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If you think the online side hustle space is just for the kids, you’re potentially missing out on a significant — and relatively easy — chunk of extra income. Those of us over 50 are out here on the internet, building skills, businesses and extra revenue. There are YouTubers in their 70s and beyond, freelancers of all ages, and top influencers who make being 50+ a big part of their brand.

If you’re 50, 60 or even 80 and just starting out online, here’s my best advice as a fellow 50-something online creator.

Don’t Be Daunted by the Technology

Everything is easier than it used to be. That doesn’t mean there isn’t a learning curve. There definitely is. But so much modern technology is simple, intuitive, and fairly drag-and-drop these days. I put off building a website for my business thinking I’d need actual web design skills, and felt pretty foolish when I first started learning to use WordPress and realised how much easier it was than I’d imagined.

My advice is to pick the simplest version of everything. That’s probably WordPress for a self-hosted blog, and something like Medium or Substack if you don’t mind using someone else’s platform (which has the advantage of a built-in potential audience). It might mean using Canva rather than Photoshop, and the social media channels you’re already comfortable with rather than those the younger generation obsess over.

Outsource if You Need To

While most modern technologies can be easily learned, it’s also fine to outsource if you want to. Some of what I’ve learned has been interesting and satisfying. Some of it has been frustrating. This really applies regardless of age. If there are things you hate doing — or don’t do well — feel free to hire someone else to do them.

Many of my contemporaries outsource the parts of their business they don’t want to do to their younger family members. You can also find people to do almost anything you might need them to on platforms like Upwork and Fiverr. Just be careful and go for people with lots of positive reviews, or better still personal recommendations from someone you know.

Use Your Existing Skills and Contacts

You probably have a whole set of life skills and experiences you can use in your online business, as well as some actual business or organisation knowledge. The creators I know in their 50s and beyond tend to have a much better idea of what they want to achieve than many younger side hustlers (and usually an actual business plan, no matter how simple).

What does your resume look like so far? What marketable skills do you have and what can you charge for them? Who do you know who might buy them? Many older freelancers end up doing something similar to what they’ve done in their career, or at least related to it in some way. This means that the contacts you’ve made over the years may well become your clients, customers, collaborators, or referrers.

Find Your Tribe

Finding a community of other people in your niche who are also the same sort of age can be a game-changer. Take a look around the platforms you use and find where the more mature crowd hang out. This might be an over-50 Facebook group specific to your niche, or a specialist publication such as Crow’s Feet: Life As We Age on Medium.

If, like me, you’re a freelance writer, you’ll find many specialist markets for older writers. You may also — depending on where you live — be able to find in-person groups who are supporting each other as they take on new challenges in mid-life and beyond. Platforms like Meet-Up may have groups in your area, and if they don’t you can always try starting one.

Starting something new over 50 may not be easy, but it’s often worthwhile from a financial point of view, not to mention the satisfaction and stimulation that comes with learning new skills and hitting new milestones. Feel like taking the first step today? This free, basic one-page business plan template is a good place to start.

About the Author

Karen Banes is a freelance writer specializing in entrepreneurship, parenting and lifestyle. She writes articles, website content, ebooks and the occasional award winning short story. Her work has appeared in a range of publications both online and off, including The Washington Post, Life Info Magazine, Transitions Abroad, Brave New Traveler, Natural Parenting Group, and Copia Magazine. Learn More About Karen

The frugal living trend isn’t new, but it is growing. And the influencers are loving it. A quick Instagram search just threw up 966,000 posts tagged #FrugalLiving.

It’s easy to see why. The cost of living crisis. Stagnant wages. Spiralling costs for education and healthcare — which are inevitably leading to higher levels of student and medical debt.

Being frugal is not a bad thing. It can impact your budget and help you pay down debt faster. But the frugal millionaire myth is misleading and the idea that frugality alone will make you wealthy is a lie.

Perhaps more concerning, the current extreme frugality movement simply isn’t healthy. The American Psychiatric Association suggests that frugality can be a symptom of obsessive-compulsive personality disorder (OCPD) if taken too far.

Too much frugality can even make you poorer. It can put all your focus on making relatively small tweaks that often come with the smug satisfaction of having saved money, without having actually saved you anything long-term, and sometimes while costing you more than you saved.

There’s still a pervasive idea that it’s designer coffee and avocado toast that’s stopping young people being able to afford things like buying a house . But It’s been pointed out many times – by many personal finance writers and vloggers – that while skipping that workday $5 latte and weekend $15 brunch makes a difference, saving $40 a week still means it will take you around 24 years to save up a $50,000 house deposit.

What’s more, the level of extreme frugality some influencers are advocating doesn’t save you $40 a week. Some people are prepared to clip coupons and drive around town looking for cheaper alternatives to save around $0.75, and that — quite frankly — doesn’t make much of a difference.

The Trouble with Extreme Frugal Living

Extreme frugality is problematic. Here are a few of the reasons why.

It’s burning up your time — you’re spending an hour researching how to save two bucks, or spending a day driving to five different stores to save $10.

It gives you the feeling you’re saving money and in control of your finances whereas if you look at the big picture, you’re talking tiny drops in a very big bucket.

It often leads to savings so small they’re not actually worth investing for the future, so they’re likely to be frittered away on something else you want or quickly sucked up by something else you need.

It distracts you from other more important things you could be doing that would actually lead to solid income, like upskilling, changing jobs or starting a profitable side hustle.

It creates a scarcity mindset where you end up very engaged with – and in some ways committed to – the concept that you can’t afford things, so you stop looking for growth opportunities that would enable you to afford more.

It has natural limits and they’re really quite low. There’s only so much you can save with constant belt-tightening, and often the less money you have to spend the smaller your savings will tend to be. Frugality, basically, doesn’t scale.

It can be expensive. Always buying cheap has big drawbacks. The car that constantly breaks down. The cheap appliances that break. The second hand stuff that wears out quickly because it was already half worn out. The wrong kind of frugality can be costly.

What to Do Instead

These are my favourite three ways to avoid the traps of extreme frugality while still being reasonably frugal in all the ways that make sense to me.

Earn more. This may sound like an obvious but ridiculously difficult to implement idea. But in fact it’s often easier to earn more than to spend less. Take the time you’re spending driving around town trying to save 20 cents on gas and spend that time on upskilling for a better job or starting a low-cost side hustle. Instead of aiming to save that 20 cents, aim to add an extra $1,000 a month to your income.

Invest the extra. It’s not worth investing 20 cents. It may not even feel worth investing the $40 a week you saved by dropping your lattes and brunches, but it’s definitely worth investing $1,000 a month. You could even spread it across different investments to create a diversified portfolio over time. If any of your investments have tax benefits, dividends or other perks, even better.

Think twice about purchasing things as cheaply as you can, and learn to recognise a false economy. It definitely is worth saving money on some things. If the generic version really does the same job as the branded version, or the second hand version will last as long as the brand new one, with the same running costs, go for it. But be prepared to invest in quality when you know it will pay off in the long run.

The aim is to keep your frugality at a level that is genuinely helpful to your long-term budget, not at the level that the APA defines as a mental illness. There’s plenty of wiggle room in there, so it’s just a case of finding a level where you’re comfortable.

About the Author

Karen Banes is a freelance writer specializing in entrepreneurship, parenting and lifestyle. She writes articles, website content, ebooks and the occasional award winning short story. Her work has appeared in a range of publications both online and off, including The Washington Post, Life Info Magazine, Transitions Abroad, Brave New Traveler, Natural Parenting Group, and Copia Magazine. Learn More About Karen

A middle-aged man with short gray hair and a slight smile, wearing a dark blazer over a patterned shirt, stands outdoors with a blurred background of greenery and buildings. — Brian Thorp, CEO of Wealthtender | Image Credit: Institute for Innovation Development

[ The rapidly evolving state of everything in the financial services industry continues in the financial marketing arena – from regulatory synchronization expanding the use of advisor testimonials to the re-evaluation of digital marketing to the new SEO – AEO spectrum.

The recent NASAA proposal to align state rules with the SEC Marketing Rule – which was slowly being adopted at the state level – has been welcomed as it allows advisors in the remaining approximately 20 states to use client testimonials. This alignment between state and federal marketing rules would eliminate a significant compliance headache and competitive disadvantage for a substantial number of state-registered advisors. The likelihood of its implementation signals marketing departments to be ready or refine their use of testimonial engagement strategies as more financial competitors will be utilizing testimonials in their community outreach.

On the other front, the technological disruption caused by the rapid mainstream client adoption of AI tools, like ChatGPT, is forcing a re-evaluation of digital marketing. A key emerging trend in digital marketing is to move beyond traditional keyword search to optimizing content to be surfaced directly by AI assistants – creating a significant shift in digital marketing from Search Engine Optimization (SEO) to Answer Engine Optimization (AEO). Advisors and their marketing departments realize that they need to evolve their digital strategy from SEO to AEO to remain visible as consumers increasingly use AI tools for search.

On the backdrop of these two significant industry marketing shifts, we reached out to Institute member and one of our Marketing professors, Brian Thorp, CEO of Wealthtender – an advisor testimonial and digital marketing platform positioned as a solution to help advisors navigate both of these evolving marketing shifts. His firm’s support includes a Testimonial Marketing Studio, the creation of the “Voice of the Client” awards, and a new feature called “AI-Optimized FAQs” to help advisors adapt to AEO. Overall, his insights positioned his firm as a thought leader and an essential partner for advisors and their marketing leaders focused on future growth.]

Hortz: Can you share your perspectives on the top trending topics around advisor marketing and regulatory compliance right now?

Thorp: The landscape for financial advisor marketing is experiencing unprecedented changes as consumers pivot to artificial intelligence tools like ChatGPT, Perplexity, and Google AI Overviews to find and research financial advisors. In my nearly 30 years in financial services, including 22 years at Invesco before founding Wealthtender, I have witnessed many industry shifts, and I believe what we are experiencing right now is just as significant as the commercialization of the internet itself.

According to our 2025 Wealthtender Study of $100K+ Households Seeking Financial Advice published this past August, 25% of consumers already plan to use AI search tools like ChatGPT when looking for a financial advisor. What is more striking is that 96% of people will research an advisor online after receiving a referral from friends or family, and 83% specifically want to read online reviews and testimonials before making contact. This shows that even a traditional “offline” referral is unlikely to result in a new client for an advisor unless they show up prominently and favorably, such as with strong client reviews, in online searches.

For financial advisors, this means their digital marketing efforts must evolve from prioritizing Search Engine Optimization (SEO) to also adopting best practices for Answer Engine Optimization (AEO).

Most online searches now end without a single click, as AI tools provide instant answers through summaries and featured snippets. Advisors and marketing teams who have invested years strengthening their SEO must now evolve their digital marketing approach to ensure they show up in AI-generated responses.

AEO focuses on generating and structuring content, both “onsite” (e.g., an advisor’s website) and “offsite” (e.g., social media accounts, industry directory listings), so AI search tools can easily and confidently surface an advisor’s information as authoritative answers to consumer queries. This includes implementing schema markup (e.g., FAQs, reviews), creating clear and conversational Q&A content, formatting content for featured snippets, thoughtful answers, and building authority signals (e.g., online reviews and testimonials, awards) across reputable platforms.

We have specifically designed our platform to become one of the most impactful digital marketing tools helping advisors optimize their visibility in AI search tools, alongside leading website hosting providers that have modernized their platforms to position advisors for success with AEO.

Hortz: That addresses major changes in advisor marketing but what about key regulatory trends that advisors and their marketing teams should also be following?

Thorp: Regarding regulatory compliance trends, there are two noteworthy concerns impacting advisor marketing, both related to the use of client testimonials in advertising and promotional activities.

First, there’s a troubling double standard affecting thousands of state-registered advisors. While SEC-registered advisors across the country have been able to collect and promote client testimonials since the SEC Marketing Rule became effective in 2021, approximately 20 states continue to prohibit state-registered advisors from doing the same. This creates scenarios where consumers can read reviews about an advisor affiliated with a national firm but cannot find a single review about the local advisor who has served their community for decades.

The recent NASAA proposal to align state testimonial rules with the SEC Marketing Rule represents a watershed moment that could finally resolve this inequity. However, several holdout states have shown troubling resistance. California indicated they are “not considering changing the regulation in the foreseeable future,” while Tennessee stated they do not plan to adopt NASAA’s recommendation. As someone who has spent thousands of hours studying the SEC Marketing Rule and advocating with state regulators, I can tell you this alignment is critical for both consumer protection and competitive fairness. Consumers deserve access to the same quality of information regardless of whether an advisor is registered at the state or federal level.

The second regulatory challenge involves the continued gray area surrounding the use of Google Reviews by financial advisors from a regulatory perspective. This is perhaps the most frequently asked question I receive from advisors and compliance officers.

While many advisors and compliance teams appear comfortable soliciting Google Reviews in a limited capacity, they acknowledge that the promotion of a Google Business Profile is problematic. Doing so likely results in “adoption” or “entanglement”, terms defined by the SEC that trigger restrictions and disclosure requirements stipulated in the SEC Marketing Rule that could prove challenging, if not impossible, to administer since Google’s platform is not designed with compliance in mind.

For example, advisory firms that invite clients to write Google Reviews only to receive testimonials containing promissory language or misleading statements clearly prohibited by the SEC Marketing Rule could prove difficult to get removed. Some firms have decided to move forward by soliciting Google Reviews, taking a calculated risk that the SEC will not pursue enforcement actions for limited use, though we have not yet seen actual enforcement actions that clarify the SEC’s position. Until we do, advisors navigate this uncertainty without clear guideposts.

Hortz: What solutions or advice can you offer for these issues?

Thorp: This is precisely why we built Wealthtender as the industry’s first online review platform designed for regulatory compliance. When reviews are collected through our platform, we require disclosures to be prominently displayed with resources provided to help advisors meet their compliance obligations.

For advisors comfortable soliciting Google Reviews, it is worth noting that we offer an import tool that brings those reviews into Wealthtender where proper disclosures can be added, transforming them into compliant testimonials that advisors can actively promote. If the SEC does eventually weigh-in that a limited use of Google Reviews is acceptable, then advisors importing Google Reviews to our platform will enjoy the best of both worlds: visibility benefits across Google’s ecosystem, and Wealthtender reviews that can be compliantly promoted on advisor websites, in social media posts, and ensure visibility in AI tools that may not acknowledge the existence of Google Reviews (e.g., ChatGPT crafts answers to consumer queries using Bing, a competing platform).

As to testimonials, while I remain optimistic that NASAA’s proposal will accelerate adoption across holdout states, advisors should prepare for a timeline that could range from several months to a few years depending on their state’s legislative process, stay informed about their specific state’s regulatory developments, and be proactive in preparing their testimonial marketing infrastructure. I encourage advisors to reach out to their state regulators and advocate for change. When regulators hear directly from advisors and understand how these outdated rules impact both small businesses and consumers seeking to make informed hiring decisions, it can help move the process forward.

These two major trends, the disruption of search through AI and the regulatory evolution around testimonials, are fundamentally reshaping the advisor marketing landscape. Advisors and their marketing teams must adapt their digital strategies to remain visible in an AI-powered world while navigating complex compliance requirements around testimonial marketing. Those who successfully address both challenges will find themselves well-positioned for outpaced growth in the coming years.

Hortz: Can you further explain the issues behind the new emergence of advisor marketing focus on AEO versus SEO? Is SEO positioning now dead?

Thorp: The emergence of Answer Engine Optimization represents an evolution in digital marketing rather than a wholesale shift away from Search Engine Optimization. Understanding the relationship between SEO and AEO is crucial for advisors who want to maintain their digital visibility as consumer search behavior evolves.

Traditional SEO focused on optimizing your content to rank highly in search engine results pages, with the goal of attracting clicks to your website. This approach has driven digital marketing strategy for the past two decades and remains important. However, the rise of AI-powered search tools like ChatGPT, Google’s AI Overviews, Perplexity, and other answer engines has introduced what the industry calls “zero-click” searches. These tools provide direct answers to user queries without requiring them to click through to websites. Recent data suggests that over 60 percent of online searches now end without a single click, as AI tools, smart summaries, and featured snippets provide instant answers. This shift fundamentally changes the digital marketing landscape for financial advisors.

AEO focuses on optimizing your content and online presence to be surfaced directly by AI assistants when they answer questions. Rather than trying to get users to click to your site, AEO ensures your expertise is cited, referenced, or recommended within the AI-generated response itself. This requires structuring your content differently, emphasizing clear, to-the-point answers to specific questions that potential clients are asking, and implementing technical optimizations like schema markup that help AI tools understand and surface your information.

As of today, I feel that AEO is not replacing SEO but rather complements it and builds upon it. While the nature of search is evolving across industries, the fundamental goal in our space remains the same: connecting people who need financial guidance with the advisors best suited to serve them.

Many search queries still result in clicks to websites, and traditional search engines remain important discovery channels. Moreover, many of the best practices that strengthen SEO also benefit AEO. High-quality, authoritative content, proper site structure, and clear answers to common questions all support both traditional search visibility and AI-powered discovery.

Advisors must adapt their strategies to include AEO practices while maintaining their SEO foundation. This means using structured content like FAQ sections with proper schema markup, creating clear, concise answers to questions prospective clients commonly ask, optimizing for conversational search patterns that mirror how people interact with AI tools, and building authority signals (e.g., online reviews, awards) across multiple platforms that AI tools can reference. The advisors who will thrive in this evolving landscape are those who recognize that SEO and AEO work together as complementary components of a comprehensive digital marketing strategy rather than competing approaches.

Hortz: What are the top concrete actions an advisor should take today to begin optimizing for Answer Engines?

Thorp: I recommend five specific actions that can immediately improve an advisor’s Answer Engine Optimization while also strengthening their traditional SEO.

First, advisors should publish comprehensive FAQ sections on their websites and on third-party platforms like Wealthtender that address the most common questions prospects who align with the advisor’s Ideal Client Profile (ICP) are likely to ask when searching for a financial advisor. Do not create generic FAQs that could apply to any advisor. Instead, focus on the specific questions relevant to your niche and your ICP. For example, if you focus on tech professionals planning for early retirement, answer the questions they are searching for about equity compensation, tax optimization, and lifestyle design. The key is providing clear, concise, authoritative answers that directly address user intent. These FAQs should be substantial enough to be helpful while remaining focused enough that AI tools can easily extract and cite your insights.

Second, implement FAQ schema markup on your website to help search engines and answer engines understand your content structure. Schema markup is specialized code that explicitly tells search engines “this is a question, and this is the answer.” When properly implemented, schema increases the likelihood that your content will be surfaced in AI Overviews, featured snippets, and direct AI responses. While implementing schema requires some technical understanding, most modern website platforms including WordPress, Squarespace, and advisor-specific platforms like FMG or Snappy Kraken can facilitate this implementation. If you are working with a website developer or freelancer, make FAQ schema implementation a priority. We have built this functionality directly into advisor profiles because we have seen how effectively it improves visibility in both traditional and AI-powered search results.

Third, optimize your content to increase the chances of appearing in featured snippets and AI-generated responses by structuring it specifically to answer questions. This means writing in a clear, question-and-answer format even within longer articles, using headers that reflect actual questions people ask, and providing concise initial answers followed by more detailed explanations. If the structure and language do not lend themselves to those formats, revise your approach to be more conversational and direct.

Fourth, leverage client testimonials strategically within your content to enhance both trust and authority signals. Reviews and testimonials serve multiple purposes in the AEO context. They provide social proof that prospects value, they demonstrate your expertise through actual client stories, and they create additional content that AI tools can reference when recommending advisors.

When someone asks an AI tool for recommendations on financial advisors specializing in a particular area, having several positive reviews that mention your niche expertise increases your likelihood of being included in the answer generated.

Fifth, publish authoritative content that demonstrates deep expertise in your specialization. While quick answers are important for certain queries, AI tools also value and cite comprehensive resources that thoroughly address complex topics. Write detailed articles, create comprehensive guides, develop educational resources that showcase your knowledge and provide genuine value to readers. This content should be written in a natural, conversational tone that reflects how you would explain concepts to clients. When AI tools are synthesizing information to answer complex financial questions, they prioritize sources that demonstrate authority, provide accurate information, and explain concepts clearly. The advisors who consistently publish high-quality thought leadership content position themselves as the sources AI tools turn to when addressing financial planning questions that require more in-depth answers.

Hortz: How should advisors and their marketing teams strategically prepare themselves for deploying or enhancing their testimonial marketing strategies?

Thorp: Getting started with testimonial marketing requires a thoughtful, systematic compliance-first approach. Having worked with hundreds of advisors and wealth management firms now successfully gathering online reviews from their clients, I recommend several important steps that separate successful testimonial programs from those that struggle or create compliance risks. And I’m happy to say the Testimonial Marketing Playbook I authored has been read by hundreds of financial advisors and compliance professionals interested in a step-by-step guide to getting started.

First and foremost, advisors must develop a deep understanding of the SEC Marketing Rule’s requirements and nuances. This is not something you can delegate entirely to your compliance team without maintaining your own working knowledge. The rule contains specific provisions around disclosure requirements, oversight obligations, and prohibited practices that should inform every aspect of your testimonial strategy.

I recommend advisors become familiar with the Marketing Rule core principles: understanding what constitutes a testimonial versus an endorsement, knowing when “clear and prominent” and additional disclosures are required, and establishing appropriate oversight procedures.

Second, develop a systematic collection process that feels authentic rather than transactional, while ensuring adherence to regulatory requirements, such as inviting all current clients at the outset to write a review to avoid cherry-picking concerns. The collection process should include simple, yet thoughtfully crafted language that makes it easy for clients to provide feedback about their experience. After the initial outreach, it is important to establish a regular cadence for testimonial requests rather than sporadic, reactive outreach (e.g., one week after annual client review meetings).

Third, choosing the right testimonial marketing platforms is critical. Not all review platforms are created equal when it comes to regulatory compliance. As an example, we designed everything from the ground up specifically to meet SEC Marketing Rule requirements. Whether an advisor chooses Wealthtender or another solution, they must ensure the chosen platform provides an ability to satisfy regulatory compliance requirements.

Finally, integrate testimonials strategically into the overall marketing plan. Testimonials should be prominently featured on advisor websites (with appropriate disclosures), incorporated into nurturing campaigns, highlighted in client presentations, and leveraged across social media platforms. To assist with the latter, we launched Testimonial Marketing Studio at the start of 2025 to provide advisors with a compliant tool to promote testimonials in social media posts with just a couple of clicks.

Create a comprehensive marketing plan that positions client testimonials as a cornerstone of an advisor’s value proposition, demonstrating through real client experiences how the advisor and firm solve problems and deliver results. The most successful advisors treat testimonials not as an isolated marketing tactic but as a fundamental component of their positioning and communication strategy.

Hortz: Any other digital marketing tips you want to share?

Sure, I’m happy to emphasize a few areas that I feel will make meaningful differences for advisors focused on sustainable practice growth through digital marketing.

First, I encourage advisors to participate in recognition programs like our Voice of the Client awards which recognizes advisors based on verified client reviews rather than revenue growth or assets under management. This also creates a level playing field where excellence in client service matters more than firm size and third-party validation based on verified client reviews rather than pay-to-play arrangements. These awards provide credibility with prospective clients who are evaluating multiple advisors and trying to identify which ones truly excel at client service. Importantly, the awards also generate impactful authority signals that both traditional search engines and AI-powered tools recognize when determining which advisors to surface in response to user queries. Being recognized by credible third parties help position you as a trusted expert in your field.

Second, implement schema markup across your entire website, not just in FAQ sections. Various types of schema help search engines and AI tools better understand your content, improving your visibility in featured snippets, knowledge panels, and AI-generated responses. This technical optimization represents one of the highest-return investments advisors can make in their digital infrastructure. While it requires some technical implementation, the long-term benefits of properly structured data significantly outweigh the initial effort.

Third, stay informed and proactive about regulatory developments affecting your marketing activities. As the SEC issues risk alerts and announce enforcement actions, advisors and marketing teams can gain useful insights that should be taken into consideration for potential refinement of marketing tactics employed. Regularly review updates from the SEC, monitor NASAA developments, and participate in industry discussions about compliance best practices. Subscribe to relevant compliance publications, attend webinars focused on marketing regulations, and maintain an ongoing dialogue with your compliance team or consultant about emerging trends and regulatory expectations.

Finally, I want to emphasize the importance of authenticity across all advisor marketing efforts. Whether you are collecting testimonials, creating content for AEO, or engaging with prospective clients on social media, the most successful advisors maintain a genuine voice that reflects who they really are and how they actually work with clients.

Consumers have become increasingly sophisticated at recognizing manufactured marketing messages versus authentic communications from professionals who truly care about helping them achieve their financial goals. Let your unique value proposition, your specific expertise, and your authentic personality come through in your marketing rather than trying to sound like every other advisor in the industry. The digital marketing tools and strategies we have discussed today are most effective when they amplify your authentic voice rather than replacing it with generic messaging that could apply to anyone.

This article was originally published here and is republished on Wealthtender with permission.

About the Author

Bill Hortz

Founder Institute for Innovation Development

Bill Hortz is an independent business consultant and Founder/Dean of the Institute for Innovation Development- a financial services business innovation platform and network. With over 30 years of experience in the financial services industry including expertise in sales/marketing/branding of asset management firms, as well as, creatively restructuring and developing internal/external sales and strategic account departments for 5 major financial firms, including OppenheimerFunds, Neuberger&Berman and Templeton Funds Distributors. His wide ranging experiences have led Bill to a strong belief, passion and advocation for strategic thinking, innovation creation and strategic account management as the nexus of business skills needed to address a business environment challenged by an accelerating rate of change.

As the end of the year approaches, it’s easy to get caught up in the rush of holidays and closing chapters. But this season also offers a powerful opportunity to make strategic financial decisions — especially if you’ve experienced a life change.

Whether you’ve gone through a divorce, stepped into a caregiving role, or adjusted your retirement timeline, the tax decisions you make now can shape your financial confidence in the new year.

Maximize Retirement Contributions

One of the most impactful ways to reduce your taxable income — and build toward long-term goals — is by maximizing your retirement contributions.

If you’re still working, review the limits for 401(k), 403(b), and IRA contributions. If you’re age 50 or older, take advantage of catch-up contributions, which allow you to save even more.

For some, this may also be a good time to evaluate a Roth conversion — moving funds from a traditional IRA to a Roth IRA. While this does create a taxable event now, it can provide tax-free growth and withdrawals later. It’s a move that requires careful planning, especially after a major transition.

Review Tax-Loss Harvesting Opportunities

If you’ve sold investments at a loss this year, you may be able to use those losses to offset gains — or even reduce your taxable income. This strategy is known as tax-loss harvesting.

In simple terms: if you sold one investment at a gain and another at a loss, those amounts can offset each other for tax purposes. And if your losses exceed your gains, you may be able to deduct up to $3,000 against ordinary income (or carry the loss forward to future years).

This is particularly helpful in years when your income has shifted — such as after a divorce or retirement.

Use Flexible Spending Accounts and HSA Contributions

If you have a Flexible Spending Account (FSA), remember that many plans require you to use the funds before year-end or risk losing them. Check your plan’s rules and spend remaining dollars on eligible healthcare expenses while you still can.

For those with a Health Savings Account (HSA), consider maximizing your contributions. HSAs offer a triple-tax advantage: contributions are tax-deductible, growth is tax-free, and withdrawals for qualified healthcare expenses are also tax-free.

HSAs can also serve as a powerful long-term planning tool — not just for this year, but for retirement healthcare expenses down the line.

Consider Charitable Giving

Charitable giving isn’t just good for the community — it can also benefit your tax plan.

If you itemize deductions, donor-advised funds allow you to bundle multiple years of charitable giving into one contribution. This can increase the tax benefit in a high-income year, while allowing you to give over time.

If you’re over age 70½ and have a traditional IRA, qualified charitable distributions (QCDs) allow you to donate directly from your IRA to a qualified charity. These gifts can count toward your required minimum distribution and reduce your taxable income.

If your financial goals are deeply connected to your values, charitable giving can play a meaningful role in both.

Life Change? Update Your Withholding or Filing Status

Major life events can directly impact your tax situation.

A divorce, a death in the family, or becoming a caregiver may change your filing status, affect deductions, or shift your tax withholding needs.

If you haven’t already, review your paycheck withholding or estimated tax payments to avoid surprises come April. Making adjustments now ensures your taxes reflect your current reality — not last year’s.

Conclusion: Be Intentional with the Time You Still Have

Year-end doesn’t have to feel rushed. With the right guidance, this season can be a chance to slow down, reassess, and make purposeful decisions — especially after a year of change.

This article was originally published here and is republished on Wealthtender with permission.

About the Author

Michelle Francis Fee-Only Financial Advisor for Women

Michelle Francis | Life Story Financial

🔗 Website | Wealthtender Profile

Do you work at Southern California Gas Company (SoCal Gas)? Get the resources you need and expert insights from financial professionals who specialize in helping SoCal Gas employees make the most of their SoCal Gas and SEMPRA compensation package and benefits.

Whether you’re a new SoCal Gas employee or you’ve moved up the ranks into a management or executive leadership role over a multi-year career, it’s important to make smart money moves with your income and employee benefits. For example:

✅ Do you know the right moves to make to get the greatest value from the SoCal Gas and SEMPRA benefits available to you?

✅If you’re thinking about leaving SoCal Gas for another job or planning to retire from the company in a few years, are you taking the right steps today to ensure you will receive all of the compensation and benefits that you’ve earned?

Get the Most Value from Your SoCal Gas & SEMPRA Benefits and Compensation Package

Throughout the year, SoCal Gas provides its employees and executives with updates about their benefits ranging from health insurance and health savings plans to retirement plans like a 401(k), deferred compensation plans, and stock options. While the company offers many useful resources and access to knowledgeable staff who can assist with questions, you’ll also find financial professionals not affiliated with SoCal Gas who specialize in helping employees make the most of their income and benefits.

Whether you work in the Southern California Gas Company headquarters in Monterey Park, California, another office location around the country, or remotely from home, you may have questions about your compensation package and benefits better suited for a financial professional who can offer unbiased advice and guidance.

For example, sensitive topics like discussing the steps you should take before quitting your job at SoCal Gas to work elsewhere, protecting yourself in advance of a corporate layoff, or deciding when you should plan to retire are all conversations that may be more comfortable with a trusted financial advisor.

Should you hire a Southern California Gas Company specialist financial advisor or an advisor close to home?

You’ll likely find dozens of nearby financial advisors well-suited to help you reach your money goals with a personalized plan. But it may be more difficult to find a financial advisor who specializes in serving Southern California Gas Company employees.

Fortunately, many financial advisors offer virtual services so you can meet online no matter where you (or they) live.

This means you can choose to hire a specialist financial advisor who lives hundreds of miles away if you decide their knowledge and experience working with Southern California Gas Company employees is a better fit to help with your unique needs.

💡 In the Q&A below, you’ll gain insights from financial advisors who work with SoCal Gas employees to help them make smart decisions to get the most value from their compensation and benefits, reduce their money stress, and prepare for a comfortable retirement.

🙋‍♀️ Do you have questions not yet answered? Use the form below to submit questions anonymously and watch this article for updates with answers to your questions. You can also reach out to the financial advisors below to set up an introductory call or contact them with your questions by email.

💸 Smart Money Insights for Southern California Gas Company Employees & Executives

This page is organized into sections to help you quickly find the information you need and get answers to your questions:

Q&A: Financial Planning Tips for SoCal Gas Employees & Executives
Get Answers to Your Questions About Your SoCal Gas Benefits and Career
Browse Related Articles

Q&A: Financial Planning Tips for SoCal Gas Employees & Executives

Answers to SoCal Gas Employee Questions with Ajay Vadukul, CFP®, EA

Ajay Vadukul is a financial advisor based in Torrance, California who specializes in offering financial planning services to Southern California Gas Company employees. Ajay helps his clients get the most value from their SoCal Gas benefits and compensation package so they can enjoy life and feel confident about their financial future.

Q: As a financial advisor with experience helping SoCal Gas employees save for their retirement, how do you help them make the most of their employee benefits?

Ajay: When I work with SoCal Gas and Sempra employees, my mission is simple: to help them maximize every benefit they’ve earned while turning those benefits into a coordinated, long-term retirement strategy.

SoCal Gas offers an excellent benefits package including a 401(k) with employer match, a defined pension plan, stock purchase options, and comprehensive health coverage, but many employees don’t realize how these pieces can work together to build true financial independence. My role is to help translate those benefits into a personalized retirement roadmap.

For example:

I help employees strategically allocate their 401(k) contributions to align with their pension and retirement income goals, optimizing tax efficiency and risk exposure.
We evaluate pension payout options, lump sum vs. monthly annuity, based on lifestyle goals, longevity expectations, and family needs.
For employees nearing retirement, I build Social Security coordination strategies that complement their SoCal Gas pension income.
I also help manage 401(k) rollovers, post-retirement investment allocation, and cash flow planning to ensure a seamless transition into retirement.

What makes me different is that I understand the culture and structure of SoCal Gas employees’ careers, long tenure, generous benefits, and a focus on stability. My approach is to turn those advantages into a plan that supports not just a comfortable retirement, but a fulfilling one.

Q: When you first speak with a SoCal Gas employee, what questions do you like to ask to better understand their unique circumstances and determine how you can best help them achieve their goals?

Ajay: When I meet with a SoCal Gas employee for the first time, my goal is to listen first and plan second. Their benefits package is incredibly valuable, but how it fits into their life depends on their story, their career stage, family situation, and long-term goals.

I start by asking questions that uncover what truly matters to them:

Career and Tenure: How long have you been with SoCal Gas, and how do you envision your next phase? Staying until retirement, or transitioning earlier? The answer helps me tailor strategies around their pension vesting, 401(k) match, and stock purchase opportunities.
Retirement Vision: What does “retirement” look like to you, full retirement, part-time consulting, or a second career? SoCal Gas employees often retire with strong pensions, so understanding lifestyle expectations helps me coordinate pension payouts, Social Security timing, and healthcare costs.
Financial Priorities: Are you focused on paying down debt, saving for retirement, or maximizing tax efficiency? I align their benefits from 401(k) contributions to Health Savings Accounts (HSAs) with those priorities.
Family and Legacy Goals: Who depends on you financially, and what do you want to pass on? Many SoCal Gas employees value family security, so we discuss life insurance, survivor benefits, and estate planning.
Tax Coordination: What’s your current tax situation, and are you using pre-tax vs. Roth options in your 401(k)? This is where I help employees optimize contributions for both short-term savings and long-term tax advantages.

Every conversation is customized. I want employees to feel like they finally have someone who understands both the complexity of SoCal Gas benefits and the simplicity of their personal goals.

Ultimately, I’m not just looking to manage investments, I’m helping them align decades of hard work into a confident, well-structured retirement plan.

Q: Is there a particular benefit available to SoCal Gas employees you feel isn’t as well utilized or understood by employees as it should be?

Ajay: Yes, without question, the SoCal Gas pension plan and 401(k) structure are two of the most underutilized and misunderstood benefits among employees.

Many SoCal Gas and Sempra employees know they have a pension, but few truly understand how valuable it is or how to integrate it with their other retirement resources. The defined benefit pension plan is a rare advantage in today’s world, but optimizing it requires understanding how your years of service, final average pay, and payout elections interact with your 401(k), Social Security, and taxes.

I often see employees leaving money on the table by:

Not contributing enough to capture the full SoCal Gas 401(k) employer match.
Overlooking the power of Roth 401(k) contributions to create tax-free income in retirement.
Not coordinating their pension and Social Security timing, which can dramatically affect long-term income and tax brackets.
Missing out on Health Savings Account (HSA) opportunities, which can serve as an additional tax-free retirement medical fund.

As a SoCal Gas financial planner, I help employees understand exactly how to layer these benefits, the pension, 401(k), stock purchase plan, and HSA into a single, efficient retirement strategy. It’s not just about saving; it’s about creating a coordinated plan that supports lifestyle, legacy, and long-term security.

Q: Beyond Southern California Gas Company employee benefits for retirement savings, are there other types of benefits offered by the company that you find valuable to discuss with your clients?

Ajay: Absolutely. One of the reasons I enjoy working with SoCal Gas and Sempra employees is that their benefits package goes far beyond just a pension or 401(k). There are several often-overlooked opportunities that can make a major difference in long-term wealth building and tax planning.

For example:

Health Savings Account (HSA): Many SoCal Gas employees have access to high-deductible health plans with HSA eligibility. I often call this the “stealth retirement account” because it offers triple tax benefits: deductible contributions, tax-free growth, and tax-free withdrawals for qualified expenses. For clients who can afford to pay medical expenses out-of-pocket, I recommend investing their HSA for future healthcare costs in retirement.
Tuition Reimbursement and Education Savings: Sempra’s tuition assistance program is a fantastic resource for those looking to advance their careers, but I also help families pair that with education savings strategies like 529 plans. This allows SoCal Gas employees to save for their children’s education in a tax-efficient way while taking advantage of employer-sponsored programs.
Insurance and Protection Benefits: Life and disability insurance are critical components of the SoCal Gas benefits package. I help clients evaluate their employer-provided coverage to make sure it aligns with their family’s needs and long-term plan and when necessary, supplement it with private coverage for full protection.

Ultimately, my goal as a SoCal Gas financial advisor is to help employees see their entire benefits package as an integrated financial ecosystem, one that supports their goals for retirement, health, education, and family security. When these benefits are coordinated properly, the results can be life-changing.

Q: For SoCal Gas employees thinking about leaving the company to accept a job elsewhere, what actions do you recommend they take before resigning and shortly thereafter?

Ajay: When a SoCal Gas employee is considering leaving the company whether for a new opportunity or early retirement, I always emphasize one thing: don’t rush the paperwork before you understand the long-term impact of every decision. SoCal Gas and Sempra offer some of the most valuable employee benefits in the utility industry, and how you handle them when leaving can significantly affect your retirement outlook.

Here are the key steps I guide my clients through:

1. Review Pension Eligibility and Options

If the employee is vested in the SoCal Gas pension plan, it’s critical to understand what happens when they leave. Depending on their years of service and age, they may have the choice between:

A lump-sum payout that can be rolled into an IRA for continued tax-deferred growth, or
A monthly annuity beginning at retirement age.
We run side-by-side projections to determine which option best fits their goals, tax situation, and family needs.

2. Evaluate 401(k) and Rollover Strategies

Employees leaving SoCal Gas can choose to leave their 401(k) in the company plan, roll it into a new employer’s plan, or move it to an IRA. I typically recommend reviewing:

Investment options and fees in each plan,
Roth vs. pre-tax contributions,
And tax implications of any distributions.
This decision alone can impact decades of future growth, so professional guidance here is crucial.

3. Maximize HSA and Health Coverage

Before leaving, employees should confirm whether their Health Savings Account (HSA) will remain accessible and portable (most do) and whether they need to bridge coverage through COBRA or a spouse’s plan. Since HSAs can continue to grow tax-free, keeping them invested is often a smart long-term move.

4. Update Beneficiaries and Financial Plan

Lastly, once they transition out, it’s time to revisit the overall plan, updating beneficiaries, investment allocations, and income projections to reflect their new employer and benefit structure.

In short, leaving SoCal Gas is more than a career move, it’s a financial inflection point! As a SoCal Gas financial advisor, I specialize in helping employees make these transitions smoothly, ensuring that their pension, 401(k), and HSA are optimized and aligned with their next chapter.

Q: For SoCal Gas employees approaching retirement age, how do you recommend they prepare to make the transition from living off their salary to relying upon other sources of income?

Ajay: For many SoCal Gas employees, the transition from earning a steady paycheck to drawing from retirement income can feel both exciting and overwhelming. After years of consistent income and predictable benefits, the challenge isn’t just stopping work, it’s replacing that paycheck with confidence and clarity.

When I help SoCal Gas and Sempra employees prepare for retirement, I focus on building a comprehensive income strategy that turns their years of hard work and benefits into a reliable, tax-efficient paycheck for life.

Here’s how we approach it:

1. Map Out All Income Sources

We begin by identifying every potential stream of income: SoCal Gas pension benefits, 401(k) accounts, HSAs, Social Security, personal savings, and any investment income. This allows us to see the full picture and create a withdrawal plan that balances growth, liquidity, and stability.

2. Optimize Pension and Social Security Timing

Choosing when to begin pension and Social Security benefits can change lifetime income by hundreds of thousands of dollars. We analyze break-even points, survivor options, and inflation protection to determine the most efficient strategy, often coordinating the pension with 401(k) withdrawals to manage taxes.

3. Transition from Saving to Spending

Many SoCal Gas employees have spent decades saving diligently in their 401(k). We reframe that mindset to focus on safe withdrawal strategies, determining how much they can comfortably draw each year without jeopardizing long-term sustainability. This often involves creating a “retirement paycheck” that mimics their working income, funded through a mix of pension, 401(k) distributions, and investment income.

4. Plan for Healthcare and Taxes

Retirement planning isn’t just about income, it’s about protection. We review healthcare options (COBRA, Medicare, or retiree benefits), ensure their Health Savings Account (HSA) is used strategically for tax-free medical costs, and build tax diversification through Roth conversions or distribution timing.

5. Align Lifestyle With the Plan

Finally, we help them test-drive their retirement lifestyle, adjusting budgets, travel goals, and charitable giving plans to make sure the numbers match the vision. The goal isn’t just financial independence; it’s financial peace of mind.

Q: For SoCal Gas employees who have managed their finances on their own to this point, what would you suggest they consider to help them decide if they should begin working with a financial advisor at this stage in their lives?

Ajay: First, I want to say this: many SoCal Gas employees have done a great job managing their finances on their own. You’ve built savings, contributed to your 401(k), and paid attention to your benefits and that’s no small feat. The question isn’t whether you can manage your finances yourself, but whether you’re maximizing the opportunities you’ve earned after years of hard work.

As employees approach retirement or major life transitions, there are several key moments where a SoCal Gas financial advisor can make a measurable difference:

1. Coordinating Complex Benefits

Between the SoCal Gas pension plan, 401(k), Health Savings Account (HSA) etc, there are a number of moving parts that can be overwhelming. A financial advisor experienced with SoCal Gas benefits can ensure these programs work together: optimizing tax strategy, risk exposure, and long-term income.

2. Transitioning From Accumulation to Distribution

Managing money while working is about saving and investing. But once you approach retirement, the challenge shifts to how to safely draw income without running out of money or triggering unnecessary taxes. This transition from saving to spending, is one of the most misunderstood parts of retirement planning.

3. Avoiding Costly Mistakes

Even the most disciplined savers can make unintentional errors — like taking a pension too early, mishandling a 401(k) rollover, or overlooking survivor benefit options. I help clients see around corners by stress-testing scenarios before irreversible decisions are made.

4. Creating Confidence and Clarity

Ultimately, the real value of professional advice is peace of mind. You’ve spent decades working hard for SoCal Gas, now it’s about ensuring every decision supports the life you want after work. My job isn’t to take control; it’s to empower you with a plan that’s clear, customized, and coordinated across every benefit and account you’ve earned.

Working with a SoCal Gas retirement planner doesn’t mean giving up control, it means gaining clarity, direction, and confidence in the next chapter of your financial life.

Q: What are some of the unique financial planning challenges you commonly see among your clients who are SoCal Gas employees and how do you help them overcome these obstacles?

Ajay: SoCal Gas employees have access to one of the most comprehensive benefit packages in the energy industry, but that also means their financial picture can become incredibly complex over time. The biggest challenge I see isn’t a lack of opportunity, it’s too many overlapping choices that make it difficult to see how everything fits together.

Here are a few of the most common challenges and how I help clients overcome them:

1. Understanding the Pension and 401(k) Relationship

Many employees don’t realize how their SoCal Gas pension and 401(k) work together to create their retirement income. I help them understand:

How to balance pension payout options (lump sum vs. annuity).
How to coordinate 401(k) contributions for maximum tax efficiency.
And how to design a withdrawal plan that creates a steady, predictable income in retirement.

We turn confusion into clarity by mapping out a personalized “retirement paycheck” that blends both benefits seamlessly.

2. Tax Efficiency and Timing

Between pre-tax 401(k) savings, pension income, and Social Security, taxes can sneak up fast in retirement. I help SoCal Gas employees structure Roth conversions, withdrawal sequencing, and tax diversification strategies so they keep more of what they’ve earned, not just for retirement, but throughout their lifetime.

3. Retirement Timing and Lifestyle Planning

Many SoCal Gas employees stay with the company for decades. When retirement approaches, it’s not just a financial shift, it’s an identity shift. I help them prepare mentally and financially for this transition by aligning their income plan with their purpose, travel goals, and family priorities.

4. Benefit Coordination and Legacy Planning

From health benefits and HSAs to life insurance and survivor options, I ensure every part of the SoCal Gas benefit package is integrated into a clear estate and legacy plan. The goal is simple: make sure their wealth supports both their life and the people they care about most.

At the end of the day, SoCal Gas employees don’t need more information, they need a trusted guide who can turn information into strategy. My role is to simplify complexity, reduce uncertainty, and help them retire with confidence knowing every benefit, dollar, and decision is working in harmony.

Q: What questions do you recommend SoCal Gas employees ask financial advisors they’re considering hiring to help them decide if they’re a good fit?

Ajay: Choosing a financial advisor is one of the most important financial decisions a SoCal Gas employee can make, especially when it comes to navigating pensions, 401(k)s, and retirement income strategies. I always encourage employees to approach this process like they would when hiring anyone else for a critical role: ask the right questions, look for clarity, and make sure the advisor truly understands your world.

Here are the questions I recommend:

1. “Do you have experience working with SoCal Gas or Sempra employees?”

This is vital. Every company’s benefits are unique, and SoCal Gas has a particularly strong and complex structure. An advisor who’s already familiar with these programs can help you maximize their value and avoid costly mistakes.

2. “Are you a fiduciary 100% of the time?”

A fiduciary is legally required to act in your best interest. It’s one of the most important protections for SoCal Gas employees looking to safeguard their retirement savings. You deserve unbiased advice, not sales recommendations.

3. “How do you charge for your services?”

Transparency matters. Ask whether the advisor charges a flat planning fee, a percentage of assets under management, or commissions. Understanding cost ensures you’re comparing apples to apples and prevents hidden surprises down the road.

4. “What’s your investment and tax planning philosophy?”

SoCal Gas employees often have large pre-tax accounts, pension income, and potential lump-sum rollover options, which means taxes become a major planning factor. Ask how the advisor integrates tax-efficient investing, Roth conversions, and withdrawal strategies into your plan.

5. “How will you communicate with me and keep me accountable?”

The best advisor isn’t just reactive; they’re proactive. You want someone who provides ongoing guidance, adapts your plan as laws and life change, and helps you stay on track toward your goals.

The right financial advisor should make your life simpler, clearer, and more confident. For SoCal Gas employees, that means finding someone who understands both your benefits and your bigger picture.

Q: Is there anything that comes up frequently in your initial meeting with SoCal Gas employees that surprises you?

Ajay: Absolutely. What surprises me most is how many SoCal Gas employees don’t realize just how powerful their benefits really are. Between the pension, 401(k) and HSA, they often have everything they need to retire earlier than they ever thought possible, they just haven’t seen how to put the pieces together.

When we sit down and map it out, most people realize they’re much closer to financial freedom than they imagined. My goal as a SoCal Gas financial advisor is to help them make the most of what they’ve already earned to turn great benefits into a plan for freedom, purpose, and the ability to live life fully on their own terms.

Q: For highly compensated SoCal Gas employees and executives, are there any special benefits you believe it’s important to take into consideration when preparing their financial plan?

Ajay: Yes, highly compensated SoCal Gas and Sempra employees have access to several unique opportunities that can dramatically impact long-term wealth and tax strategy if used correctly.

One of the most important is the Deferred Compensation Plan (DCP), which allows eligible employees to defer income beyond traditional 401(k) limits. This can be a powerful tool for reducing taxable income during peak earning years and strategically spreading income into lower tax brackets in retirement.

Additionally, high earners should pay close attention to tax diversification, combining pre-tax, Roth, and after-tax accounts for flexibility and asset protection strategies such as umbrella liability insurance, estate planning, and advanced trust structures.

As a SoCal Gas financial advisor, my goal is to help executives go beyond accumulation, building a cohesive plan that protects their wealth, minimizes taxes, and creates freedom for future opportunities, philanthropy, and legacy.

Q: Is there a particularly memorable experience or a moment you recall with a client who worked at SoCal Gas when you realized they have unique opportunities and circumstances when it comes to their financial planning needs?

Ajay: Absolutely. I worked with a SoCal Gas employee who came to me thinking they were still five years away from retirement. They almost didn’t see the point in meeting with a financial planner, they were diligent savers and assumed they still had a long road ahead.

Once we organized their pension, 401(k), HSA, and other SoCal Gas benefits, it became clear they were in a far stronger position than they realized. With the right strategy, they were able to retire years earlier, travel more, play more golf, and spend more time with the people they love.

That moment reminded me why I do what I do, to help SoCal Gas employees see that financial freedom isn’t a distant dream; it’s often closer than they think. When their benefits and hard work are aligned with a clear plan, life opens up.

Get to Know Ajay Vadukul, Financial Advisor for Southern California Gas Company Employees:

Endeavor Advisors Ajay Vadukul, CFP®, EA

Torrance, California

Serving Clients Nationwide

You only get one retirement. Make it a great one.

264 Certified Advisor Reviews™

Areas of Focus

Education Funding Employee Stock Options Estate Planning Financial Life Planning Insurance

Book Intro Call with Ajay

View Ajay’s profile page on Wealthtender or visit his website to learn more.

Are you a financial advisor who specializes in working with employees at Southern California Gas Company or another large company?

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Brian Thorp

Founder and CEO, Wealthtender

Brian is CEO and founder of Wealthtender and Editor-in-Chief. He and his wife live in Austin, Texas.

With over 25 years in the financial services industry, Brian is applying his experience and passion at Wealthtender to help more people enjoy life with less money stress.

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Do you work for the Advocate Aurora Health System? Get the resources you need and expert insights from financial professionals who specialize in helping Advocate Aurora Health System employees make the most of their compensation package and benefits.

Whether you’re a new Advocate Aurora Health System employee or you’ve moved up the ranks into a management or executive leadership role over a multi-year career, it’s important to make smart money moves with your income and employee benefits. For example:

✅ Do you know the right moves to make to get the greatest value from the Advocate Aurora Health System benefits available to you?

✅If you’re thinking about leaving Advocate Aurora Health System for another job or planning to retire from the company in a few years, are you taking the right steps today to ensure you will receive all of the compensation and benefits that you’ve earned?

Get the Most Value from Your Advocate Aurora Health System Benefits and Compensation Package

Throughout the year, Advocate Aurora Health System provides its employees and executives with updates about their benefits ranging from health insurance and health savings plans to retirement plans like a 401(k) and deferred compensation plans. While the company offers many useful resources and access to knowledgeable staff who can assist with questions, you’ll also find financial professionals not affiliated with the Advocate Aurora Health System who specialize in helping employees make the most of their income and benefits.

Whether you work in the Advocate Aurora Health System headquarters in Milwaukee, Wisconsin, Downers Grove, Illinois, another office facility around the country, or remotely from home, you may have questions about your compensation package and benefits better suited for a financial professional who can offer unbiased advice and guidance.

For example, sensitive topics like discussing the steps you should take before quitting your job at Advocate Aurora Health System to work elsewhere, protecting yourself in advance of a corporate layoff, or deciding when you should plan to retire are all conversations that may be more comfortable with a trusted financial advisor.

Should you hire an Advocate Aurora Health System specialist financial advisor or an advisor close to home?

You’ll likely find dozens of nearby financial advisors well-suited to help you reach your money goals with a personalized plan. But it may be more difficult to find a financial advisor who specializes in serving Advocate Aurora Health System employees.

Fortunately, many financial advisors offer virtual services so you can meet online no matter where you (or they) live.

This means you can choose to hire a specialist financial advisor who lives hundreds of miles away if you decide their knowledge and experience working with Advocate Aurora Health System employees is a better fit to help with your unique needs.

💡 In the Q&A below, you’ll gain insights from financial advisors who work with Advocate Aurora Health System employees to help them make smart decisions to get the most value from their compensation and benefits, reduce their money stress, and prepare for a comfortable retirement.

🙋‍♀️ Do you have questions not yet answered? Use the form below to submit questions anonymously and watch this article for updates with answers to your questions. You can also reach out to the financial advisors below to set up an introductory call or contact them with your questions by email.

💸 Smart Money Insights for Advocate Aurora Health System Employees & Executives

This page is organized into sections to help you quickly find the information you need and get answers to your questions:

Q&A: Financial Planning Tips for Advocate Aurora Health System Employees & Executives
Get Answers to Your Questions About Your Advocate Aurora Health System Benefits and Career
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Q&A: Financial Planning Tips for Advocate Aurora Health System Employees & Executives

Answers to Employee Questions with Robert Dignan, CFP®, AIF®

Robert Dignan is a financial advisor based in Brookfield, Wisconsin who specializes in offering financial planning services to Advocate Aurora Health System employees. Robert helps his clients get the most value from their Advocate Aurora Health System benefits and compensation package so they can enjoy life and feel confident about their financial future.

Q: As a financial advisor with experience helping Advocate Aurora Health System employees save for their retirement, how do you help them make the most of their employee benefits?

Robert: As the spouse of a 30 year Advocate Aurora physician, I’ve had the opportunity to watch the company (Aurora) grow from a leading regional healthcare system into a national healthcare powerhouse. In that growth process, the benefits have evolved as well, resulting in major financial planning opportunities for employees at every level of compensation, whether they be part- or full-time. By integrating company-offered retirement benefits with our clients outside portfolios, we find ways to maximize the opportunities that are provided by the AAH 401(k) and/or Deferred Compensation Plans, without the need to pay for additional “in plan management fees.”

Q: When you first speak with an Advocate Aurora Health System employee, what questions do you like to ask to better understand their unique circumstances and determine how you can best help them achieve their goals?

Robert: The most important question for anyone in healthcare today is “How are you doing, and do you still love what you do?” Healthcare today has become a never ending battle to maintain your sanity and life balance, especially for the Nurses, Nurse Practitioners, Med Techs, and Physicians on the front lines. First and foremost, we always need to find out how our clients are doing mentally, because the “when and how” of retirement is hugely dependent on “are you doing okay?” We expect these people to give us great care, and they should expect that to be our first concern too.

Q: Is there a particular benefit available to Advocate Aurora Health System employees you feel isn’t as well utilized or understood by employees as it should be?

Robert: For those who qualify, the AAH Deferred Compensation Program is absolutely a “must consider”. Not everyone qualifies, and not everyone should fund it, but it must be discussed, especially for anyone in a more highly compensated role.

Q: For Advocate Aurora Health System employees thinking about leaving the company to accept a job elsewhere, what actions do you recommend they take before resigning and shortly thereafter?

Robert: While no company is perfect, it’s important to understand what you are giving up before you leave. So many advisors first want to talk about what to do with your retirement plan assets, but that’s incredibly short-sighted. The first questions need to be around the topic of the heath insurance that you’re leaving (and examining where you are in your “paid deductibles” for the year) and what your new situation will be going forward. In a few cases we have recommended waiting for just a month or two to more completely capitalize on making the most efficient use of Flex Spending dollars, health insurance deductibles that were already fully met, and even sneaking in a pair of spare eyeglasses (under the vision plan) before an employee departs.

Q: For Advocate Aurora Health System employees approaching retirement age, how do you recommend they prepare to make the transition from living off their salary to relying upon other sources of income?

Robert: This isn’t a straightforward transition that applies equally to all employees. If an employee has had the benefit of funding a Deferred Compensation account, in addition to their AAH 401(k), those assets can be triggered to create income in a manner that should compliment their Social Security income, or that may even allow them to defer their Social Security to a later age to maximize their lifetime Social Security payouts. Once an Advocate employee is within three years of retirement (or believes that they are) we begin a transition process that involves a very specific examination of their current expenses, their projected expenses in retirement, the anticipated changes in their personal income tax situation, and the manner in which we will utilize their assets to replicate the equivalent of a monthly paycheck.

Additionally, if that retiring employee is under the age of 65, we will also work with them to ensure that they are positioned to have great health insurance until age 65, when Medicare begins. This can include the use of their AAH COBRA benefits, a referral to a trusted independent health insurance agent, or collaborative assistance with an ACA health plan. And as the client draws closer to age 65, whether retiring or not, we work to connect them with an independent advisor who specialized in Medicare Supplement or Medicare Advantage policies to assist them in filling in the gaps in their Medicare coverage.

Get to Know Robert Dignan, Financial Advisor for Advocate Aurora Health System Employees:

Highland Investment Advisors Robert T. Dignan, CFP®, AIF®

Brookfield, Wisconsin

Serving Clients Nationwide

Building and Sustaining a Life Worth Living

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Areas of Focus

Business Owners Divorce Financial Planning Education Funding Estate Planning Financial Life Planning

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View Robert’s profile page on Wealthtender or visit his website to learn more.

Are you a financial advisor who specializes in working with employees at Advocate Aurora Health System or another large company?

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✅ Sign up today and join financial advisors attracting their ideal clients on Wealthtender
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Brian is CEO and founder of Wealthtender and Editor-in-Chief. He and his wife live in Austin, Texas.

With over 25 years in the financial services industry, Brian is applying his experience and passion at Wealthtender to help more people enjoy life with less money stress.

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A financial advisor who knows the unique needs of liveaboard cruisers can help you make smarter money moves as you navigate new ports and plan for adventures ahead.

Are you a liveaboard cruiser? Or are you considering the benefits of trading life on land for full-time cruising aboard your vessel?

A financial advisor who understands the unique needs of liveaboard cruisers can help you make smarter money moves as you navigate harbors near and far (or as you prepare to cast off your dock lines and embrace life on the water).

You’ll likely find dozens of financial advisors in your hometown well-suited to help you reach your money goals with a personalized plan. But it may be difficult to find a financial advisor who understands the unique financial planning opportunities and challenges faced by liveaboard cruisers who may frequently move between marinas, live off-grid at anchor, or cross international waters while making their boat their primary residence.

Fortunately, many financial advisors offer virtual services so you can meet online no matter where your travels take you, whether you’re docked in the Florida Keys or dropping anchor in the Caribbean. This means you can choose to hire a financial advisor who lives thousands of miles away from your current port if you decide their knowledge about financial planning for liveaboard cruisers could help you achieve better outcomes.

Financial Planning for Liveaboard Cruisers

💡 In the Q&A below, you’ll gain insights from financial advisors who work with liveaboard cruisers to help them make smart decisions to enjoy life more today while preparing for a comfortable retirement in the future.

🙋‍♀️ Do you have questions not answered below? Use the form on this page to submit your questions, and we’ll update this article with answers from the financial professionals and educators in the Wealthtender community. You can also contact the financial advisors featured in this article directly to set up an introductory call or ask your questions by email.

💸 Smart Money Insights for Liveaboard Cruisers

This page is organized into sections to help you quickly find the information you need and get answers to your questions:

Q&A with Financial Advisors Specializing in Serving Liveaboard Cruisers
Get Answers to Your Questions About Liveaboard Cruising
Browse Related Articles

Q&A: Financial Advisors Specializing in Serving Liveaboard Cruisers

Answers to Questions About Liveaboard Cruisers with Kevin Caldwell

We asked Chester, Maryland financial advisor and liveaboard cruiser specialist Kevin Caldwell to answer questions about this lifestyle on the water.

Q: For liveaboard cruisers (and those who are aspiring to become liveaboard cruisers) who are unsure whether or not they should hire a financial advisor at the current point in their lives, what guidance can you provide to help them make a more informed and educated decision?

Kevin: One of the biggest challenges liveaboard cruisers face is managing cash flow in a lifestyle with highly variable expenses and income sources. Unlike traditional homeowners, cruisers deal with fluctuating costs for fuel, marina fees, maintenance, provisioning, and sometimes international travel. On top of that, many cruisers have irregular income streams—retirement withdrawals, rental income, or seasonal work.

As an experienced boater myself, I fully understand the realities of life on the water—including the unpredictability of maintenance costs, the impact of weather on travel plans, and the nuances of provisioning in remote areas. That firsthand knowledge allows me to build financial plans that are not only technically sound but also practical and realistic for the cruising lifestyle.

To help clients overcome these challenges, I work with them to:

Assess your financial readiness: Are you confident in your budget, reserves, and income strategy for cruising? Do you have your boat yet? If not, a financial advisor with extensive boating experience can help you build that foundation and figure out your boat buying budget.
Clarify your goals: Whether you’re planning a seasonal cruise or a multi-year journey, selling your dirt home or maintaining it while cruising, aligning your financial plan with your cruising goals is essential.
Evaluate complexity: If your financial life includes investments, retirement accounts, early retirement, rental properties, or business income (see bullet point about business owners below), professional guidance can help you optimize and simplify.
Build a flexible cash flow plan that accounts for seasonal variations and unexpected repairs.
Create a cruising reserve fund for emergencies so they don’t have to disrupt their long-term investments.
Use forecasting tools to project expenses for different cruising regions (e.g., Great Loop vs. Caribbean) and align withdrawals or income accordingly.
Support business owners who cruise full-time by offering strategic financial planning through both Islands East Advisors and our sister company, Islands East Financial Solutions. IEFS provides fractional CFO services and business consulting to help owners manage and grow their businesses while living aboard.
Consider peace of mind: Many cruisers find that working with an advisor gives them the confidence to enjoy the journey without constantly worry about money.
Evaluate the unknowns: If you sell your dirt home, how will you obtain a street address for your license, residency, credit cards, and mail? If you cruise internationally, how will you manage healthcare or even medevac insurance? If you want to spend extensive time in one place, do you understand how that can affect your tax liabilities? Do you travel with pets and understand the complexities this can bring to international destinations? These are just a few of the many intricacies that liveaboard cruisers face. When you hire IEA, you get an Advisor who understands these issues and has partners and contacts that can help you through each of them.

This approach gives cruisers confidence that their lifestyle is sustainable without jeopardizing their financial future—and it’s grounded in a deep understanding of both finance and the realities of life aboard.

Q: For aspiring liveaboard cruisers ready to become a boater, what actions do you recommend they take before making their way to the marina?

Kevin: Transitioning to the liveaboard lifestyle is exciting—but it’s also a major shift that requires thoughtful preparation. Here are the key actions I recommend before casting off:

Understand the financial realities of cruising. Life aboard can be more or less affordable than land life, depending on your situation and goals, but it comes with variable costs—fuel, maintenance, marina fees, insurance, and provisioning. I help clients build realistic budgets and cash flow plans tailored to their cruising goals.
Get hands-on boating experience. Take boating safety courses, spend time crewing with experienced cruisers potentially on some offshore runs, and practice docking, anchoring, and basic maintenance. The more confident you are on the water, the smoother your transition will be.
Purchasing your boat. Figuring out the style of boat that best fits your needs and determining whether to pay cash or finance is a daunting task. There are many details that make this a critical decision point that requires several areas of expertise. Taxes, insurance, and financing are much more complicated than purchasing a home.
Plan for boat maintenance. As an experienced boater myself, I know firsthand how unpredictable and costly maintenance can be. I advise clients to set aside a dedicated reserve fund for repairs and upgrades—and to understand the systems on their boat before departure. Understanding the spare parts needed to keep your cruise going until you reach an appropriate marina where you can get assistance is imperative.
Review your insurance and legal documents. Make sure your boat insurance covers your cruising plans (especially if international), and update your estate plan, medical directives, and travel documents.
Test your lifestyle. Before committing full-time, try living aboard for a few weeks or months, especially before you sell your home. It’s the best way to discover what works for you—and what doesn’t. It also ensures your boat, if recently purchased (new or used), is ready to cruise full-time and you obtain the required experience and confidence in your home waters.
If you’re managing a business while cruising, plan ahead. Islands East Advisors specializes in helping both liveaboard boaters and business owners. Our sister company, Islands East Financial Solutions, offers fractional CFO services and business consulting to help you stay financially organized and operationally effective while living aboard.

Preparing well before you reach the marina ensures your cruising lifestyle is not only adventurous—but also sustainable and financially secure.

Q: When you first speak with liveaboard cruisers, what questions do you like to ask to better understand their unique circumstances and determine how you can best help them achieve their goals?

Kevin: Every cruiser’s journey is different, so I start by asking questions that help me understand both their lifestyle and financial picture. My goal is to tailor a plan that supports their cruising dreams while protecting their long-term financial health. Here are some of the key questions I ask:

What kind of cruising are you planning? (e.g., Great Loop, Caribbean, coastal hopping, international)
This helps me estimate regional costs and plan for seasonal variations.
What’s your current income structure?
Whether it’s retirement withdrawals, rental income, remote work, or a business, I want to understand how money flows in and how stable it is.
Do you own or plan to manage a business while cruising?
If so, I introduce our sister company, Islands East Financial Solutions, which offers fractional CFO services and business consulting to help owners stay financially organized and operationally effective while living aboard.
What’s your comfort level with boat maintenance and repairs?
As an experienced boater, I know how quickly costs can escalate. Understanding their skill level helps me plan for realistic reserve funds, maintenance schedules, and risk assessment.
What is your overall boating experience?
Clients with no prior boating experience require a different level of service than clients that have owned many boats throughout their lives and have a 100-Ton Master Captain’s License.
Do you have a financial safety net or emergency fund?
Cruising can be unpredictable, so I help clients build buffers that allow them to handle surprises without derailing their plans.
What are your long-term goals—both financial and lifestyle?
Whether it’s cruising for a few years, retiring aboard, or transitioning to land life later, I want to align their financial strategy with their vision and their life transitions.

These conversations help me build a financial plan that’s not just numbers on a spreadsheet—but a roadmap for a sustainable and fulfilling cruising lifestyle.

Q: What are the biggest financial risks cruisers face, and how do you help mitigate them?

Kevin: Cruising full-time is a dream for many, but it comes with unique financial risks that can quickly derail even the best-laid plans if not properly managed. The biggest risks I see include:

Unpredictable maintenance and repair costs.
Boats are complex systems, and unexpected breakdowns are part of the lifestyle. With all of today’s technological advancements, the more systems you install on your boat, the more difficult it is to diagnose and the more expensive it is to maintain. As an experienced boater, I understand how quickly these costs can escalate. I help clients build realistic reserve funds and plan for routine maintenance, so surprises don’t become financial emergencies. This understanding also helps me give advice to clients when purchasing their boat, so they don’t overspend.
Variable living expenses.
Costs for fuel, marina fees, provisioning, and insurance can fluctuate dramatically depending on location and season. An advisor that lacks experience in boating will not typically dig into the details of a client’s living expenses on a boat because they are unaware of what questions to ask. I combine traditional forecasting tools and my knowledge of cruising to help cruisers anticipate regional cost differences and adjust their cash flow accordingly. We also review scenarios such as what if fuel costs increase by 50%?
Irregular income streams.
Many cruisers rely on retirement withdrawals, rental income, or seasonal work. These sources can be inconsistent, so I help clients structure their finances to ensure steady cash flow and avoid shortfalls.
Limited access to financial services while underway.
Cruisers often travel in areas with limited internet or banking access. I help set up systems that allow for remote financial management, automated transfers, and secure access to critical accounts.
Managing a business while cruising.
For cruisers who are also business owners, staying organized and financially effective can be a challenge. That’s where our sister company, Islands East Financial Solutions, comes in. We offer fractional CFO services and business consulting to help owners maintain control and growth—even from the deck of their boat.

By identifying these risks early and building a flexible, forward-looking financial plan, I help cruisers enjoy the freedom of the lifestyle without sacrificing financial security.

Q: What questions do you recommend liveaboard cruisers ask financial advisors they’re considering hiring to help them decide if they’re a good fit?

Kevin: These are the top questions I would encourage asking:

Have you ever purchased a boat larger than 30 ft and have you ever lived aboard or spent extended time cruising yourself?
Do you have experience working with liveaboard cruisers or full-time travelers?
Do you have extensive contacts and referrals in boat specific areas like financing, boat insurance, health insurance, boat brokers, etc.?
Are you familiar with the financial challenges unique to boating – like maintenance, marina fees, internet connectivity, and provisioning in remote areas?
Are you able to help me build a budget and cash flow tailored to my new lifestyle?

Get to Know Kevin Caldwell, Financial Advisor for Liveaboard Cruisers:

Islands East Advisors Kevin Caldwell

Chester, Maryland

Serving Clients Nationwide

Serving business owners, liveaboard cruisers, and other successful professionals

Areas of Focus

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View Kevin’s profile page on Wealthtender or visit his website to learn more.

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Most people think legacy planning begins and ends with writing a will. In reality, a complete legacy plan is far more comprehensive – and far more powerful.

A thoughtful legacy plan gives you control over your assets, provides clarity to your loved ones, and protects your wishes at every stage of life. And yet, too many families leave this planning unfinished, or worse, never start at all.

Whether you’re approaching retirement, navigating a divorce, or managing a business, now is the time to get your legacy documents in order.

What Is Legacy Planning?

Legacy planning is the process of organizing your financial, legal, and personal affairs to ensure your wishes are honored during your life and after your death.

Unlike basic estate planning, which typically focuses on distributing assets through a will, legacy planning takes a broader view. It coordinates financial documents, medical directives, personal letters, and digital assets—everything needed to provide a clear and complete roadmap for your family.

This type of planning isn’t just about death. It’s about how you want to be cared for if you’re ever incapacitated. It’s about easing the burden on your family. And it’s about passing on not just your assets, but your values.

Why Legacy Planning Is Often Overlooked

Despite its importance, many people delay or avoid legacy planning. There are a few common reasons:

1. Emotional Discomfort

Planning for end-of-life care or imagining a world after you’re gone is never easy. These are deeply emotional topics, and many people avoid them entirely until a crisis forces the issue.

2. “It’s Only for the Wealthy”

There’s a widespread belief that legacy planning is only necessary for the ultra-wealthy. In truth, anyone with a home, a bank account, retirement savings, or a family can benefit from a well-structured plan.

The Essential 7 Documents for Legacy Planning

So, what documents do you need for legacy planning? Here’s your essential legacy planning checklist:

1. Last Will and Testament

This is the most recognized estate planning document, but it’s only one piece of the puzzle. A will outlines how your assets should be distributed and names guardians for minor children. Without one, the courts will decide who gets what—often with delays and costs your family could have avoided.

2. Trust (Especially a Revocable Living Trust)

A revocable living trust allows you to transfer ownership of your assets into a trust during your lifetime while maintaining control. It can help your estate avoid probate, reduce delays, and ensure privacy. Trusts are especially helpful for blended families, business owners, or those with property in multiple states.

3. Financial Power of Attorney

This document designates someone to manage your financial affairs if you become incapacitated. Without it, your loved ones may need to go through a lengthy and expensive court process to gain control of your finances.

4. Healthcare Proxy / Advance Directive

Also called a medical power of attorney, this document names someone to make medical decisions on your behalf if you can’t speak for yourself. Your advance directive outlines your wishes for life support, resuscitation, and other treatments. Together, these documents help ensure your preferences are respected—and relieve your family from making agonizing decisions without guidance.

5. HIPAA Authorization

This lesser-known but critical document allows your chosen representatives to access your medical records. Without it, even your spouse or children may be blocked from getting the information they need to make informed decisions about your care.

6. Beneficiary Designations

Retirement accounts, life insurance policies, and some bank accounts allow you to name beneficiaries. These designations override your will, which is why it’s crucial to review and update them regularly. It’s common to find outdated beneficiaries listed, such as an ex-spouse or deceased relative.

7. Letter of Intent

While not legally binding, a letter of intent adds a personal dimension to your legacy plan. It can include your funeral wishes, the values you want to pass on, and guidance for how you hope your heirs will use their inheritance. It’s also an opportunity to express love, gratitude, and encouragement—things no legal document can fully capture.

Bonus: Digital Asset Inventory

In today’s world, digital assets are often overlooked. This includes your email accounts, financial platforms, social media, cloud storage, and any digital files or subscriptions. Documenting usernames, passwords, and account instructions can save your family enormous frustration. Consider using a secure password manager or digital vault.

Coordinating Across Generations

Legacy planning isn’t just about documents – it’s about communication.

Start by having open conversations with your loved ones. Let them know where your documents are located and who is responsible for what. If you have a trust or healthcare directive, make sure those named understand your intentions.

Many families also benefit from working with financial advisors, estate planning attorneys, and tax professionals. These experts can help you structure your plan to minimize taxes, avoid legal pitfalls, and reduce the risk of family conflict.

Conclusion: Control, Clarity, and Protection

Legacy planning is one of the most thoughtful gifts you can give your loved ones. It prevents confusion, preserves family harmony, and ensures your voice is heard even when you can’t speak for yourself.

This article was originally published here and is republished on Wealthtender with permission.

About the Author

Mitchell J. Thompson, CFP®, CDFA®, ChSNC®, AEP® Family | Fixer | Fiduciary | Advisor | Wealth Manager

Mitchell J. Thompson, CFP®, CDFA®, ChSNC®, AEP® | MJT & Associates Financial Advisory Group

🔗 Website | Wealthtender Profile

Navigating a business transition can be both exhilarating and overwhelming. The sheer complexity means that even important details can get overlooked. There are several components to selling a business.

First, and most self-explanatory, is the business side of things. Is your business ready to sell?

Next, is the personal and emotional component. Are you ready to sell? You may be selling something you’ve worked on your whole life and you’re not sure what’s next. Have you thought through what that means?

Finally, the personal and financial side of things. Do you know if you’ll have enough money after the sale to live the life you want?

Wrapped up in all of these complex emotional and financial decisions are taxes. The tax implications of a sale can significantly affect your outcome, and they can turn what appears to be a smart financial decision into a costly one without proper planning. Ironclad Wealth Management can help you preserve more of what you’ve earned as you chart your path towards an eventual exit.

Why Tax Planning Matters in Business Transition

Without business transition tax planning, entrepreneurs and small business owners risk giving away a significant amount of their sales proceeds to the IRS. This is probably your last bite of a large meal that’s fed you and your family for years. If you’re like most people, you want to make the most of it.

So, what does this look like from a practical perspective?

When selling your business, you need to sell for enough that your investments can then provide your desired lifestyle for you and your family. The problem is that you may be going from a business that has a 25% profit margin to an investment portfolio that supports a 4% withdrawal rate. That’s a pretty big difference!

The amount that you need to sell your business for to provide your lifestyle is what I call the “Wealth Gap.” The Wealth Gap is the difference between what you need to provide for your lifestyle and what you have in personal, outside investments today. That Gap is the amount that you need to sell your business for after taxes.

Wealth Gap = Amount Needed to Generate Desired Income – Personal Investment Assets

With a desired income of $250,000 and a 4% withdrawal rate, it would take $6,250,000 to retire today. If you had $2,000,000 of personal assets, that would mean you need to make $4,250,000 from the sale of your business. That’s your Wealth Gap.

However, that’s excluding taxes. Including taxes at a 25% tax rate, you need $5,666,666.67 to reach your Wealth Gap of $4,250,000. That means that without tax planning, your Wealth Gap is much higher!

That’s the point of tax planning during a business transition. Lowering your tax bill means that you can either meet your goals with a lower sales price or receive a higher income if you plan properly.

The first step in preparing financially to sell your business should be to identify your personal Wealth Gap. If you haven’t, take the time to do so before starting any tax planning.

Want to calculate your own Wealth Gap?

Key Tax-Saving Opportunities for Sellers

One of the main financial goals of any business owner looking to sell is to save capital gains taxes. The good news is that there are several tax saving strategies available to small business owners who are looking to sell their business.

The magic happens when you find the right strategy for your personal situation. Jamming the wrong strategy into your life purely to save taxes can cause more problems than the tax savings are worth.

Even worse, you may hear about a strategy that’s too good to be true…and is. Don’t get swept up in the emotions of a sale and make a decision that that could trigger IRS scrutiny and distract you from the peace of mind you hoped to enjoy post-sale.

So which tax savings strategies are out there? Here’s a brief list with commentary on what they do and who they may work for.

Installment sales

The easiest way to reduce your taxes is to spread your gain over multiple years in an installment sale. In an installment sale, you receive your proceeds over a set period instead of all at once. The main benefit is that you may be in a lower tax bracket during the installment period. The highest tax bracket for capital gains is 20% and the lowest is actually 0%. However, if you’ll be in the highest bracket no matter how you spread this out, there’s really no benefit. Remember, you are also loaning the buyer the money, so you must be comfortable with their ability to pay.

Best for: Business owners who are comfortable taking the loan risk and will be in a lower tax bracket post sale.

Qualified Small Business Stock Exclusion (QSBS)

The QSBS exclusion is the most beneficial part of the tax code for business sellers but does not apply to all businesses.

The QSBS exclusion excludes up to $15m or 10x your investment, whichever is higher, from capital gains taxes. To qualify, you must be a C-Corp, have received stock directly from the corporation, the corporation must have had less than $75m in assets at the time of issuance, and 80% of assets must be used in a qualified trade. You receive a 50% exclusion after 3 years, 75% after 4 years, and 100% after 5 years of holding. These rules were recently changed in The One Big Beautiful Bill Act (OBBBA) and your exact terms will vary based on when your shares were issued.

Best for: C-Corporations who qualify. There is no better tax saving strategy than the QSBS exclusion. If you didn’t start as a C-Corp, you may still be able to convert and partially qualify if you have a 3+ year window.

Structured Installment Sale

A structured installment sale has the same tax treatment as an installment sale with one major change – there is no loan risk. This is because the buyer deposits the full purchase price with an intermediary. This intermediary then pays you according to your schedule. This is an irrevocable election as part of the sales agreement.

Best for: Business owners who think an installment sale may work for the reasons above but are expecting a lump sum sale.

Charitable Remainder Trust

This trust allows you to gift your shares of the company to a trust and receive a charitable deduction. When the trust sells the business, it pays no income taxes. While you live you receive a set payment each year and then whatever is left passes to your named charity at death. As the income comes to you, you do pay personal taxes on it in the same manner your trust earned the income. However, you get to earn 5% on $10,000,000, not $7,500,000! This must be done in advance of a sale and S-Corp stock does not work with Charitable Remainder Trusts.

Best for: This option could be good for a business owner with charitable intent who has a good understanding of their possible sale timeline. Also, if you are concerned with your heirs losing their inheritance, it is common to pair this with a life insurance policy to provide for them.

Opportunity Zone Investing

Investing in an Opportunity Zone allows an investor to defer eligible gains for a period of time. After a sale, you must invest within 180 days in an eligible Qualified Opportunity Zone. Currently, you can defer your gains until Dec. 31, 2026. Beginning Jan. 1, 2027, you can defer your gain for 5 years. The main benefit of OZ Funds is that you can then exclude the appreciation of the OZ investment itself if you hold the fund for 10 years. OZ Funds are in a state of flux right now with this waiting period from the OBBBA. However, they can provide substantial tax benefits for the right person and it is one of two strategies on this list that can be done after a sale! OZ Funds are complicated and if you are interested, here is a good overview of the current state of affairs.

Best for: A business owner who has already sold and is comfortable investing their money in a new investment for 10+ years.

Tax Loss Harvesting

Finally, there is tax loss harvesting. In tax loss harvesting you take your proceeds and invest in a taxable investment account that generates losses while still generating market returns. The main benefit is that this can be done post-transaction. The losses generated offset your capital gains. This is probably the most flexible option.

Best for: The business owner who has already sold or doesn’t want to have any complicated lockups with their money. Check out our detailed guide here.

Key Tax Strategies for Buyers

While this blog is mainly geared towards sellers, I do want to address buyers briefly. While there are fewer strategies available to buyers than sellers, you can structure a deal to help you save money on taxes.

Most buyer tax benefits are directly derived from the structure of the deal. If the purchase is an asset purchase, it becomes very straightforward. You can depreciate the fixed assets that you purchase, and they are usually eligible for bonus depreciation. You can also amortize intangible assets like goodwill over a 15-year period. When you buy the business, it’s highly likely that you will pay less in taxes than the previous owner for the first several years, which can help with early cash flow.

If you buy a business in a stock sale, you would think that you may be ineligible for asset level depreciation; however, with proper business tax strategy and planning you can still achieve this in some cases. If your transaction is eligible, you may be able to utilize a Section 338(h)(10) election. This allows buyers to treat the transaction as an asset purchase for tax purposes while still executing it as a stock purchase.

This gives a buyer both the ease of a stock sale and the tax benefits of an asset sale. However, the seller will most likely incur some additional taxes and may need to be compensated for that.

What to Avoid: Common Tax Mistakes in Business Sales

Unfortunately, more exits than not go poorly or leave business owners with a sense of regret. Most of these regrets tend to happen on the personal, emotional side where a small business owner feels like they’re losing a piece of their identity after the sale. However, improper tax planning can also cause issues.

I see three major issues when it comes to tax planning during exit planning:

Reactive, not proactive planning – As you saw above, some strategies need planning before a sale is executed. By waiting too long, you may limit the possibilities available to you and cause issues for yourself down the road.
TOO much focus on taxes – Sometimes business owners can become TOO focused on the tax aspects of a transaction and ignore other factors that may hamper them in the future. It may sound funny coming from a financial planner, but remember, taxes aren’t everything!
Falling for “Too Good to be True Strategies” – When you’re looking at a big tax bill, schemes that promise to eliminate all your taxes start looking pretty tempting. Some business owners take tax positions that I would charitably call misguided, and uncharitably call fraudulent, in the pursuit of tax savings. Don’t do it. When in doubt, check the IRS Dirty Dozen list for common scams.

Avoiding these pitfalls is just as important as identifying the right strategies for good tax planning.

The Role of Exit Planning with Ironclad Wealth Management

A trusted advisor like Ironclad Wealth Management is an integral part of any exit planning process. The tax piece is critical, but it’s just one part of a much bigger puzzle.

We help business owners:

Calculate their personal Wealth Gap
Determine if they’re financially ready to sell
Prepare their family for life after the business
Coordinate with their team of attorneys, CPAs, and investment bankers
Make sure their business goals and personal goals actually align

The goal isn’t just to save on taxes, it’s to make sure the entire transition sets you up for the life you want afterward.

The Bottom Line

Buying or selling a business is one of the biggest financial decisions you’ll make. The tax implications can dramatically affect your outcome, but they don’t have to derail your plans.

The key is planning ahead, understanding your options, and working with advisors who see the big picture, not just the tax bill.

Whether you’re preparing to sell the business you’ve built or looking to acquire your next opportunity, proper tax planning can save you significant money and set you up for long-term success.

This article was originally published here and is republished on Wealthtender with permission.

About the Author

Patrick G. Moore, CFP®, EA Helping small business owners make sense of their money

Patrick G. Moore, CFP®, EA | Ironclad Wealth Management

🔗 Website | Wealthtender Profile

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What Is Legacy Planning?

Why Legacy Planning Is Often Overlooked

The Essential 7 Documents for Legacy Planning

1. Last Will and Testament

2. Trust (Especially a Revocable Living Trust)

3. Financial Power of Attorney

4. Healthcare Proxy / Advance Directive

5. HIPAA Authorization

6. Beneficiary Designations

7. Letter of Intent

Bonus: Digital Asset Inventory

Coordinating Across Generations

Conclusion: Control, Clarity, and Protection

About the Author

Why Tax Planning Matters in Business Transition

Wealth Gap = Amount Needed to Generate Desired Income – Personal Investment Assets

Key Tax-Saving Opportunities for Sellers

Installment sales

Qualified Small Business Stock Exclusion (QSBS)

Structured Installment Sale

Charitable Remainder Trust

Opportunity Zone Investing

Tax Loss Harvesting

Key Tax Strategies for Buyers

What to Avoid: Common Tax Mistakes in Business Sales

The Role of Exit Planning with Ironclad Wealth Management

The Bottom Line

About the Author