Robert T. Dignan, CFP®, AIF®
Building and Sustaining a Life Worth Living
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Highland Investment Advisors
Robert T. Dignan, CFP®, AIF® He/Him
Brookfield, WI
Serving Clients Nationwide
Building and Sustaining a Life Worth Living
5 out of 5 Stars
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Areas of Focus
- Divorce Financial Planning
- Education Funding
- Estate Planning
- Financial Life Planning
- Inherited Wealth
- Investment Management
- Job Loss
- LGBTQ Couples
- Loss of Spouse or Partner
- Owning a Business
- Retirement Planning
- Retiring Early (F.I.R.E)
- Saving for College
- Taxes
About Robert T. Dignan, CFP®, AIF®
Over the last three decades, Robert "Bob" Dignan has had the pleasure to develop incredible relationships with his clients that are uniquely personal, and focus as much on quality of life as they do on “the numbers.”In a time when so many advisors focus exclusively on your account values, Bob’s goal for every client is to help them to discover how much control they possess, and how their decisions can lead them to living their greatest possible life outcomes. Because these types of outcomes are only possible with a significant investment of time and trust, Bob makes it a point to limit his client base to a more controlled number of clients, and may take only a few new clients per year.
When Bob’s clients give him the permission to collaborate directly with their preferred accounting, estate planning, and risk management professionals, the likelihood of that client enjoying consistent, successful outcomes increases dramatically. He employs a fully collaborative approach with his clients and their most trusted inner circle of advisors, all of whom should be striving to protect that client’s best interests. In doing so, the client’s “team” unites to help them to find sustainable, higher quality outcomes, as well as a sense of empowerment over their financial situation. Our goal is not to tell you what to do, but instead to listen to you, and then provide you with the best possible options from which to choose, so that you can make the best decision for your family.
Bob is a firm believer in the idea of getting the very most out of life, while finding a responsible balance that allows for a sustainable and repeatable series of life opportunities. While we are always striving to use our professional and technical knowledge to maximize your tax efficiencies and investment opportunities, the fact remains that this process must always be fundamentally anchored to those goals and priorities that are unique to you and those you love.
If your goal is “to win life” by dying with the largest portfolio (solely for the sake of bragging rights), then Bob isn’t your guy. But if you are willing to share your dreams and fears openly and honestly, and aren’t afraid to put in the effort to make great things happen for your family, you’re going to discover an advisory relationship unlike any other.
Professional Designations
- Accredited Investment Fiduciary (AIF)
- CERTIFIED FINANCIAL PLANNER ®
Primary Location
175 Patrick Blvd, Suite 120, Brookfield, WI 53045
Video
Meeting Options
- Video Conference
- In-Person
- Phone
Compensation Methods
- Fee Based
- Percentage of Assets Managed
What to expect in the first meeting
If you're interested in getting started, or just learning more about how I engage with my clients, please click the 'Contact Me' button to share your best contact information. With that, we will schedule an introductory conversation to get to know each other, and begin to determine whether we are a great fit. If we finish that call and share a mutual belief that there is value that we can bring to your situation, we will follow up with actionable steps and set a follow up meeting to begin your financial planning journey.Offers Investment Management
Yes
About Highland Investment Advisors
As an Investment Advisor Representative of Highland Investment Advisors, LLC, Bob utilizes a model that is fee-based. Because he holds an active insurance license, and prefers to be able to assist his client with specific insurance challenges in situations where discretion and privacy are requested, he believes that not being able to refer to himself as "fee-only" is a small sacrifice. To put this in perspective, in 2024, 0.06% of his income was derived from commissions of this type.Because Bob is a proud CFP® Practitioner, and because Highland operates as an independent SEC Registered Investment Advisory firm that acts as a fiduciary, recommendations that are presented to you are always made with your best interests in mind. It is always important to understand how your advisor is compensated, but being able to access the most effective tools and solutions for his clients remains one of Bob's primary objectives, from a practice management standpoint.
Tailored Strategies for Every Stage of Life
✔️ Build Your Wealth
Your hard work is paying off, and now it’s time to compound your wealth. From tax strategies to investment guidance, let Highland create a plan that aims to maximize every opportunity to move you closer to financial independence while safeguarding your family.
✔️ Secure Your Future
As retirement nears, you may be thinking about slowing down, switching careers, or stepping away entirely. Highland will help you plan your income and lifestyle so you can retire with confidence, knowing you have the financial security you need.
✔️ Retire with Financial Peace of Mind
In retirement, you may have concerns about spending, withdrawals, taxes, and Social Security decisions. Highland provides a dynamic planning process that adapts as your needs and circumstances change.
Is Highland the right "fit" for my family?
Bob's clients range in age from age 18 to 88, and unlike advisors who focus primarily on "those approaching retirement age," he prefers to get involved as soon as possible so that he can help his clients to build, enhance, and diversify their wealth at the earliest possible stage. For some this might be as they step into their very first professional role, while for others it may come after years of "spinning their wheels," or upon finding themselves suddenly single after a major life event. We know how much most advisors like to focus their marketing dollars on new prospects who are on the brink of rolling a large 401(k) out of their employer's retirement plan, but Bob prefers to help his clients earlier so that they have larger retirement reserves and greater opportunity when that day comes. Proper investment and income tax planning is critical at all stages of life, not just when you approach your end goal.
While Bob has developed a practice that includes a significant focus on physicians, engineers, and public school teachers, the professions of his clients are wonderfully varied. From analytic minds to creative geniuses, he has the most interesting group of friends that an advisor could hope for. The one consistent theme throughout all of Bob's clients is that they are people who take their opportunities and responsibilities seriously, and are willing to work as hard to reach their best outcomes, as he is for them. Bob lovingly refers to this as "painfully Midwestern," because at the core his clients are high quality people who are willing to make a strong effort to ensure that they and their families have the greatest likelihood of finding long-term, sustainable happiness. Of course the other side to this coin is that Bob also works with them to encourage them to make the most of their lives at every step of the journey to minimize the likelihood of future regrets and missed opportunities. Like everything in life, the key is a responsible balance.
Education
University of Wisconsin-Madison, Bachelor of Science, Natural Resource Management, May 1992
Hobbies and Interests
- Baseball
- Cycling
- Family
- Hiking
- Hunting
- Music
- Photography
- Volunteering
SEC Lookup
View DisclosureFINRA Lookup
View DisclosureWho We Serve
- Attorneys
- Baby Boomers
- Blended Family
- Business Owners
- Corporate Executives
- Couples
- Creative Professionals
- Divorce
- Dual Income Family
- Educators
- Engineers
- Entrepreneurs
- Families
- Financial Independence Retire Early (FIRE)
- Gen X
- Healthcare Professionals
- Individuals
- Intergenerational Families
- LGBTQ
- LGBTQ Couples
- Living in Retirement
- Nonprofit Employees
- Physicians
- Sales Professionals
- Single Women
- Technology Professionals
- Widow
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Write a Review
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Profession prepared polite
✅ Wealthtender Certified Advisor Review™
Nov 17, 2025
Thoroughly prepared with a history of experience and knowledge to be trusted.
Relationship to Financial Advisor: Client as of Nov 17, 2025
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Disclosure: This review is being shared by a local attorney who is both a client, as well as a trusted resource with whom I have had the pleasure of working on client-related matters.
An Advisor Who Has Always Put My Quality of Life & Financial Wellbeing First
✅ Wealthtender Certified Advisor Review™
Nov 8, 2025
For the nearly 20 years that Bob has been my financial advisor, he has consistently demonstrated a deep knowledge of a broad range of topics critical to ensuring one's overall financial wellbeing--not only relating to specific investments but also helping the client assess the level of investment risk that they are comfortable with, maintaining a healthy balance of different types of financial assets, carefully evaluating the impact of taxes on any potential financial transaction, among others. This vast understanding of the multiple factors that influence one's financial decisions adds tremendous value to the services that Bob provides.
Apart from Bob's skills and expertise as they pertain to the specifics of financial planning and advising, he is efficient, extremely responsive and a pleasure to work with. Even though I imagine that Bob must work with 50 to 100 clients or more, his attentiveness to my requests and his commitment to helping me achieve my goals in life make me feel very often that I am Bob's only client. That's an extraordinary feeling and a testament to Bob's dedication to his clients.
And...results matter. With Bob's thoughtful management of my assets, I was able to retire before age 50. That's a pretty solid testament to his skills as a financial advisor.
Relationship to Financial Advisor: Client as of Nov 8, 2025
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Our advisor for over 20 years
✅ Wealthtender Certified Advisor Review™
Nov 7, 2025
Bob has been our financial advisor for over 20 years. He is attentive, thorough, not-pushy, and never self-interested. Highly recommend.
Relationship to Financial Advisor: Client as of Nov 7, 2025
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
A True Partner in Your Future Planning
✅ Wealthtender Certified Advisor Review™
Nov 6, 2025
We have worked with several financial advisors over the years, but Bob and the team at Highland have shown us what we'd been missing for so long. Bob has taken the time to understand our finances and our goals, both now and in retirement, to ensure we are prepared for each phase of our lives. He is extremely generous with his time, connections, and experience and this goes well beyond our investments. He has helped us to make sound decisions around taxation, college funds, estate planning, and even caring for aging parents. We consider Bob a dear friend who just happens to manage our investments.
Relationship to Financial Advisor: Client as of Nov 6, 2025
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Proactive, Ethical, Great Communicator
✅ Wealthtender Certified Advisor Review™
Nov 6, 2025
We have been working with Bob for over 10 years. From day one he took the time to get to know us and understand what we wanted to accomplish financially. He certainly has earned our respect and trust. We have found him to be proactive, an excellent communicator, and very ethical. With Bob's guidance, we were able to retire early and we're relying on him to continue to help us navigate our finances during retirement. You'll enjoy working with him.
Relationship to Financial Advisor: Client as of Nov 6, 2025
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
A Trustworthy, Professional, Knowledgeable Advisor!
✅ Wealthtender Certified Advisor Review™
Nov 4, 2025
What more can we say? When we switched to Bob at Highland we feel we made an excellent decision. It really paid off. We are very comfortable in that we feel Bob knows us and our ongoing retirement needs. He is quick to respond to our phone calls and visits and his wide experience has kept us on track and we feel comfortable in our financial matters with his advice.
Relationship to Financial Advisor: Client as of Nov 4, 2025
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Full 360 view, support, and advice
✅ Wealthtender Certified Advisor Review™
Nov 4, 2025
Bob takes the time to get to know you and your family. This is essential in a shared understanding of where you are in your personal and family life, your present and future goals, and how to work together to make those goals happen. Bob also has many important contacts and associations to help with the inevitable challenges that most of us face at one time or another. This "feature" of partnering with Bob has been and continues to be a great comfort. As my wife and I are both now fully retired our world is changing and our approach to life and what we wish to do is quite different from the days of 60 - 70 hour crunch mode work weeks and all the struggles raising a family. Bob has been there for us and best of all he is eternally positive and a true optimist. We heartily recommend Bob to anyone!
Relationship to Financial Advisor: Client as of Nov 4, 2025
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Tops in integrity, knowledge, and service!
✅ Wealthtender Certified Advisor Review™
Nov 4, 2025
I've worked with Bob for over 2 decades and these are a few of the reasons I continue to do so:
1) Unquestionable integrity. I've not found another person more worthy of my trust.
2) His top concern is that his clients sleep well each night by taking the term 'fiduciary' to the next level.
3) Long term planning specifically tuned to each individuals needs, including age related changes to risk tolerance, are discussed at least twice every year.
4) Bob answers his own phone and ALWAYS returns my calls, emails and texts, frequently within minutes!
5) He notifies me prior to taking vacations plus his backup folks share his ideals and are first rate in every respect.
6) Bob goes out of his way to make sure I FULLY understand the ramifications of every financial decision. The decisions are ALWAYS mine. When we disagree, due to his patients and guidance, I'm able to make an informed decision.
Relationship to Financial Advisor: Client as of Nov 4, 2025
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
A personal professional
✅ Wealthtender Certified Advisor Review™
Nov 4, 2025
We have been with Bob for over 30 years. He has that personal touch, making visits not only informative but meaningful. We always enjoy our one-on-ones with him. He is not only knowledgeable about his profession but cares about his clients. Every meeting make us feel more comfortable about placing our finances in his care.
Relationship to Financial Advisor: Client as of Nov 4, 2025
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
More than an advisor
✅ Wealthtender Certified Advisor Review™
Nov 4, 2025
Bob Dignan was referred to us by a friend 20 plus years ago. Since that time we have found him to be not only a trusted financial advisor, but a trusted friend who has helped us through the financial & legal processes when dealing with family members who had passed and their estates. He has even directed us to excellent home remodeling sources that made our dollars go much further. He has always shown an interest in us as a family and makes times for a cup of coffee and enjoyable conversation. We have full confidence is his handling of our financial future and for our estate for our children.
Relationship to Financial Advisor: Client as of Nov 4, 2025
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Simply the Best
✅ Wealthtender Certified Advisor Review™
Nov 3, 2025
Bob takes the time to listen and understand more than just your financial goals, but also your hopes and dreams without judgment. He then does everything he can to walk you through how to prioritize and start achieving both the immediate and future goals. We have been working with him for a number of years now and have never looked back. We trust him fully and would not hesitate to recommend him as an advisor.
Relationship to Financial Advisor: Client as of Nov 3, 2025
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
An Advisor That Takes Care Of Your Time and Treasure
✅ Wealthtender Certified Advisor Review™
Nov 3, 2025
Bob has been a lifesaver in helping us manage our investments! Numbers are not my thing but Bob explains everything in a way that even I can understand. Even better - before getting into the numbers, Bob takes the time to get to know you and what's going on in your life. He appreciates time is just as important as money and may point you to the choice that considers both instead of just more $$$. You don't see that very often in this industry. Everyone needs a Bob in their life to help sleep better at night!
Relationship to Financial Advisor: Client as of Nov 3, 2025
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Fortunate to have Bob Dignan as financial advisor
✅ Wealthtender Certified Advisor Review™
Nov 3, 2025
Bob Dignan has been my financial advisor for a couple decades. Fortunately, I have known Bob since he was a teen and have enjoyed seeing his successes through the years. He clearly explains the impact of any financial decisions I make or need to make and has served as a trusted advisor through those years. He is friendly, knowledgeable, and works diligently to make wise investments and lessen the tax burden on my money.
Relationship to Financial Advisor: Client as of Nov 3, 2025
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Wonderful Advisor and Guide
✅ Wealthtender Certified Advisor Review™
Nov 3, 2025
Bob has been a wonderful advisor that has helped us navigate the changing course of our lives. Whether it be buying a home, having a wedding, or starting a family of our own, Bob has helped translate what that would mean for our financial present and future. He has also guided us when it was necessary to press pause on our financial journey, and focus on the now.
Relationship to Financial Advisor: Client as of Nov 3, 2025
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Highly professional
✅ Wealthtender Certified Advisor Review™
Nov 3, 2025
We have had Bob as our financial advisor for years. We can't say enough about his prompt actions in either returning a call or checking on things we have questions for. We would highly recommend him. We have been extremely happy with how he has handled our accounts and would not have any hesitation in having him for your own advisor.
Relationship to Financial Advisor: Client as of Nov 3, 2025
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Our Highly Trusted Financial Advisor
✅ Wealthtender Certified Advisor Review™
Nov 3, 2025
Bob has been our financial advisor for a number of years and I cannot say enough good things about him! I am not knowledgeable about investing. Bob answers any question I have in a way I can understand. My husband knows a little more and Bob is open to any of his thoughts.
Bob is extremely knowledgeable, keeps very up to date and is very responsive. He is a good listener and we feel very comfortable with him.
As much as anything, we trust him! We have every confidence in the world and can highly recommend him!
(Unpaid review and we’re not related!)
Relationship to Financial Advisor: Client as of Nov 3, 2025
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
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Wealthtender Awards
Robert T. Dignan, CFP®, AIF® received the 2025 Wealthtender Voice of the Client Highly Rated Advisor award.
Award Disclosures
Wealthtender awarded Robert T. Dignan, CFP®, AIF® with its 2025 Voice of the Client Highly Rated Advisor Award on 11/05/25. Rating criteria based on eligible client reviews published on Wealthtender between 1/1/24 and 11/05/25. Although Highland Investment Advisors compensates Wealthtender for marketing services (including eligibility to be considered for this award), Wealthtender’s award criteria is objective and not influenced by compensation. This award is not a guarantee of future performance or success and client reviews may not be representative of the experience of all past or future clients. ↗️ View additional award details and FAQs (wt.reviews/awards)
