How Do You Retire from Your Friends? My Decades of Fulfillment as a Fiduciary Advisor

Here’s Why I May Never Be Ready To Retire: Purpose & Fulfillment

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Over the past few years I’ve been asked the following question with increasing frequency: “Are you planning to retire soon?” Folks see my white hair and assume that I’m ready to sail off into the sunset. Yet, every time I consider the idea, I think to myself, “Retire from what?” Or better yet, “How do I retire from my friends?” That question always makes me smile, because my clients have become far more than a list of accounts on a spreadsheet. They’re people I’ve grown to care about deeply. They’re the reason I rise each morning, eager to see what the day might bring.

Sure, I handle the numbers, graphs, portfolio allocations, diversifications and retirement and tax plans. But for me, being a fiduciary advisor is so much more than crunching data. It’s about sharing life’s moments—both big and small. It’s about having conversations that help people see the path ahead more clearly. It’s about giving folks the confidence to spend on the experiences they’ve always wanted, or the reassurance to save for the future they envision. Over the years, I’ve realized that this isn’t just a job; it’s a purpose-filled life.

In this article, I’ll walk you through why I’ve remained so passionate about this work for decades. I’ll share real client moments that remind me why I’m not ready to hang up my hat. I’ll also show you how a simple pension decision can change the course of an entire family’s future. My hope is that by the time you reach the end, you’ll understand why I cherish this role. Maybe you’ll also see why it’s something I can’t imagine giving up.



A Career of Meaningful Work

I’ve been at this for decades now. With every passing year, I gain new perspectives on how money intersects with life. It’s not about piling up assets in an account or outsmarting the markets. Instead, it’s about seeing how goals evolve, how family dynamics shift, and how dreams can become reality with the right financial approach. It’s about how a conversation about money could transform into a conversation about life aspirations, concerns, and family legacies. I realized very early on, that I wasn’t just moving numbers around on a chart. I was helping shape futures.

Over the years, I’ve been privileged to share in the lives of many wonderful people. Clients have become friends, friends have become like family, and those relationships keep me passionate about what I do. My work is fulfilling because I get to be there through all sorts of transitions—marriages, children going off to college, job changes, retirements, and sadly, even funerals. Through it all, I’m in the background, ensuring that each financial plan adjusts to life’s inevitable twists and turns.

Finding Joy in Ongoing Service

You might wonder why someone so involved with retirement planning, like me, isn’t interested in retiring as soon as possible. After all, isn’t retirement the ultimate reward for a career of hard work? The truth is, I already have the reward: I get to do something I love every single day. I work with and for people I respect and admire, I solve interesting problems, and I watch lives improve as a result of our planning.

That never gets old, (even during tax season). Each time I help a client buy their dream home, navigate a challenging market, manage an inheritance, coordinate their family’s estate plan, or set aside funds for a grandchild’s education, I feel an immense sense of purpose. I feel I’m part of something that truly matters to them. And that’s priceless.

"I work with and for people I respect and admire, I solve interesting problems, and I watch lives improve as a result of our planning." –Chip Addis
“I work with and for people I respect and admire, I solve interesting problems, and I watch lives improve as a result of our planning.” –Chip Addis

From Clients to Friends

Over time, my relationships with clients deepen. I learn about their families, their hobbies, and their personal wishes for the future. I celebrate their milestones: a child’s graduation or wedding, a big promotion, or the birth of a first grandchild. I’m there for the heartaches, too. I’ve sat across the table and listened to tearful goodbyes to a spouse, or watched as someone faced unexpected health issues.

These are the moments that bond us. When a client has a pressing question about their portfolio, I suspect they don’t just see me as a financial advisor. I hope they see me as someone who’s known and supported them through many stages of life. We share stories, laughs, and sometimes frustrations about the curveballs life throws. That’s why the notion of retiring is so strange to me. It feels like stepping away from a group of dear friends. Who would want to do that?

Staying Passionate and Purpose-Driven

I’ve learned that if you’re not improving someone’s life—helping them achieve their financial goals, lowing stress, reducing a burden, clarifying financial complexity, etc.—then you’re not doing your job as a fiduciary financial advisor. Fiduciary means that I’m legally bound to put my clients’ interests first. Yet, for me, that’s not enough, it’s a personal ethics matter as well—I want to add value too!

The True Mission: Improving Lives

Money can be a powerful enabler. It funds our dreams, provides security, and offers freedom of choice. But without the right plan, money can also create stress, uncertainty, or confusion. My mission has always been to help clients see how their finances can support their broader life goals. Maybe it’s traveling the world while you’re still healthy, or setting up a trust that ensures your grandchildren can attend the college of their choice.

I love seeing the look on a client’s face when they realize they can do more than they thought. That flash of joy when they say, “Wait, so you’re telling me I can afford this trip and still be on track for retirement?” is one of my favorite parts of the job.

The Fulfillment of Guiding Through Life’s Ups and Downs

Being a financial advisor means sharing in the full spectrum of life’s milestones. I help clients navigate major transitions like retirement, estate planning, real estate purchases, and job changes. I also handle smaller day-to-day concerns, such as routine portfolio rebalancing and minding clients’ financial to-dos.

I check in with clients regularly to see if their needs have changed. Over the course of a lifetime, priorities evolve. Maybe your primary focus shifts from saving for college to funding a comfortable retirement. Or perhaps you move from corporate life to entrepreneurship. When these shifts happen, we readjust the plan. My role is to remain informed, relevant, transparent and thoughtful about every recommendation I make.

Supporting Major Transitions

Retirement is a big one. People often feel overwhelmed when the paychecks stop and their investments become the main source of income. A major shift like that can be scary! That’s where a calm, steady hand can be invaluable. I run projections, discuss realistic spending rates, and ensure there’s enough buffer even for big emergencies.

This advice extends to how pension funds are allocated or how Social Security might fit into the bigger picture. Tax laws are forever changing and some are quite complex, so sometimes, clients need guidance on when to take distributions. Other times, they need reassurance that a market downturn won’t doom their retirement prospects. In those instances, my job is to provide that clarity and stability.

Inheritance and legacy planning are other major transitions. It can be sensitive since it involves discussions about mortality, family dynamics, legacy and generational wealth. I try to approach these conversations with empathy. For many clients, passing something on to their children or grandchildren is a final act of love. For that reason, it’s clearly of great importance to them. Ensuring that the paperwork, trusts, and wills reflect their wishes is something I take seriously.

Consistency Amid Uncertainty

Markets are unpredictable. Elections bring uncertainty. Headlines can stir up panic. And social media, well, you get the idea. In those moments, I become a steady voice that reminds clients of our long-term strategy. Emotional investing often leads to mistakes. People try to time the market or get spooked by temporary news. My approach and value here is to help them stay the course.

I prefer diversification over prognostication.” By spreading out risk, we’re less affected by any single downturn. This approach isn’t flashy, but it’s time-tested and true. It doesn’t promise to beat every market cycle, but it does offer a kind of stability that protects investors from huge losses. It’s also less stressful. Over the years, I’ve seen how consistent, steady investment strategies tend to outperform hasty, emotional decisions.

We can change lives, protect legacies, and give people peace of mind in their final years. That’s the kind of fulfillment that energizes me every day.
We can change lives, protect legacies, and give people peace of mind in their final years. That’s the kind of fulfillment that energizes me every day.

Impactful Moments That Fuel My Passion

A Pivotal Pension Decision—a Little Story About Jack & Diane

Certain client experiences stick with me forever. They remind me why I still (figuratively) jump out of bed in the morning, eager for another day of helping people find financial security and peace of mind. One story in particular stands out. It’s about a couple—for the sake of anonymity, let’s call them Jack and Diane—who made a pivotal pension decision that affected not only their own future but their children’s future as well.

Jack worked for three decades at a large corporation. When he was ready to retire, he faced a big decision about how to receive his pension. He could take a higher monthly benefit for the rest of his life, but that benefit would end if he passed away before Diane. Alternatively, he could choose an option that provided a smaller monthly benefit that would continue for Diane if he died first. Another possibility involved a lump-sum payout.

During our meetings, Jack leaned toward maximizing his monthly checks. He felt good about his health. He joked that he had plenty of years ahead of him to enjoy his retirement. Diane, on the other hand, was quiet. She nodded through most discussions, but didn’t say much unless prompted.

The Moment that Mattered

Then at some point in the meeting, Jack needed to step out of the room briefly. While he was away, Diane quietly revealed that Jack’s health wasn’t as great as he claimed. She worried that if he opted for a benefit that ended upon his death, she could be left with little or nothing. This was crucial information. Jack never mentioned any serious concerns, perhaps he thought he could overcome his health challenges. He also seemed committed to the choice that gave him the bigger monthly payout.

But, I took Diane’s concerns to heart. My fiduciary duty means I have to look at the entire situation, not just the immediate benefit, not just one spouse’s perspective. Jack’s pension was a sizable portion of their retirement savings. But if they chose the higher monthly benefit, Diane would face serious financial stress if Jack were to pass away sooner than expected. With this in mind, we ran multiple scenarios. We considered the potential risks and evaluated different payout structures.

The Outcome

Ultimately, they chose a lump-sum option that provided a substantial amount of money to the couple.

Sadly, Jack passed away only six months into his retirement. Because of the lump-sum choice, Diane had a safety net that supported her through this devastating time. She didn’t need to worry about running out of money or rushing back to work. Three years later, Diane herself passed away. The remaining funds from the pension payout then went to their two adult children.

If Jack had chosen either monthly payment option, that benefit would have ended when Jack or they both had passed. Their children would have received nothing. Instead, Jack and Diane’s decision financially secured Diane’s final years and allowed their children to inherit a significant sum. This changed the course of the couple’s and their children’s lives. It also illustrated the real power behind engaged thoughtful financial planning.

Why It Mattered

This story reminds me why I do what I do. Simple financial decisions can have profound outcomes. By listening to Diane’s fears, we found a plan that made sense for both of them. Her willingness to speak up and my duty to act in their best interest combined to create a lasting impact for their family.

Moments like these keep me passionate. They show how a caring advisor can do more than just handle assets. We can change lives, protect legacies, and give people peace of mind in their final years. That’s the kind of fulfillment that energizes me every day.

Measuring Success Beyond Returns

People sometimes assume that financial professionals measure success by account balances or returns on investment. While these metrics are important, I find more satisfaction in the peace of mind my clients gain. When they say, “I can sleep at night knowing I’m covered,” I consider that a job well done.

Money is just one piece of the puzzle. The bigger picture includes relationships, dreams, health, and personal well-being. A solid financial plan supports all these elements. I feel my role is to empower you financially while weaving a safety net that catches you when life events threaten your stability.

Embracing the Future: “Retire? To What?”

When I am asked, “Why don’t you retire and enjoy life?” My question back is, “I’m already enjoying it. Why would I stop now?” Some of us work hard so that someday we can do what we love. I’ve been lucky enough to do what I love as my career. It challenges me, keeps me learning, and lets me form meaningful bonds with people I care about.

Why Walk Away From Fulfillment?

I don’t see a compelling reason to walk away from something that fulfills me. If I retired, I’d be stepping away from clients who have become like friends. I’d miss the satisfaction of guiding someone through a tricky market situation or helping them find new ways to fund a dream vacation. What’s better than helping your friends?

Certainly, there may come a time when my energy or health forces me to slow down. But for now, I’m grateful that I can keep doing what I love. Clients often say they appreciate my enduring tenure. They trust me to continue looking after their finances because what I’ve seen runs the gamut—markets fluctuate, economies shift, and countless life events unfold.

Legacy in Action

As I move through these later stages of my career, I’m mindful that it’s important to pass along what I’ve learned to younger advisors. I want the next generation to understand that being a fiduciary financial advisor isn’t just a legal obligation. It’s a moral one. It’s about empathy, compassion, and genuinely caring about the people on the other side of the table.

I’ve shared my story of ‘Jack and Diane,’ to explain to new advisors why it matters to ask the right questions, and to pay attention when spouses have concerns. I stress the importance of building relationships on trust and open communication. That’s how you go from working with a “client base” to working with a “community” of people who rely on you to be there through life’s ups and downs.

I also try to instill the idea that money is only part of the conversation. Advisors who truly excel do so because they understand people’s hopes and fears. They understand that behind every account there’s a human story waiting to be heard.

When I reflect on the many years I’ve spent in this role, I realize my approach can be summed up in a simple piece of advice: Do the right thing and always add value.
When I reflect on the many years I’ve spent in this role, I realize my approach can be summed up in a simple piece of advice: Do the right thing and always add value.

My Simple Advice: Adding Value Wherever You Can

When I reflect on the many years I’ve spent in this role, I realize my approach can be summed up in a simple piece of advice: Do the right thing and always add value. If you’re not improving someone’s financial life, then reconsider your strategy. If you can’t answer the question, “How is this making my client’s life better?” then you’re not living up to your role as a fiduciary advisor.

Here’s a short bulleted list that helps me stay true to this principle:

  • Listen more than you talk: You can’t add value if you don’t understand a client’s real concerns.
  • Ask deeper questions: Finances are personal. Encouraging clients to share more about their life helps you craft a plan that truly fits their lives—needs, goals, values— all of it!
  • Stay calm in a crisis: Your reassurance can prevent emotional decisions that harm long-term goals. When the professional remains calm, it’s can have a powerful calming effect on the clients.
  • Celebrate the wins: Recognize personal and financial milestones, because these moments build stronger relationships.
  • Keep learning: The financial world changes rapidly. Stay current on new regulations, market developments, and planning strategies.

This list acts as a reminder to remain humble, curious, and client-focused. It ensures that I never lose sight of why I started in this profession.

In Conclusion: Me, Retire? Why?

I sometimes wonder if I’ll ever truly retire. Then I think about the relationships I’ve built and the folks I’ve had the privilege to serve. I think of the young couple that came to me full of questions about buying their first home, who later returned for advice about college savings, and who now consult me on their retirement plans. I think of Jack and Diane’s family, whose futures changed for the better because we approached a tricky pension choice with care and foresight.

The truth is, this job has become part of my life’s fabric. There’s something deeply fulfilling about helping guide people through the ebb and flow of finances, emotions, and life changes. I can’t imagine waking up one morning and saying, “Well, that’s it. Time to leave it all behind.”

I measure my success in the trust earned, the friendships formed, and the lives made richer by thoughtful financial planning. I’m still here because there’s always someone else to help, another problem to solve, and another dream to realize. If I can offer comfort or clarity to people juggling so many of life’s demands, then I’ve found my purpose.

So, when someone asks me about retiring, I just grin. Maybe someday I’ll slow down, but for now, I’m far too passionate about what I do. I’ve been blessed with meaningful work, lasting relationships, and countless rewarding experiences. It’s more than I could have asked for or expected in a career. After all, how do you retire from your friends?

I don’t have an answer for that yet, and I’m in no rush to find out.

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