From Debt to Financial Freedom

My Journey to a Fulfilling and Work-Optional Retirement

gravity well (Rob Tomlin)
6 min readSep 10, 2024
Source: Author’s view

As I sit on my upper deck overlooking the peaceful lake, with the breeze gently rustling the trees, I find myself reflecting on the journey that led me to this serene moment. After decades of work, meeting deadlines, attending meetings, and navigating the daily grind, I have finally entered retirement — or, more accurately, became work-optional at age 65 when Medicare kicked in. Now, I work if I want to, but the beauty of it is — I don’t have to.

The Initial Adjustment: A Period of Uncertainty

I’ll admit, the first few weeks of retirement felt strange. For so long, my life had been defined by routine — work gave me structure, a sense of purpose, and a constant stream of tasks to accomplish. The sudden freedom that came with retirement was both liberating and unsettling. Suddenly, my days were wide open, and I found myself wondering, “What do I do now?”

It took time to let go of the idea that productivity was synonymous with worth. After years of having my sense of self tied to my professional life, the shift to a more relaxed, self-directed routine felt like stepping into the unknown. I had to remind myself that it was okay to slow down and that my value didn’t depend on a to-do list. I’ve always hiked, cycled and kayaked. So I started there. I did more of that. But also rekindled my interest in physics and mathematics.

Financial Preparation: The Debt Payoff at 53

My financial journey towards retirement didn’t truly begin until I reached the age of 53 and was faced with the reality of having over $60,000 in credit card debt. I knew I had to make a change, and while I didn’t particularly care for Dave Ramsey personally, I couldn’t deny the effectiveness of his approach. His method, especially the debt snowball, worked for me.

I focused intensely on paying off that debt, and little by little, I chipped away at it. Starting with the smallest balances and using those victories to build momentum, I finally cleared the slate. Once that burden was lifted, I could finally turn my attention to building wealth and preparing for retirement. While it took discipline and sacrifice, the payoff was life-changing.

The Power of No Debt

With my debt gone, I was able to fully invest in my SEP IRA, IRA, and 401(k) accounts. Over time, I built my savings to $800,000, giving me a solid foundation as I approached retirement. Even though I started late, I focused on contributing consistently and wisely. One of the best financial decisions I made was paying off one house with the proceeds from another, leaving me completely debt-free before retirement.

Now, sitting here on my deck overlooking the lake, I can say without hesitation that being debt-free has given me the freedom to enjoy retirement without the financial stress that many retirees face. No mortgage payments, no credit card bills — just the peace of knowing that what I have, I own.

Managing Finances in Retirement: Social Security and Burn Down Rate

In retirement, I follow a strategy I call my burn down rate. I’ve calculated how much I need each year and decided on withdrawing $75,000 per year from my savings and investments. But the beauty of it is, not all of that comes from my investments.

I receive $3,100 per month in Social Security, which covers a large portion of my living expenses. That means I only need to withdraw around $37,800 per year from my investments. With my $800,000 portfolio earning about 8% annually, I’m able to maintain a comfortable lifestyle without significantly depleting my savings. This careful balance between my withdrawals and investment growth allows me to confidently know my money will last for decades to come.

Retiring at 65: The Work-Optional Life

One of the biggest milestones in my retirement planning was hitting 65 and qualifying for Medicare. That was the moment I truly became work-optional. Knowing that my healthcare was covered took away one of the biggest financial burdens that many retirees face.

The freedom that comes with being work-optional is something I cherish. I can choose to take on work or projects that interest me without worrying about financial necessity. There’s no pressure — if I want to work, I do. If I’d rather spend my days relaxing by the lake, hiking , kayaking, cycling or pursuing hobbies, I have that luxury. It’s the best of both worlds: freedom and security.

Slowing Down: Finding Joy in Simple Moments

One of the unexpected gifts of retirement has been the ability to truly appreciate the present moment. In the rush of working life, it was easy to overlook the beauty of simple things — a quiet cup of coffee in the morning, a good conversation with a my partner, or the pleasure of a home-cooked meal.

Now, without the constant pressure of work looming over me, I find that I can be more present. I take my time with everything, savoring moments I would have rushed through before. Time spent with family and friends feels richer, and I’ve grown to appreciate the little things that often go unnoticed when life is filled with deadlines.

Challenges and Reflections

Of course, retirement hasn’t been without its challenges. There’s a sense of loss that comes with stepping away from a long career. The camaraderie with colleagues, the satisfaction of completing a big project, and even the structured routine are things I sometimes miss. But because I followed a solid financial plan and entered retirement debt-free, I’ve had far fewer worries in this area than I expected.

Living on a fixed income required a shift in mindset. While I used to have a steady paycheck, now my income comes from careful planning and withdrawing from my savings. But with a solid 8% growth and a reliable burn-down rate, I feel confident that my money will last long enough to support me for many years to come.

A New Kind of Fulfillment

Looking back, retirement has given me the opportunity to redefine what fulfillment means to me. It’s not about reaching goals or climbing the career ladder anymore. Instead, it’s about pursuing what truly brings joy and contentment. For me, that’s spending time with loved ones, nurturing my curiosity, and giving back to my community in small ways.

There’s a kind of peace that comes with knowing that I no longer have to prove anything to anyone — not to myself, not to my employer, not to the world. I’ve come to appreciate the rhythm of slower days and the freedom to shape my time in whatever way I choose. And because I prepared financially, I have the freedom to truly enjoy these days without worrying about running out of money.

Advice for Those Approaching Retirement

For those nearing retirement, my advice is to focus on becoming debt-free before you step into retirement. Whether it’s through Dave Ramsey’s method or another approach, getting rid of debt will make everything smoother. After paying off debt, make consistent contributions to retirement accounts like SEP IRAs, IRAs, or 401(k)s. It’s never too late to start, but the earlier you can contribute, the better.

Once you’re retired, set a clear burn down rate. Figure out how much you’ll need each year, and stick to it. If you have Social Security coming in, use that as part of your income plan, so your investment withdrawals are smaller. You’ll feel much more in control of your finances and less worried about the unknowns.

Take the opportunity to explore new hobbies, reconnect with old passions, and most importantly, allow yourself the grace to rest. Remember that fulfillment doesn’t have to come from productivity — it can come from relationships, creativity, or simply taking joy in the present moment.

As I continue this journey, I look forward to the adventures that lie ahead, even if they are quieter and more reflective than those in my past. Retirement, for me, has been a chance to slow down, savor life, and rediscover who I am beyond a work title and face on a video call. And for that, I am grateful — both for the financial stability I worked hard to create and the freedom it now affords me to truly live.

Disclaimer:

The information provided in this article is intended for informational purposes only. I am not a certified financial planner, advisor, or accountant. Any financial strategies or methods mentioned should not be construed as financial advice. Before making any financial decisions, you should consult with a licensed financial professional to discuss your individual situation and goals.

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gravity well (Rob Tomlin)

Manager-Software Development. Focusing on SaaS based microservices