The Evolution of Enough

May 13, 2026

How does your definition of "enough" money change over time?

Your definition of enough changes because you change. It's not a flaw in your thinking. It's evidence that you're paying attention. Most people move through at least three versions of enough over a lifetime: accumulation, escape, and meaning. Understanding which stage you're in right now might be the most clarifying financial question you can ask.

Me, I had around $750,000 in assets and didn't believe I had enough. It took cancer, burnout, and walking away from a paycheck before I realized that $36,000 a year on top of my wife's salary was all we actually needed.

That gap – between $750,000 feeling insufficient and $36,000 feeling like freedom – isn’t about the math. It's about mindset. And it's something I've watched play out with clients at every asset level, from people just crossing $200,000 in savings to people sitting on several million wondering why they still can't stop.

Here's what I've learned: the number almost never does what you think it will. But when you understand why your definition of enough keeps shifting, you can finally start working with it instead of chasing it.

What follows is my own evolution through those three stages, as well as the lessons I’ve learned. Think of it as a framework. Because if you can see yourself somewhere in this arc, you're already closer to clarity than you think.

What does money mean to you when you're just starting out?

When I first started my career, I cared a lot about how I was perceived. Like a lot of young professionals, I tied money to identity. Wealth represented success, status, and proof that I was accomplishing something meaningful. I wanted people to see me as successful, and I believed money was the clearest way to signal that.

At that stage, I had no concept of enough. I simply wanted more. More money, more recognition, more evidence that I was "winning."

The problem with chasing an undefined version of success is that there's no finish line. Someone will always have more. There'll always be a bigger house, a better title, a person further ahead. And if your enough is built on comparison, it can never actually arrive.

What happens when enough becomes about escaping work?

After several years in a career that didn't fully align with who I was, my motivation started to change. I'd come to believe that work was simply something to endure until you had enough money to stop.

My definition of enough became this: "If I can just save enough, I'll never have to work again."

That represented progress, in one sense. I was at least starting to think in terms of a destination rather than endless accumulation. But it was built on an unhealthy scarcity mindset. I routinely robbed myself of enjoying nice things and memorable experiences in the present because I needed to save for the future.

And ironically, I even robbed myself of greater future financial security. As a young, healthy guy, I saw no point in paying premiums for a private disability insurance policy. I exercised regularly, had a relatively healthy family history, and worked in a safe white-collar environment. I thought I was better off saving that money.

This decision would come back to haunt me, because once you’re diagnosed with a serious illness, you can’t just go back and get coverage.

How does a health crisis change what enough looks like?

In January 2015, I was diagnosed with cancer. Thankfully, it was an indolent (slow-growing) form of non-Hodgkin's lymphoma.

My oncologist assured me I still had plenty of time ahead of me. His estimate was another three decades, based on treatment options available in 2015. Given how rapidly blood cancer research was evolving, he believed I could potentially live even longer.

The diagnosis didn't immediately change my perspective on what enough looked like. But it changed my perspective on time.

Before my diagnosis, fatherhood felt like something that would happen eventually. After it, "eventually" felt less certain. I didn't want to postpone fatherhood any longer.

And that shifted my definition of enough in the opposite direction. Now I felt like I needed more. Not just enough to stop working someday, but enough to support a family.

What finally pushed me to walk away from the paycheck?

In early March of 2020, my wife and I found out we'd be having a second child. And once again, my definition of enough expanded. Now I needed even more.

A couple of weeks later, the world shut down. For me, the stress was amplified on multiple levels at once: a new baby on the way, COVID anxiety because lymphoma had weakened my immune system, and an unsustainable workload.

By that point, I was working with hundreds of clients who relied on their investment portfolios to support their lives. Overnight, I was essentially doing two jobs: financial advisor and therapist, as the stock market crashed more than 30% in a matter of weeks. I was working 50 to 60 hours a week, and a large chunk of that was on the phone helping others through what felt like an existential crisis to them. I didn't even have time to process what I was going through personally.

Eventually, the burnout became too severe to ignore. By summer, I'd walked away from my job.

On paper, that decision made very little sense. If you believe you'll never have enough money, leaving a paycheck looks irrational. But sometimes you simply reach a point where your nervous system can no longer tolerate the environment you're in. If you've ever felt that, you know exactly what I mean.

How do you recognize enough when scarcity is your default?

After leaving, I had no income. My definition of enough felt further away than ever. I spent the next several months studying for the CFP exam, believing it would increase my earning potential within the financial services industry.

Then my cancer returned.

Only this time, it was aggressive and life-threatening. Given the timeline for surgeries and chemo treatments, my next paycheck wouldn't be for a while. And that was when I really started kicking myself for not getting that disability insurance.

But it wasn’t all bad news. Coming out of COVID, the stock market experienced the fastest and strongest recovery I'd ever seen in my career. Through a combination of fortunate timing and aggressive positioning, my assets had grown to around $750,000. At the time, I was heavily invested in high-growth technology stocks that performed exceptionally well during that period.

Looking back, much of this was luck. But I kept my foot on the gas pedal. In my mind, I still didn't have enough.

Had I applied the framework I now use with clients, I could have designed a more resilient portfolio, withdrawn a modest percentage annually, paid taxes and penalties where necessary, and created meaningful monthly income – all while the assets kept growing at a reasonable rate over time.

And this isn’t limited to a high-net-worth situation. The same math works at the $200,000 level. It’s not about the balance; it’s about the question you're asking. But when scarcity becomes your default setting, abundance becomes difficult to recognize. Even when it's sitting directly in front of you.

What does it feel like when the number finally stops mattering?

It took about a year of cancer treatment, therapy, uncertainty, and soul-searching before my perspective finally shifted. By then, my portfolio value had declined significantly, and my other savings had largely been depleted.

And yet I felt more grounded than I had in years.

I stopped asking how much money I needed to feel safe. Instead, I began asking a different question: "What do I actually need to live a meaningful life?"

I realized that if I earned roughly $36,000 per year on top of my wife's salary, we could fund our lifestyle and fully preserve our retirement savings. Assuming the portfolio kept growing at a reasonable rate, our long-term future looked more than stable. That realization changed my definition of enough from several million dollars in the bank to simply earning $36,000 a year.

And that gave me the freedom to take a risk and start my own business.

Why doesn't the math feel like enough even when it works?

After everything I went through, it was clear that planning is never just about the numbers. It’s about the emotional impact those numbers have. From a financial standpoint, $36,000 worked perfectly fine for our situation. But emotionally, it became harder to accept over time.

Having my wife assume the bulk of our financial obligations affected me more than I expected. Every time we went out to dinner and she paid the bill, for example, I felt a quiet sense of discomfort. Every time I needed a little extra financial support, it felt like little daggers in my heart. Not because she made me feel inadequate or was judgmental, but because I simply wanted to contribute more.

That led to my definition of enough evolving yet again. Now, it means reaching a level of income where my wife has the option to stop working if she chooses. She's dealt with a tremendous amount of pressure throughout all of this, and while she still enjoys her work, it’s not as fulfilling as it once was.

I want to earn enough for her to be able to step away when she’s ready so she can set her own schedule every day.

What does enough look like when it's driven by generosity instead of fear or scarcity?

I suspect my definition of enough will keep evolving, and I think that's healthy. Once my wife and I reach our next milestone, there are other things I'd like to do. I'd like to help my kids more. I'd like to support extended family members. I'd like to invest in my community and contribute to causes that matter to me.

Maybe I'll never have enough in the strictest sense. But that's OK, because my definition is no longer driven by greed or fear. It's driven by generosity, abundance, and impact.

That's the real evolution: moving from a number to a mindset of meaning. Because enough isn't simply a financial destination. It's a perspective. And when you define it intentionally, you give yourself permission to enjoy the life you already have while still building toward the future you hope to create.