How FI Led Me to FINE: A New Way to Think About the Second Half of Life
It was early on a Saturday morning. I was driving solo to one of my favorite desert hiking spots, further out than my usual trails but worth it for the rugged open landscape, the solitude, and the wide views. I was catching up on a podcast from the week, half-listening while the desert scrolled past the windows, when the host made a passing comment about something called a Next Endeavor.
He offered two or three sentences about how part-time meaningful work could hedge against sequence of returns risk in early retirement, and then moved on.
I turned off the podcast and drove the rest of the way in silence.
That concept awakened a deep curiosity, a sense of possibility and hopefulness that could solve a tension I was feeling acutely.
My wife and I had crossed a financial milestone, and we were getting closer to some level of financial independence, but I knew it was not close enough to sustain the life we wanted to live in retirement. Not yet. The number was real but the gap between where we were and where retirement required us to be was still significant. There were income events on the horizon that could move the needle, our home was paid off, our savings rate was the highest it had ever been. I could see how we would eventually get there. What I could not see was how we would get there on a timeline that made sense for the life I actually wanted to live. Sure, I could work another five to ten years and retire in my late fifties or early sixties, still early but closer to what has traditionally been a retirement age. But there was a deep sadness and frustration about having to work that long, and I had been looking for a solution.
Part of that was the Minnesota season. If you have not read that story, it is worth a few minutes. It reshaped everything about how I think about work, success, and what it costs to build a life that looks impressive from the outside while feeling misaligned on the inside. After that season, I knew I did not want to make it to 65. I was not sure I could, even if I wanted to.
Part of it was a conversation with a good friend, a peer and client I have known for years, who had recently settled into a demanding senior role at a new company. He said something I have never forgotten. There are two ways you leave a role like this, he told me. You get fired or you leave the company. There is very little chance you get to stay in it and retire from it. He was not being cynical. He was being honest about what he had observed at the top of large organizations: the role above him was a rotating cast of executives proving their mettle on the way up, and they almost always wanted to bring in their own people.
A third part of it was the cautionary tale of my father-in-law, who had retired around 60 and died at 62. While we were not related by blood, it burned into my consciousness that tomorrow is never guaranteed. I wanted a way to retire responsibly with a spending level similar to what we had in our later working years. While in the more stressful weeks the idea of travelling, hiking, kayaking, skiing, and playing pickleball all seemed appealing full time, I could not help but wonder if there was some kind of phased retirement or middle ground. The problem was I did not know anyone who had actually done that. Or more precisely, I did not have a framework to categorize the people I knew who had.
So when the podcast host mentioned a Next Endeavor as a sequence of returns hedge and then moved on, I did not move on with him. I drove in silence and started doing what I always do when something financial grabs me: I went home, I researched, and I built a spreadsheet.
What the Math Showed Me
Over the next several weeks I played with future value calculations, built in a downshift at different ages, and modeled what a flexible Next Endeavor income might do to the retirement timeline. Not a full second career or a demanding job, but something purpose-built: meaningful work on my own terms, done for clients and projects I chose, tapering gradually toward a more traditional retirement as the years passed.
At first I modeled larger sums, thinking that if I wanted to retire in the next few years, the number would need to be large. But what I found surprised me.
Even a modest Next Endeavor income, the kind you could generate from part-time consulting, teaching, artistic expression, or work in a field you had always wanted to explore, could change the retirement math dramatically. It could allow you to retire sooner, protect the portfolio during the years when sequence of returns risk is most dangerous, and fund a better lifestyle in the early years when energy and health are still abundant. It would bring structure and meaning to the weeks, keep the mind sharp, build relationships, and frankly help control spending through more structured days in a way that pure retirement often does not.
The more I modeled it, the more compelling it became. And the more I went looking for what others had written about this idea, the less I found.
There were fragments: passing references to Barista FIRE, which involves part-time work often in retail primarily for health insurance coverage, and vague mentions of semi-retirement and phased transitions. The idea of working on someone else's schedule after forty years of work since my early teens did not appeal in any case. But there was no developed philosophy, no rigorous math, and no clear framework that differentiated purposeful part-time work from the FIRE community's general suspicion of any work after the number was hit.
I was building this for myself. But as the framework took shape, I began to realize I might be building something worth sharing.
Fritz Gilbert of The Retirement Manifesto and others have written honestly about the depression and loss of identity that can accompany the early years of retirement, particularly for high-achieving people who have spent decades deriving meaning and structure from their work. The transition from a demanding career to complete leisure is harder than the savings rate suggests. FINE is not just a financial strategy. It is a psychological one. Meaningful work on your own terms, even a few hours a week, preserves the identity and the engagement that pure retirement can quietly erode.
That realization is a large part of why Desert FI exists.
What Financial Independence Actually Means
Financial independence is simple at its core. You have enough invested assets to cover your desired lifestyle without needing a paycheck. Not total net worth, not home equity, not feeling comfortable. Invested assets, accessible funds, sufficient cash to weather market corrections, sustainable withdrawals, and a spending level you can support for decades.
The math behind it comes from William Bengen, a financial planner who in 1994 analyzed historical market returns and discovered that a retiree could withdraw 4% of their portfolio in the first year of retirement, adjust for inflation each year, and have a very high probability of never running out of money over a thirty-year horizon. This became known as the 4% rule. The Trinity Study later popularized it, but Bengen was the original voice.
Bengen has since updated his figure to 4.5% and even 4.7%, based on thirty years of additional data showing that most retirees actually see their portfolios grow over time. But the core idea remains: your retirement number is roughly twenty-five times your annual spending at 4%, slightly less if you adopt his more recent figures. Know your number and you know your target.
Financial independence is also not a binary event, even if the math sometimes makes it feel like one. The 25x rule gives you a number, but what that number actually buys depends entirely on what you plan to spend. Is it your basic necessities only? Your current spending minus the commuting costs, dry cleaning, and work wardrobe you will no longer need? Or does travel expand once you have the time for it? Does healthcare, often heavily subsidized by an employer, become a significant new line item? And what about the subtler risk: that after decades of deferred living, more time and fewer obligations quietly encourage spending you did not budget for. I have found financial independence to be a spectrum. Crossing the 25x threshold on basic necessities felt meaningful, but it would still be several more years before we could reach the level that would sustain the life my wife and I had been building toward for thirty years. Knowing which version of financial independence you are targeting changes everything about the plan.
What FIRE Got Right and Where It Stops Short
FIRE, Financial Independence, Retire Early, proved something important: if you earn well, save aggressively, invest consistently, and avoid lifestyle creep, retirement does not have to wait until 65. The math is real. The community that built up around it, the blogs, the forums, and the podcasts, has helped millions of people think more seriously about financial independence than they ever would have otherwise.
But for many people, FIRE stops short of the real question.
Extreme early retirement often requires extreme savings rates and a dramatically compressed lifestyle, both before retirement and during it. And even when the math works, the life it produces is not always what people imagined. The identity question, who am I without the work that defined me, is real and underexamined in the FIRE conversation. This may be because the goal of FIRE is to escape or be free from work entirely. It is hard to retain some vestige of employment and be considered truly FIRE, unless it is retail work for health insurance.
For the full math on how Traditional, FIRE, and FINE compare across savings rates, portfolios, and Monte Carlo success rates, The Harder Trail walks through all of it and the results are compelling.
What FINE Actually Means
FINE is Financial Independence, Next Endeavor.
It is the stage after FI where you stop optimizing for escape and start optimizing for alignment. The shift from how do I get out to what am I moving toward. Financial independence with direction, purpose, and emotional clarity.
I thought about what a Next Endeavor might look like for me: teaching high school part-time, being adjunct faculty at a university or community college, consulting in my current profession but only on projects and with clients I chose, a few hours a week or for a few months at a time on a retainer or short-term project basis. Desert FI itself, which was in its earliest stages at the time, was a potential Next Endeavor I was still developing.
When I was thinking about retiring in my late fifties or early sixties, traditional retirement activities sounded more appealing. But the idea of stepping away from meaningful contribution in my early fifties felt like a loss rather than a reward. I still had energy. I still had things to give. I wanted to redirect that energy toward work I was genuinely passionate about, toward helping others, toward building something that mattered, rather than simply stopping. Some of that is my faith, where I believe every person is given God-given talents to use for the benefit of others. Another part is knowing that talents, like muscles not used, can atrophy, and I did not want to lose decades of accumulated wisdom and intellectual engagement at such an early age.
The best illustration of FINE I have seen up close is a man I will call Robert.
Robert was a Regional VP at a nationwide retailer, responsible for hundreds of employees and tens of millions in revenue across an entire region. By any professional measure, he had made it. He had also, years earlier, heard about a leadership development program called The Masters Program, the kind that meets at country clubs with workbooks and curated reading lists and a cohort of accomplished peers. The nearest cohort was across the country, and so he flew from the Southeast to the West Coast each month because the program had such a great reputation and he wanted to be part of it.
The program was transformative for Robert. And as he moved through it, he began to see something. The content, the framework, the investment in developing leaders at the highest level, was reaching only a narrow slice of people: executives who could afford the cost and the travel, people who had already made it.
Robert had a different vision. He went to the founder and got permission to run a pilot version of the program at his church on the opposite coast, at a fraction of the cost, open to leaders in their twenties, thirties, and forties who would never have access to the original. He did not bring in outside speakers or facilitators. He taught it himself. He recruited volunteers to lead table discussions. He showed up once a month for two years and gave everything he had learned about leadership, calling, and building a life that actually fits.
It became more meaningful to him than the demanding corporate role that had funded everything.
That is FINE.
An Invitation, Not a Mandate
Robert is one example. But the question underneath his story is not really about Robert. It is about you.
What did you always want to do that your career never gave you time for? What would you do with ten or fifteen hours a week if the income pressure were lighter but the structure and engagement remained? What would it mean to leave a demanding full-time career a bit earlier, not because you had finally accumulated enough to do nothing, but because you had built enough to do something on your own terms to help fill the gap? If these themes resonate with you, or awaken some hope, it may be worth some time with a journal, a spreadsheet, or a yellow pad and a cup of coffee to think through the possibilities.
FINE is compelling, and I want to say directly that it is an invitation and not an obligation. If you have built enough, and the beach, the hobbies, and the long unhurried mornings are genuinely what you want, that is a worthy and complete answer. This post is not for everyone, although you will find other posts here about retiring well. It is for the person who feels something unfinished when they imagine that version of the future, the one who suspects they have more to give and wants to give it on their own terms.
You do not have to pursue a Next Endeavor. But if the idea appeals even a little, it is worth exploring before you decide.
Here is the practical invitation underneath all of this: if you are willing to do something meaningful and flexible, even for a few years, FINE may allow you to leave the demanding full-time career sooner than the math of pure retirement would permit. You trade the all-or-nothing exit for something more gradual and more human. The gift of time, reclaimed earlier than you expected, in exchange for the gift of meaning, preserved longer than traditional retirement often allows.
When I turned off that podcast and drove in silence, I was solving a personal problem. When I went looking for what others had written and found almost nothing, I started to understand that the problem was not just mine. The gap in the conversation was real, the need was real, and the math, once I ran it, was more compelling than I had any right to expect.
FINE is the lens I keep returning to, but Desert FI was never meant to be only about FINE. The broader question, how do you build a financially wise and deeply meaningful life along the way, not just at the end, runs through everything here. The financial milestones matter. So do the stories of the people hitting them and what comes next.
FI is the foundation. FINE is the future. And the trail between them is worth walking carefully, with honesty about what the math actually shows and what the life actually feels like.
If you want the full comparison of Traditional, FIRE, and FINE across savings rates and Monte Carlo success rates, start with The Harder Trail.
If you want the story of why any of this started, start with The Moment I Realized the Life I Built Was Not the Life I Wanted.
Let's make wise choices and live a great life together.
🌵 Desert FI
New here? A few good places to continue:
The 10-Year Window Most People Miss— why the decade between 45 and 55 changes everything
The Financial Conversations Most People Avoid— finding the people who will walk this trail alongside you
Not yet on the trail? Weekend Reflections goes out every Sunday morning: a personal letter on money, meaning, and the courage to build a life that finally feels like your own. Join us at DesertFI.org/join.
