The Seven Signs You're Ready for a Next Endeavor

It started on a hike. It always does.

After years of following the same personal finance philosophy with 15% savings, paying off debt, creating an emergency fund, and saving in my 401K, I was getting bored. The plan was proscriptive and clear, but black and white advice in a world of vibrant color.

I yearned for more, so I branched out, searched for new podcasts on personal finance, and began listening on the drive to one of my favorite desert peaks. Alone on a Saturday morning in 2018, at the trailhead, I popped in my AirPods and listened to a then-foreign language about tax credits, Roth conversions, higher savings rates, and different levels of something called FIRE. I wasn't fully sure what FIRE was, but apparently it involved working at a coffee shop for health insurance, coasting at work while waiting for investments to catch up, and it came in different varieties: Lean and FAT.

Over the months that followed, I learned more and more from podcasts and several high-quality blogs. A whole new world was opening to me and, like the Western sky I had recently moved to, it was expansive.

In the years that followed, I made specific and targeted moves. I was past the age of a truly early FIRE and wasn't sure the austere lifestyle I read about was for me, but I respected the higher-than-typical savings rates, the Boglehead emphasis on low-cost index funds, and the discipline behind both. These became real accelerants in my own FI journey.

Then earlier this year, my view expanded even further. I wasn't disillusioned or hemmed in this time. I was looking for an answer I couldn't quite find in the existing literature: how do you retire earlier, at a comfortable spending level, but continue to serve others and do work that genuinely matters? Retirement is often framed as leaving something: the work, the pressure, or the politics. I did want to leave those things, but I still wanted to stay mentally sharp, contribute in a meaningful way, and positively impact the lives of others but on my terms. Frankly, after working since my preteen years, I wanted to keep the small rush of earning even a modest income for at least a season longer, not in a One More Year Syndrome way, but for protection in the early years of retirement when my portfolio would be the most vulnerable.

That question, and the gap it exposed in the FI literature, is what this post is about.

What a Next Endeavor Is (and Is Not)

A Next Endeavor is not a second career, not a side hustle optimized for maximum revenue, and not going back to what you left.

It is also not Barista FIRE, the concept of working retail part-time primarily for health insurance coverage. There is nothing wrong with that path, but a Next Endeavor is something different. It is work rooted in passion, purpose, and genuine contribution, with enough schedule flexibility to travel when you want to, pursue the hobbies that give your life texture, and be present for the people who matter most, spouse, children, grandchildren, aging parents, and old friends you never had enough time for.

It's meaningful, flexible work you genuinely want to do, built from what you already know and love, on your own terms and your own schedule. Ten to twenty hours a week on average. Some weeks more, some weeks nothing at all. Work that keeps you sharp, connected, and contributing, without the politics, the pressure, the Sunday night dread, or the early Monday morning alarm clock.

The financial case for a Next Endeavor is made in detail in Why $20K a Year Changes the Retirement Math More Than You Think and The Harder Trail. The philosophy behind it lives in How FI Led Me to FINE. This post is about something different: how to know whether you're ready.

The Seven Signs

Sign 1: You've Hit Basic FI, But Not the Life You Actually Want

This is the financial threshold sign, and it comes first because without it the conversation is premature.

I think of FI as a spectrum rather than a finish line. Essential FI covers your basic needs: food, housing, transportation, and healthcare at a sustainable withdrawal rate. Comfortable FI funds a genuinely good life with reasonable travel, flexibility, and margin. Dream Life FI funds the retirement you actually spent thirty years building toward. I wrote about the emotional dimensions of these three levels in Three Versions of Enough.

The FI community often defines financial independence as hitting 25 times your annual spending. The question worth asking is: 25 times which version?

I'll be honest: I'm a little reluctant to share this publicly. But it's an honest point and I think it matters.

In my forties, when we crossed $1,000,000 in total net worth, home included, we celebrated. We were genuinely, deeply thankful. It's a milestone most Americans never reach and we didn't take it lightly.

Then I ran the math.

Four percent of $1,000,000 is $40,000 a year. Home equity aside, our liquid invested assets were a fraction of that total. Even if they weren't, $40,000 was not going to sustain the life we had spent thirty years building toward. So I filed it away: grateful for the milestone, clear-eyed about what it meant. Liquid net worth was the metric that mattered. We still had work to do.

That is the Basic FI moment almost nobody talks about. You hit a number that sounds like the finish line and discover it was really just the beginning of a longer journey.

Let me be precise about what I mean. If your invested assets at today's value would require a 4% or lower withdrawal rate to fund the retirement you actually want, you may not need a Next Endeavor at all. If the life you've dreamed of requires drawing somewhere between 4.5% and 6.5% of today's portfolio, and you don't want to spend several more years working full-time to close that gap, you're a strong FINE candidate. The alternative paths are straightforward: retire today at a more modest lifestyle, keep working and saving until the assets grow to support the life you want, or pursue a Next Endeavor that bridges the gap on a shorter timeline without requiring either sacrifice. A modest NE income during the sequence of returns risk window can move you from fragile to sustainable without requiring you to work longer or downgrade your dreams.

If you're still building toward Essential FI, keep building, or file this framework away for the future and start testing things you enjoy now. The Next Endeavor conversation will wait. If you've crossed it and find yourself wondering what's next, keep reading.

Sign 2: You've Stopped Caring About the Game

This sign arrives whether you work in a corner office, a classroom, a hospital, or a production floor. It looks different depending on where you work. The feeling underneath it is the same.

You're still doing good work. The results are there, but somewhere along the way, you stopped tracking who was in and who was out of the inner circle. The re-org announcements or office gossip wash over you rather than activating you. You're no longer managing face time or building alliances or engineering the optics of your presence. You're doing your job and letting the results speak.

This is not burnout. Burnout wants relief from the current situation. This is something deeper: the quiet recognition that the role no longer feels authentically yours. You wear it competently and the results are real, but the fit has changed and you know it.

A few years ago I went through a recovery year, a season of lighter work and unexpected margin that I wrote about in The Moment I Realized the Life I Built Wasn't the Life I Wanted. When I came back to full speed, something had changed. The re-org announcements still came. The inner circle still shifted. The face time expectations were still there. But I could see the game more clearly now, and I found I had less appetite for playing it. It wasn't because the work had gotten worse or I was quiet quitting. It was because I had gotten a taste of something better, and the gap between the two was no longer invisible to me.

Sign 3: You're Looking Past Work

Not dreading it or counting down the days, but looking past it, the way you look past a conversation you're having toward the door you're about to walk through.

On a flight, in a meeting, during a commute you've made a thousand times, you find yourself not thinking about the next deliverable or the next review cycle but about how to shave two years off the retirement timeline. You're actively thinking about which accounts to maximize, or what a week of Saturdays would feel like after a downshift or retirement. A meaningful portion of your mental energy has quietly redirected itself toward the problem of getting out, and you're approaching it not with frustration but with the focused curiosity of someone who has a problem to solve, knows an answer exists, and is determined to find it.

This is different from escapism. Escapism wants out of the present. This vision leans into a specific future. If you're daydreaming about what you'll do rather than just dreaming about being done, that's a sign.

I wrote recently about what my ideal Tuesday looks like. If you want a specific picture of what the first day of that different life might feel like, that post is worth a few minutes.

Sign 4: The Accolades Have Stopped Working

There's a season in most careers when recognition lands with real weight: the promotion you worked for, the award you received, or the bonus that rewarded the sacrifice. It could even be the recognition from someone whose respect you had spent years trying to earn.

Gradually, they don't mean as much as they used to. The work that once felt like a calling or at least meaningful increasingly feels transactional. The people you most respected may have retired, left the organization, or been exited through restructuring. The culture that once energized you may have shifted, or you may find yourself less connected to the mission than you once were. You're still performing well by every external measure, but you're just no longer motivated by those measures or infatuated with the organization in the way you once were.

I had a moment recently that illustrated this more clearly than anything I could explain abstractly.

There is a business growth opportunity I'm working on right now, the kind that a few years ago would have felt like a badge of honor. The financial upside is still real and meaningful, but five years ago, it would have been a much bigger part of my identity than it is now. Chasing and winning it would have been all consuming: late nights, early Saturday mornings, and thinking about it while lying awake at night.

I still want to win it. I care about doing the job I've been hired to do, using my skills and talents to the best of my ability, honoring the relationships that made the opportunity possible, and being generous with the team behind me. But the financial upside barely registers as the point. It's almost an afterthought to all the other reasons to work hard at it. The work matters. The relationships matter. The money is almost beside the point. It's a strange feeling and I'm still processing it.

That shift didn't happen overnight. It accumulated gradually over several years of the financial foundation growing, the career achieving what it was going to achieve, and the question of what the second half of life should look like becoming more urgent than the question of what the next deal would pay.

When you notice that the stakes that used to feel enormous have quietly reclassified themselves to business as usual, that is a sign worth paying attention to.

Sign 5: You're Asking "Is This All There Is?"

This is the sign almost everyone experiences and almost nobody recognizes for what it is.

It arrives not as despair but as a quiet restlessness. I once went backpacking with friends for five days in the Blue Ridge mountains of Southwest Virginia. We hiked through a state park on a foggy morning, eventually summiting Mount Rogers, the tallest peak in Virginia at 5,700 feet. While the surrounding area is stunning, this particular mountain is covered in a dense, mossy spruce forest. After all that effort to get to the top, the view was sub-optimal.

Sometimes work can be like that. You achieved what you set out to achieve. The career has been meaningful and the accomplishments have been real and the life has been genuinely good. But somewhere beneath all of that is a voice asking whether the second half of life deserves something different from what the first half required. You climb the mountain only to realize that view wasn't what you envisioned, and you may want to be on a different peak entirely. So you reset the GPS, grab your walking stick, and begin taking steps toward the path you want in the second half of life.

The people who hear that voice and dismiss it as ingratitude or entitlement miss something important. The people who hear it and mistake it for burnout often make lateral moves, or worse, climb the next mountain hoping to find that rush again. Neither addresses the deeper question. The people who hear it and get curious are the ones ready to have this conversation. They start asking what a different kind of contribution might look like, imagining a version of the second half that uses everything they've built in service of something they actually care about.

Sign 6: You Have a Direction Worth Testing

You don't need to know exactly what your Next Endeavor is before you're ready. But you need a direction.

A skill people already affirm in you. A field you've spent decades mastering that smaller organizations need but can't afford full-time. A creative outlet that keeps pulling you back that you squeeze into early mornings and weekends just for the love of it. Something you've done on the side, occasionally, and found that it energized you rather than depleted you.

For me it was two things arriving at roughly the same time. The consulting calls in my field I had been blowing off for years, one-hour conversations where someone wanted my perspective on a market trend or a business decision, started feeling less like interruptions and more like previews of something I might actually want to do. The writing, rekindled after years of neglect, reminded me of something I had known since high school: that putting ideas on paper and finding the right words to carry them is one of the things I'm genuinely made for.

Neither required a business plan or a website or a revenue model. They required a direction. The direction came first. The rest follows.

Sign 7: You've Started Pre-Testing

This is the most underrated sign of readiness, and the most actionable.

Readiness is not a feeling. It's an accumulation of low-risk evidence. You take the consulting call. You write the first post. You teach the personal finance class. You lead not just another multi-day meeting, but a leadership team retreat in the desert and notice people's perspectives transformed, a fresh vision for the business and a more deeply connected team. You sit around a kitchen table and help a couple build a budget and realize the enjoyment is entirely in the work and the money is secondary.

The clearest evidence I was pre-testing came not from what I was pursuing but from what was finding me.

Over the past year or two, executives I know and respect started coming to me with questions I didn't expect. How do you think about savings rates at this stage? What does your retirement math look like? How do you get out earlier without sacrificing the life you want? I wasn't advertising any of this. The questions found me. Friends and family members followed with their own financial questions, laying out their situations carefully and asking for specific guidance. Younger professionals at work sought me out for career advice, wanting to hear stories from a longer road with its own twists and turns. I found I loved those conversations in a way that had nothing to do with obligation.

The things you know so deeply that people seek you out before you've hung a shingle are usually the things worth building toward. Someday I hope to help other high-achieving professionals and families find their own version of FINE, their own path to freedom and meaning on the other side of full-time work.

The writing confirmed something I hadn't fully admitted to myself. Even in the busiest weeks, the high-stakes weeks, the weeks where I had every reason to skip it, I couldn't. It wasn't because I had to. It was because I didn't want to live without it. That is a different kind of evidence than anything on a spreadsheet.

If you've had versions of any of those moments, people seeking you out rather than you seeking them, work you can't stop doing even when you could, you already have your answer.

The False Positive Worth Naming

Before you take these seven signs as confirmation, one clarification worth making.

Stress alone is not a sign of readiness. A brutal quarter, a difficult boss, or a re-org that left you feeling displaced: these are real and legitimate reasons to make a change. But they are reasons to change roles or companies, not necessarily reasons to downshift out of full-time work. The difference is that those problems have a solution. A different job, a different team, a different company would solve them.

Readiness for a Next Endeavor is deeper than that. It's not about the role or even the company. It's about what you want to do with the remaining years of life energy you have left.

I know this distinction personally. A year into my recovery year, I was asked to step into a new role with high results expectations. It's meaningful work with people I genuinely like. Earlier in my career it would have been my absolute dream. Right now I'm giving it everything I have, because the people who put me there deserve that, but something in me has shifted. I want to do this work well while keeping some of the balance rhythms I learned in my recovery year. While I enjoy the role, I know there are bigger things ahead for my life in the long run.

That is not disengagement, quiet quitting, or burnout. My goal right now is not more accolades or more responsibility. It is to do excellent work without being consumed by it, and to build toward something that uses everything I have learned in service of something I feel called to.

If you can honestly say a better role or a better company would fix what you're feeling, go find that role. If the honest answer is that the role is actually pretty good and that feeling is still there, that is the sign worth taking seriously.

A Note on Readiness and Your Spouse

You may be further along in this thinking than your partner is. That gap is not unusual, and it's worth naming early.

I love my wife and I want her to have full confidence in the plan before we make any major move. That means coming to her not with anxious questions but with a clear vision, a developed plan, and the honest belief that the math works. I've spent a lot of time running those numbers, more than she probably wants to know about, and I feel confident in what they show.

But I also know that confidence built on my own spreadsheet is still just my spreadsheet. So we're working with a fee-only CFP on a project basis to get an independent validation, not because I expect the numbers to change materially but because I want her to hear it from someone else. For her peace of mind, for our unity going into this next chapter, and frankly for mine too, having an expert review the plan and confirm the assumptions is worth every dollar of the fee. The decision is too important and too irreversible to rest on one person's analysis, however thorough.

Come to your partner with a developed plan rather than an open question. Show your work. Consider getting an independent set of eyes on it before the conversation happens. Your partner deserves that confidence. So do you.

Where Are You?

Nearly everyone reading this falls into one of three places.

Some of you are not ready yet. The signs aren't there or the financial foundation isn't close enough. That's honest and that's fine. Keep building. The Next Endeavor conversation will still be here when the time is right, and the earlier you start thinking about what your direction might be, the better positioned you'll be when the foundation is ready.

Some of you are almost ready. One or two of these signs resonate but not five or all seven. You're in the pre-testing phase, trying things, gathering evidence, running the numbers with more seriousness than you were a year ago. That's exactly where you should be.

Some of you are ready right now and haven't said it out loud yet. You've been reading this list nodding at things you've felt for a while but haven't had language for. You're not burned out. You're not disillusioned. You're done with what you were doing, ready for what comes next, and looking for a framework to make it real.

If that's you, the next step isn't waiting. It's deciding which direction is worth testing first.

My own motivation runs deeper than the math. I believe we're put here to serve others and to use the gifts we've been given, not to spend the last decades of life in self-indulgence. A Next Endeavor is how I intend to keep contributing on my own terms, for as long as I'm able. Whatever your motivation, the path is the same: find the direction, test the idea, and let the evidence tell you whether you're ready.

A reflection question worth sitting with:

Which of these seven signs do you recognize in yourself, and what would it look like to take one small step toward testing your direction this month?

Let's make wise choices and live a great life together.

🌵Desert FI

A few good places to go deeper:

• How FI Led Me to FINE— the philosophy behind the Next Endeavor and why it matters for the second half of life

• Why $20K a Year Changes the Retirement Math More Than You Think— the math behind why a modest income ramp during the SORR window changes everything

• The Harder Trail— the full Monte Carlo comparison of Traditional, FIRE, and FINE

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.