🌵 From the River to the Corner Office — And Back Again
Your career has seasons. Here's what I wish someone had told me about each one.
In my early twenties, I spent summers wading through the bubbling rapids of the New River in the Blue Ridge Mountains, backpack held above my head, books inside. I’d find a flat rock, sit in the sun, and read for hours while kayakers and inner tubers drifted lazily past.
I wanted to dive in. Every single day, I wanted to drop the books and jump into that cold, clear, moving water — the laughter, the freedom, the people fully alive in the moment.
Instead, I sat on the rocks.
On weekdays, while others played, I was studying — graduate coursework to grow my skills for the nonprofit work I loved. Even then, I understood the season I was in had a purpose. The reading, the long conversations over coffee, the slow accumulation of ideas — they were building something I couldn’t yet see. The river would always be there. The window for formation was shorter than it looked.
That tension — between the life you’re living and the life calling to you from the water — never fully goes away. It just changes shape.
Your career has seasons. They don’t follow a calendar. They don’t care how old you are. A doctor finishing residency at 34 is just entering Spring. A mom returning to the workforce at 45 is beginning a new Spring of her own. An entrepreneur who sells their company overnight enters Winter whether they’re ready or not.
The question isn’t which season you’re in right now.
The question is whether you recognize it — and embrace it.
Spring — The Season of Newness
I didn’t walk into my first corporate office until I was 32. A decade of nonprofit work, graduate study, service trips abroad, fundraising, speaking — and then, with a newborn at home and an MBA freshly in hand, I put away the backpack and bought a charcoal grey suit.
Cufflinks. Black oxfords. I was out of central casting.
I arrived ninety minutes early on my first day because I had no idea how to park in an urban canyon of thirty‑story towers. When I finally made it upstairs, I found the breakroom — and discovered they had fancy coffee drinks before fancy coffee drinks at work were a thing. I had clipped coupons for years. I drank seven dollars of free beverages that first day and felt like I was living like a king.
It sounds small. But that moment told me something important: a new season had begun, and I had a lot to learn.
I had walked into what I expected to feel like a prison — the soul‑sucking, fluorescent‑lit opposite of everything I loved about my twenties. Instead, once I found my footing, I discovered something I hadn’t expected.
I actually loved the work.
The spreadsheets, the client pitches, the problem‑solving under pressure — it turned out my decade of leading people, managing projects without a playbook, and fundraising for a cause I believed in had built skills I didn’t even know I had. When I delivered results, people noticed. When I exceeded a goal, it showed up in my paycheck. That connection between performance and reward was new. It was motivating in ways I hadn’t anticipated.
But Spring has a way of teaching you before it rewards you.
A few weeks in, I double‑booked two meetings — one on my laptop, one on my Blackberry, each invisible to the other. I got the call from the one I wasn’t attending. He was a serious client. His time was valuable. And there was nothing I could do.
I rebooked the meeting for lunch at Ruth’s Chris. I paid out of pocket — the corporate card stayed in my pocket. Nobody asked me to. I owned the mistake completely.
I have not missed a meeting like that in twenty years.
John — the President of the firm, a straight shooter who took a genuine interest in me from the beginning — noticed how I handled it. I was deep in imposter syndrome those first months, convinced that everyone in the room knew more than I did and that it was only a matter of time before they figured out I didn’t belong. John pulled me aside early and said: “We’ve already hired you. Just be yourself. You’re on the inside now. Loosen up.”
I needed to hear that more than I knew.
In the Spring season — wherever yours falls:
Find someone like John in every new season. The person who tells you the truth and says 'you belong here, loosen up' is worth more than any training program.
Build systems early. A calendar discipline, a communication rhythm, a way of keeping your word — these compound for decades.
Go where people are. The relationships you build in Spring will carry you through every season that follows.
Capture every dollar of your employer's 401K match. A 50% match is a guaranteed 50% return on day one. Nothing else comes close.
Invest early with consistency. Every dollar invested early has decades to compound. The math is quietly unforgiving in both directions.
Summer — The Season of Building
Summer doesn’t announce itself. One day you realize people are coming to you instead of the other way around — and you understand something has shifted.
The Great Recession hit while I was still finding my footing at Boutique Co. The firm scaled back by three quarters. I found myself unemployed in the middle of mass layoffs, with a young family and a résumé that said MBA but not much corporate experience behind it yet.
When there are no jobs, you take whatever door opens.
My wife sold her car. She biked our toddler around in a trailer while I chased clients across the city as a commissioned broker at a National Brokerage — one of the largest in the country. On my first day, I was handed a digital database of cold leads and dead deals. I eventually convinced the managing director — over golf — to let me dig through boxes of old paper sales files gathering dust in a back room. Everyone had the database. Nobody had the files.
I turned prospecting into a game. One point for an email. Two for a phone call. Four for a live connection. Ten for a meeting. C‑suite executives and Fortune 500 CFOs were reachable between five and seven in the morning, before their assistants arrived to filter calls. So that’s when I started. If someone said call me in two weeks, I wrote down the exact date and called without fail. Every time.
The checking account hit three digits more times than I care to remember. But the mortgage was never late.
Survival was the new success — and by that standard, I was successful.
Landing meetings with Fortune 500 CFOs — something first‑year brokers simply didn’t do — caught the attention of the professional services side of the brokerage. They won one of those pitches and created a role for me. Steady salary. Bonus. The Summer season had truly begun.
Within a year I was promoted. I spent two more years delivering measurable results in a role I had grown to love. After three years of results that spoke for themselves, I had multiple offers when the contract ended — including one from a Fortune 10 company.
I turned it down. The brand was impressive but the mission was smaller, and I'd learned enough by then to know which one I'd regret.
Instead I joined a small supplier with a mission I believed in — innovative technology that reduced water consumption, with a portion of profits funding wells in communities without access to clean water. Within a year I had doubled the revenue of my business segment and built an offshore back‑office team drawing on relationships from my nonprofit days a decade earlier.
I wanted to do it forever.
But small companies are volatile by nature. And when the largest firm in the industry called with an offer that doubled my salary, I took that call — with gratitude for what the Supplier had given me and clarity about what came next.
After leaving the Supplier, I was handed my first real team at Global Corp — five people who had been doing things the same way for years and had no particular reason to change.
I asked about their families first. Learned their names and what mattered to them outside of work. When I needed something done I said, “Would you mind helping me with this?” rather than issuing directives. They were skeptical. Then curious. Then all in.
Together we delivered fifty‑percent improvements in metrics that had been flat for years. The team grew from five to ten. Then David arrived.
High energy, fast‑talking, going places — and completely willing to stretch me past what I thought I could handle. He told me six months in advance that he was going to move a team of over a hundred tradespeople under my leadership. I was a suit‑wearing MBA. I knew nothing about that world.
He sent me into the field first. I rode in trucks. Climbed on roofs. Asked the people who would eventually become my team what they actually thought about management.
They did not hold back.
It was undercover boss — and the best leadership preparation I’ve ever received. The team grew from ten to one hundred twenty. The Summer season was in full bloom.
Meanwhile, at home, something equally important was happening.
I coached my son’s baseball team. We played board games on weekday evenings. I made it home for dinner and put the phone away until he was in bed. The early morning hours were for work — he was sleeping anyway. The evenings were ours.
As Gretchen Rubin once wrote, “The days are long, but the years are short.” I didn’t fully understand that line until I looked up from the grind one day and realized my son had grown up somewhere between the early morning calls and the evening board games. The toddler in the bike trailer was suddenly in middle school.
Summer moves faster than it looks from the inside.
In the Summer season:
Seek a mentor outside your direct chain of command. Someone who will tell you the truth and stretch you before you feel ready.
Serve people exceptionally well. Your boss, your team, your customers, your peers. The size of your paycheck is often determined by how many people you serve and how well you serve them.
Build margin for your family. Even when the career is accelerating. The years are short. They don’t pause for quarterly reviews.
Take whatever honest door opens when the floor falls out. The skills you build surviving a hard season follow you into every season after.
Keep investing through downturns. The worst time to stop contributing to a retirement account is also the best time to be buying.
Don’t be afraid to take the mission‑driven detour. The skills, relationships, and clarity you build there will surprise you.
Fall — One of the Most Beautiful Seasons
After years of pushing the boulder uphill, you start to feel it move on its own.
Trust has accumulated. Your network — built through years of genuine relationship rather than calculated positioning — turns out to be more valuable than any credential. People you mentored in Summer have moved up. Doors open from directions you never anticipated.
My Fall brought Arizona.
A promotion I almost didn’t take because it meant moving a family to a state I had never visited before my interview. But my wife was ready — hungry for a new adventure, tired of the urban grind and suburban sameness, eager to see and live a genuinely different part of the country together as a family.
Three hundred days of sunshine. Mountains in every direction. The desert as a place of clarity and rest. Hiking a canyon trail in fifteen minutes. Skiing ten‑thousand‑foot peaks near Flagstaff in the morning, then driving back down to the Valley of the Sun — still in ski clothes — and sliding into the outdoor hot tub at seventy degrees as the stars came out.
We fell in love with a landscape we hadn’t known we were missing.
Fall is generous that way. It rewards the long investment. It surprises you with gifts you didn’t know to ask for.
The momentum of Fall also brought opportunities that earlier seasons hadn’t. Responsibilities grew to a scale I once couldn’t have imagined. From a team of five to a team of hundreds, across countries and time zones. The boy who arrived ninety minutes early to find parking had somehow become a senior leader in a global organization.
In the Fall season:
Let your network breathe. Relationships built on genuine interest pay dividends in ways and timelines you cannot predict or manufacture.
Be geographically flexible. Say yes to the move your spouse is ready for before you are. The best chapter of my career was in a state I'd never visited before my interview. Your version is waiting somewhere you haven't considered yet.
Take the detour. The small company chapter, the unexpected offer, the role you’re slightly underqualified for — these are often the seasons that define everything that follows.
Maximize your 401K, HSA, and backdoor Roth in Fall. These are likely your highest-earning years. The window is shorter than it looks.
Bring your family into the adventure. The best relocations aren’t sacrifices — they’re shared stories.
Winter — The Quiet Before What's Next
Eventually the leaves that were so beautiful begin to fade.
What was once vibrant grows quieter. The pace that felt exhilarating starts to feel like weight. You find yourself sitting in meetings you’ve sat in a hundred times, thinking thoughts you haven’t quite said out loud yet.
This is not failure. This is Winter.
My father had a saying he returned to throughout his life: “You’re either growing or you’re dying.” He didn’t mean it grimly. He meant it as a compass. Growth looks different in Winter than it does in Summer — it turns inward, becomes more deliberate, quieter — but it still has to be there. The form changes. The direction matters more than ever.
Winter is a season of preparation and honest reflection. Of sharpening what you’ve built and beginning to sense what comes next. The bears hibernate. The ants, as Solomon wrote, store up for the season ahead. Both are wise.
In the Winter season:
Shift from building to protecting. In Winter you stop just building wealth — you start learning to protect it. Sequence of returns risk, Roth windows, Medicare premiums: the map is worth reading before you're standing at the trailhead.
Build your emergency fund to twelve to eighteen months. Cash is a shock absorber when markets drop at the wrong moment.
Study the financial terrain of late career. Penalty‑free withdrawal timing, Medicare premium planning, Roth conversion windows — all of it rewards people who study up early or hire a professional who knows the terrain. The podcasts, the books, the fee‑only fiduciary advisor — all of it pays for itself many times over.
Begin imagining what’s next. Not escaping what you have. Moving toward what’s calling.
The biggest mistake people make in Winter is staying too long because they haven’t yet named what they’re moving toward. The season changes whether you’re ready or not. Better to choose the timing yourself.
My Winter has been asking a question I've come to call FINE — Financial Independence, Next Endeavor. Not retirement from life. Direction for the next one. If you want to see the math behind why a meaningful Next Endeavor changes everything — financially and personally — The Harder Trail lays it out completely.
Back to the River
Here’s what I know now that I didn’t know sitting on those rocks in my twenties:
The seasons are not a ladder. They’re a cycle.
Retirement works the same way. It isn’t the end of the seasons — it’s the start of a new cycle. Some people step into a Spring of reinvention, others settle into a quiet Fall of enjoyment, and some linger in Winter until they name their Next Endeavor. The season changes either way.
The mom returning to work after years raising kids is beginning a new Spring — with everything life has given her since the last one. The doctor leaving medicine to teach is entering a fresh Summer. The executive stepping away from the corner office to build something meaningful is not going backward. They’re going around again, carrying everything the previous seasons gave them.
I am the caterpillar in the cocoon right now. Something is forming that I can’t fully see yet. Desert FI is part of it. The river is still there — clearer now, warmer somehow, more inviting than it ever was from those flat rocks in the Blue Ridge.
The question isn’t whether a new season is coming.
It is.
The question — your question, wherever you are on the trail today — is the same one I sat with on those rocks all those years ago:
Are you going to keep holding the books above the water?
Or are you finally ready to jump in?
If this resonated, share it with someone who's between seasons right now.
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Let's take the harder trail together.
-🌵 Desert FI
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