Careers Don’t Have Linear Paths. Only the Résumés Do

I was thirty minutes into a call with a Korn Ferry recruiter about a search she was running: a $100 million + company, right in my wheelhouse, seven figure compensation and equity when I said something I hadn’t planned to say out loud yet.

“I’m not looking to run other people’s companies anymore. I’m going to start my own and help others do the same.”

It wasn't the first time I'd had the thought. It was the first time I'd said it out loud to someone who recruits for B2B CEO roles. I'd already formed Uphoff Advisory the week before that call.

I read something recently, a first-person piece on careers, that really resonated with me: the vast majority of successful careers aren’t the product of a plan. They’re a combination of aptitude, planning, environment, and following your own curiosity, wherever it leads, whether or not it looks strategic from the outside. I’ve spent thirty-five years, five CEO roles, and several exits proving that thesis without knowing it was a thesis.

Colleagues kept complimenting my career strategy. There wasn’t one.

For most of my working life, people I respected would comment on how deliberately I’d planned my career. I’d smile, chuckle, and let them believe it. If they only knew.

The actual formula was four simple questions, asked in the same order every time a real career decision came up: What am I good at? What am I going to learn that I don’t already know? Who am I going to learn it from? How much does it pay? Lately I’ve added a fifth: what brings me joy? That’s the whole strategy. It’s pattern recognition applied in real time, not a five-year plan pinned to a wall.

None of that is unique to me. What’s unique is that thirty-five years of applying it happened to produce a resume that reads like a straight line: publisher, CEO, CEO again, exit, CEO, exit. The line is real. It’s also an illusion. The resume is the only part of any career that was ever actually linear, because a resume looks like every stop along the way was planned ahead of time. Even when they weren’t.

The timing wasn’t ambition. It was the environment finally catching up.

Turning down a large operating role to start a solo advisory practice looks, from the outside, like either a reinvention or a risk. It was neither. It was the same four questions, applied to a different environment than the one I’d been operating in for three decades.

My early exposure to agentic AI convinced me a new kind of services business could be built around the skills I’d spent a career accumulating: one that scales like software instead of like headcount. I’ve written about the mechanics of that shift at length, most directly in “Solo Scale” where I laid out why the ratio of expert time to revenue that has trapped professional services firms at 10 to 20 percent margins for decades is finally breaking, and why domain experts, not developers, are best positioned to exploit it.

Since making that call, I've built three tools myself. The Uphoff Value Index™ scores the decisions that build a business's worth before a banker ever puts a multiple on it. The Sales Talent Matrix™ and Marketing Talent Matrix™ do the same for people: built with input from a panel of experienced B2B operators, to give business leaders online tools to help hire, coach and manage Sales and Marketing talent.

I didn't need a development team to ship what's live today. Thirty-six months ago, there was no version of a solo advisory practice that also builds and ships its own software, on its own timeline, without a product team or a funding round to get there. Agentic AI didn't just make the old way of doing this faster or cheaper. It made a way of doing this that didn't exist before.

What I hadn’t fully appreciated until I actually started doing the work: agentic AI is both more powerful and more complicated to deploy well than I expected going in. Working directly with founders and operators to help them build, run and grow their businesses turned out to be even more rewarding and fun than I anticipated. And the thing I worried about most, whether my identity would survive giving up the title, turned out to be the thing I should have worried about the least.

Giving up the CEO title didn’t shrink my ego. It set it free.

For thirty years, a meaningful chunk of my identity was as “CEO,” with the size and growth rate of whatever company I was running attached to it like a subtitle. Launching a small advisory practice instead of taking on another large operating role should have dented that. It didn’t. It brought me joy instead, and it liberated a level of thinking and creativity the operating roles never allowed for.

As family, friends and colleagues can attest, my ego did not go away. I believe I'm in the top one percent of operators in this industry, and I'm not going to pretend otherwise to sound humble. But once I took off the yoke of running a company, I stopped seeing every business challenge or opportunity through that single filter. It was the difference between watching something in black and white and seeing it in color.

The calls that told me this wasn’t just me

As the advisory practice found its footing, I started fielding calls from people who wanted to understand "the model." One was a veteran private equity investor. He told me he'd been working on a plan to build his own advisory business. He just hadn't found the right model yet. He's now looking hard at "Solo Scale." I've heard versions of that since, including from two veteran B2B CMOs: one who moved into fractional and advisory work five years ago and hasn't looked back, and another who just came through a successful exit and is weighing the same move, out of a senior operating role and into something like this.

What surprised me wasn’t the interest. It was the range. Plenty of the people calling were mid-career, some early-career, curious whether a model like this could let them apply what they already knew, build something of their own, and get more flexibility and freedom out of the deal than the traditional career ladder ever offered.

What I told them, and what I’ll tell you

A long career in an industry I had real aptitude for, that paid well and built equity along the way, gave me a cushion not everyone has the chance to build, whatever stage of their career they're in. I earned it, and I don't take it for granted. But the disruption underway isn't going to respect it as a prerequisite much longer.

The same agentic infrastructure let me build a substantive, multi-client advisory practice in a hundred days. Thirty-six months ago, that would have cost a quarter million dollars and taken years to assemble. It doesn't check anyone's resume before it goes to work. That's the bet underneath everything I've written about Solo Scale, and it's the bet I'm making with my own career right now: this is the beginning of the biggest opening for people to build something of their own that I've seen in thirty-five years of watching this industry change, and it's going to reach careers before it finishes reshaping the enterprises those careers grew up inside.

What built my career hasn't changed. It was aptitude, environment, and the thing I couldn't stop paying attention to, applied one decision at a time. What's different is the environment itself: disrupted enough that it's now opening that same formula to more people, at more stages, than it ever has before. Thirty-five years taught me to treat disruption as the opening, not the threat. That's the bet I'd make on your career too.

The views expressed in Uphoff on Media are entirely my own. They don’t represent the opinions of any company I’ve led, any board I’ve sat on, or any investor who’s had the pleasure of debating strategy with me over the years. If something I write here sounds brilliant, I’ll take full credit. If it turns out to be wrong, I was clearly misquoted by myself.

”Uphoff on Media” is published by Tony Uphoff, Founder and Managing Partner of Uphoff Advisory, LLC: a strategic advisory practice for founders, CEOs, and investors in B2B information, marketing, and technology. The businesses that drive business.