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Careers Don’t Have Linear Paths. Only the Résumés Do · Uphoff on Media Podcast

• 0:01
  SPEAKER_00: The funny thing about careers is how different they look from the outside.
• 0:06
  SPEAKER_00: The career narrative of the successful business leader reads like a story where
• 0:11
  SPEAKER_00: the hero executed a carefully planned,
• 0:13
  SPEAKER_00: mapped out strategy and was in control of every step along the way.
• 0:18
  SPEAKER_00: But when you talk to veteran executives,
• 0:20
  SPEAKER_00: you learn that the path their career journey took was less strategic than it appears
• 0:25
  SPEAKER_00: from the outside.
• 0:28
  SPEAKER_00: In reflecting on my own 35-plus year career journey leading B2B information,
• 0:33
  SPEAKER_00: marketing,
• 0:33
  SPEAKER_00: and technology companies,
• 0:35
  SPEAKER_00: what also hits me is that several of the businesses I led wouldn't have existed in
• 0:39
  SPEAKER_00: the previous decade as the disruptive technology we were using hadn't mainstreamed
• 0:45
  SPEAKER_00: yet.
• 0:47
  SPEAKER_00: No need to tell you that we are in the midst of one
• 0:49
  SPEAKER_00: of those disruptive technology waves with Agentec AI.
• 0:53
  SPEAKER_00: Now, what's unique about Eugenic AI, though,
• 0:56
  SPEAKER_00: is that it is enabling new business models
• 0:58
  SPEAKER_00: that I believe will ultimately reshape careers
• 1:02
  SPEAKER_00: in ways previous technology waves didn't.
• 1:05
  SPEAKER_00: I've been doing more than just researching, writing, and analyzing this trend.
• 1:09
  SPEAKER_00: I've been living it.
• 1:10
  SPEAKER_00: In today's episode,
• 1:11
  SPEAKER_00: Careers Don't Have Linear Paths,
• 1:13
  SPEAKER_00: Only the Resumes Do,
• 1:15
  SPEAKER_00: I'll share how Agendic AI is creating more career opportunities,
• 1:18
  SPEAKER_00: not less,
• 1:19
  SPEAKER_00: and why we may well be about to witness the largest unlock
• 1:23
  SPEAKER_00: of entrepreneurial activity we've ever seen.
• 1:26
  SPEAKER_00: Okay, let's get to work.
• 1:29
  SPEAKER_00: This episode is called Careers Don't Have Linear Paths, Only the Resumes Do.
• 1:34
  SPEAKER_00: What builds a career hasn't changed.
• 1:36
  SPEAKER_00: What has is the environment, which will change how both careers and businesses are built.
• 1:43
  SPEAKER_00: I was 30 minutes into a call with a corn fairy recruiter about
• 1:47
  SPEAKER_00: a search she was running,
• 1:49
  SPEAKER_00: a $100 million plus company right in my wheelhouse,
• 1:53
  SPEAKER_00: seven-figure compensation and equity,
• 1:55
  SPEAKER_00: when I said something I hadn't planned to say out loud yet.
• 2:00
  SPEAKER_00: I'm not looking to run out of people's companies anymore.
• 2:03
  SPEAKER_00: I'm gonna start my own and help others do the same.
• 2:06
  SPEAKER_00: Now, it wasn't the first time I'd had the thought,
• 2:09
  SPEAKER_00: but it was the first time I'd said it out loud to someone who recruits
• 2:13
  SPEAKER_00: for B2B CEO roles.
• 2:15
  SPEAKER_00: I'd already formed Uphoff Advisory the week before the call.
• 2:20
  SPEAKER_00: I read something recently, a first-person piece on careers that really resonated with me.
• 2:25
  SPEAKER_00: The vast majority of successful careers aren't the product of a plan.
• 2:29
  SPEAKER_00: They're a combination of aptitude,
• 2:31
  SPEAKER_00: planning,
• 2:32
  SPEAKER_00: environment,
• 2:32
  SPEAKER_00: and following your own curiosity wherever it leads,
• 2:36
  SPEAKER_00: whether or not it looks strategic from the outside.
• 2:40
  SPEAKER_00: I've spent 35 years,
• 2:41
  SPEAKER_00: five CEO roles,
• 2:42
  SPEAKER_00: and several exits proving that thesis without even knowing it was a thesis.
• 2:48
  SPEAKER_00: Colleagues kept complimenting my career strategy.
• 2:52
  SPEAKER_00: There wasn't one.
• 2:53
  SPEAKER_00: For most of my working life,
• 2:55
  SPEAKER_00: people I respected would comment on how deliberately I'd planned my career.
• 3:00
  SPEAKER_00: I'd smile, thank them, chuckle, and let them believe it if they only knew.
• 3:05
  SPEAKER_00: The actual formula was four simple questions asked in the same order every time
• 3:11
  SPEAKER_00: a real career decision came up.
• 3:13
  SPEAKER_00: What am I good at?
• 3:15
  SPEAKER_00: What am I going to learn that I don't already know?
• 3:18
  SPEAKER_00: Who am I going to learn it from?
• 3:20
  SPEAKER_00: And how much does it pay?
• 3:22
  SPEAKER_00: Lately, I've added a fifth.
• 3:23
  SPEAKER_00: What brings me joy?
• 3:26
  SPEAKER_00: That's the whole strategy.
• 3:27
  SPEAKER_00: It's a pattern recognition applied in real time, not a five-year plan pinned to a wall.
• 3:34
  SPEAKER_00: None of that is unique to me.
• 3:35
  SPEAKER_00: What's unique is that 35 years of applying it happened to produce a resume
• 3:40
  SPEAKER_00: that reads like a straight line.
• 3:42
  SPEAKER_00: Publisher to CEO, CEO again, exit, CEO again, exit.
• 3:47
  SPEAKER_00: The line is real.
• 3:48
  SPEAKER_00: It's also an illusion, though.
• 3:50
  SPEAKER_00: The resume is the only part of any career that was ever actually linear because
• 3:55
  SPEAKER_00: a resume looks like every stop along the way was planned ahead of time,
• 3:59
  SPEAKER_00: even when they weren't.
• 4:02
  SPEAKER_00: The timing wasn't ambition, it was the environment finally catching up.
• 4:07
  SPEAKER_00: Turning down a large operating role to start a solo advisory practice looks from
• 4:11
  SPEAKER_00: the outside like either a reinvention or a risk.
• 4:15
  SPEAKER_00: It was neither.
• 4:16
  SPEAKER_00: It was the same four questions applied to a different environment than
• 4:20
  SPEAKER_00: the one I'd been operating in for three decades.
• 4:23
  SPEAKER_00: My early exposure to agentic AI convinced me a new kind
• 4:27
  SPEAKER_00: of services business could be built around the skills I'd spent
• 4:30
  SPEAKER_00: a career accumulating, one that scales like software instead of like headcount.
• 4:36
  SPEAKER_00: I've written about the mechanics of that shift at length,
• 4:38
  SPEAKER_00: most directly in SoloScale,
• 4:41
  SPEAKER_00: where I laid out why the ratio of expert time to revenue
• 4:44
  SPEAKER_00: that has trapped professional services firms at 10 to 20% margins
• 4:48
  SPEAKER_00: for decades is finally breaking and why domain experts,
• 4:52
  SPEAKER_00: not software developers, are best positioned to exploit it.
• 4:57
  SPEAKER_00: Since making that call, I built three tools myself.
• 5:01
  SPEAKER_00: The Uphoff Value Index scores the decisions that builds a business worth before
• 5:05
  SPEAKER_00: a banker ever puts a multiple on it.
• 5:07
  SPEAKER_00: The Sales Talent Matrix and the Marketing Talent Matrix do the same for people built
• 5:11
  SPEAKER_00: with input from a panel of experienced B2B operators
• 5:14
  SPEAKER_00: to give business leaders online tools to help hire,
• 5:17
  SPEAKER_00: coach, and manage sales and marketing talent.
• 5:20
  SPEAKER_00: I didn't need a development team to ship what's live today.
• 5:23
  SPEAKER_00: 36 months ago,
• 5:24
  SPEAKER_00: there was no version of a solo advisory practice that also builds
• 5:28
  SPEAKER_00: and ships its own software on its own timeline without a product team or
• 5:32
  SPEAKER_00: a funding round to get there.
• 5:34
  SPEAKER_00: Agentic AI didn't just make the old way of doing this faster or cheaper.
• 5:38
  SPEAKER_00: It made a way of doing this that simply didn't exist before.
• 5:42
  SPEAKER_00: What I hadn't fully appreciated until I actually started doing the work,
• 5:46
  SPEAKER_00: Agentic AI is both more powerful and more complicated to deploy well
• 5:51
  SPEAKER_00: than I expected going in.
• 5:54
  SPEAKER_00: Working directly with founders and operators to help them build, run,
• 5:56
  SPEAKER_00: and grow their businesses turned out to be even more rewarding and fun
• 6:00
  SPEAKER_00: than I anticipated.
• 6:01
  SPEAKER_00: And the thing I worried about most,
• 6:04
  SPEAKER_00: whether my identity would survive giving up the title,
• 6:07
  SPEAKER_00: turned out to be the thing I should have worried about the least.
• 6:11
  SPEAKER_00: Giving up the CEO title didn't shrink my ego, it set it free.
• 6:15
  SPEAKER_00: For 30 years,
• 6:16
  SPEAKER_00: a meaningful chunk of my identity was as CEO with the size and growth rate
• 6:21
  SPEAKER_00: of whatever company I was running attached to it like a subtitle.
• 6:25
  SPEAKER_00: Launching a small advisory practice instead of taking
• 6:28
  SPEAKER_00: on another large operating role should have dented that.
• 6:31
  SPEAKER_00: It didn't.
• 6:32
  SPEAKER_00: It brought me joy instead and it liberated the level of thinking and creativity
• 6:36
  SPEAKER_00: the operating roles never allowed for.
• 6:39
  SPEAKER_00: Now, let me be clear here.
• 6:40
  SPEAKER_00: As family, friends, and colleagues can attest, my ego did not go away.
• 6:46
  SPEAKER_00: I believe I'm in the top 1% of operators in this industry,
• 6:49
  SPEAKER_00: and I'm not gonna pretend otherwise to sound humble.
• 6:52
  SPEAKER_00: But once I took off the yoke of running a company,
• 6:55
  SPEAKER_00: I stopped seeing every business challenge or opportunity through that single filter.
• 7:00
  SPEAKER_00: It was like the difference between watching something in black and white and seeing it in color.
• 7:06
  SPEAKER_00: The calls that told me this wasn't just me,
• 7:08
  SPEAKER_00: As the advisory practice found its footing,
• 7:10
  SPEAKER_00: I started fielding calls from people who wanted to understand the model.
• 7:15
  SPEAKER_00: One was a veteran private equity investor.
• 7:17
  SPEAKER_00: He told me he'd been working on a plan to build his own advisory business.
• 7:20
  SPEAKER_00: He just hadn't found the right model yet.
• 7:22
  SPEAKER_00: He's now looking hard at solo scale.
• 7:25
  SPEAKER_00: I've heard versions of that since,
• 7:26
  SPEAKER_00: including from two veteran B2B CMOs,
• 7:29
  SPEAKER_00: one who moved into fractional advisory work five years ago and hasn't looked back,
• 7:33
  SPEAKER_00: and another who just came through a successful exit and is weighing
• 7:36
  SPEAKER_00: the same move out of a senior operating role and into something like this.
• 7:40
  SPEAKER_00: What surprised me wasn't the interest, it was the range.
• 7:44
  SPEAKER_00: Plenty of the people calling were mid-career,
• 7:46
  SPEAKER_00: some early career,
• 7:47
  SPEAKER_00: curious whether a model like this could let them apply what they already know,
• 7:51
  SPEAKER_00: build something of their own,
• 7:53
  SPEAKER_00: and get more flexibility and freedom out of the deal than
• 7:56
  SPEAKER_00: the traditional career ladder ever offered.
• 8:00
  SPEAKER_00: What I told them and what I'll tell you.
• 8:03
  SPEAKER_00: A long career in an industry I had real aptitude for that paid well
• 8:07
  SPEAKER_00: and build equity along the way gave me a cushion not everybody has the chance
• 8:11
  SPEAKER_00: to build, whatever stage of their career they're in.
• 8:14
  SPEAKER_00: I earned it and I don't take it for granted,
• 8:16
  SPEAKER_00: but the disruption underway isn't going to respect it as a prerequisite much longer.
• 8:22
  SPEAKER_00: The same agentic infrastructure let me build
• 8:24
  SPEAKER_00: a substantive multi-client advisory practice in 100 days.
• 8:28
  SPEAKER_00: Thirty-six months ago,
• 8:29
  SPEAKER_00: that would have cost a quarter million dollars and taken years to assemble.
• 8:33
  SPEAKER_00: It doesn't check anyone's resume before it goes to work.
• 8:36
  SPEAKER_00: That's the prediction underneath everything I've written about Soloscale.
• 8:40
  SPEAKER_00: We're at the beginning of the largest unlock of entrepreneurialism we've ever seen,
• 8:45
  SPEAKER_00: and it's going to change the course of careers long before it finishes reshaping
• 8:49
  SPEAKER_00: the enterprises those careers grew up inside.
• 8:54
  SPEAKER_00: What built my career hasn't changed.
• 8:55
  SPEAKER_00: It was aptitude environment and the thing I couldn't stop paying attention
• 8:59
  SPEAKER_00: to applied one decision at a time.
• 9:01
  SPEAKER_00: What's different is the environment itself.
• 9:04
  SPEAKER_00: Disrupted enough that it's now opening that same formula to more people
• 9:08
  SPEAKER_00: at more stages than it ever has before.
• 9:11
  SPEAKER_00: 35 years taught me to treat disruption as the opening, not the threat.
• 9:16
  SPEAKER_00: That's the bet I'd make on your career too.
• 9:21
  SPEAKER_00: Hey, that's it for the episode.
• 9:22
  SPEAKER_00: If you found this useful, please do one thing.
• 9:25
  SPEAKER_00: Follow the Uphoff on Media podcast on Apple or Spotify and leave a rating.
• 9:29
  SPEAKER_00: It's the single best way to help another operator find this.
• 9:33
  SPEAKER_00: I'm Tony Uphoff, back at it next week.