From Rock Star to Tech Innovator: Breaking Free When Your Career Gets Stuck
Watch the full interview: Mastering Career Evolution: Professional Musician to IPO with Bec McIntosh on the Career Jam YouTube channel
How a Liverpool kid who questioned everything became a polymath with 13 patents—and what that means for your AI-anxious career
Feeling stuck? You're not alone. That nagging sense that AI is coming for your job, that your hard-earned expertise might be obsolete—it's very a real fear among mid-career professionals right now and this article has your executable action plan.
Finbar O'Hanlon's journey from professional musician to serial tech entrepreneur who's launched IPO companies and raised $40 million in startup capital offers a masterclass in career reinvention. And his insights on navigating the AI revolution? They might just change how you see your future and where your career focus needs to be now.
The Uncomfortable Truth About Mastery
Here's the paradox: The expertise you've spent years building might be the very thing holding you back.
"When we get good at something, we start to relax, we start to run it out of mastery," O'Hanlon explains. "Our brand and our identity gets wrapped into that Mastery. So when we take on something new, we're trying to bring that across and that's fear."
Sound familiar? You've climbed the ladder in your field. You're the go-to expert. But now the landscape is shifting, and that expertise feels more like an anchor than a rocket ship.
O'Hanlon's solution is radical: treat your mastery like Lego blocks.
"Now I've got my mastery, now I'm going to treat it as Lego because I'm going to break all my Mastery tools and put them in the shed cause I could pull them on at any time. Now how about I reorder them in new ways and new sequences to see what happens?"
When Did You Stop Experiencing New Things?
O'Hanlon has a diagnostic question that cuts deep: "What in the last week have you done that you've never done in your life before?"
If you're drawing a blank, try the last month. Still nothing? The last year?
"Take yourself back to when you were 17—how often do you think you were experiencing something new?" he challenges. "Quite a bit, okay. So why has that stopped?"
The answer usually boils down to comfort, packed schedule, exhaustion, or fear. But here's the kicker: "Are you in control of your life or is life in control of you?"
That "stuck" feeling isn't about lacking opportunity. It's about unconsciously choosing stasis over growth.
The Adult Condition of Being Stuck
Kids don't get stuck. They're perpetually curious, constantly learning, always in motion. Somewhere in adulthood, we trade exploration for expertise, curiosity for certainty.
"Our subconscious is our systems, our plumbing, our heartbeat, our lungs—all the things that are running our physical being, but it's also the autonomous behaviour," O'Hanlon says. Your career can be on autopilot for years.
His prescription is simple: Build a practice of curiosity.
"When you're driving in the road, question why was that signpost there not over there? You can ask yourself questions to build a practice of curiosity. Programming your mind to be curious and asking ‘stupid’ questions—you don't have to ask them, no one has to hear you, just in your own mind—it starts to build that curious mindset."
The Information Diet You Desperately Need
Feeling overwhelmed by the constant firehose of information? O'Hanlon has a filtering system he calls the "binary method."
"Everything is a zero or a one. The information I can actually action is a one, and a zero is information I can't affect the outcome of."
Start categorising the incoming flood: LinkedIn posts, news alerts, Slack messages, emails. Can you actually do anything about this information? If not, it's a zero.
"Just being aware of information and categorising it will start—I've worked with hundreds of people on this—you start to subconsciously start eliminating information 'that's not serving you.' Without actually actioning anything, you actually start to naturally do this."
The result? You suddenly have more time than you thought. Time you can redirect toward that curiosity practice.
AI: Your Career's Biggest Threat or Greatest Amplifier?
Now for the elephant in the room that's got everyone anxious: artificial intelligence.
O'Hanlon's take might surprise you: "AI is going to be the most amazing tool to amplify humanity than we've ever seen in the past."
But—and this is crucial—only if you upgrade your operating system.
"When we have a new chip in PlayStation 5 over the PlayStation 4, we build a new operating system to get the most out of that chip. AI—we're the operating system. We need to upgrade our operating system to get the best out of it."
The fear driving most mid-career professionals? It's the wrong question entirely.
"If you want to compete against something that works 24/7, that's trained on trillions of data sets, that can recall them in a second, that can cross-pollinate and analyse the data in ways that a human could never do—" he pauses. "It's a zero-sum game."
Instead, reframe: "How might AI help me be the best version of myself where I still get paid the same amount of money?"
The Skill You Already Have That AI Can't Touch
Here's the counterintuitive truth that should reassure every anxious professional: "AI is the first technology in the history of humankind that requires you to know nothing about technology."
An English professor will get better results from AI than a software developer, O'Hanlon argues, because it processes natural language.
"You don't need to know everything about the electrical system of a car. Do you just need to get in and drive it? You can drive AI."
What AI can't replicate? The human elements you've been devaluing: emotional intelligence, gut feelings, contextual understanding, collaborative nuance, your professional network but on years of developing trust.
"There's a lot of things that humans can do in understanding, making decisions that are based on the hidden language in language—the emotional response. AI can do some of that but not like a human can."
Your Multidisciplinary Advantage
O'Hanlon's secret weapon wasn't being the best musician or the best coder. It was connecting the unconnected.
"I love horse riding, I love everything about horses, I'm an accountant—they don't fit together. Go to an AI engine and go 'how can I build a business which takes my two skills, horse riding and accounting? Give me 10 options for a future where I'm super valuable.' You can do that right now on ChatGPT, on Claude, on any of these engines."
This is where your seemingly random career experiences become assets. That stint in retail before you moved into finance? The creative writing degree before your MBA? The volunteer work that seemed unrelated to your day job?
"When you see someone who doesn't connect with you, who you go 'oh, he's not in my tribe or she's not in my tribe, that person is a bit of a weirdo'—I gravitate towards those people because that's where the biggest innovation comes from."
Start Small, Start Now
The paralysis comes from overthinking. O'Hanlon's career didn't leap from musician to tech CEO overnight. It was curiosity compounded daily.
"We think so much about doing the thing that if we just did it, it would be so much easier than thinking about doing it."
Your action plan:
This week: Do one thing you've never done before. It can be as small as using a new software feature or reading an article in a field completely outside your expertise.
Practice the binary method: For three days, mentally categorise incoming information as 0 (can't action) or 1 (can action). Notice what happens to your sense of time and control.
Ask your ‘stupid’ questions: Even if only in your head. Why does your company do things this way? What assumptions are you making? What would happen if you connected two completely different domains?
Experiment with AI: Open ChatGPT or Claude. Ask it to help you connect your disparate skills into future career possibilities. Don't judge the output—just explore.
The Bottom Line
O'Hanlon's parting wisdom keeps it simple: "All you can do is just try it. What have you got to lose? It might seem scary, but it's only scary because you think it's scary. It's just going against your programming, that's all."
That stuck feeling? It's not permanent. It's not a verdict on your worth or your future. It's feedback that your operating system needs an upgrade.
The question isn't whether AI will change your career. It will. The question is whether you'll be a passive recipient of that change or an active architect of what comes next.
Your mastery isn't obsolete. It's the foundation. But foundations are meant to be built upon, not lived in forever.
