#95 Your Messiest Career Decision Was Your Best

Why the iGaming executives who wore every hat are now the most valuable people in the room

I think this is something a lot of people in iGaming can relate to, can you? You’re in a meeting, maybe it’s a hiring panel, maybe it’s a pitch and someone squints at your career history and says, “So you’ve done a bit of everything, haven’t you?”

It’s not a compliment. It’s a polite way of saying: you’re scattered. No clear lane. No obvious specialism. You started in affiliates, ended up in product, then in brand marketing, and now you have a job title that doesn’t quite explain what you actually do.

The subtext is clear. They’re looking for the specialist who went deep and stayed there.

Here’s the thing. They’re wrong. And the data is starting to prove it.

What David Epstein figured out

In his book Range, David Epstein dismantled one of modern business’s most sacred assumptions: that specialisation is the path to greatness. The 10,000 hours rule. The early start. The single lane. Master one thing, and master it young.

Epstein’s research showed the opposite. In complex, unpredictable environments, the kind where the rules change, markets shift, and no two problems look the same, the people who win in the long run are the ones who sampled widely. Who didn’t commit too early. Who collected experiences across disciplines that specialists never knew were even connected.

He called it “match quality.” The ongoing process of finding where your skills best meet the problem in front of you. It requires breadth. Not the absence of depth, but the addition of range.

Sound like anyone you know in iGaming?

The iGaming executive in the wild

Think about the senior people you respect most in this industry. I’d bet most of them don’t have a tidy career story. They started in one place and wandered somewhere else. They worked in one vertical, and got pulled to another. They built something in one market and got asked to do it again in three more. They have had titles that never quite captured what they actually did.

That’s not a lack of focus. That’s range.

And in iGaming, it’s one of the most valuable things you can have, because this industry does not reward tunnel vision. Regulation changes overnight and you need to understand compliance, commercial reality, and player behaviour all at once. A new market opens and you need to read the culture, restructure the product, and rebuild the acquisition funnel simultaneously.

No narrow specialist navigates that alone. The executive who has lived in multiple disciplines can.

Silicon Valley just figured it out

The most competitive talent market in the world has quietly changed what it’s looking for.

AI mentions in job postings have exploded by over 120% year-over-year. But the twist is that most of the most in-demand skills in those same postings aren’t purely technical ones. They’re design thinking, systems judgment, ethical reasoning, and cross-functional adaptability. Human skills that work alongside technical depth. The so-called T-shaped professional: genuine expertise in one area, paired with the range and adaptability to operate across an entire business.

Shopify’s CEO banned new hires last year until managers could prove the work couldn’t be automated first. PwC found that skills in AI-exposed roles are now changing 66% faster than any other category. The old model of hiring a specialist, give them a lane, and leave them alone is breaking down. Because AI is handling the lane-specific work faster and cheaper than any individual ever could.

What AI cannot do is think across a whole system. It cannot hold the commercial tension of a new market entry, the regulatory sensitivity of player protection, and the product implications of a new mechanic all at once, and make a judgment call. That’s what range builds, over years and across functions.

The person with the messy career has been training for this moment without knowing it.

What to do with it

Three things.

Stop apologising for your breadth. The next time someone raises an eyebrow at your CV, don’t shrink. Your cross-functional history is a leadership credential, not a confession. Call it what it is.

Find your anchor. Range without depth is just being good company at a conference dinner. Epstein is clear that the best generalists still carry genuine depth in at least one domain. Pick yours — whether it’s data, product, regulation, or commercial strategy — and go deep there. That’s what turns breadth into a T-shape, and a T-shape into a genuine edge.

Use AI to extend your reach. This is the generalist’s great unlocking. AI lets the T-shaped executive move faster and cover more ground than entire specialist teams once could. The person who combines cross-functional judgment, domain expertise, and AI fluency is not just valuable, they’re very hard to replace.

The uncomfortable truth

The executive hired for one specific skill set, in a world being rapidly automated, is quietly at risk. The person who can think across the whole board, connect two ideas no one else saw, and adapt when the market moves underneath them?

That person is harder to automate than any piece of software.

You spent years being told your career lacked focus.

Turns out, it had exactly the right kind.

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