The Art of Being a Jack of All Trades

Why entrepreneurs need to master multiple skills, manage their mindset, and ditch the guru hype.

Photo by: Pixabay

I’ve been in business for over 20 years. Studied it, too—first at university, then at business school in Europe, where I earned my master’s degree. I was doing everything “by the book,” gearing up for that pristine, polished corporate career. But you know what I learned? The world doesn’t follow the textbook. Even if it pretends to.

I figured out pretty quickly that the corporate ladder wasn’t for me. Why? Because I did my MBA too early. I was 25, freshly armed with an expensive degree and a head full of strategy—and that terrified people! A lesson I’ll never forget came from the HR Director of one of the country’s biggest companies: “You’re aiming for positions that managers won’t give you. It’s a threat to them—and most don’t have your level of preparation.” And no, starting from the bottom wasn’t an option either. “Overqualified” rings all sorts of warning bells in the hiring world.

Turns out, the ideal time for an MBA is while you’re already moving up the corporate ladder—preferably on the company’s dime. But the real takeaway? Education is often just theoretical. Even in business school, you’re studying “real-world” cases that happened 10 years ago which is just another form of theory. Trust me, I have been teaching at three different Business Schools through my career. Reality doesn’t play by Harvard’s rules.

At some point (ideally sooner than later), you’ve got to stop searching for advice, certifications, tutorials, or the perfect moment—and just roll up your sleeves and start the darn thing. And that is exactly the reason why I have been contacted by Business Schools. They want someone with the right degrees but teaching out of experience. The thing is that nothing provides more experience than Entrepreneurship and having to wear all sort of hats. becoming a Jack of all trades.

The thing is, that education and theory is just one part of the equation in which many people is still covering with as a blanket, but listen, If you don’t have hands own experience you don’t know what you are doing. Plain and simple.

So, ask yourself the question—do I have what it takes?

It’s a valid one. And honestly, not everyone does. The strength, the attitude, the tenacity, the mental fortitude… and let’s not forget the ability to pivot like a caffeinated ninja. Being a bootstrapper isn’t for the faint of heart. That’s why not everyone is out there building unicorns.

But here’s the good news: there are a few hacks that can help more risk-takers actually take the plunge.

First off, starting a business can feel massive—like standing at the base of Everest in flip-flops. The trick? Break it down. Chunk tasks into bite-sized action steps. That way, you’re making visible progress every day and avoiding that looming sense of “what am I even doing with my life?” Visual momentum reduces anxiety, and anxiety, by the way, is often a self-inflicted beast. It’s born from catastrophizing, overgeneralization, filtering, anticipation, and a good ol’ dose of worry.

So yes, becoming a Jack of all trades means learning how to hack yourself too.

You acknowledge the risk. You know that bad outcomes are possible—and probable at some point. But you also understand that failure is the best professor you’ll ever have. The key is showing up, taking the hit, learning the lesson, and coming back smarter.

If you are following until now, then you have what it takes to apply to be a Jack of All Trades. 

Let’s assume for a second that you get it—you know you’ll need to learn a whole bunch of things. It doesn’t matter if you went to college for arts, literature, medicine, or interpretive dance. I know PhDs in AI who don’t know the first thing about business, economics, or even how to manage their personal finances. Forget about marketing—they think it’s some sort of dark art.

Here’s the reality: if you’re building a venture, you need to understand how every area works. Every. Single. One. You don’t have to be a world-class expert in each, but you do need a working knowledge of operations, optimization, and the importance of iteration. You’ll have to become fluent in progress.

And yes—your life will become one long masterclass in lifelong learning. Especially today, with tech moving at warp speed, resisting new tools or platforms won’t stop the world from adopting them. It just puts a target on your back and a “Do Not Disturb—Outdated” sign on your forehead.

What I’m trying to say is: you’ll have to do stuff you don’t enjoy. Like accounting. (Sorry, accountants.) But here’s the trick—you’ve got to get good at switching hats.

Once you’re done with a task, take a breath, change perspectives, and ask: What’s best for the goal right now? Whether it’s your company, your product, or your overall mission—your decisions should serve the bigger picture, not your personal preference.

Photo: Ketut Subiyanto

To wrap this up, let’s talk about balance. Yes, that elusive, underrated thing that actually keeps your brain functioning and your ideas fresh. You don’t need to work 14-hour days—or even 10, to be honest. What you do need is to hack your most productive hours and use them wisely. That’s when you do your thing. No distractions. No multitasking madness. Just focused, deep work.

Most people are terrible at managing time. They confuse busyness with productivity and wear their exhaustion like a badge of honor. But ask yourself: Who are you comparing yourself to? If it’s someone who needs 14 hours a day to complete a task you could do in five, you’re setting the bar way too low.

Balance, focus, and self-awareness—these are the real game-changers. Take walks. Lift weights. Laugh. Get bored on purpose. Some of your best ideas won’t show up while staring at a screen—they’ll hit you mid-shower or halfway through a playlist on your run.

And finally, be extremely mindful about who you’re taking advice from. We live in the golden era of snake oil salesmen—YouTube “gurus” reading ChatGPT scripts they don’t even understand, peddling recycled nonsense with a flashy thumbnail and a funnel behind it.

Skills matter. Experience matters. And in an over-informed world, discernment is your most powerful tool.

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