Jack of All Trades, Master of None: The Success Formula

6 min readJan 26, 2021

For as long as I can remember, I’ve always been a Jack of all trades, master of none.

Hobbies, skills, sports — I’ve taken a swing at almost everything that made sense. But, I never committed to becoming exceptional at any of them.

I tend to get bored quickly. I obsess over something for a few weeks, and then step off the gas. Sometimes never putting my foot back down. This irritated me when I was younger. I would often fail to match up to friends at their chosen skill or watch on as classmates achieved straight A’s.

But, things changed over the past few years.

I watched the same friends give up the skill they spent years working on or stick with it only to realize that it was never a viable long term strategy. Similarly, my classmates with the best grades ended up in the same positions as those who focused their attention elsewhere.

But, how does this make sense? You work hard and get rewarded for it, right?

The main issue, however, is our inability to make a smart decision when choosing what to work hard at. And since we are all working with incomplete information, it might be smart to hedge your bets.

I think everyone should focus on becoming a Jack of all trades, master of none (or, as I like to say, Jack of most trades, master of some).

Here are a few reasons why:

Technology has changed the world forever

Up until the 20th century, people usually chose one career for the entirety of their lives. Most men followed in their father’s footsteps (who did the same a generation earlier), and women usually stayed at home. Glimpses of this exist in common last names such as Miller, Smith, Potter, Mason, Taylor, Baker, Fisher, and Cook. All taken on by those in each profession.

At that time, specialization made sense. People rarely moved, industries developed slowly, and competition was low.

But, the world is a different place now.

According to a study of Baby Boomers by the Bureau of Labor Statistics, on average, men held 12.5 jobs, and women held 12.1 jobs during their careers. That’s a good number, and it’s a solid bet that it’ll be higher for millennials and gen z’ers.

A big driving force behind these numbers is technology. Many jobs, companies, and industries are becoming obsolete, with the threat of higher efficiency and automation impacting nearly every worker.

Now, that’s not to say that the sky is falling and robots are going to take over. I’m a firm believer that more jobs will be created than lost, but, no one knows what the world will look like in 20 years. And if you’re thinking you’re fine because you work in an emerging field, you might be, but you’re still playing a risky game.

You’re only an expert for as long as the market says so

There are few instances where aiming for the 99th percentile may seem like it makes sense.

One of the most obvious is professional sports. To make it to the big leagues in sports such as football, basketball, soccer, baseball, and hockey, you have to truly be the best of the best. Perhaps even in the 99.9th percentile.

Millions of people worldwide play these sports, but it is only a very select few that actually make it. Sometimes it’s due to luck and being in the right place at the right time. But, usually, it’s because you are damn good.

Unlike other professions, if you’re a top player in a popular sport, you’re paid an obscene amount of money. For example, in 2020, Patrick Mahomes, QB for the Kansas City Chiefs, topped the NFL’s highest-paid athletes by raking in $45 million for the season. In circumstances like these, perhaps it makes sense to become a specialist.

But, players like Mahomes are the exception, not the rule. The NFL player’s association found that the average career for an NFL player lasts only 3.3 years. Meanwhile, after retirement, 78% of players are penniless within 3 years, and 15.7% file for bankruptcy within 12 years.

The problem isn’t the retirement. The issue is that most of these players have few marketable skills to fall back on. They bet everything on football, won big and then lost everything.

It’s not all about protecting downsides

Being a Jack of all trades isn’t just a back-up plan. It provides an opportunity to become un-unemployable, gain freedom, and achieve true long term success that outweighs almost anything that could be gained by putting in your 10,000 hours.

From a career perspective, learning many skills is one of the highest leverage activities that you can do. It allows you to excel in all aspects of a role, and even do more than is expected. This is probably the fastest way to get promoted and climb the corporate ladder.

Additionally, most modern-day CEOs and entrepreneurs are Jacks of all trades. They have the skillset and experience needed to make decisions for a company as a cohesive group and delegate to specialists when needed. Consider Elon Musk for example. He isn’t anywhere near being the top engineer, physicist, marketer, or salesperson at Tesla. His value, however, is significantly higher than any of these. He knows enough about each to see the bigger picture, and how they all fit together. Without him, Tesla wouldn’t be Tesla.

Having a broad skillset also grants you significant freedom. It means that you are no longer bound to a job, field, or geographical location. You are free to pursue the things you enjoy, and avoid the things you hate. If this isn’t one of the main reasons why people become unhappy, I don’t know what is.

How do I become a Jack of all trades?

The simplest way is to try a bunch of things, and pursue the ones that you enjoy and present a viable commercial opportunity. I think that you should be free to sample an unlimited number of skills but pick 3–5 to focus on. These will make up your personal skillset, your brand and your personal monopoly. They are what make you, you.

In his book, How to Fail at Almost Everything and Still Win Big, Scott Adams describes what has now been coined as skill stacking. His theory is that for every skill you learn, it doubles your chances of finding success.

This is because similar skills complement each other and add a deeper layer to your work. Whereas, pairing skills that are a rare combination separates you from the crowd by offering a unique perspective.

For example, by combining a master’s degree in economics and experience running your own business, you gain an understanding that most people lack. How many economists know how to create, market, and sell something? And how many entrepreneurs understand game theory and international relations?

On the other hand, imagine someone pairing a degree in business with a degree in cinematography. This is a rare combination that grants you the ability to see the story behind a business, and the data behind art.

This is what I like to call the Success Formula (Skill + Skill = Success).

“Jack of all trades, master of none, but oftentimes better than a master of one.”

Being a Jack of all trades isn’t perfect for everyone. But, it is the best option for most people, especially if you’re young and ambitious.

Simply focus on developing 3–5 marketable skills, some that complement each other, and some that don’t. You’ll find yourself in high demand, immune to industry changes, and an all-around interesting person.

You’ll become a Jack of all trades, master of none.