Pros and Cons of Being a Jack of All Trades

I was an executive at a publishing company until last September. 

Now, I'm nine months into a long-threatened sabbatical. Taking time off is a great way to reflect on where you've been and where you'd like to go. I'm not entirely sure about the latter point, but I have a clear picture about where I've been: lots of places.

I'm a "jack of all trades." 

Earlier in my career, people warned me not to describe myself that way. "Master of none" is the part that would stick out in employers' minds. Maybe it's true. I don't set out to master many things. My goal is more to become very good at as many things as I can. Almost everything is interesting to me, and if I get the bug to learn about something, I'll teach myself until it's no longer fun.

This is a choice and, like any other choice, it has consequences and benefits.

I'm going to jump right into the pitfalls in case you're a jack-of-all-trades who is just starting out. You should know what you're signing up for. Don't get me wrong: I don't regret my career choices and I'm not trying to dissuade you of yours. I'll touch on that later. But for now:

Some People May Find You Deathly Boring

I pride myself on being able to hold a conversation with just about anyone. For the most part, it works: Business, sports, politics, world affairs, health, science, pop culture and many hobbies are all within my comfort zone. But, that's not enough for some people.

There are conversations where I can feel the boredom oozing from others. These are people who value obsession as the ultimate form of mastery. That's not me. 

I'm passionate about many things (and about life in general), but it's unlikely that I'll be discussing achromatic doublets with a photographer or rhabdomyolysis with someone who keeps fit.

You Might Not Get Rich Quickly (Possibly, At All)

The people I know who are wealthy and self-made have something in common: focus. They're the young men and women who went to college for business and became investment bankers or studied medicine and became doctors. They do one thing and they do it well.

On the flip side, I know plenty of people who are smart and equally driven, but not nearly as financially successful. (I put myself in this group.) They've made pivots and taken career risks rather than climbing straight up the ladder.

Some of them are one break away from hitting it really big, but that break may never come. Only time will tell.

Luck May Lead You Astray

Beginner's luck is a form of bad luck. It teaches your brain that if you put a little effort in, you get a big result out. But, that's not how things actually work. Just because you're good at something and have an early success doesn't mean you'll have continued success or that something is actually worth pursuing in the first place. I've made this mistake often (and continue to do so).

Toes Will Get Stepped On (and Some People May Hate You)

You may have a hard time working with someone if you have a better grasp on his or her "thing." (There are many people who are employed to do something that they're not particularly good at.) If this person happens to be your boss or your boss' boss, get out. 

You don't want to be in a place where competence is considered a feather-ruffling activity.

You Might Suffer From Impostor Syndrome

Impostor syndrome is when you feel like you're a fraud even though you have a track record that proves otherwise. (I used to confuse this with the Capgras delusion, a disorder where people think their loved ones have been replaced with impostors.)

I don't think jacks-of-all-trades are any more or less susceptible to feeling like frauds, but the more things you're good at, the more chance you have to feel like an impostor (or to feel like you aren't good at anything). Always remember that luck is real, so count your blessings, learn from your failures and try not to get down on yourself too much.


OK. Let's move on to the good stuff now that we've gotten those unpleasant things out of the way. When you're a jack of all trades:

You Can Do Things Quickly and Cheaply

Those who are both creative and technical can do pretty much anything they want to.

Robert Rodriguez is an award-winning director who made his first movie, El Mariachi, for around $7,000. He wrote, produced, directed and edited the film. Plus, he operated the camera and did the sound work, music editing and special effects. 

Rodriguez took this same approach, albeit to a lesser degree, with blockbusters like Spy Kids and Sin City. All of these films earned multiples of what they cost to produce.

Creative freedom is a by-product of being able to do many things well.

A Hobby Can Lead to an Opportunity

Years ago, one of the hobbies listed on my LinkedIn profile was "reading financial statements and annual reports." (Yes, it was true.) A recruiter who happened across my profile noticed this and sent me for an interview. I got the job and, within two years, I had gone from an entry-level marketer at a women's fashion magazine to director of business intelligence at a top-10 financial media company. Not bad.

You Meet Cool People

I've had the pleasure to meet with TV personalities, artists, executives and even a U.N. peacekeeper from Sudan. My former boss (and ongoing friend) is an accounting major who can shred the guitar: He opened for Poison in the 1980s. 

Having a lot of interests is like a platonic form of speed dating.

Going With the Flow Comes Naturally

I graduated from film school with a ton of debt and no prospects for getting hired, so I took the first job that came my way (public relations). It was at a video game company and they made me a designer when they saw I had Photoshop skills. 

When a friend from school raised money to start a magazine, I left my design job to co-found it with him.

The magazine failed during the recession, so I became an online marketer (and so on).

You Get To Do Lots of Fun Stuff

Many of the coolest things that I've done haven't benefitted me financially and don't appear on my resume. If I ever created a CV that combined personal and professional accomplishments, here are some of the things it might contain:


In Conclusion

Focus, concentration and hard work are prerequisites of success, no matter if a person has one talent or many. Yet, success has many definitions.

I view success as a type of freedom: the ability to live life the way a person wishes to.

Focusing on financially-rewarding activities may seem like selling out, but I don't think it is. To do so can give you the freedom to focus on other passions throughout life. For example, Jeff Koons worked as a commodities broker before he became an artist.

I was lucky enough to find an in-demand career that celebrates a generalist. "Search engine optimization" is a rare field that demands collaboration among creative, technical and analytical people. It's a perfect crossroads for me.

Like the brilliant Yogi Berra once said, "When you come to the fork in the road, take it."


Did I miss something important? Tell me on Twitter or LinkedIn. Thanks for reading!