6 Things People With Interesting Careers Have in Common

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A good amount of my work at The Unmistakable Creative is centered around finding not just successful people, but people with interesting careers who stand out in an incredibly distinctive way, and highlighting their differences. Earlier this week, in an interview on the Creative Warrior podcast, the host asked me what all of these people had in common, and the list below is what emerged.

1. Their Path is Never Linear

I’ve said before that straight and narrow paths rarely lead to interesting destinations and that the greatest work of your life will be done with a compass, not a map. People with interesting careers never have a linear path.

Jerry Colonna spent time working as a journalist and a professor before he ended up joining forces with Fred Wilson as a venture capitalist at Flatiron partners. Today he heads up Reboot.IO, where he coaches CEO’s and has been referred to as the CEO whisperer. His path was far from linear.,

elle luna didn’t get into law school, applied to art school, worked at multiple startups and found herself at the crossroads of should and must, which eventually resulted in her becoming a full-time artist.

In my own life, author, speaker, and podcast host were never part of any grand plan. In fact, when people used to ask me what I’d do after business school I would tell them “as long as it has nothing to do with the internet, that’s all that matters.” Fate it seems has a sense of humor.

But early in life, we are taught a linear path is the key to success, and all the evidence of outliers seems to point to the contrary.

2. They’ve all Gone Through Something Difficult

In the hero’s journey, the crucible is the right of passage, the thing that ultimately turns a hero into the person he is destined to become. Nearly every single person I’ve interviewed has had moments like these.

  • Joe Loya spent 7 years in prison after robbing more than 30 banks, before he became an author and a talking head on the criminal justice system.
  • Janelle Hanchett found herself in a hospital with no more moves left because of her alcoholism before she became known as a writer with an unmistakable voice and popular blog.

The worst hands that we are dealt, the most difficult things that we experience, and the darkest moments of our lives are usually what stand between us and our destiny. The lessons from such a chapter can be only be imparted by experiencing one.

3.They Turn Disadvantages into Disproportionate Advantages

Often what on the surface appears to be a disadvantage provides people with a disproportionate advantage. Many of the most interesting and successful people I’ve interviewed have mentioned their dyslexia in our conversations (Todd Herman, Phillip Mckernan, and Michael Port to name a few). Because of their challenges with reading, all three of them compensated by developing a disproportionate advantage in their ability to deal with people.

Being fired from most of the real jobs I’ve been at forced me to give people a reason to find me interesting. It also gave me a reason to persist throughout my 7-year journey from blog to book deal. If I’d had a job waiting for me upon graduation from business school, I would have never done any of what I’ve done in the last 7 years. l. My biggest disadvantage, a resume of failures, become a disproportionate advantage.

Sometimes piss poor results at something are actually better than average results because they light a fire under your ass to go out and change something.

When we’re forced to make our disadvantages work for us, they can become our greatest strengths.

4.They Have Bold and Compelling Points of View

Look at any wildly successful media personality, author, musician, or artist and you’ll see that they have people who hate them with a passion and people who think the world of them.

Glenn Beck has people who hate his guts and the people who work for him say he’s the most misunderstood man in the world. And some of his good friends are people that you probably have a lot of respect for. Whether you love him or hate him, it’s clear that he has a bold point of view.

A strong opinion will piss some people off, but it’s also the very thing that will cause people to be magnetically drawn to you.

5. Their Behavior isn’t Dictated by Social Programming

Everything is programming: everything you’re told by a parent, teacher, coach, boss or mentor, every book you read, and every piece of media you consume. But there’s a point somewhere in our lives when the social programing becomes like water to a fish. We’re unaware of it, yet it dictates many of our choices.

When I spoke with my friend Justine Musk about the psychology of visionaries she said the following about Elon Musk:

He has a way of taking the world in his head and imposing it on the world around him until it looks like the world in his head.

People who have interesting careers never stop questioning the programming. Because of that, their behavior isn’t dictated by it and they see the world as malleable, something that can shaped and be molded to their own liking… a blank canvas.

6. They are Lifelong Learners

Many of the people I’ve interviewed have enough money that they don’t have to work again. Yet they are still building companies and starting new projects. Why? Because humans are meant to grow and evolve. Every pinnacle is a plateau, the start of another journey, and a new chapter.

For the most part, we spend our lives completing things.

We complete our years of schooling. 
We complete courses, certifications, etc

It’s not uncommon for me to run into people who have surfed for 40+ years. Most people don’t have careers that long. Surfers commit to their journey for a lifetime.

Commitment is different than completion. When you’re committed you’re not ever finished. You’re a lifelong learner, and a perpetual student.

One of the things Chase Jarvis said to me in an interview when I asked him about the outcomes they’ve seen in people’s lives because of Creative Live was they aren’t focused on completion. But most learning in our formal education system focuses on completion.

I completed a degree in Environmental Economics at Berkeley. And I can’t tell you a damn thing about it. You can complete something without being committed to it, and gain absolutely nothing of value from it.

Commitment leads to mastery. 
Completion leads to crossing things off lists.

It’s a deceptively simple choice, but the implications of which choice you make are profound.

Interesting careers are rarely the result of simply choosing from the options that are put in front of you (i.e job listings/recommendations from other people). They are the result of detours disguised as debacles, wrong turns, highs, lows, and false horizons.

Before You Go…

If doing the best work of your life is important to you, you’ll love my free guide: “Optimizing Productivity & Creativity.

The tactics I’ve packed into this guide allowed me to write over 1 million words in the last 2 years. What could it do for your life’s work? Don’t miss it.


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