How to Take That Big F*cking Career Risk (Without the Consequences)

image You really gonna let Swayze and Keanu down by not taking risks? Didn’t think so.

I debated putting the asterisk there. I went with it for my 11 year old readers, ya know? Out of respect.

Regardless, I’m adamant about taking risks, and I get really sad when I think about people with great ideas and potential who stagnate way before the window slides shut. Yes, people, it does close (or at least, it gets much harder to pry open). That thought alone should light a serious, smoldering fire under your ass.

Think about it. In your 20’s, or at least before you (maybe) get married and have kids, you can afford to take a huge hit. Your bank account can hit zero, and you can still bounce back.  You can take a year off and backpack, learn some new skills on the weekend at a local university, or just simply, dedicate yourself to enjoying life a bit more, with whatever that may entail.  You’ve got less strings attached.  Freedom, essentially.

The New York Times Style Magazine had a great article entitled, Kids These DaysIt highlighted a few uber accomplished 20-somethings who are making an impact, one way or another.  Chris Hughes (Facebook cofounder and New Republic Chief Editor), Helen Oyeyemi (young novelist), Alexander Wang (renowned fashion designer), Ezra Klein (blogger), Samantha Shannon (fantasy writer), and the unnecessarily wealthy founders of my favorite addiction, Instagram.


Instagram founders with Avicii in Vegas the day after they sold their baby

The article starts out with a clear case on the unique potential that we hold as we begin our careers, and look to find our path:

“So what is it about that youthful decade after those awkward teenage years that inspires such shoot-for-the-moon success? Does age really have something to do with it?

It does. And that leaves the rest of us — even those of us just a little older — at a bit of a disadvantage.

The conventional wisdom is that young people bring fresh eyes and a new perspective to confronting problems and challenges that others have given up on. Michael Moritz of Sequoia Capital, a venture capitalist who backed Google, Yahoo and YouTube, once described the phenomenon of 20-something entrepreneurs as a generation of people “who see no boundaries, see no limits, see no obstacle that they can’t hurdle — it is the most stimulating environment that you can ever be in.” Vinod Khosla, another venture capitalist, goes further. “People under 35 are the people who make change happen,” he said at an international conference. “People over 45 basically die in terms of new ideas.”

So, you’re scared of taking risks? Your job is too stable. Life is good. Brunches.  But, something’s missing. You know you have creative bones in your body that you haven’t stretched since preschool.  So, how do we take risks…without really taking risks?  …First, we need to set goals.  Do you want to learn photoshop? Illustrator? Programming? Painting?  Anything.  That’s it, just express what you want to do and then all you have to do is ONE THING in order to begin dipping your toes into new waters:

1st: Dedicate 1 weekend (JUST 1), to researching and beginning to learn the foundations of whatever it is you want to do. Straight up, you can figure out whether or not you truly want to go in one direction, or at least begin to invest time in learning a new skill with ONLY two full days of work and research. (aaaand we’ll throw in a BRAND NEW CAR)  Would you do that knowing it could positively change the course of your life? What are you truly missing out on?

Go ahead, schedule it in your calendar now.  Tell your friends and family that you’re going to be a hermit for two whole days.  It’s not that bad.

There are some insanely cheap and free resources out there today to help ignite a new passion, or brush up on new skills.

Here are a couple of my favorites: – Classes taught by experienced humans (some free, some very cheap). It’s got everything from How To Program iPhone Apps in Three Weeks to How To Write (Smart) About Pop Culture

Khan Academy - “A Free World Class Education for Anyone, Anywhere.” Get better at math, learn computer science. This site has it all, for free. Absolutely amazing.

Open Culture - It’s basically an aggregator site of all the free learning resources on the web – if you’ve ever wanted to find all of the available Harvard lectures on the internet, this is your place.

The world of learning has never been more open and accessible. Those who are taking advantage of these resources allow a certain nimbleness and adaptability into their lives. They are the ones who will live a life of color and variety.

We’re not all going to be millionaires and billionaires. But, when you’re doing things that you love doing, even if they are on the side while you keep your day job, you will feel more motivated, and complete.  “Busy hands are happy hands,” as the cliche goes. And when those hands are being constantly massaged by the fruits of your creative labor, them handz will get REAL happy. Make a small investment in yourself, or forever ride the track to becoming a boring old fart full of gassy regrets.

If you have any questions about how I’ve structured my time, and made use of a full weekend of learning, feel free to e-mail me at


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