The 5 Things I’d Tell My 21 Year Old Entrepreneurial Self

12 years ago I set out on my first foray into the world of entrepreneurship. The company was called (we later changed the name to the equally obtuse and while it wasn’t a huge success by dot com era standards we did sell it for a tidy profit. But looking back I’m shocked at how little I knew about entrepreneurship.

As I’m sure any entrepreneur would love to do, I’d give anything to step back in time 12 years and have a chat with my 21 year old self. And while I can’t do that I do love to share lessons with as many young entrepreneurs as I can. I’ve spoken a bunch at colleges and other organizations for young entrepreneurs. I love passing along lessons while realizing that my experience is far from complete and I have many lessons yet to learn. Still, here are 5 things I’d tell myself if I could step back to 1997 and take myself out for coffee (yes, I know that sounds strange…)

#1 – Take as much risk as you can as early in life as you can. My choice at the time was to either be an investment banker or start a company with some friends. Starting a company sounded way riskier. Which is the main reason why I think I took it. Yogi Berra may have said when you come to a fork in the road take it but I’d merely add when you come to a fork in the road take the riskier path.

I’m not talking stupid risks. But smart, calculated ones. Look, at some point in your life you’ll have kids and a mortgage and a spouse who might not be super understanding of your crazy business ideas. But when you’re young you usually don’t have any of those things. Which means you can swing for the fences. Please do so. I promise you won’t regret it.

#2 – Nail the fundamentals. There are things that you know you’ll likely be doing for the rest of your life. Reading, speaking, typing, etc. Get really good at those things when you are young. When you’re young you typically have a lot more time on your hands. My gosh, I think about all the thousands of hours I wasted when I was at college…

Take some of that time and use it to build skills that will make you more effective and productive the rest of your life. Learn to type faster (David Allen impressed upon me that this will save you thousands of hours during your lifetime). Practice various speed reading techniques (I’ll blog on that soon). Hone your speaking skills by doing something like Toastmasters. Later in life when you’re a busy executive and balancing running a company and raising a family you’ll have a lot less time to devote to this stuff. So nail these things when you’re young and you’ll benefit for your entire lifetime.

#3 – Surround yourself with people who expect you to succeed in a big way. Two quotes have had a tremendous influence on me in this area of my life:

“You are the average of the five people you spend the most time with.” -Jim Rohn

“The quality of your life is a direct reflection of the expectations of your peer group” -Tony Robbins

Simply put, if you want to succeed surround yourself with people who (a) are succeeding and (b) expect you to do likewise. That simple piece of advice will do more to put you on the path to success than anything else I can think of.

I’m lucky. I gained this awareness around the age of 27 or so. Some people don’t gain it until much later in life. Some people never do. If you can realize that at 21 you’ll be way, way ahead of the game. I think whether this means peers, mentors, etc. is less important. What’s most important is that the people you are around expect you to do big things with your life. That will serve like a tractor beam that literally pulls you towards some major accomplishments.

#4 – Follow your bliss. This phrase originates (I believe) with Joseph Campbell. It basically means do something your passionate about. OK, you’ve heard that advice a million times. But I think the turning point for me was when I was reading Keith Ferrazzi’s excellent book Never Eat Alone. In it, he talks about the concept of the “blue flame” which he defines as “a convergence of mission and passion founded on a realistic self-assessment of your abilities.” Then he goes on to describe Joseph Campbell’s blue flame.

After graduation, (Campbell) moved into a cabin in Woodstock, New York, where he did nothing but read from nine in the morning until six or seven each night for five years.

I’m not suggesting that you hole up in a cabin and read for five years but what I will suggest is that you should be able to, in the words of Steve Jobs, wake up and say to yourself if I was going to do what I’m about to do today for the rest of my life I would be insanely happy. Or, to put it in Campbell’s words:

“If you follow your bliss, you put yourself on a kind of track that has been there all the while, waiting for you, and the life that you ought to be living is the one you are living.”

#5 – Give the big middle finger to the “good or bad opinion of others“. When you’re 21 people are going to tell you you should “build your resume”, “get a full year of experience with a big company” or (my personal favorite) “be a doctor or a lawyer” (apologies to all my doctor and lawyer friends…God bless you and the world most definitely needs you!). These people (often your family and closest friends) have good intentions. They want what they think is best for you. But while their advice often comes from a pure place it also is very often misguided.

The people who truly change the world often don’t care too much what people think of them. They may have an inner circle who they go to for advice but they are not about to let the opinions of most people sway them from their mission. This removal of the baggage that comes along with trying to win the approval of others frees up a tremendous amount of time and energy to focus in the direction of being who you truly are, not who someone else wants you to be. Because let’s face it, if you’re going into law/medicine/big corporate life/etc because you feel someone else wants you to do that, you’re not going to be happy. Nope, that’s not true. You’re going to be totally miserable. Across the board. No exceptions.

I was way too self-conscious at 21. Heck, I’m still way too self-conscious at 33. But I think the difference is that the older I get the more aware of that I am and the easier it is for me to let little bits of that go. Get started early on that in life and you won’t regret it. Plus, it makes life a whole heckuva lot more fun. By the way, if you want a cool exercise (one that I admittedly have yet to do) to help eradicate your self-consciousness try this one out from Tim Ferriss:

…simply lie down in the middle of a crowded public place. Lunchtime is ideal. It can be a well-trafficked sidewalk, the middle of a popular Starbucks, or a popular bar. There is no real technique involved. Just lie down and remain silent on the ground for about ten seconds, and then get up and continue on with whatever you were doing before.


I hope you all enjoyed this and I would love (love!) to hear what you would tell your 21, 31, 41, whatever year old self. Fire away in the comments!!