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 MCSETutor.com (we later changed the name to the equally obtuse 2000Tutor.com) 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…)

risk#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.

flyhigh#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.”

middefinger#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.

Fantastic.

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!!

24. April 2009 by Jon
Categories: Entrepreneurship, Inspiration | 240 comments

  • Brp127

    hoping that while you are there, they will teach you the difference between “then” and “than” and the difference between singular and plural verbs. Good luck!

  • @kiltedbroker

    Found this on Stumbleupon, thanks for the article, I am relatively new to blogs but I will subscribe to your RSS and look forward to reading more! Very informative!

  • Mehgan

    I am freshly 22 and struggling with the ideas and concepts that are being forcefed to me by my professors.  At a state school, ideas like this would be hushed away.  I feel very inspired by this article.  Although education is expensive, in the long run starting a business requires capital that must be earned through other jobs.  With the help of my degree, I can find employment that will help me attain my start- up business goals.  I am currently managing my own office for someone else's company wondering, “why the hell am I not doing this for myself!”  I have so many ideas that just needed a jump start and spark of epiphany! THANK YOU!

  • james

    ya im only 14 and i dropped out of middle school, started 4 companies of my own, and im now a multi-billionaire about to buy my first sports franchise

  • leshan

    I am an Account Manager at an IT firm selling fibre optics so far i don't regret what i have archived though am so worried about the future i am 20 turning 21 in two months time gone through college for two years i am adventurous and stubborn i have crazy ideas and i do crazy things that amaze people sometimes i hope to own a company already working on it. Thank you for the message to my 21 year old self hope my 45 year old self is appreciating the article

  • BE

    I'm a 21 year old in the business school at Clemson University.  For me, the hardest thing about following your dreams and doing the things that you love is the tension that other people give.  More than a few times, I have told my parents about ideas that I have, or an adventure that I want to go on, and all I get back is doubt.  While my parents are intelligent and want me to have a good life, they are not in my shoes.  The same thing goes for friends, professors, and acquaintances.

    If you have something that you want to pursue in life, do it.  I am learning to do this right now, but it is hard because I feel like the people that I need to have my back are not there.  Nevertheless, it is my life and I need to take the risks to experience life to the fullest.  Number 5 is absolutely crucial for me!  Don't let others dampen the fire inside!

  • Tina_a8

    im 21 and this post… well has ignited the fire of ambition in me, once again. Thanks Jon !

  • Trevor

    Great article. I love it. It's ideal for any budding entrepreneur. I just posted this to my son.

  • Sudhasubedi

    I appreciate it. I ll be 21 tomorrow. And this really gonna help me.. U rock :)

  • PhillyV

    I just turned 21 today and after reading this article I have come to the realization that I need to get on my own track to get my life moving in the right direction. This article I came across was a huge push in the right direction as I have been trying to pursue an entreprenuership since 18… just want to say thank you and any other advice you have please post.

  • Imani

    that was wonderful i gained a lot from this message im 21 now and im still trying to figure out where to start with the things that i want to do i know i have to take it one at a time i just dont want to be 30 still thinking of a master plan.. lol… i want to make something happen before im 25…. thanks for the tips

  • Huh09

    awesome!!! :) I'm 21 and i struggle most with the last point… i care oo much about other peoples opinions!  i leave conversations kicking myself for the stupid comments i say. 

  • Ah

    I am 21 i work with a big apparel company for a year but i been in the industry for 3  i have decided to follow my blitz.

  • Rcutej

    This post just made me realize that its high time i start taking risk..Im 21!!!!Thank You…..

  • http://viruscaptive.com/ eBay

    I can say. I stopped going to school, because it meets my “business” class, the need seems to have been. Instead, I took what I learned in accounting, and surrounded me in successful people. I have more of those people who have experienced the business world than I ever could learn from the school.

  • David

    I think you hit the nail on the head Jon. I am 63 years old and wish someone told me this when I was 21 years old because I believe that I would be a lot better off today. However, since it's better late than never, I have decided to start my own entrepreneurial journey and although I am being encouraged to find a job even one that pays minimum  wage, I am dead set on doing what I want at this point in my life.

    My children are all grown up and I am near retirement with nothing to look forward to from anyone but me. I do not want to be a burden to my children, so I am going after my dreams now.

    To all the young ones out there, don't wait until you are old, do it now, you will not regret it.

  • Spaceman

    More than ever, people need to hear this. Im 24 and its a shame to see people who are only a few years younger at me focus on some of the most insignificant parts of their lives and allow these to determine who they are. They need direction and they need to read articles like these! Thank you Jon, will share.

  • your number 1 fan

    Thank you, that was a really inspirational read for me. I will share it with all my friends!

  • Dlabadini

    im 21 and i need a job just got fired from Sales at Toyota i found alot of clients in a managers desk that no one knew where they were i told someone and they wanted to fire someone so they picked me. i didnt fight it cause i dont wanna be in an environment run like that. My mom has forced me to look online for careers and jobs for the past 4-5 weeks suggesting nothing but Machinist and Nurse…and i dont think i wanna do either. what is your company?

  • http://inspiringtravellers.com/ Andrea and John

    Love this! I think it's hard-wired into my brain to take risks. For years I felt bad/guilty for not taking the corporate road like many of my friends. Like there was something wrong with me. Now I realize it was the best thing I could have ever done for myself. Cheers for a great post! ~AS.

  • Ashwin

    Hi.., I really like and read the complete article .. its so meaningful , I really like it ..,   Thanks a lot !!!!!!!!!!   :D   Ashwin 

  • http://twitter.com/hannahlah Hannah Redmond

    Agreed. I am currently at the tail end of earning my MBA and it seems to
    be a shock to people when I don't want to go the corporate route. I Love
    entrepreneurship and innovating and inventing. The MBA has absolutely
    been useful to teach me how to pitch, create a business plan, and teach me the foundations, but overall I have learned more from the other entrepreneurs in the program who have given me support, expanded my network and even helped get me investors. Same with my professors. Having them as my advisors and investors is one of the greatest things I have gained in B-school. You absolutely learn just as much or more from the people sitting in class next to you.

  • 1990banks

    Pure Inspiration.
    Thank you.

  • Anonymous 31

    Stay true. Work hard. Try it.

  • http://www.crevo.co/ CREVO

    Amazing article… (Y)

  • sera

    thank you!!! i am 21 and i keep putting being entrepreneurial off! so thanks!

  • http://twitter.com/RCONNOR111 ROBERT CONNOR III

    Good story on your 12 yrs lessons-Have a great day on purpose!

  • Jmcarumba

    Fantastic finally someone telling it like it is.  I wish I would have read this when I was younger. Now if I could just invent the time-machine fax I'll have it made. 

  • http://topcaribbeantours.com/ Bioshatta

    Great advice, thanks for sharing 

  • K Norden

    I'm 19 and will take this advice strongly!

  • Bkag

    You are definitely a Mormon . . . “by gosh!”

  • Jaroninthesis

    These are all really important things, thanks for sharing! I have read 4hww when Timothy Ferris challenges to lie down in a public place, and have done it my self. it was while working at a Starbucks and all day constantly getting bossed around and feeling like I was one of their robotic slaves. (which I can say since I sell my time for money that really sums up what I am). So I decided to act on Tims advice and just lie down in the middle of a rush out in the lobby in front of everyone. No body said anything to me while doing so, and even after the fact. And now, a few weeks after the spontaneous “f&$?you” lie down stunt my co-workers and bosses really admire and understand why I did it. I know it wasn't done for the reasons Tim intended it to be, but it made people view me as someone who does not care what they think I am. Whether that is a normal everyday barista or a robotic slave. By being yourself and not settling for anything less than who you are can really change how others (and yourself) view and act towards you.

  • Jaroninthesis

    These are all really important things, thanks for sharing! I have read 4hww when Timothy Ferris challenges to lie down in a public place, and have done it my self. it was while working at a Starbucks and all day constantly getting bossed around and feeling like I was one of their robotic slaves. (which I can say since I sell my time for money that really sums up what I am). So I decided to act on Tims advice and just lie down in the middle of a rush out in the lobby in front of everyone. No body said anything to me while doing so, and even after the fact. And now, a few weeks after the spontaneous “f&$?you” lie down stunt my co-workers and bosses really admire and understand why I did it. I know it wasn't done for the reasons Tim intended it to be, but it made people view me as someone who does not care what they think I am. Whether that is a normal everyday barista or a robotic slave. By being yourself and not settling for anything less than who you are can really change how others (and yourself) view and act towards you.

  • akhilesh

    I am 21 rt now and am tellin myself-”Hey this makes good sense, gotta think on this”
    It was a great read John, thankyou :) .
    Would like to talk more about this with you ,i have sent you a friend request on Facebook. Hope we can connect and have a chat sometime :)

  • Dougalberts

    The proplem is now,  what risk do i take?   im 21 years old i have an amazing 10 month old that i want to give the world to.   i currently work in a factory welding third shift.   i hate that it seems i have no control over my own life.   i have to have this job to make ends meet.   i cant afford any big risk in my life at the moment.(or in in the foreseeable future)   Everyone around me seems to be happy barely making it.   i dont know what to do.  you said to surrond myself with people who expect you to do big things in life.  i see myself doing big things in life.  i just dont know how to get started.  coming from a farming comminity i have drive to work at things that seem inpossible. i guess what im wondering is how do i get started down this path? 

  • Retyyyh

    This is cool,The lord will enlighten the eyes of your understanding the more.God bless you for this.

  • http://inventikasolutions.com/ Inventika Solutions

    Each and every sentence in this article is true. I’m 22, started my webdesign company simply because I love designing websites. Within a short time I’ve come across almost every scenario Jon has mentioned.

    The thing which irritates me most is when neighbors and unrelated relatives try to give me career advice.

    But I’m glad that I choose this path.

  • Ally

    I typed in “I am 21 what should I be doing in my life”
    this article was a pleasant surprise. Ive managed to get myself to what I thought was “what I want” out of a job, with being a manager of a popular hotel at only 21… only to find im miserable…
    I know I need to fly…and I have little spurts of gut to quit my job and just go anywhere…after reading this I realize only I can hold me back, and only I can let me go… Thank you

  • Mia

    Thank you so much for the advice! I’m currently 20 years old, currently working as a wedding/bridal consultant in downtown from where I am. My passion is bridal which motivated me to apply when I was 19 to put myself out there and see what happens. I will be finishing Human resources by end of 2014. Then 2015 I will be applying to be a certified wedding planner. I plan to own my own bridal shop one day. Reading your article inspired me to push forward and educate myself more to become a true entrepreneur. Thank you!

  • RN

    I’ve been on the fence on starting a business. I am currently 20 and in college. It’s articles like these that make me want to go for it.