Make Your Mistakes As Early As Possible

Posted on September 20, 2007

Note: This is a true account from my life but the names of people and places have been changed to protect the innocent.

It was a bright, sunny, crisp fall day in Chicagoland (well, maybe just the names of people were changed) and I was lucky enough to be having lunch with a wise man who we’ll call Chris (see, name changed and innocent protected). Chris and I were talking tech, start-ups and VC, the usual stuff he and I like to ponder. It seemed like a pretty typical day for me until we walked into the parking lot (queue dramatic music).

Once in the parking lot Chris and I began to talk more about my career and a piece of advice emerged that really got me thinking. The crazy thing is that this particular piece of advice was so basic and, yet, it hadn’t occurred to me before Chris said it. The advice was this:

Figure out who you are and what you enjoy career wise and get to that place as soon as you can. That way, as you make mistakes, which you undoubtedly will, the lessons learned from those mistakes will be directly applicable to where you want to be down the road.

Of course, I thought. That’s dead simple reasoning and yet I hadn’t thought of it. Here’s an example of this reasoning in action:

Let’s say Jonathan wants to be an entrepreneur down the road but he is currently a VC. Well, he should get to the entrepreneurial side of the fence as soon as possible because mistakes he makes as a VC won’t directly apply to the entrepreneurial side (for the most part). The implications are that Jonathan is losing time.

Adding in some numbers… If Jonathan started his entrepreneurial life now, at 25, he could make mistakes and start to get good, by, oh let’s pick an arbitrary number, 30 (of course I understand that one always makes mistakes, learns from them and grows but I want to keep the example simple). That gives him another 25 - 30 years to hit the ball out of the park. However, if Jonathan did VC until I was 30 and then jumped to the entrepreneurial side he would start to get good around 35 and then he would only have 20 - 25 years to hit the ball out of the park.

This is a very interesting concept and one that is directly applicable to entrepreneurship because of the fact that the most successful entrepreneurs have simply tried more times than others.

So, some food for thought on this fine day in Chicagoland. As always, I would love to hear your feedback in the comments section or directly at eric [at]

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2 Comments so far
  1. Ann Bernard September 20, 2007 11:05 pm


    Is there anything else in life more worth doing than figuring out who you are and what makes you happy? I think part of the saying goes a little something like this “Do what you love and the money will follow”

    Not everyone has what it takes to be an entrepreneur. That’s a FACT. If someone is wondering if they have what it takes…the only way to find out is by giving it a shot. If you fail and you are willing to try all over again, then you might have what it takes.

    I failed my first time around…but, I never questioned if I had/have what it takes. I know I have the heart, passion, knowledge, leadership and abilities needed. I made rookie mistakes and needed to learn a few things that I am now applying to my new company.

    I learned a few things about business, but more importantly, I learned exactly what I wanted out of my business and for my life.

    I agree in that you shouldn’t waste time in positions that won’t get you to where you ultimately want be, but remember that where you are now will somehow matter down the road. Life has a funny way of working out that way.

    Age is a number. What matters in life is not making excuses for yourself, not allowing fear to stop you, grabbing opportunities as they present themselves and to always explore and discover WHO you are and what makes you tick.

    Life is not a race, and it’s not a contest or competition.

    Best to live with no regrets, no guilt and no looking back!!

  2. Eric Olson September 21, 2007 9:39 am

    Great points Ann. Thanks for sharing them. Can’t wait to see Why Go Solo emerge. :-)