I have found that there’s a simple test for whether you are learning in your career. Look back 3–5 years from today and ask yourself if you could have been substantially more effective at your past job in your present form. If you look back a few years and feel like in comparison to who you are today, you had little idea of what you were doing and would have done things a lot differently given what you now know, that’s a telltale sign of learning and growth.
I have been in the venture business 11 years now, and whenever I look back even a few years, I feel like I was pretty clueless. Now, it’s not to say that I was actually clueless (though perhaps some of my partners or CEOs would disagree!), but the differential is just a testament to the slope of the learning curve that takes place every day, month, and year in this business. I was sharing this with Mitch Free, founder and CEO, MFG.com, and he said that he feels that way in all the important things in life. After thinking about that, I have to agree.
I used to think that looking back and feeling like you’ve made so many mistakes is not such a great thing. Now I’ve come to believe that the thing to really be worried about is looking back a few years and being impressed with your past self. If that were to happen, it probably means your learning has stalled altogether.