Weave Your Past Experience Into One (Of Many) Options for Success

You should not feel trapped by your career success. I harbor this core belief that's likely to strike you as pretty odd, but I hope you'll let me explain:

You should run your firm as if it's an arbitrary choice to be a successful entrepreneur, and you could have been successful in countless career choices.

This is counter the idea that you were somehow destined to be a successful principal of a dev shop or creative firm or advertising powerhouse or UX research firm or....

Here are the two reasons I believe this.

You should not be afraid of failure.

If your firm must continue to exist at all costs, you'll do your best to hold on rather than doing your best to thrive. Thriving requires risks with such an upside that the attendant downside is fatal. Next March will bring this enterprise to the "30 years" mark, and normally this would be the time to relax. But instead, we (there are two of us full-time now) are renaming the firm, completely redoing our website presence, releasing a new book (Tradecraft), editing and re-releasing a classic twelve years on (Financial Management), launching sold out events (six this year), and building a SaaS application to help you monitor performance. Oh, and rounding out a $110,000 spend on a new index that measures your internal culture. We have also waisted a fair bit of time and money on two failed ventures!

There should be this wonderful balance of steadily making money with proven offerings...and innovation to stay on top of your game. Those risks, if they are to provide a meaningful contribution, need to present real risks, and one of the reasons you take them is this: "I could be successful in multiple ways, but whatever I'm going to put my name on needs to be a worthy addition to the marketplace." I regularly ask myself "what's the worst that could happen?" The answer is business failure, and I can accept that. It's happened before, and those memories are fresh. Big deal.

You should seek to weave your past into your present, gratefully.

We are all the sum of the experiences that we have had, and each person is a beautiful quilt made of a lot of very strange squares that don't seem to fit until you step back far enough to see the whole, made up of the parts.

I learned something from working in a vault at Purolator Armored, as a meter reader at NIPSCO, running a trimmer at an R. R. Donnelley printing plant, and having a lawncare business with 24 weekly customers. I've also learned from speaking to a live audience of 5,000 people that including a country's VP...days after being threatened with a lawsuit over my incompetence. Learn from everything, as a parent or a child or a success or an imposter.

This Steve Jobs quote is very inspiring:

You can't connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something—your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.

I don't think you need some big master plan as much as I think you need to constantly be growing, folding past experience into current opportunities, viewing your entrepreneurial ventures as a lovely dance between maximization and stretching for more.

You really think you can arrange all of these experiences to create a perfect exit? Phooey. Just keep moving and you'll get...somewhere even better.