Living Vicky Blog

Entrepreneurs: Fail Until You Don’t

Screen Shot 2014-05-09 at 6.40.06 PMShortly after graduating from law school in the mid 90s, I took off for London and a glamorous career as an international corporate lawyer. A decade of advising investment bankers and huge multinational businesses taught me a little something about how entrepreneurs create, and manage, success and failures.

The good news: If you have an entrepreneurial bone in your body, this is your time. Technology now puts the solution to nearly any problem in the hands of anyone who is self-motivated enough to fix it. If you’re enough of a risk taker to monetize the solution, you are on your way.

Bridging an experience gap is a real, but manageable, challenge for young entrepreneurs. The internet is alive with excellent free advice on how to turn out a viable business plan. We won’t cover that here. We will focus instead on how to develop some of the soft skills – the savvy – that makes it easier to create, and manage, success.  And how to use a failure as a valuable “lesson learned”.

light bulb1. Get to Know Yourself: Nothing can prepare you for how quickly things move when a business takes off. You will be asked to make snap decisions with high stakes about unfamiliar topics. Putting some thought, now, into who you are and what you want will help you avoid passive choices and uninformed delegation.

  • Do you want to build and sell businesses or build and run them?
  • Do you want to be involved in the details or just think big thoughts
  • What sort of people do you want working for you?
  • What sort of a boss do you want to be?
  • What are your basic values?

Know yourself, inside and out, find advisers who you trust to advise you consistent with your values and objectives, and you will be able to minimize course corrections later on.

2. Get a thick skin. Let’s talk some baseball: R. A. Dickey, a pitcher for the Toronto Blue Jays, began his baseball career in 1996. He spent the next decade failing miserably until, broke and washed-up, he reinvented himself as a knuckleball pitcher. After yet another six years, Dickey broke through with one of the most phenomenal seasons of the modern era. He now earns $12.5 million a year.

The story of successful entrepreneurs is much more R.A. Dickey than Mark Zuckerberg. Dogged tenacity and self-belief in the face of repeated, iterative failure is an indispensible character trait that can’t be taught, but can be learned. You have to try publicly, and fail publicly, and then sit down with that failure, and wring out every last lesson to be learned. The natural reaction to failing is embarrassment and a desire to move on more quickly than you should. Resist this. Failure has value. Don’t waste it.

3. Get a network. There is a fine line between believing in yourself and being delusional. Ideally, you want to locate yourself at the edge, without crossing over. You can’t do this part alone. You need to build a network. Begin with a good mentor. Add allies and skeptics. Get out of your social circle, your age group, and your comfort zone. Start now.

How to start? Ask. The nicest thing about the human race is that people love to help (they also love to give opinions so this is win-win). You will be amazed at the number of people with relevant expertise who will be willing to meet with you and kick over an idea for the price of a latte. Be considerate of their time, be respectful in your approach, and remember that the number of people you add will be a function of the number you ask. Make it a habit to ask a few people a week.

Police this network completely and carefully. You do not need a group of people who will tell you nice things about yourself when you are down. You do need a group of people who will keep you on (or kick you back to) the self-belief side of the line.

Failure4. Get Transparent. Your network does you no good if you don’t leverage it. The natural tendency with an idea is to guard it so someone doesn’t steal it. Relax. Few people see the potential in something they haven’t thought of and fewer have the drive to make it work. Use your network to figure out if your idea has legs or if you are so attached to some version of it that you’ve lost the perspective needed to make it work.

The story of businesses is like the story of relationships: They all fail, until one doesn’t. But that doesn’t mean you stop looking for either. Get to know yourself, get some people on your side, and go fail, until you don’t.

Lorraine Charlton is a member of Living Vicky’s Bridges Committee. She is taking a break from a career in international corporate and humanitarian rights law to keep up with a four-year old hellion and his two-month old sister. During the summer, she can usually be found at a baseball game. She spends the off season losing to her iPad at backgammon and editing the occasional article on public international arbitration.

This entry was published on May 9, 2014 at 6:44 pm. It’s filed under VickyEntrepreneurship, VickyInspiration and tagged , , , . Bookmark the permalink. Follow any comments here with the RSS feed for this post.

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