Risk Takers

Narrative #1: Life is dangerous! Working for yourself is a risky, uncertain proposition. Better to take the safe road and work for a larger company.

Almost every entrepreneur or self-employed person hears this narrative when heading out on their own, especially from well-meaning friends or family members. I heard from a woman last week who has built a million-dollar company with more than ten employees, and her family still tells her she should try to find a job “to be safe.”

Narrative #2: Leap and the net will appear! You can do it. If you don’t want to work completely on your own, something is wrong with you or you’re afraid of change.

This narrative is also problematic. Not everyone wants to be an entrepreneur, but almost everyone wants to create freedom and independence. Sometimes we leap, and no net appears.

Entrepreneurs and creatives tend to be regarded as risk-takers. But what if there’s a third way between the undesirable choice of two all-or-nothing options? What about those of us who know better–we know that creating independence for ourselves is the right path, but we don’t necessarily have an aggressive mindset? We know that the cautious person doesn’t always win the race, so how can we avoid being left behind?

Our group in the Times Center lobby began with a risk-o-meterwhere we looked at how we view the roles of risk and uncertainty in our careers, based on questions like these:

“Working for myself is the only option. I never want to work a ‘real job’ again.”

“It’s better to do one thing very well than to be a jack of all trades.”

“I’d rather have less money and more freedom.”


The main part of our time together was focused on a pre-mortem. I stole the idea for the pre-mortem from a fun book on facilitation exercises. (Whenever you have no idea how to lead a 90-minute workshop, it helps to learn what other people have done.)

A pre-mortem is like a debriefing–where you meet to reflect on a recent project or experience–but conducted in advance. With a pre-mortem, you look ahead to a project or experience and identify everything that could go wrong. It helps to raise the stakes by asking, “How will this end in disaster?”

The goal is to find the problems in an upcoming scenario before they happen. In this case, we were looking at concerns related to independent careers. Many of the problems raised related to finances. Others related to a changing marketplace, and still others related to inertia, or concerns about our own ability to produce.

After spending a good length of time thinking about problems and disasters, the next step is to move to premptive action phase. In this phase, you identify which problems are the most pressing and also the most likely to be resolved through a change of course. For example, one group identified “the world will come to an end” as a potential disaster, and another group identified an earthquake. Those would indeed be serious problems, but there’s not much that most of us can do to prepare for either of them.

After we identify the pressing and actionable issues, we then focus on solutions. If we’re worried about money, we can establish an emergency fund. We can also establish a “fun fund”–in my case, I started a fun fund for my travel expenses a couple years ago, and it’s made a big difference in mentality. Even though I have no more or less money in my cumulative bank accounts, having the travel money in an account on its own has helped me feel more secure.

If we’re worried about a changing marketplace, we can create an opportunity list. An opportunity list is an idea list of opportunities we could pursue if we needed to generate more income. (My list is five pages long–I don’t have time to pursue most of the ideas now, but they are there if I need them.)

If we’re worried about inertia, we can use a carrot-and-stick approach: over here, I’m busy writing a manuscript for the AONC book sequel, and as soon as the first draft is complete, I’ll buy a Round-the-World plane ticket. Having the “carrot” in front of me keeps me focused, even though there’s no practical need to wait until the manuscript is finished before getting the ticket.

Your solutions may be different from these, but the goal is to increase confidence. Often, we’re worried about vague concerns and problems. This exercise forces us to bring the real problems to the surface, and then get serious about preventing them from actually taking place.

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