Having built over 20 start-ups in my life, I am no stranger to risk. You might even say we are kindred spirits. From renting out Seattle’s football stadium to leasing the biggest space in Pike Place Market with no experience to leasing 10,000 square feet of warehouse space to make muffins for espresso stands to bringing CRAVE guides to Vancouver hoping that someone would help me sell them, I’ve taken leaps that probably shock some people. Over time, however, my risk taking style has evolved.

It was much easier for me to take risks when I was younger and more naive. I think the less you know about business, the easier it is to jump in headfirst and figure it all out as you go.  I am the kind of risk taker that loves to come up with an idea and gets the ball rolling practically the next day.  Sometimes it works and sometimes it either needs to be tweaked or abandoned altogether.

As I get older and (hopefully) wiser, I find that I am slower to take risks.  I guess I have so many experiences under my belt that it has created a bit more fear.  When I was 18, I opened a furniture store because my boyfriend was a custom woodworker and I thought, “why not open a retail store and fill it up with contemporary furnishings to compliment his pieces?”.  I didn’t even think twice about signing a five year lease.  It turned out just fine and the only reason I moved on is that I got bored.  Several years and many signed leases later I was sitting in front of another 5 year lease for a fitness business without fear.  Soon after I opened the doors I realized I did not have the patience for inspiring people to get fit.  I since have discovered you can actually get out of a lease.  I am pretty sure (but never say never) that I will not sign another lease again.

Some risks I take end up okay, some turn out really well, and others don’t work at all.  Something I’ve learned is that the worst time to make a decision is when you are in a desperate situation.

I’ve been in the food business for almost 30 years and have taken varying degrees of risks with each project or new division of the company throughout that time.  One time, when I was really low on cash and didn’t know how I was going to make the next payroll, an opportunity came my way to sell strawberry shortcake on a national tour with rock star Peter Gabriel.  It would start in New York and travel across the country to San Francisco.  In retrospect, this is a risk that I wish I hadn’t taken. What can I say? At the time, I thought it would be quick cash!  I sent my staff on the road in a 15 foot truck full of strawberries from Seattle to New York and flew in additional staff to man the concession stand.  The wind got knocked out of me by the time they hit Chicago and I had lost money in each city.  The event coordinator kept telling us to hang on, that in the next city we would hit gold.  We couldn’t keep losing, so I pulled out.  Huge bummer!  Not only did I have to borrow money to pay the payroll but I was deeper into debt than before because my quick cash scheme tanked. This was a case where doing NOTHING would have gotten me further ahead.

Since then, I resolved to think through decisions more thoroughly and talk them over with my husband and other mentors to see if I’m on the right track. I have my mental checklist of what constitutes a valid risk, which has helped me immensely. Being headstrong as I am, I might still move forward with something if I’ve got a fire in my belly.

I took time this last year to write down all the mistakes made and lessons learned from my numerous businesses, including that jaunt across the country with a rock band.  The book will be out soon.  I wish I’d done it much sooner so I didn’t have to continue to learn the same lessons over and over again. Seeing it all in writing has helped me come up with some real key messages that I’ve been using in my decision-making ever since.  I’m not saying that I will never again make a mistake, but now I’m much more aware of consequences based on decisions made.

For me, having the courage to do nothing was a hard lesson learned.  Sometimes you just have to say no, and I  think we are programmed to say yes way more than no.  There’s hope and excitement  in saying yes and going for it. And who knows? Maybe you can do it all and go for everything you dream, but probably not all at the same time.  Saying no now doesn’t mean you can’t try it down the road when the timing is better. I guess what I’m saying is to beware before you dare, but definitely dare if you can!

Having been through it all, I feel a bit schizo about risk taking. I still think you should go for your ideas and take big risks.  I also believe in listening to your gut and taking some baby steps before you leap. What I know for certain is that it’s crucial to use your personal experiences (and mine!) as a risk-taking guide and learn from your mistakes as quickly as possible.

What is your risk taking style?