Risk Vs. Reward

October 25, 2023

written by
Barbara O Stephenson

When I made the decision to take over 300FeetOut, it was with the phrase “fuck it, why not?” I was in my early 40’s, newly divorced, and didn’t have to answer to anyone about how I spent my time, my money, or my future. I could either go look for a job or take the clean slate of getting to nurture 300FeetOut my way, so I did. And I failed. 

Again and again I made bad hires, I remember one who even said to my face that I was an idiot for hiring him because there was no way he was ever going to put me over his family (WTF?) because he couldn’t do both (turned out he was taking business for himself). I hired people who were incompetent. I hired people who lied on their resumes. And I learned how to let people go. 

I thought because I’d been running departments for the last few years I understood finance….wrong. I was running the business like a hobby (putting in more than I got out), we barely made it through covid, I didn’t understand how to guide accounting in the difference between a pass-through cost vs revenue. I took classes and learned how to hire people smarter than I was to guide us to financial success. 

I listened to people who told me I wasn’t a creative and wasn’t qualified to judge the work of my staff or their choices.  Design is a bit like being a chef (Kitchen Confidential anyone?) because for years designers have been taught to tear other people down.  I had people literally outright laugh at my opinions in dismissal and yet I kept making them. 

The risk of being made fun of was smaller than the reward of building something great.

I made bad decisions and we’ve lost a lot of RFPs. But when we were approached by the San Francisco Ballet, a world class organization, to respond to an RFP I was initially excited about the prospect- this was a chance for us to play with the big agencies!  We had a fabulous partner in The Content Bureau for messaging, we knew the San Francisco arts scene, and we knew our creative chops were on par with the biggest agencies in the world. But as we got closer to submitting, the little voice in the back of my head said ‘no way’. It said we were not good enough. It said we were too small and too new, it said who were we to take on this work. I started getting doubts and those doubts led to a decision not to submit the RPF. Poof! The weight off my shoulders was gone. I wasn’t scared of failing because I’d simply decided not to play.

And when I realized that,  I remember looking at Greg, knowing that while we had a lot to lose, we were going to play to win. I said “fuck it” and hit send on the email. We won 5 awards for that campaign. 

Playing to win instead of not to lose will always be a struggle. But if you’re going to walk up to the edge, you need to take the leap. 

Everyone knows the higher the risk, the greater the reward or the failure. Not all of us are born gamblers and not all of us have enough of anything to be able to afford to lose. I’ve learned that if I power thru my imposter syndrome and my fears, pure grit and determination will usually get me to an outcome I can be satisfied with. Because failing and getting up again to try once more is the key to risk vs reward in business for me. But I have good people around me and together we risk and win together.