A.K.A How I Learned (For The Most Part) To Stop Doubting Myself & Start Taking Risks

I don’t want this post to be a bunch of clichés. In thinking about writing it, so many good quotes come to mind to cite—“You miss 100% of the shots you don’t take”; “If not now, when?”; “Only those who risk going too far can find out how far one can go.” I could keep going. This isn’t about clichés, although there is truth to some of them. It’s about finding the tipping point and this time, going over the top.

A few years ago—three or four—I reached a tipping point. My business was doing well, and we were basically at capacity. The demand for our services was exceeding our ability to supply them. At the time, I felt I only had one option: I started saying “no.” We turned down business because we didn’t have the capacity to take it on, and “lost” a lot of potential clients. In hindsight, I realize now that I had other options. I could have hired more employees. I could have raised our rates. I could have done both. But instead, it was frankly safer and easier to just focus on the clients we had and stay the same size. I mean, things were working, right?

Reva in front of her computer

Working away at 1871

Now, I’m making different choices. At first, I took baby steps. I started working with freelancers. I started asking for a little more money, but would then often come down if there was any push back at all. The business was growing a little, but it was not where I wanted it to be. Then one day I realized that my business was never going to grow if I didn’t take the risks to let it grow. I made a full-time hire. I became less apologetic about my rates and did a better job at sticking to my guns. I pursued opportunities that were bigger and better than what we’d done before. And when an opportunity came my way, even if it was a little scary, I started to ask myself, “What’s the best choice for my company? What’s the best next step that will lead me where I want to go professionally?” And I started saying “yes.” We’re now having our best months of growth ever.

I think I’ve developed this calm resoluteness and confidence with time. After repeatedly finding myself in the same situation, I needed to figure out how to move forward and get beyond that tipping point. I’ve learned that saying “no” didn’t move me or my business ahead—it just kept us where we were. In doing something different, I found my “yes.”

I’m not advocating that everyone should go jump off the deep end and say “yes” to everything with abandon. You get one shot with a new customer, and it’s important to be ready to give them a great experience. You don’t want to under-deliver. You also owe it to yourself to stay healthy and sane, and you have to listen to your body and mind. At the same time though, while being an entrepreneur is an already risky decision, if you don’t take risks once you’re there, you will never move ahead. So even if it’s a little thing, start saying “yes.” Trust yourself a little bit more. Think about what you would do if you weren’t afraid—and see where it takes you and your business.