The Thoughts of Max Keilson

Today, I read a some thoughts that Ryan Caldbeck, founder of CircleUp, shared on Twitter. CircleUp is an amazing financial platform that has democratized finance. It’s the kind of idea that I see, and think “Wow, that guy is brilliant. He has it all together. He had an idea, was able to execute, and now runs a very transformative, successful business.” On Twitter, he shares that as his company has grown, so too have the pressures, worries, and insecurities. Along with those, he feels his ability to talk about his feelings have decreased.

His thoughts resonate deeply with me. I’m not the CEO of a widely known, well respected business. I’m the co-founder of a small beverage company that maybe a couple thousand people have heard of. We have big aspirations, but right now we exist in obscurity in Brooklyn.

Yet, I have all the same fears. If we fail, how will that impact my own identity? How will my friends and family react? Would I have to go out and get a job? How could I sleep at night knowing that I’ve lost hard earned money that people entrusted to me? How could I react knowing that we failed the farmers we partner with, or that we have failed at mainstreaming Radical Sustainability?

I want to succeed. I don’t want to fail. As a result, I let work consume me. I work seven days a week. I regularly have difficulty sleeping. When I do things that I used to find fun, I think about how I could be working. It’s not healthy, and I know that. I meditate. I workout obsessively. Those are about the only real escapes that I have. Worst of all, I often feel like I can’t share these fears with people, because I have to be confident in my business. How else could I encourage people to buy my product, or to invest in me? I worry that expressing my fears makes me seem less confident, less marketable, so I only express them to a handful of people.

But these aren’t things that only apply to CEOs, or entrepreneurs. These apply to everyone. No one wants to fail and everyone wants to succeed. People are often consumed by their fears and anxieties. Everyone wants to appear confident.

I often ask myself the question, “What’s the worst that could possibly happen?” Weirdly, it helps put my fears and anxieties in check. In most cases that I deal with, the worst that can happen isn’t so bad. If I failed, the worst thing that could happen is I’d have to go out and find a job. I’d have to make a few difficult phone calls, and start saving up to pay some people back. Life would go on. That fear shouldn’t control me, because the worst case scenario isn’t so bad.

Being vulnerable about our fears is a good thing. You can look at how it impacts human connection, like Brene Brown talks about. You can also think about how transparency and honesty leads to improved outcomes, like Ray Dalio has long advocated. Whether that be writing your fears out on a blog that some complete strangers on the internet might read, or telling your best friend, or encouraging such openness in your workplace, it will only bring catharsis. The sooner we do that, and overcome those fears, we can get back to doing the things we love.