Welcome to issue #035 of Unsubscribe. Each week, I send two essays that help you step off the default path to build a life you love, supported by work you enjoy. If you need support on your entrepreneurial journey, join our network of over 1,000 entrepreneurs. You’ll instantly join our group chat, weekly live Q&As, monthly workshops, and private in-person events.
Last week, I had lunch with a successful CEO who runs a company worth hundreds of millions.
As we were eating our appetizer salads, I started digging into his story and asking him questions about how he built the business. At one point during the conversation, I said something to the effect of, “I don’t think I know enough to build a business that big.” After I said it, he smiled, leaned across the table, and said something that surprised me:
"I have no idea what I'm doing half the time. I just try stuff and see what happens."
This is a guy who has hundreds of employees, an office that costs something like $60,000 per month, and whose decisions impact entire industries. And he's basically out here experimenting.
The most interesting part about it is that he seemed totally fine with that.
Most of us act the exact opposite way. We walk around acting like we have everything figured out, nod along when someone says something we don't understand, and avoid asking a basic question because we don't want to look dumb in front of everyone in the room.
The truth is, most of us are just scared little kids wearing business outfits, afraid that someone will discover we don't actually know what the heck we're doing a lot of the time.
And that fear keeps us from building better lives and businesses.
When you're too worried about looking stupid, you stop taking risks. You don't ask the obvious questions that everyone else is secretly wondering about. You avoid trying new approaches because failure might expose you as ignorant.
But successful people are completely at peace with looking foolish. What a way to live.
They ask embarrassing questions in front of important people, admit when they don't understand something, and try approaches that might fail spectacularly.
I know a young lady who built a multi-million dollar business. One of her best qualities was that she wasn't afraid to sound unsure when talking to potential customers. While her competitors worried about “knowing everything”, she was saying things like, "I'm probably wrong about this, but..." or "This might not actually work, but what if we tried..." Most people opened up to her because her honesty was refreshing.
The irony is that being willing to look a little silly actually makes you look smarter. People trust someone who admits their limitations over someone who pretends to know everything.
Your boss doesn't have all the answers. Your successful friend is making it up as they go. That confident person on social media is probably just as confused as you are. I know I am.
We're all figuring this stuff out in real time, together.
The people who get ahead aren't the ones who never look foolish. They're the ones who understand why they looked foolish, educate themselves on how to keep it from happening again, and then implement what they learned.
So ask the dumb questions, try the risky approach, and tell people when you're confused.
Everyone else is just as scared as you are.
The difference is that some people do it anyway.
What’s your take on today’s topic? Do you agree, disagree, or is there something I missed?
If you enjoyed this read, the best compliment I could receive would be if you shared it.
Join our private network of 1,000+ entrepreneurs who have access to the following upcoming events and previous workshops from 6 and 7-figure entrepreneurs, CEOs, multiple New York Times Bestselling Authors, creators, makers, and more. You’ll also gain access to live weekly Q&As and invitations to members-only networking events worldwide.
Love this one, especially Justin. Calling out what you don't understand also stops people who talk fancy to impose superiority. Or at least slows them down a notch 😉
Writers are the same. Or can be. I know I am, even after 65 odd years of being a published one. It's why I am always taken aback by those who follow up their first novel with a second book/course/long running podcast on how to write a novel. I have never really known how I do it, I just sit down and start, and I certainly couldn't teach anyone else..except to advise them to, er, just sit down and start. Only advice I ever give is short & sweet. 'There are no rules.' If there were, I'm pretty sure I'd never have been a writer at all.