Where I've had to be confident when I wasn't.

We’re here to help you love work & life more. At Creative Conversations, we’ve invited 13 of our favorite bosses to talk about how they’ve used Courage, Confidence, Creativity & Commitment to build their dreams.

Join us.

cleveland-flea-SHP-121723.jpg

Maybe I’m doing it wrong- or maybe this is what it’s like- living a life where things matter. Money. Relationships. Words. Outcomes.

From the moment I began Cleveland Flea, I’ve always felt the weight of this business. The inadequacy of my training. The mountains ahead. The valleys and peaks. The rivers I’m stuck in. The huge potential I’m blessed to have.

I’m probably pretty strong- but I keep taking on bigger challenges, which leaves me feeling tired and unprepared.

And smarter.

And wiser.

And grateful.

It is NOT easy. But I want to live an entrepreneurial life. One filled with real challenge. One that has the capacity to change lives for other people. One where things matter.

I’ve had to leap before I felt ready. I’ve had to launch when the t’s weren’t crossed nor the i’s dotted. I have to be vulnerable in front of people I admire. I’ve had to be in conflict with those I love.

I have to convince others to follow me into the fog. Where there’s no map- except for my own determination lighting the way.

And so on and so on.

My business journey has been filled with about 80% moments where I had to fake confidence and 20% where I KNEW things would work out. And what I truly mean by that is that I’m in situations where I am out of place or have never been before about 80% of the time. I am confronted with new situations ALL THE TIME. Whether that’s in leading or letting people love me or developing new products or writing a business plan or starting a new collaboration. When you’re doing remarkable things you’ll likely be doing things you’ve never done before.

And that’s ok.

And the thing is, that’s what it means to grow. To be the boss. To be the leader. To venture into new territory. To take a leap. To go in a direction that most people avoid.

They avoid it for a reason- because it’s uncomfortable and scary.

But it also leads to greatness- to an emotional world that excites you. To a life full of adventure.