Let's Play Another Round

Every Thursday night I play pickleball with a group of guys from a local church. I really enjoy it, but I’m not that great. I hold my own, but I'm probably the weakest player in the group.

Now, I like to think I'm a pretty positive and even-keeled guy. I'm generally confident in my ability to do good work and show up well for the people around me. But the pickleball court is one place where my confidence gets shaky. When I'm on, I'm decent. When I'm off, I'm really off. And I can get really down on myself. And other negative thoughts start seeping through the cracks that open up when I miss a shot. It’s like all the pent-up frustration and self-doubt I’ve been holding at bay see an opportunity to attack, and they rush in to kick me while I’m down.

Last night, I got especially broody after a disappointing loss. I stood in the hallway, stewing for a few minutes. I'm out of my league. Everyone's just tolerating me. I’m holding others back; they'd have more fun without me. I was considering calling it a night and heading home. Then one of the guys called out to me. "Hey Dave, you playing?" A court opened up. They waved me over. So I went back inside and played another round.

I still sucked. But I got over myself. And I had fun.

I've been showing up for over a year now, and some of these guys have been genuinely encouraging: giving me pointers, pointing out how much I've improved, reminding me I belong there. I'm really grateful for that.

That kind of community is invaluable. Especially when you're a solopreneur.

There's a lot to juggle when you’re running a business on your own, and there are plenty of opportunities to struggle with doubt and disappointment.

A proposal gets declined. You've been troubleshooting a technical issue for hours with nothing to show for it. You miss a tax deadline. You feel overwhelmed by the financial and legal-schmeegal stuff. You fall down a doom-scroll rabbit hole about economic collapse and wonder what any of this is even for. Or you come downstairs and your family already started dinner because "I’ll wrap this up in 10 minutes" turned into an hour, and you feel like you let down the people who matter most to you.

Self-employment can feel lonely. And when you're already down, it's easy to stay there. I’m speaking from experience.

But if you have people in your corner who nudge you back onto the court - who are invested in your progress, give you honest feedback, and remind you that you belong - it changes everything. I’m speaking from experience.

If you don't have those people in your life yet, please seek them out. Look into joining a mastermind group, or working with a coach, or just meeting regularly with a friend who’s also growing their own business. Make those connections. And if you're not sure where to start, feel free to reach out. I'd love to help.

Shoot me a message. All you have to write is “I could use a nudge” and we’ll set up time to chat.

In the meantime, keep playing.