On Asking For Help

Borrowed

"In elementary school, you were taught that getting help from others is 'cheating.' You were not taught to enlist the help and capabilities of your peers. Yet in the world of business and life, collaboration is the name of the game."

From "Who Not How" by Dan Sullivan and Benjamin Hardy [Book]

Learned

I used to have a tough time asking for help.

From a young age, I liked figuring things out on my own. I taught myself guitar and piano. Started writing songs instead of playing covers. There was something deeply satisfying about taking things on myself. The same feeling, I think, my 2-year-old son Mylo gets when he sees his artwork on our wall. “I made that.”

And a lot of that spirit is still in me. I’m the guy who wore a pink blazer and laceless shoes without socks to my wedding and didn’t tell anyone ahead of time because I didn’t want the feedback. Same reason I’d rather get my hands dirty building stuff with AI than wait for someone to explain it to me. In leadership, I like hands-on learning and building before I expect anything of anyone on our team.

But what’s changed for me over the years is recognizing that living in your own little world is limiting. There’s so much to learn from other people. I can’t read music as well as I’d like. I can’t drop to my knees and bang out a Jimi Hendrix solo or sit down and play a Bach piece on piano.

No regrets, but there’s this part of me that thinks if only I had taken some instruction early on, maybe I could.

What changed my perspective on all of this? I attribute a good bit of it to powerlifting. I fell into it through a CrossFit gym and felt totally out of my comfort zone, but my coach saw potential in me that I didn’t. I loved the feeling of not knowing what I was doing or what I was capable of. Before I knew it, I was deadlifting nearly 400 lbs and competing.

That’s really what asking for help has come to mean to me. It’s less about needing to be rescued and more about loving the process of learning and staying open. Open to perspectives I don’t have, to people who’ve walked a path I’m just starting down, to insights I can take and apply in my own way. And honestly, the right person at the right time can get you somewhere in weeks that might have taken you months or years to find on your own.

Today, I think about this through two lenses in my life.

The first is books. I try to read widely and with genuine curiosity, approaching every author as someone worth learning from. Not to follow their playbook, but to find the pieces that resonate and see how they might apply to how I show up each day in my life and work. I also take book recommendations from people I respect and dig in right away.

The second is the people I've intentionally brought into my orbit. My fitness coach. Our sales consultant, who challenged how I was thinking about proposals and helped us design a new approach. Other consultants across CPG and client services. And a growing network of agency folks, founders, and potential collaborators. When I lived in NYC, I made it a habit to meet with people weekly for coffee or breakfast. These days, it can happen virtually with anyone, anywhere.

The independence thing never fully goes away. But I’ve learned that doing things on your own and being open to others aren’t in conflict. One just makes the other better, and life is a lot richer for it.

Which is part of why I write this newsletter and share thoughts on LinkedIn. Every time I put something out here, I create the opportunity to learn from the responses, the conversations they spark, and the people they invite in.

Thought

What's one area where I've been the bottleneck to my own progress?

Where am I confusing effort with progress?