Hey Lyle Letter #002

Permission Granted

This is the second installment of my periodic Hey Lyle advice column. I need more of your questions to answer. Please click on this blue button and ask me something (it’s completely anonymous).

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Hey Lyle,

I feel like the most valuable experiences come from settling in, going deep, and building relationships and community. However, I feel this constant pull to travel, explore new ideas, and make new connections. I find myself freeing up parts of my life and seeking freedom, and wondering where this is leading me. How do I balance these two important parts of life?

Aspiring Wanderer

Hey Wanderer,

For the first several years of our relationship, I was jealous of my wife Allison.

She was working at Sonoma Valley Hospital as a dietitian at the time. She’s a Registered Dietitian (RD) with a Master’s degree in Nutrition, which—she would like me to point out—is not the same as a nutritionist because becoming an RD involves more advanced requirements and education. She loves cooking and eats incredibly healthy all the time. And it’s not difficult for her to eat healthy because she genuinely likes those foods more than unhealthy options. She likes the occasional piece of chocolate, but even that is of the low-sugar, dark chocolate variety.

At the time, she seemingly had everything figured out. The perfect career-life fit, if you will.

Meanwhile, I had been hopping from job-to-job and tried and failed to successfully launch a startup on nights and weekends with some friends before we met. Then I got into tech startups and joined some early-stage companies, all of which eventually ran out of money or were acquired for a measly outcome (read: the acquiring company really just gave us all jobs).

The one time in my life when I felt like I truly had a career-life fit was when I was in my old band Pressure 4-5. But that was nearly twenty years ago now.

I just painstakingly counted all the job roles I’ve had, startups I’ve launched, or side projects I’ve worked on in my career going all the way back to when I would help out in my parent’s real estate office to make some extra cash during high school. If you count writing this newsletter, they total up to twenty-four. It’s been twenty-six years since I graduated from high school. I’m no expert, but twenty-four seems like...a lot.

I’m a generalist at heart. That’s part of the reason why I call this publication Just Enough to Get Me in Trouble. I’m often in awe of people who have seemingly found their “thing” and have made it their life’s work. But now I know that my awe is somewhat misplaced.

Eventually, Allison grew disillusioned by her work. She would routinely make the same suggestions to her patients over and over. And then over and over, they wouldn’t follow through on them. She felt like she was talking about the same things constantly and not getting any results. And the crazy thing is that almost all her patients already knew what they should be doing. We all know we could probably stand to eat more healthy. But food is deeply tied to our emotions. I often joked that she played the role of a therapist more often than that of a dietitian a lot of the time.

Now she’s working on something completely different within the healthcare space, which is only tangentially related to diet.

The two words that stand out in your question, Wanderer, are “balance” and “important”. You intuitively know that going deep and branching out are both important. But I wouldn’t think of trying to balance the two perfectly against one another. They will ebb and flow throughout the years.

When I look back at all the things I’ve attempted, I don’t give myself enough credit for how deep I’ve gone on a lot of them. Music is only a hobby for most people who play an instrument, but I was able to record an album and play in front of tens of thousands of people. Poker is just a game most people play at home with friends, but I qualified to compete in the World Series of Poker Main Event with the largest field they’ve ever had. Sure, those both didn’t pan out as well as I’d hoped, but I still got further than 99.9% of people.

None of those things would’ve happened without exploring something new. And they’re some of the best experiences I’ve ever had.

I’ve thought about your question a lot, Wanderer. I wonder if there’s more complexity below the surface of what seems like a relatively simple question. Maybe I’m projecting a bit, but I get the feeling that you’re struggling with your identity. What are you meant to do with your life? What’s your purpose? What if you screw up and waste your time on the wrong things?

First of all, I’m giving you permission right now to screw up. Even if you go down a path and it blows up in your face and it doesn’t amount to anything in the long-run, you’re going to be okay. In fact, you’ll be more than okay. You will have learned, very concretely, that it wasn’t the path for you, instead of wishing you had tried and wondering about it for years on end.

Identity isn’t a fixed, innate thing we’re all born with. It can change over time. I guarantee it will change over time. You can even change it intentionally.

A year ago today, I wasn’t a writer. Yet I wrote all the time. I wrote in my journal, in work and personal emails, in texts, and in the occasional tweet. I didn’t consider myself a full-fledged writer then but now I do. So what changed? I just started writing more and then declared myself a writer publicly. That’s it. And now I show up as a writer consistently and it’s an important part of my identity.

So, Wanderer, get out there and travel (safely during COVID, of course), explore those new ideas, and make new connections. Go deep on the ones that feel right at the time. Try them on for size. It’s okay if you exchange them for something else later on.


Thanks for reading. I’d love to answer one of your questions in a future installment of Hey Lyle. Tell me what’s on your mind.

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