I sat down with Jim Thompson on The Great Unfamous podcast, and he asked me a question that stopped me in my tracks: if someone out there is struggling with a non-traditional path, maybe college wasn’t for them, maybe their current job is a bad fit, maybe they don’t know what they’re passionate about, what’s the one thing they should start doing?
My answer was simple, but it took me decades to learn it: invest in yourself.
The Reinvention That Started With 30 Minutes a Day
When I unpacked the early days of the last reinvention I went through, the turning point was when I started to dedicate some time for myself rather than just running from one chaotic event to another.
I’m talking about purposely taking even a half an hour or an hour of the time that we’re given in a day and making it just for you. It could be something as simple as:
- Getting your clothes set out for the next day
- Making the bed
- Going for a walk
- Reading a book or listening to a podcast
- Teaching yourself something new on a piece of software
That first step, that investment in yourself, is the key.
20 Years of Not Investing in Myself
If I look back at the 20-year stretch before my 10-year reinvention, I can break my career into two chapters: 10 years of early work and 10 years of grinding through. During those first two decades, I wasn’t investing in myself. Not meaningfully. And the data shows it.
Here’s what I’ve found to be true: if you look back and measure what you’ve been investing in yourself, you’ll usually discover that you’re not investing at all, or you’re investing very little. The minute you start making significant investments in yourself is when you’ll start to see exponential improvement.
The Dinner That Woke Me Up
I remember sitting at a dinner at a very famous place in New York City. I used to have this annual dinner with a colleague, and he asked me what my goals were for the year. It was March, and I said, “Oh, I haven’t really set my goals yet.”
He looked at me and told me exactly what I needed to hear. We’re in March and I hadn’t even set my goals for the coming year.
That was a good wake-up call. It’s those people you surround yourself with that tell you what you don’t want to hear but need to hear.
Learning to Be Vulnerable
One of the things I told Jim that I still need to improve is being vulnerable. For the longest time, I didn’t want people to know how broken I was. But now I’ve realized something: if I don’t talk about it, some person out there might not be able to learn from it. And that’s worse than any discomfort I feel sharing it.
If I can share the hard lessons from those early years and the way I’ve thought about rebuilding, then those 20 years of struggle actually mean something beyond my own experience.
The Prairie Farm Analogy: Getting Out of the Rut
I gave Jim a prairie farm analogy because I grew up with plenty of them. When you’re a kid on the prairies, you’re on that hour-long bus ride into town where there’s only one road. And sometimes the ruts in that road get so deep from rainfall that they won’t even risk putting a school bus through because it might flip over.
That rut is something I can now look back on and see clearly in different periods of my life. I was in a rut, and I couldn’t see over the edge. It wasn’t the edge of the earth. There was better stuff outside of that rut. But I couldn’t see it.
Sometimes you just need a jolt to get out. That jolt might come from a trusted colleague, a friend, a partner, or a circumstance. But if you’re in that rut, just peek over the edge and remind yourself of what might be if you could jolt yourself out of there.
The Danger of Inertia
Here’s the real danger: inertia. When you’re stuck in a rut, inertia is what carries you through. And that rut might end up in a ditch because you’re following the path of others and not your own.
After a while, you’re sitting there going, “Three years are gone.” I don’t want that to happen anymore. I make decisions now based on one question: am I just going forward because of inertia?
I find that I work better when I’m challenged, when I’m moving off into new paths. Not recklessly, because I also have a higher level of risk tolerance than I used to. But I take a good hard look at the path I’m on. Is this getting me the outcome I’m looking for, or am I just doing it because that’s what I did yesterday?
Be very careful of inertia. Because that’s when you wake up and go, “Five years are gone, and I’m no closer to the goals I didn’t set and the outcomes I was looking for.”
The Bottom Line
If you’re stuck, start small. Dedicate even 30 minutes a day to yourself. Set your goals. Surround yourself with people who will be honest with you. And most importantly, peek over the edge of whatever rut you’re in, because there’s something better on the other side.
This conversation with Jim Thompson on The Great Unfamous reminded me why I started sharing these lessons in the first place. If my 20 years of struggle can save someone even a fraction of that time, it’s worth every uncomfortable moment of being vulnerable.
Listen to the full episode on The Great Unfamous podcast.