Thief of joy.

When I was 27, my friend Cassie bluntly asked me how much money I was making.

We were sitting at Bar Louie in Columbus, Ohio, after I'd driven two hours from Toledo to visit her for the weekend. We were ten minutes into our dinner conversation when she came right out with the question.

"How much are you making now at your job?"

Up until that moment, I hadn't really thought about whether my salary was good enough. And I certainly didn't think it was a problem. I was making $45K plus some measly commissions, and that wasn't keeping me up at night. None of my friends in Toledo were making much more than that. Most of my colleagues were in the same range, give or take $10K, and that was based on their experience.

I was a 27-year-old kid from a small farm town in Ohio, and it had never occurred to me that I should be earning some massive salary, like $100,000, by age 27. In my head, people who made $100K+ lived in penthouses in NYC, and that just wasn't my world.

So when I told Cassie my salary, I wasn't expecting a competition of any sort. I was just answering a question. But she let out a big laugh. She hadn't intended to be mean. It was more like a laugh of disbelief. I can still remember her voice and response:

"Oh, my God! I can't believe you're not making six figures yet! I'm making $110K. I always thought you'd make it way before me."

And Cassie had every reason to think that. We'd interned together in college, selling Yellow Pages ads door-to-door for a company called University Directories. I won the sales pitching contest at our training program, and everyone expected me to be successful at sales when we got out in the real world. But I was immature, had zero discipline, and I was completely lazy. The talent was there, but everything around it was missing.

After college, our careers went in completely different directions. Cassie got a sales job at a big box flooring company and steadily worked her way into bigger roles over the next six years. Meanwhile, I got into pharmaceutical sales and spent that same time getting fired from jobs in tiny Midwest towns I didn't even want to live in. Three towns in seven years, bouncing from one to the next, underperforming, and repeating the cycle of failure.

But I wasn't sitting in that booth at Bar Louie feeling sorry for myself before Cassie told me her salary. I was fine, just catching up with a college friend over dinner. And then a few sentences about her salary blindsided me. Suddenly, I was losing at something I hadn't even known was a competition.

The drive home

I drove back to Toledo a few days later, and I remember the drive more than the rest of that dinner. Snaking through Route 23 with nothing but my thoughts and a big coffee. I turned the radio off and drove along in silence, replaying Cassie's laugh in my head. And I started doing the math I'd never done before. She was making more than twice as much as I was, and she wasn't even bragging. She was genuinely confused about why I hadn't figured it out yet.

Ten minutes before Cassie asked the question, I was doing fine. I was content. And 30 seconds after I heard her salary, I fixated on how far behind I was. How many years would it take to close the gap? Had I been deluding myself about my potential this whole time? It stung.

That feeling of being behind rarely comes from an honest assessment of your own life. It comes from moments like my dinner at Bar Louie. From learning about someone else's number or title or milestone. Ten minutes before you knew it, you were okay. And ten minutes after, you're an utter failure. But the only thing that really changed was you learning information about someone else.

What the scoreboard missed

If you'd asked me on that drive back home what my career would look like in 10 years, I wouldn't have had much good to say. Probably something vague about hoping to find a sales job I could keep for more than a year.

Within two years of that night in Columbus, I'd stumbled into a job at a startup in New York City and started winning real sales contests. Within four years, I'd run sales teams across multiple cities. And within eight years, I was a Chief Revenue Officer at a $500M company in Los Angeles. A decade after that night in Columbus, I began building what would become an eight-figure, one-person business.

None of that was visible from the driver's seat of my Ford Escape on Route 23 back in 2008. I couldn't even get a whiff of this career. And if Cassie had asked me that night where I'd be at 37, I probably would have said something depressing (and inaccurate).

You feel behind because you only know how to read the current scoreboard, and scoreboards are just snapshots of a specific moment. They can tell you exactly where things stand right now, but they're terrible at predicting what happens next.

Cassie's timeline

This isn't a story about me winning and Cassie losing. We both ended up winning.

She's still working at the same flooring company and living in Ohio 18 years later. And she's thriving. She found her thing early on and has been building on it for almost two decades. That's a career almost anyone would be thrilled to have.

Cassie wasn't ahead of me at Bar Louie. She was just earlier on her timeline. And I wasn't behind. I was just a bit later on mine. Two completely different trajectories, pacing on different schedules. The comparison that felt so devastating at 27 turned out to be meaningless. I was comparing two people on completely different paths using the same measuring stick, and that ruler couldn't capture what would eventually happen for either of us.

I didn't start building my online business until my late thirties. Almost any snapshot of my career along the way could have looked behind compared to someone else. In retrospect, the timing was exactly what it needed to be. I just couldn't see it while I was living it. I'm not sure anyone can.

The bottom line

The worst thing about feeling behind is that it makes you rush. I know because that's how I responded.

After that conversation, I jumped at an open Territory Associate job in St. Clair Shores, Michigan, with a big medical device company. It actually paid $5K less than what I'd been making before, but I took the role because I heard reps got their own territories after a year and "made the big bucks." The rep I was supporting made $600K, and I'd never heard of such a thing in my life. So I chased it. I took the pay cut to chase someone else's number.

And when I finally got my own territory in Allentown, PA, I ended up getting fired again. So there I was, back where I started, in another small town I didn't like, and feeling even further behind than before.

Careers, businesses, and even relationships don't follow straight lines. They can flatline, or dip, or stall for what feels like forever before they compound into something massive that nobody saw coming.

If I could go back and talk to my 27-year-old self, driving back to Toledo on Route 23, I wouldn't tell him to work harder or find a better strategy. I'd tell him the scoreboard is going to start looking wildly different in a few years. That he doesn't need to compare himself to anyone other than previous versions of himself. And that he has no idea what's coming. But I'm not sure 27-year-old me would have listened to any of that.

So here's my question for you this week: Where in your life are you rushing because you feel behind? And what would change if you stopped comparing your timeline to someone else's?

Reply and tell me about it. While I can't reply to everyone, Jennifer and I read every response, and we love to hear from you.

That's all for this week.

See you next Saturday.