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The Joy of Striving · May 13, 2026

When Comfort Became Uncomfortable

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The Joy of Striving · The Joy of Striving

I was a solid B student K through 12. I played sports but mostly sat on the bench. When I went to college, I had no idea what I wanted to do with my life. So, my grades sucked for two years. In my third year, something clicked. I was doing well in my computer classes, so I found a major. By default. More importantly, I also started leading student organizations that same year. I was finally starting to strive, even if just a little.

As graduation approached, I was ready to land my first real job. I bought the suit, attended campus recruiting days, and made a list of the companies where I would apply. My brother even gave me a leather briefcase — remember those? 🤣

But I stopped. I did the easy thing.

I went to work for my father. Not that he needed me. In fact, there was nothing for me to do there. My parents were great, but this just pulled me right back down into my spoiled childhood — only as an adult this time. And I knew it. But I did it anyway. I eventually found a way to add value to his company, which gave me the tools I needed when I finally found the courage to leave for my first real job. Which is what I should have done directly out of college.

I loved that job. And it loved me back. I was striving again. I quickly became a high-potential young leader. But when the president — who had become my mentor — took off for a better opportunity, I went back to my father’s company.

It was different this time. Really.

I had a specific purpose and some hard-earned success under my belt. We agreed up front that I would run the company as general manager and lead the charge to add equipment sales to his technical services company. I had never sold anything in my life, but I was up for the challenge.

I was Striving.

I tripled his revenue in three years. After five years, my father finally agreed to name me president — with one caveat. My older brother had to agree. No problem! Or so I thought. To my surprise, he didn’t. To make it worse, my father took his side.

I should have left that day, but I had just bought a big house I could barely afford. And a family of four to support. I earned every penny of my paycheck, but I knew it was bigger than I would likely get somewhere else — at least in the beginning. We were living beyond my “marketable” means.

I was stuck. I stayed five more years feeling diminished and defeated – which took a toll on every relationship. My parents. My brother. My marriage. When I finally found the courage to leave the company, my wife left me. Our marriage had been eroding for years, so this was actually the inflection point I needed. I was 36. Divorced. Essentially unemployed. And starting over.

I didn't find a job. I started my first company instead.

A single wireless retail store. I worked in that store for fifteen months to learn the business model. Then I bought another existing store with 100% seller financing since I had very little cash to bootstrap my startup. The same day I took over that store, I also opened a new third store. Thirty months later, I owned 11 stores.

Every day was long and hard. And yet, I was having the time of my life!

I didn’t always know how I was going to make payroll, but I always knew why I was there. That was the difference. I was driven by a meaningful purpose each time I found myself Striving — my first real job, the intentional return to my father’s company, and the wireless startup.

Contrast that with the years when I was uncomfortably comfortable. No purpose. No direction. No idea why I was there. Just feeling safe.

Years after selling both of my startups, I read a book that changed my life – The Happiness Advantage by Shawn Achor. He shared an idea from Aristotle that underpins everything I do today.

Happiness is the joy you feel while striving to reach your potential.

Not after. While. Don’t wait to be happy until after you’ve already made it. This type of joy is only accessible while you’re still in the messy middle of your pursuit. Happy people are more likely to reach their goals.

I even changed my license plate to BHAPPYR after I read that book, and it still reminds me every time I get in my vehicle today…

Never let comfort get uncomfortable again.

Not just at work. Throughout your life.

I was 25 when I lost 50 pounds and set a Big Hairy Audacious Goal (BHAG) — before I learned that term from Jim Collins — to live 100 Healthy Years. I thought that only meant eating right and being thin until…

25 years later I added exercise to my health plan. The first day I ran for one minute. The next day I ran two minutes. Three minutes on the third day. So on and so on until I was running 6 miles at a time. And then I added CrossFit for strength. Seven months later I ran the first of my many Spartan obstacle course races.

Spartan races are hard. Training for them is hard. That’s why I do them. Not to win. Not a final destination. The whole journey.

Overcoming obstacles is what Strivers do.

Keep Striving ✈️
Eric

👉 Read What Exactly is The Joy of Striving?

Read the original on joyofstriving.substack.com

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