Reinventing your career

Lessons learned from hitting the career reset button

👋 Hello to the 483 Intentional Wisdom’ers receiving today’s newsletter! If you’re new here, welcome! So this week, I spent a lot of time thinking about the idea of reinvention, specifically when it comes to our careers. I shared the thread below on Twitter, and judging by the ~100 new followers I gained, I’m thinking that it’s a subject that hits home for a lot of people. As such, I’ve decided to dive in a bit more and see if I can’t provide a useful bit of insight or two on the subject based on my own experience. I hope you enjoy.

The big idea 💡

I remember wondering if I had just made the biggest mistake of my life.

There’s thinking about quitting your job and then there’s actually doing it.

That day, one by one, I sat down with all of the senior managing directors in the equities division of the investment bank where I worked. And I told them I was leaving. After 12 years. Not for another job. Not to go across the street to the highest-bidding competitor like they were used to hearing. But leaving the industry. Leaving the region. Starting over. Gone.

The responses were varied. Everything from “you’re not thinking clearly,” and “how could you possibly walk away from THIS?” to “good for you, I’m jealous.”

It was terrifying and liberating all at once.

Despite fearing that I would live to regret “throwing away” all the hard work—including the 12 years I’d spent showing up to the trading floor at 6 am!—I felt deeply that it was the right move for me. And there were a few simple reasons why:

  1. Family — Hands-down, this was my top priority. My oldest child was less than a year old at the time and my wife and I knew we wanted to raise our family in a different part of the country, specifically in North Carolina.

  2. I had stopped growing — No one, and I mean no one should have been complaining about the role I had. I was paid very well. I had incredible perks (front-row seats at Fenway Park for client entertainment! I mean…that was actually pretty hard to walk away from…). And I had the full confidence of the firm’s top brass. But all of that gloss couldn’t cover up the fact that I was bored. I had stopped learning. And I didn’t feel like I was leveraging my true skills (in my case, writing), and each day that I stayed in the job I felt like a little bit more of my time on this Earth slipped away—time I couldn’t afford to waste.

  3. I saw what was coming — If I didn’t leave when I did, it was going to get harder, not easier to extract myself. The ‘golden handcuffs’ would get tighter—sure I’d probably make more money, but the expenses of my lifestyle would almost certainly rise in lock-step.

So it was time to go. And unless you want this to be a book instead of a newsletter, I’m going to spare you all of the details and point you to the “10 lessons learned” at the bottom of this article.

But I will say this.

  • There was fear. — Moving to a city where I knew literally no one, having no job, and no immediate prospects, and taking out a mortgage (just for good measure), can have that effect.

  • There was an identity crisis. — It was an eye-opening experience for me to understand just how much of my self-worth was tied to my job, and what a hit to my self-confidence it was to be “in-between jobs.”

  • There was a massive serving of humble pie. — Convincing people to have coffee with me; getting way too familiar with navigating HR gatekeepers; and ultimately, once I did find the right role, suffering through the inevitable pain of being clueless in a new job and a new organization.

But there was also:

  • Calm. — In knowing that I had been brave enough to get off the wrong path and was now on the right one, even if it might take some time to grow into it.

  • Excitement. — In being able to pursue a role that allowed me to learn, grow and sharpen the skills that I truly wanted to focus on.

  • Pride. — In having actually pulled the trigger on quitting something that from the outside no sane person would walk away from, but that I knew I was doing only for the money.

The point of this article is not to get you to quit your job.

Hitting the career reset button is painful. The grass is always greener on the other side, but when you get there, you often just inherit a new set of equally complicated problems.

Rather, the point is encouraging you to make sure that you are on the right path.

  • That means you’re engaged.

  • That means you’re growing.

  • That means your work is supporting the life you want to live outside of it.

  • That means you’re making progress in the right direction.

If you are, that is amazing. Keep going.

If you’re not, you might want to consider what changes you can make to adjust course.

And adjusting course may mean minor tweaks rather than massive, life-changing transitions. Today, there are so many opportunities to move from one role to another within the same company, or to develop your current role into something more satisfying.

Ultimately, these things we call careers are going to be over in a flash. I am over 20 years into my career. I can’t believe that. But it’s real. Time marches on. Relentlessly.

So if we want to get to the end and look back and say with pride “Wow. I did that,” well then, the time to ensure we’re on the right path is now.

Thanks as always for reading, and below is that thread from Twitter that I mentioned. — Greg


Thanks again for reading. See you next Thursday. — Greg


Image credit: Whrelf Siemens @ Free Images

Extra credit: The Gold Rush, Bad Science, and Mimetic Thinking

For your content diet nutrition, here are a few of the best things I’ve consumed recently.

Book: The Age of Gold by H.W. Brands — Just finished this epic history of the California gold rush and late nineteenth-century America. Was hoping to get a few clues as to how history might help predict how some of today’s gold rushes (crypto, the creator economy, etc.) could play out. I think I did. Will share more on this soon.

Podcast: Gary Taubes and Peter Attia on The Drive — I’m a fan of Peter’s and increasingly diving into Gary’s work especially as I’m experimenting with a quasi low-carb, keto-ish diet at the moment. But this one surprised me. It was a much deeper philosophical conversation than expected, covering everything from nutrition to bad science to what makes writing good. Two very smart people in a field where I struggle just to keep up.

Podcast: Luke Burgis and Jim O’Shaughnessy on Infinite Loops — I mean I just love everything the O’Shaughnessy’s do (both Jim and his son, Patrick). Is it too late to ask them to adopt me at 43? Listen, with all the life-extension talk these days, I don’t think it is. Anyhow, Burgis recently published a book called Wanting on the subject of mimetic thinking. I don’t claim to be an expert on this—at all—but just this small taste of the topic has me fascinated by the idea that our ‘wants’ or ‘desires’ are essentially learned behaviors and influenced by people we probably have no idea have this much power over us. I’m not doing it justice. Give it a listen. Read the book. You’ll get smarter. That’s my plan.

Anyhow, that’s really it! See you next week.