The best career advice

posted by Jeff | Tuesday, May 16, 2023, 6:53 PM | comments: 0

We are fast approaching the decade anniversary of my arrival in Orange County as a new resident. I think that even accounting for the 2009/2010 season, when I moved to Seattle with my new wife and had a baby, this has been the densest of my almost-five decades so far, in terms of change and life events overall. But one of the things that triggered the move was a conversation I had almost ten years ago to the day.

If you know me, you know that back then I had an unusual amount of access to the CEO of a then-billion-dollar public company. I didn't work for him, but I had a lot of contact with him, and he always answered my email. To that end, he became an unintentional mentor of mine. I really respected his path, even though it was not without its missteps. He made hard decisions, he empowered people and it seemed like his priorities were all correct.

So one day in May, of 2013, we're at an event, and in a break in the action, we get a few moments to catch up. He described the progress that he was making on a few fronts, and I told him I was working in a contract job that was lucrative, but I hated it. I said that we thought that we wanted to move to Orlando, and that we could do it without any specific plans. I also told him that I was flying out to Seattle in a week to interview at Microsoft again, despite not really being sure if it was even the right fit for me. It was a weird time. I didn't like what I was doing, but it enabled some degree of freedom to improve the situation.

He told me something that has stuck with me since. In fact, I heard him say it to others, and even in a public speech once. He said that all of the things that I was talking about regarding my career were "rounding errors" relative to the big picture. My contentment, and little family, including then-3 Simon, were the more important things. Yes, it's important that you can provide, but not at the expense of your contentment. There's nothing wrong with building a career, but as he said, you can get burned if you're just chasing the money. I was chasing the money in that shitty contract job.

That really settled it. We had to move. I couldn't deal with another Cleveland winter. There was little upside to staying.

I won't say that making more money is bad as you move through your career, but in the last decade, I've never actually changed jobs because of pay. When I left my first full-time job, it was a totally lateral move to a much smaller company where I felt I could have more impact. (That one didn't really work out, but chasing start-ups can be like that.) I am more aware of income than I ever was, but that's largely because of my failure to really save anything until my mid-30's. I can catch up if I remain disciplined.

I'm not going to chase money, but I'm not going to let myself be undervalued. That seems like the sweet spot, and that's the advice that sticks with me.


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