From the Archives asked

answered Oct 28, 2022

I'm reaching out about your article in Business Insider.  It really hit home.  I'm going through a similar phase in my life where I'm feeling burned out and questioning taking the "big" role.  I'm a CFO for an MSP.   Anyways, I'm at a crossroads because I'm seriously considering taking a step or two back in my career.  I really miss the hands-on work that I consider myself really good at.  What are your thoughts on going backwards in your career after having the big roles?  Do you think this is a mistake?  I'm finding that its difficult to find company's willing to even look at me for these mid level roles.   I'm not sure if its because they consider me "over qualified"?  Would really appreciate your thoughts.

Philip's answer

Thank you for reaching out. I struggled (and still struggle) with the same things.

It's hard to give accurate advice without knowing a person's situation more deeply, but I can at least speak from my own experience (which may or may not apply in your case).

First, the empiric fact is that the moment I added my Amazon warehouse job to my LinkedIn profile, recruiters stopped contacting me. And in social engagements, people get visibly uncomfortable, not knowing what to say, when I tell them I worked at an Amazon warehouse. These things made me feel a bit ashamed at times, but I forced myself to continue saying that I was, at first, unemployed, and then eventually a worker at Amazon in the warehouse. I talk more about the subtleties of all of this, along with my self doubt, in my podcast, Peak Salvation. It's hard to describe it all here, but if you're curious, please give the podcast a spin.

Second, there's the practical emotional side of stepping down. I saw former coworkers, even people who worked for me, get promoted beyond where I was in my career. I began to doubt my ability to get back into work. This doubt, by the way, got worse and worse as the months went by. When you tell people you've been "looking for the next thing" for a few months, it's no big deal. When you tell them you've been away from the industry for 18 months, people start asking what happened.

One particularly low point happened when I interviewed with Apple after being out of tech for more than a year. I tried to mumble and explain a few things about why I had left the industry, and what I hoped to do as an individual contributor on one of their small teams. At the end of the interview, the interviewer revealed that we had met previously. Apparently, when we first met, I had been the Site Director of Meta in London, reporting to the CTO; we had declined to offer this person a job because we didn't feel he qualified for an individual contributor role on the team. Now he was interviewing me as the lead of the team I wanted to join. I felt so ashamed. It's hard to describe how mortifying this was, unless you've experienced a fall of similar altitude.

If this were the classic American movie, I'd tell you that, after a period of struggle, I emerged happier than ever, glad I seized the narrative of my life and did what I wanted to, regardless of social opprobrium. That I slept well, resting in the confidence that what I had saved up to this point would last even through the types of economic circumstances that seem likely to develop in the coming months. That friends, true friends, continued to respect me and talk to me the same way.

But I don't direct this movie. It's an unscripted reality TV series, where every actor says and does what they want. I've made my choice, and I'm overall very glad I did, but I can't recommend it wholeheartedly to others without warning you that there may be some rough times ahead. Only you know what's best in your own situation.

Wishing you the very best in a tough world.

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