On Making Big Career Changes

By Dann Berg

Published or Updated on

Wintery fork in the road Photo from Usplash

Most people hate change. Their initial gut response is that change is bad. A company redesigns its logo? Updates its app? Initial gut-checks usually lean fairly negative, even if hindsight tells a different story.

I’ve had many career changes in my life, and witnessed a similar reaction from those around me. The only real exception being my first big move — out of retail and into tech journalism — and that’s only because it’s a path many of my peers also hoped to take.

I was a staff writer for a couple years, first at Laptop Magazine and then at The Verge, and it just wasn’t for me. I was never able to push past the imposter syndrome, which meant I spent 5x as long writing articles that I judged to be 10x worse than anyone else’s writing. I imagine the objective reality of my writing was different than my internal reality, but I just couldn’t get the two to sync. So I made the difficult decision to quit.

I had made several decent friendships with other journalists, but staying connected after I left proved difficult. There were a few people who I actively tried to stay in touch with, but it felt one-sided. And so I naturally drifted apart from nearly all these colleagues, with mutual1 Twitter follows being our only remaining link.

Sometimes you lose old colleagues when you make big moves, and leaving journalism was a huge move. Nearly every single one of my peers from that time are still journalists. People just don’t have a model for what that new quasi-friendship/most-professional relationship should look like.

It was after leaving journalism that I found a career that really fit me. FinOps as a professional specialty was in its infancy when I first started, and I happened to be lucky enough to be in the right place at the right time.

The hard work I did at MediaMath, Datadog, and FullStory ended up giving me many multiples in returns thanks to the FinOps Foundation. The combination of working at a high-profile company, hosting the monthly NYC virtual meetup, and occasionally publishing content on my website helped advance my career even further.

But all that work has put me in a unique place as I find myself unemployed and meditate on my future career options. There are so many open doors in front of me2, and it’s important to make a decision based on what feels best to me, and what I really want my day-to-day work to be.

I’ve been thinking about my future both deeply and loudly. Since I was laid off early February, I’ve had career-based discussions with a total of 19 people spanning multiple companies and careers (thank you to everyone I’ve talked to!). It’s helped me navigate this period of abundant choice in a diverse and thoughtful way.

Some options are along the same path I’ve been following for the past decade-ish. Other options are down a different path. And it’s been interesting try to focus on any external pressures I sense as I feel out these different paths.

You can lose touch with people when you make big career moves. To begin with, these relationships are a mix of personal and professional, and when the dynamics of the professional relationship fundamentally change due to a big career move, the personal side must find a way to adapt and adjust or it will disappear. It’s real work, and takes effort on both sides.

My personal experience has taught me that when considering a big career change, you need to make sure you consider the move from all angles. But you can’t let potential consequences hold you back from making the big career change thats best for you.

  1. I say “mutual” here, but the truth is that most of them are mutual only because these former workmates never actively unfollowed me. A follow on another platform (ie Mastodon) doesn’t initiate a follow back. C’est la vie. ↩︎

  2. There is a massive article coming soon about all these possible FinOps career paths, as well as the pros and cons of each. ↩︎

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