Adapting or Choosing?

Through your career, have you changed your behaviors to fit into a career that excites you? Or have you pursued a career that excites you because of how much it fits your existing behaviors?

I have struggled with this paradox mightily throughout my career. Working at big companies, I saw what it would take to get ahead and often wasn’t willing to make the changes or sacrifices to become the person that would succeed in those environments.  

In the latest iteration of my career, I am thankfully leaning into behaviors that fit very naturally with what I love to do and what I am good at. This shift has been incredible for me. Work flows. It feels meaningful. It gives me energy rather than taking energy away. 

And yet, I carry some regret about my unwillingness to change or sacrifice in service of my career. 

Work is supposed to be hard right? Getting ahead takes sacrifice right? You have to EARN success right? These are the stories we are told. As I think about the choice I made to leave behind the world of leadership in tech companies, I wonder if I just “couldn’t hack it.”  Or was I just too selfish to make the sacrifices required to be successful?

What could I have built if I just… stayed later, worked smarter, managed up, influenced without authority, built a following, and followed all the rest of the cheesy but true business advice.

Don’t get me wrong - I am aware that all that sacrificing would have been to line someone else’s pocket. I’m aware that we are put on this earth for a short period of time, and that it’s about more than “line goes up and to the right.” But that doesn’t change the fact that I feel a sense of loss for what could have been and a sense of shame for not trying harder or doing more.

Why do I get to be the one who does a job that I like when so many people toil away in unsatisfying jobs? What privilege and arrogance do I have to have to opt out of a path so many would dream of? How is that even remotely responsible or optimal?

I think what happened when I left the traditional path and started out on my own was I finally realized how little traditional “success” in the corporate sense of the word mattered to me. And simultaneously I realized all of the ways struggling for it made me unhappy day to day. And even if I changed a ton to meet the moment (which would have been very painful), the result would have been a bit more money and a lot more stress.  Woo!! Looking back, I am glad I didn’t take that deal.

Now of course, being an entrepreneur hasn’t eliminated this dilemma for me. While for the most part I am doing things I love, running a business comes with all sorts of unpleasant work that I have to contort myself into doing. But at least I know it is in service of something I really believe in.  And it is thankfully a much smaller percentage of the work I do day to day.

Would love to hear your experience on this topic - it’s one I continue think about all the time.