Pivoting Careers

Is there a limit?

I have pivoted careers 5 times. Since I was 22, I've been in hospitality, retail, SaaS, freelance filmmaking, and now — consulting. I am 37. Most people would have graduated college, nestled into their degree-based career, and would have been satisfied. But no, I have this urge to feel fulfilled and challenged while working, and when that feeling dulls, I pivot.

I am not the only one that pivots. People pivot when their career becomes unfulfilling or they want more of a challenge, like me. They also pivot because they see an opportunity for more money, growth, recognition, and a myriad of other reasons. I have yet to meet anyone who has pivoted as much as me, but I know they are out there.

The question that I pose today — is there a limit? Should we stay in our lane, doing a similar job for 40 years? Then collect a pension, a 401k, and of course social security, or your country's equivalent.

Curiosity

From my experience, pivoting careers has a direct correlation to curiosity. Most people that I know who have serially pivoted have craved more out of their careers. They wanted to learn new things, they wanted to be challenged, they wanted fulfillment. Most people just want to make it through the week. In order for you to seek more money, recognition, or challenge, you need to be curious about the opportunity for change.

Most adults are not curious. Based on this research study, less than 2% of adults are actually curious. If my theory is correct, that means a very small number of people are willing to pivot.

I can go on about curiosity, how to foster it, and how it is your most valuable asset, but I will save that for another edition.

How to Pivot

As mentioned, I have experience pivoting. How have I done it and have they always been successful? Most of my pivots were successful, with a few exceptions.

Like applying for that promotion, pivoting careers successfully requires you to do a lot of upfront work. Most managers will tell you, do the job you want. If you want to be a product manager and you're a designer, start approaching your problems through a business mindset. When going for that promotion, I do not think anyone should do more work than they are being recognized or monetized for, but you can shift your thinking towards the new role.

Pivoting requires that mindset, plus learning and practicing. So when I was a product manager and I wanted to be a filmmaker, I spent my nights and weekends reading, watching videos, and stowing away money for gear. When I knew enough, I bought some gear and took on free gigs. Once I started to become good enough, I started charging for my services.

While this pivot ended up being a bit of a failure, I learned a lot from it. I learned that some career pivots are not just a knowledge and skill problem. Depending on the career, you also need to have a certain type of personality. If you were wanting to pivot into sales, but disliked talking to people, I would not recommend it. For me, I did not have the ego-stroking personality for filmmaking. I couldn't make the talent feel the way I needed them to act. I had the artistic eye, the technical skills, and the grit, but that one piece was hindering me.

Once you have acquired the skills and tested your ability to excel at it, then determine if you should ditch your current thing and go all in on what is next.

Limits

So, is there a limit to how many times you can pivot? Absolutely not. Well, as long as you keep your curiosity sharp and are willing to put in the effort. Of course, age and situation play a part, but I have known people who were in their 60s and people who were in challenging life situations that pulled off numerous pivots with great success. If you are curious to try something new, even if the timing seems shit and the cards are stacked against you, don't give up. Pivoting is hard, you might fail, but when you do it well, you will thank yourself for not staying complacent.