The Anatomy of a Career Pivot



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The Lowest Risk Path To Making a Career Pivot I’ve changed my career 5-6 times depending on what counts as a career change. Here’s a list of changes:

  • Changed to unrelated industries: finance —> space electronics —> internet content—> insurance

  • Changed how I work: employee —> freelancer —> employee —> freelance consultant —> founder/business owner

  • Changed roles: trader —> sales/operations —> writer —> GM —> innovation consultant —> CEO

Clearly not all of this was well thought out, but my point in writing this is that change happens: either we choose it or it is forced upon us.

I want more people to choose to change rather than be forced.

Whether you want to change jobs, change companies or blow it all up and work for yourself, change takes some thought and planning.

How you go about breaking your career depends on your risk profile, just like with investing. The more risk tolerant you are, the bigger, faster change you can make. If you have more obligations, children, expenses, the slower and more planned out this should be.

Maybe there are readers that feel like they can join the great resignation and quit their jobs cold turkey. I wouldn’t want to do that right now with three kids, a home and staring down the barrel of inflation and recession.

So we need a low risk approach to making a career change. Here it is (this has worked for me). At a high level here it is:

  • Extend your runway.

  • Be good at something (the bar is lower than you think. We are all good at something)

  • Figure out how that thing can be used in a different context, and prove your hypothesis (new industry, on your own, etc)

  • Give, give give to open opportunities.

Here’s the process from my own story.

1. Extend your runway. In startup financing land, a startup team is always trying to bring in cash (from investment or revenue) that covers their monthly spend (called “burn” rate) to get to breakeven. The amount of time until the startup runs out of cash and has to raise new investment is called the “runway”.

Similarly, you have your own income and expenses to manage. You need time to enact the plan above. There is so much talk online about “being bold” by quitting your job cold turkey to purse work you love. The cold reality is not having an income source even for a short time, puts you at risk. You can cut expenses and have savings, but the easiest way to keep your runway is to stay in your current job as long as possible, even if your situation is unbearable. This gives you breathing room and the ability to be patient as you work out how to enact your career change.

My latest career “break” was going from corporate consulting in insurance to becoming an internet entrepreneur. I hatched my plan and worked on it for a year and a half while still working my consulting job. I got the entire plan to where I was making the same income (but had more upside to working for myself). It took time, but I recognized that it was very important as a father and husband that I not take any unnecessary risks. It took more time, but I was more precise and executed the pivot the right way.

2. Be good at something. We all have skills. Figure out what makes you stand out. For so long I didn’t know what mine were. I built an anonymous survey about my skills and sent it to friends and colleagues. My biggest skill? Apparently I could get work accomplished with very little direction.

3. Figure out how that thing can be used in a different context. For me this was freelancing. Freelancing is easy because you simply take your skill from step one and find just one person or company that will pay you on the side for your skill. Now you’re a freelancer. Freelancing gives you a low cost, low risk way of figuring out if you want to work for yourself or not. Even more important, by finding and working for multiple clients, you build a portfolio of relationships and options for future employment. It’s an options-based approach to discovery of what you really want to do.

In discovery mode, you want options. Options lower risk.

In the ultimate move of naïveté, I stared a consulting business to “help startups”. My first startup failed. What the hell did I know about helping startups? But my intention was to build relationships with at least 3 growth startups and eventually join the one that was the best fit. That is a real options approach applied to career development!

4. Give, give, give. A good network generates options for you and opens doors. I don’t know anyone who has made a significant career change who has not leaned on their network. But, if all you do is ask your network for favors, you’ll end up shrinking it. You build a network by giving, not asking. When you give, people think of you when they have open opportunities.

The easiest way to give to your network? Be a connector. You know people. Figure out who should know each other. When you give enough, new opportunities find you, you don’t have to ask.

Within one month of starting my freelance business I had 3 clients. How? I had previously connected a few people in the Chicago startup ecosystem. When I told them what I was doing, they immediately connected me to a few opportunities. I was soon making more money than my previous job.

What’s Happening on the Pod? I was recently interviewed by Liz Herrera on the Career Coaching Podcast about job search tips for people over 40. I’m a strong believer in network, so I talk a lot about how to build a solid network.

My favorite question I got was what Inspires me at about the 36:30 mark in the video.

“Resilience is brilliance” is my motto and resilience is all about taking more control and dealing well with change or uncertainty. Goes very well with the topic of this weeks newsletter above!

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