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Celebrating Setbacks · Jan 20, 2026

On Taking Control Back of Your Career: Reflection #13

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Lessons learned from an intellectual historian about why we should take career setbacks less personally — and how to restore your agency.

Whether you like or hate your job — or are currently working or looking for a role — we all have a lot of feelings about work. But how many of us know all of the intellectual and historical reasons why we might feel the way we do?

Last time, I had the pleasure of speaking with Alex Randall Kittredge. With his background in intellectual history, he distills complex economic and historical theories to help us understand why the modern economy is the way it is. He is a writer, strategy consultant, and spokesperson for the “portfolio career” —the idea of cultivating a variety of skills and income streams in your career, rather than being tied to one full-time job or company forever.

His newsletter, “ARK Strategy” — one of the fastest growing on the internet — has helped thousands of people dealing with layoffs and industry volatility to feel more empowered and in control of their professional lives. If you didn’t have a chance to read the conversation, you can see it here. Here are my 5 takeaways below from our fascinating conversation about work — and the history of it.

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#1: Your title might not always translate in your career, but your interests will.

Alex mentioned at the beginning of our interview that his childhood dream was to be a judge. Today, if you looked at his career — as an author, strategy consultant, and modern champion of the “portfolio career” — it might not seem like an obvious connection. But the fundamental skills he uses today are the same.

In college, he became interested in political philosophy— and this led him to grad school in England, where he became enraptured with the theory of “human capital” that developed in the 1960s. While the term might seem standard today to refer to the skills and training of people to make them more productive, it’s actually a fairly new concept. Previously, investments were only thought to be possible in physical things — like equipment — and not in our own knowledge or abilities. (This is where the idea of “invest in yourself” comes from!) Since then, Alex has studied extensively how this concept has shaped our world.

So one crucial skill of being a judge is there: understanding the ideas that shape our society and understanding how they should be applied to our actual world. I love that I could see that connection looking backward — because I know it’s an area that a lot of people struggle with, feeling like they aren’t tapping into the creative desires they had as a child or are doing something totally they didn’t necessarily plan on with their lives. But looking backwards applies more clarity about how your own story makes sense.

What did you want to be as a child? How might that inform what you do today?

#2: Don’t always take things too personally at work — there might be larger forces at play.

It’s so easy to take things personally when things don’t go our way — whether it’s in a company re-org, a layoff, a bad work environment, etc.

Alex shared a story about his first day at a college internship at Barclays, where he and all the other interns were excited to join the prestigious bank. But before their first day, they got a notice not to come in — and that their entire division was being sold off. They would be able to intern, but there would be no return offers. It was his first real introduction to the workforce —and many of the people mentoring him there were former Lehman Brothers employees, so they especially knew not to take things too personally, post the 2008 financial collapse.

Interestingly, Alex also mapped his own career ups and downs to the broader M&A cycle in the market — and they line up nearly perfectly.

Of course, it’s important to take accountability for what we can control — but some things, we just can’t.

#3: That said, be reminded of the control you do have.

I asked Alex how one could feel empowered when there were so many macroeconomic forces out of our control. His answer? The portfolio career. Yes, it’s partly about hedging your bets and developing a variety of skills so you’re not overly invested in just one skillset or job. But what I took away is that you are the owner of your career — not your employer, or the industry you work in. Even if you have a full-time job, and one that you enjoy, it doesn’t have to be the be-all end-all of your professional life. You are allowed to develop other interests and skills that seem different from what you do day to day.

Even that subtle shift in framing — that you get to sell your time to different organizations, and that your identity isn’t just based on the mercy of whoever happens to hire or not you — can make us feel much more empowered.

#4: You are truly not alone, even when it feels like it.

Alex talked about the lonely feeling of layoffs — especially remote ones, where you might be sitting in your home, alone, wondering what happened. While that might be a very isolating feeling, he shared that 25% of the workforce has experienced this type of job loss at some point, so nearly everyone has been affected in some way, whether it’s themselves directly or someone they love.

A major antidote to feeling less alone is being able to name what you’re feeling. And through Alex’s ultra-zoomed out lens on history and the economy, he’s helped thousands of people recontextualize the struggles they thought were unique to them.

Thanks for reading! What did you take away from Alex’s story? Comment below!

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