I've changed careers 3 times and learned 6 critical lessons about work and life

Steven JohnThe author, Steven John, has changed careers multiple times, and now works as a freelance writer.
  • I’ve changed career tracks three times during my time in the working world.
  • Doing these vastly different jobs has taught me six key things about what it means to change careers and try vastly different professional paths to find one that fits you.
  • Though not all skills are transferable, experience can be an important benefit taken from each opportunity you have in your professional journey.
  • Visit Business Insider’s homepage for more stories.

Within a year of graduating college, I found myself on a fast track toward a mid-level management role with a major Los Angeles entertainment company.

I was going on business trips, meeting with executives from across the industry, and helping plan sizeable acquisitions of new ventures.

But it all fell apart when the head of my division was caught in an embezzlement scandal involving fraudulent invoicing and a cover company. My coworkers and I were shocked. My division was promptly shut down, and I was out of a job.

I was still in the first half of my 20s, and with a sparse résumé, there was no way I was going to find another position with the same responsibilities and pay as my old job. So I swallowed my pride and took a position as an assistant at a talent agency a few miles down the road.

After a short stint there, and then multiple years at another agency, I finally decided to change careers for a third time, working full time out of my house as a self-employed writer.


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It was a move that was equal parts liberating and terrifying, but I’ve come to see it as the best move I could have made. Only with the benefit of hindsight do I see how dissatisfied I was with both of my previous careers.

With that in mind, here are six crucial things I’ve learned about work thanks to my multiple career changes – things that anyone contemplating a change of scenery could use.

1. I couldn’t tell just how unfulfilling my work had become until I left it.

When I used to hear people say they loved their jobs – like, they genuinely enjoyed going to work – I was always a bit confused. Happy for them, sure, but a bit dubious, too.

After having changed careers multiple times, I see that I had been comparing apples to oranges, because I strongly disliked my own workplace and the greater culture beyond it.

Though I have been self-employed for nearly a decade, not a week goes by where I don’t see the clock hit 7 p.m. and think that, in my former role, I would just be getting dismissed for the day, just in time for a 45-minute drive home.

2. Not all skills are transferable, but all experience is.

Warehouse workerScott Olson/Getty Images

Like any worker, over the years, I’ve built up a body of knowledge relevant to my work. Switching to a totally different line of work rendered a lot of that information essentially useless.

But one thing that is always applicable from one career to the next is experience.

The abilities I honed, like being able to educate myself on previously foreign topics, work with multiple different personality types, and manage several projects simultaneously, have been a priceless and compounding asset.

3. You won’t keep most of your work friends after you leave a job – and that’s OK.

In my days at the entertainment agency, I had six or seven close friends in the office, and I was close with a handful of people who worked at other companies in the same industry.

We hung out at each other’s homes, went to bars and shows, and played beach volleyball every few weekends, too. At work, the jokes and chatter were constant.

But within a year of leaving the entertainment industry behind, I was only in meaningful touch with four or five of these people. And now, years later, though I am loosely in touch with some of the gang, only one former work friend has become a genuine, lifelong friend.


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I was surprised and somewhat saddened that I lost touch with some many people in such a relatively quick time. But I’m also clear-eyed about it. After all, it’s not as though I was constantly finding time to head downtown for lunches with my work friends, or making plans with them via phone or email, as opposed to just leaning into an office as I walked past for coffee.

4. Many companies are going too far in trying to control their workers.

I understand that a workplace needs to have certain systems in place to keep people on the same page and keep operations running smoothly.

But now with an outsider’s perspective, I can see that many companies have gone too far in how they control their workers.

In my last regular position, if I wanted to take a personal day or even a few hours off to go to the dentist, for example, I would need to fill out at least two forms have have a multi-step back-and-forth with HR. Taking a longer vacation? That required planning weeks out.

I remember once feeling genuine guilt for having to leave in the middle of the day as I was overcome with a high fever. I would think: “Sorry, listen, my vision is swimming and I’m sweating and shivering and I can’t really think right now. Is it OK if I head home? Sure, I’ll find someone from the mail room to cover my desk before I go – that’s exactly what I want to be worrying about right now.”

5. The way you use your time is immeasurably important.

These days, I work for about six hours a day, sometimes five.

But I get more done in any day now than I ever did when I worked full-time for a company. Sometimes I get more done in a day than I did in a week.

That’s because working from 9:30 a.m. to 7 p.m. for several years taught me how valuable time really is. So now when I sit down at my desk, I’m laser-focused and I work with only a few short breaks, like going upstairs for a cup of coffee and a piece of fruit.

That way, I can get done what needs to be done professionally and then get to all the other things in life.

6. It’s hard to see the writing on the wall unless you’re really looking for it.

Frustrated investorMario Tama/Getty

After working in Hollywood agencies for so many years, I made a conscious choice not to ever work in that field again.

But had my first real career not been cut short by my boss’ corruption scandal, I’m not sure I would have ever quit, despite my lack of passion for the work. The pay was good, but the fulfillment wasn’t there, and that’s a toxic combination for wasting years of your life.

Only once the rug was pulled out from under me did I realise I wasn’t where I belonged. It took switching careers to recognise that.

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