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How to branch out into a new industry without quitting your job

The author began a process of ‘prototyping’ different work experiences she was considering by shadowing or volunteering alongside an accomplished professional.

How to branch out into a new industry without quitting your job
[Source illustration: nadia_bormotova/iStock]
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If you’re stuck in a job you hate, you’re unfortunately not alone. In fact, astonishingly, more than 80 percent of Americans are dissatisfied with their jobs.

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I too was unhappy with the career path I entered just after graduation from university. Like many people, I’d put more thought and effort into getting the job than into figuring out if it was something I actually wanted. There’s plenty of research and advice out there on how to write the perfect résumé and ace that interview. But when it comes to figuring out what you want to do with your life, the strategies aren’t so clear.

I realized that although I could predict and pontificate about a career path that might make me happier, I’d never actually know until I was in the thick of it. I had an idea that I might like to do something related to entrepreneurship but didn’t exactly know what that meant. Did I want to join a startup? Start my own? Try to get into venture capital? Join or start a non-profit? Do international development work?

More importantly, I didn’t know how I could figure it out without a huge investment of time, like starting another full-time job with a new company.

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But then I had a different idea. I decided to enter a competition to shadow the founder of the accelerator 500 Startups. Being selected as one of the finalists gave me the kick I needed to quit my job, fly down to Silicon Valley, and begin what I call a “self-education program” on something they don’t teach you in school but is arguably the most important thing of all: what I wanted to do with my life.

What is that? I run my own company. I control my days and who I spend time with. My company makes a difference in the lives of our customers, staff, and community members — and has strong potential to grow. Sometimes I have bad days, but many are good. Certainly, there are many more good days than I used to have. And the work is fulfilling.

So what did I do during my self-education program? Over the course of a few months, I began cold emailing anyone I could think of who I was interested in meeting and learning from. To my surprise, I had a shockingly high response rate. I met with the founders of Airbnb, Square, Kiva, Color, and many more, and also with various investors and professors in the Bay Area. I asked them about their career paths, how they’d come to be where they were now, and what recommendations they had for figuring out my next move.

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And I didn’t stop there. I also volunteered at major conferences such as DEMO and Founder Showcase so I could meet more people and attend the talks for free. I checked out various events and lectures in the region, and even sat in on classes at Stanford University.

One of the most important conversations I had was with John Krumboltz, an international career expert who taught career coaching at Stanford. He shared an idea that stuck with me: testing out the different career experiences I was interested in, in the most low commitment way I could for each option. I had just been introduced to the entrepreneurial concept of “minimum viable product” — an interesting parallel, I thought — so I decided to apply these same principles to deciding what to do next with my career.

I began “prototyping” the different work experiences I was considering — dipping my toe in each, so I could figure out which I liked best.

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Using the tactic of cold emailing, I reached out to and secured “shadow experiences” with companies, including Launchrock (a 500 Startups company), Dojo, Causes (started by Sean Parker), Kiva, the Stanford d.school, and Ashoka (a non-profit that supports entrepreneurship). I spent one to five days with each company, not only learning from them but also assisting them wherever I could. At Causes, I helped produce reports for clients and sat in on strategy meetings and interviews with potential hires. At Kiva, the then CEO Matt Flannery let me follow him around for the day (the literal definition of a shadow) and experience “a day in the life,” complete with accompanying him on his daily walk in the park to clear his head.

So what did I learn through all of this? I realized that I wanted to pursue my own business as soon as possible. In one of the classes I sat in on at Stanford, the professor asked the students how they wanted the world to be different when they died. I knew then that not only did I want to be passionate about what I was doing—I wanted others to be, too. I wanted my business to do something that helped other people find and pursue career activities they were passionate about, and I’ve worked toward that objective ever since.

But looking back, I’m so happy I took the time to prototype my different career options and am grateful for the fact that it was nearly free to do so — much cheaper than an MBA, which many people say they take to figure out what to do with their lives. I learned more in those few months than I had in years. I realized I had created a career design process that others could use, leveraging principles from the quantified self movement, design thinking, lean startup methodologies, and more.

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And whether or not you can spare a few months off work, you can learn like that, too. If you’re not quite sure about your career path, you can pick a few things you think you’d rather be doing and then prototype them yourself by setting up experiences in which you can try out your different options. Find companies you’d like to work for and individuals whose career paths you admire and then reach out to them to see if you can shadow them. And don’t be surprised when they say yes, or even if many of these experiences lead to job offers — without you even asking for them.

One thing that really surprised me during my experience was how easily approachable, open, and helpful most people are. Cold emailing has become perfectly normal. This is the first time in history that people’s career interests and hobbies are listed online and are easily searchable—and it’s an amazing opportunity to create your own network.

Take it from me: if you’re trying to decide on your next step, it’s an opportunity you can—and should—take advantage of.

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Jennifer Turliuk is an entrepreneur, writer, and speaker who has been featured in the New York Times, Wired, Forbes, and more. She lives in Toronto.

Excerpt from How to Figure Out What to Do with Your Life (Next) by Jennifer Turliuk © 2021. All rights reserved. Published by Dundurn Press Limited.