If you’re stuck in a job you hate, you’re (unfortunately) not alone. In fact, an astonishing more than 80% of Americans are dissatisfied with their jobs.
I, too, was unhappy in the corporate job I took right after college. 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 resume 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 would never actually know until I was into the thick of it. I had an idea that I might like to do something related to entrepreneurship, but I 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 abroad?
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.
But then I had a different idea. I decided to enter a competition to shadow Dave McClure, who runs the accelerator 500 Startups. Being selected as one of the top six 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.
Over the next 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 got to meet with the founders of Airbnb, Square, Kiip, Mint, Color, and many more, and also various investors and professors in the Bay Area. I asked them about their career path, how they’d come to where they were now, and what recommendations they had for figuring out my next move.
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 talks in the region, and even sat in on classes at Stanford (which the professors were kind enough to let me observe). Finally, to get a full holistic experience, I lived in a co-op in Palo Alto and had an amazing time learning about cooking, co-operative living, and alternative lifestyles.
One of the most important conversations I had was John Krumboltz, an international career expert who teaches career coaching at Stanford. He advocated an idea that stuck with me: testing out the different career experiences I was interested in, in the most low commitment way that 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 that I was considering—dipping my toe in each—so I could figure out which I liked best. Again using my favorite 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 1-5 days with each company, not only learning from them, but also helping them out wherever I could. At Causes, I helped produce success reports for clients and sat in on strategy meetings and interviews with potential hires. At Kiva, the 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 that they were passionate about.
Since then, I was accepted into an incubator called Startup Chile and an academic program called Singularity University (started by the founders of Google and based at NASA), which have helped me to work towards that objective ever since.
But looking back, I’m so happy that 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 say, 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.
And whether or not you can take a few months off from work—you can learn like that, too. If you’re not quite sure about your career path, pick a few things you think you’d rather be doing, and then prototype them yourself by setting up experiences where 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 with them for an afternoon, a day, or a week. Try informational interviews, volunteering, even internships, and more. 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, as has saying “I saw you on Twitter and thought you seemed interesting, so I wanted to reach out.” 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 beyond just the people you meet in person.
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.
Want help deciding on your next steps or prototyping your own career? Get in touch with me about my career coaching services at email@example.com.