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This is how to decide whether you’re ready to work for yourself

Whether the motivation is inspiration or frustration, branching out on your own can be both exciting and totally terrifying. Here are a few simple steps to measure your readiness.

This is how to decide whether you’re ready to work for yourself
[Photo: Christina Morillo/Unsplash]

Many of us have thought about being our own bosses at some point, says Josh Grau, a lecturer at Stanford Graduate School of Business and Northwestern Medill Integrated Marketing Communications Program. “Maybe that idea stems from a killer business idea you’ve wanted to execute. Or perhaps you have a challenging manager who isn’t enabling you to do your best work.” Whether the motivation is inspiration or frustration, branching out on your own can be both exciting and totally terrifying.

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So when do you know it’s time? Unfortunately, there’s no perfect answer to that question, but there are some things you can do to help make a more informed decision about whether or not to take the leap.

Grau says a great place to start is by making a list of what you really value about your work— such as culture, industry, role, and compensation—then ranking them in order of importance. “That can help you understand what are must-haves and nice-to-haves when it comes to your career,” he says.

For example, if you rank team culture the highest, then working as an independent consultant might actually be unfulfilling for you. However, if it’s a role like founder or CEO you’re after, then it’s probably time to think about entrepreneurship, he says.

“Of course, starting your own endeavor often means taking a major financial haircut, at least until you can raise some capital,” he says. “Even if compensation isn’t one of your most important work values, you should definitely take a hard look at your personal finances and understand how much time you can comfortably go without a steady paycheck while you pursue your dream of independence,” Grau says.

If this exercise reveals that you’ll be happiest going out on your own and that you can swing it financially, “then you need to have something unique to bring to the world,” Grau says. “Your area of specialization might be crowded with competitors, so it’s key to determine what white space you can occupy in a particular market,” he says.

“Identifying your unique audience and understanding their pain points will enable you to develop the best product or service and move towards product-market fit,” says Grau. “After you’ve answered those important questions and have iterated on your idea, you’ll want to develop a launch plan, as well as sketch out a longer-term vision of what a scaled version might look like if your pilot is successful,” he adds.

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Grau recommends putting together a group of advisers, both for guidance and networking. “Be sure to pick mentors who you know will give honest feedback,” he cautions. “If you can build a compelling story and win their support (and in some cases, their investment), then you’re one step closer to working for yourself,” says Grau.

Karina Sobieski, partner at Human Capital at SoftBank, says that you know the time is right when your desire for change overcomes your fears. “For me, I was being driven by constantly challenging myself with new, bigger goals and knowing I want to grow and learn. It all stemmed from my desire to make a bigger impact on the world, and I knew I couldn’t do that by remaining stagnant.”

There’s one important caveat that Sobieski underscores. “Don’t let others tell you whether you should or shouldn’t do this—it’s about the vision you have for yourself and the mindset you carry with it,” she contends. “If you can envision yourself going off on your own, then go for it,” says Sobieski.

She suggests creating the vision and building a plan first. Then, execute and don’t stop believing in your capability just because you hit bumps along the way, she says. “Surround yourself with resources to make this plan work, and then monitor all of this as you go,” Sobieski recommends. “If something doesn’t work, create a new plan and continue to execute,” she adds, “See this all as the part of your journey and take away as much as possible from the experience.”

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About the author

Lydia Dishman is a reporter writing about the intersection of tech, leadership, and innovation. She is a regular contributor to Fast Company and has written for CBS Moneywatch, Fortune, The Guardian, Popular Science, and the New York Times, among others.

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