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Advice / Career Paths / Exploring Careers

The Risky Steps You Have to Take Today if You Want a Career You Love

No one I know has ever claimed that changing jobs, making a major career transition, and figuring out what it is you truly want to do is a piece of cake. While it may not require blood, sweat, and tears exactly, a career pivot undoubtedly requires deep self-reflection, hard work, and, drumroll, please: risk-taking.

Because you don’t know the outcome, taking career risks is scary. You have to get over the fear factor though if you really want to carve out a life you love, not merely tolerate.

I spoke with Wendy Sachs, author of Fearless and Free: How Smart Women Pivot—And Relaunch Their Careers, about this very thing, and I walked away from the conversation with a fresh outlook and tons of ideas for how this looks in real life.



The truth is, while a small handful of people may be considered extremely lucky, most of us don’t have awesome professional opportunities and dream jobs just falling into our laps. Our success and achievements aren’t handed to us on a silver platter. They are worked toward—and gained by risky behavior. (When you put it like that, doesn’t it start to sound a bit intriguing?)

Think small at first. You don’t need to quit your job, apply to MBA programs, or launch a business. You need to share your plans with your friends, family, and your network. You need to meet people who are doing what you want to be doing. You need to find tiny ways to begin moving in the new direction and away from where you’re now stuck.

  • Want to make a move from finance to healthcare? Volunteer at a nonprofit hospice center and get a feel for the organization.

  • Ready to ditch that career in advertising so you can start a wedding planning business? Reach out to a local wedding planner and ask if you can shadow for a weekend.

  • Thinking about turning your love of photography into a full-blown career? Take a class, buy a book, start an Instagram account and begin marketing yourself.

  • Ready to leave your job in book publishing for a full-time freelance career? Set yourself up to make this transition by taking on freelance assignments you can focus on outside of work.

  • Prepared to make the leap from business development to engineering? Excel in a side gig first to show you have the skills necessary to make the move.

Know that you may experience rejection—a natural part of any endeavor. Not everyone you tell your plans to is going to be excited for you. Not everyone you reach out to on LinkedIn or following a networking event is going to respond favorably; some people may not respond at all. It’s OK. It’s a part of the process. They key is to take those rejections in stride. Move on to the next person or ask, and keep your eye focused on the big picture.

The more comfortable you get taking small risks, the more confident you’ll become. And the more confident you become, the easier it’ll get to make those risks bigger and bigger. Plus, as Sachs points out, “confidence begets confidence.” At the end of the day, if you believe in the moves you’re making and you have faith in yourself, you’ll succeed.

Photo of woman making strides courtesy of sturti/Getty Images.