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How to Be a Risk Taker


How to Be a Risk Taker

Doing your homework and taking risks might be a better career strategy than slowly climbing up the ladder

I am a risk taker, and I urge others to take risks too.

That doesn’t mean I encourage hasty or reckless decisions. Mine have actually been pretty well thought out. But I do say: trust your instincts, listen to your gut, and take chances.

It is something that has worked for me, although it has also raised some eyebrows. Take my first job out of college. I went on countless interviews and turned down multiple offers. My family was about to have a meltdown. I remember my 94-year-old grandmother’s advice to “ … just accept something already.”

The jobs didn't feel right, but even I began to wonder whether I should settle. About that time, an interview at Bain Capital presented a great opportunity. I took it, and within three years I was doing marketing and event planning, serving on the children's charity committee, and coordinating recruitment efforts worldwide. I quickly realized to never settle. And I haven’t since.

Because of that, a lot of risk-taking happened during the following two years:

  • I left my family and a job I loved at Bain Capital to experience the West Coast, where I was technically unemployed for fourth months.
  • I accepted a job as recruitment coordinator at Google in San Francisco, taking a career step back for an opportunity at a great company. (I ended up proving myself and being promoted to recruiter within five months.)
  • I got a call from Bain Capital looking for someone to head up talent at a local startup. 

The call from Bain Capital threw me for a loop. Had I maxed out my risk-taking? I was settled and happy. But it was an intriguing prospect. I met with the startup company’s CEO and co-founder, debated taking on a bigger job role, and talked to a lot of people. I also asked myself one question: “Would you regret not taking this opportunity and just seeing if it's something you'd be interested in?” The answer was a resounding “yes.” 

It got me wondering: What does it take to be a successful risk taker, even if you weren’t born that way?

  • Weigh out your options
  • Talk and listen to others, bounce your ideas off mentors, friends and family
  • Have resources to fall back on, and a back-up plan if things don’t work out; be ready to adapt
  • Don’t burn bridges, explain why you are making your decision
  • Listen to yourself and trust your instincts
  • Live with no regrets; don’t be hard on yourself if it wasn’t the perfect choice

I’m not sure if I was born a risk taker. But I did learn early on how to be independent. At the age of 14, I was experiencing family issues and made a tough decision: move out of my house and live with my aunt and uncle to avoid the foster care system. Having to be independent at an early age gave me that fuel and fire.

When Bain Capital called, I did join the startup, and I am happy heading up the talent acquisition team at BloomReach. If you know you can do something and decide not to do it because you feel that another route is easier, you are cheating yourself out of something that could have been great.

Alissa Rogers '06 is Talent Acquisition Lead at BloomReach. She has seven years of experience in recruiting in financial and tech industries. She is originally from the Boston area and relocated to San Francisco in 2009. And yes, she’s still open to taking risks in the future…


by Meredith Mason  September 12, 2017

U.S. News & World Report ranked Bentley No. 2 among regional universities in New England and the Mid-Atlantic states, up from No. 3 last year, highlighting Bentley’s high-quality faculty and academic programs along with the strong value that students receive from a Bentley education.



Crain's | November 14, 2017
Huffington Post | November 13, 2017