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Career Bites #04: Be a Risk Taker

Picture of Angela Guido

Angela Guido

The number one regret of the dying is failing to live a life true to oneself. Living the life (and having the career) you want takes courage. Courage is cultivated by taking small risks, then bigger ones, and slowly transforming your relationship with fear. Want to become a Risk Taker? Do two small things today that scare you: speak up in a meeting, volunteer for a stretch assignment, or schedule an informational interview at your dream firm. When you live to tell about it, you’ll be eager to embrace bigger risks and make choices that are true to who you really are and not the you that others expect you to be.

More to chew on

Are you a Risk Taker? Would you call yourself a brave soul? Do you take calculated risks, or just jump in without fear of failure?

We all have at least one of those friends – you know, that person who’s always doing big things, following their dreams, and seizing the day. The Risk Taker. It’s the person who vacations in fun countries. The one who quit a six figure job to follow a less lucrative passion, but offered better personal opportunities for growth. The one who sometimes has to cancel your lunch date because he has a sprained ankle from marathon training, a ski accident, or a hip-hop dance move gone wrong. It’s the person you can count on to challenge you, the one whose company always leads to positive outcomes and, yes, adventure!

If you’re like most of us, you probably envy the Risk Taker a little bit. A source of inspiration to you and a reminder that life is short, their life might look messy at times, but you can tell they’re having a blast just being alive.

Not only do Risk Takers tend to have more fun than the rest of us do, but they are also less likely to suffer from regret.

Living with Expectations

Bronnie Ware, a hospice nurse, recorded the dying epiphanies of hundreds of her patients. In her book, The Top Five Regrets of the Dying, the number one regret she recorded was, “I wish I’d had the courage to live a life true to myself, not the life others expected of me.”

Everyone tells you to be true to yourself (including me!). But no one tells you that living a life true to yourself takes courage. That’s a revelation we tend to have too late in life. We tend to go with the flow without stopping to question if and when we should be swimming upstream.

Countless expectations befall us even before we are born. Our parents have big hopes and dreams for us, and these range from the vague: “I want her to be successful,” to the highly specific: “We come from a family of doctors and so of course that’s what he’ll be when he grows up.”

Then come the ideals of our teachers who want us to conform to classroom norms and perform well in our studies, and those of our peers who expect us to dress and act and talk a certain way.

Then pile on top of two decades of these amassed expectations the demands of employers: understand firm culture, work hard, don’t let them see you sweat, fear of failure, be scrappy, be polite, don’t be entitled, deal with negative feedback, do more, keep the status quo,  do good work but don’t expect too much praise.

By the time you are one year old, you’re swimming in a soup of hopes and ideals that others dumped on you. Never mind the ocean of potential risks you’re bobbing in by the time you have your first, second, or third job.

But this is all part of what it means to be human. It’s no big deal. In fact, it’s an asset. When other people expect great things of you, it makes it easier for you to expect those things of yourself. Parental pressure is a form of support, as is the prodding idealism of your teachers and mentors. You couldn’t have become who you are now without it.

You’ll never be able to stop the onslaught of expectations others have of you. And that’s OK. UNLESS, you don’t stop to examine, question, and challenge these expectations and decide which ones you want to keep and honor.


Here’s a really simple example of what I mean. My Dad always wanted to be a lawyer. He would have been a great one, and he considered it a kind of personal failure that he gave into his own father’s influence and became an engineer instead. So growing up, I always imagined I’d go to law school. It was my father’s hope that I’d fulfill the dream he abandoned. I never thought about it much until after I was admitted to three top US Law Schools. A law degree seemed interesting to me, but as I looked ahead, I couldn’t picture myself being satisfied with a legal career.

I decided to defer admission and take a few months to temp in a law firm and see what lawyer life was really all about. Within three weeks I knew I would never go to law school because that particular set of tasks and problems weren’t meaningful to me, and I am the kind of person who can’t work hard at a task I find meaningless (none of us can, actually). I would have made a miserable lawyer, and I knew it. I would have to find a new career path.

Thank goodness I had the wherewithal to stop and ask those questions. Although I never knew it, all that time, I was living up to my Dad’s expectations of me: ones that didn’t fit my own passions and interests at all. I was 24 when I figured that out. The process of examining and leaving aside the expectations of others takes a lifetime, and it is part of what allows us to achieve our full potential.

Courage Required

But the process of defying the expectations of others takes courage. There is no question about it – no matter what kind of relationship you have with your parents, friends, life partner, or colleagues, NO ONE likes courting potential failure, to disappoint others. You have to be willing to do that to live a life true to yourself.

And that brings us back to our Risk Taker.

What the Risk Taker has is the ability to try and fail, to challenge herself, and to live with the consequences.

What’s worse? A skinned knee and a bruised ego or a lifetime full of regrets? Surely we’d all agree that the latter is worse. The problem is, the downside risk always seems greater than skinned knees BEFORE we take the risk.

When I was four, my parents invited me to jump off the high dive at our local swimming pool. The high dive was three meters, roughly 10 feet high. At the time, that was five times my height. “When I’m five,” I said, imagining that time would never come.

Then five came, and I still refused to do it. I walked up to the edge, looked over, and made my mom carry me back down. Later that day, my three-year-old sister made the jump. Sibling rivalry is a great thing. I basically HAD to do it then.

I still don’t remember how I got myself to jump that first time, but once I did it, I wanted to do it again and again. I think I jumped 20 times that day. Eventually I was doing dives and backflips. Each of those was a new fear, but each one was less potent than the last.

This is how life works. If you’re standing on the edge of the high dive for the first time, it might certainly seem like the downside risk is death. But as the millions of people who jump of high places into deep water each year will tell you, it’s far riskier to drive a car in rush hour traffic. The actual threat of death or even serious injury is statistically insignificant.

When contemplating a risk, understand the true downside first. That’s an important step when facing career choices – speaking up in a meeting versus staying silent, volunteering for a project that feels out of your current league, or leaving a cushy job of a more adventurous one. Usually, you will find the actual downside of career risks is far less significant than the possibility of a lifelong regret.

But knowing the actual downside risk is low will not obliterate your fear. Because the mind doesn’t have that much power over our emotions. The threat of death feels very real when you are standing at the edge of a diving board, or contemplating quitting your job, or entertaining the notion of telling your parents you’re not going to be the doctor they always wanted you to be. Fear has this nasty ability to overpower our rational thinking.

But there is an easy solution to this problem. Take risks.

Living a life true to yourself takes courage. And courage is cultivated. You earn courage by confronting challenges and taking risks. When you do things that scare you just a little bit and survive anyway, you teach yourself to view fear as excitement instead of as a limitation. You turn that high dive jump from something that seems like a sure death drop into a sport and a pleasure. Chances of success? They just increased with your risk-taking growth mindset.

How to Cultivate Courage and Become a Risk Taker

Start small and then take on bigger risks. Here are some ideas:

In School

  1. Raise your hand in class before you’ve formulated what to say.
  2. Apply for that internship you feel unqualified for.
  3. Take that extra hard chemistry class instead of the basic one.
  4. Step up to a leadership role in a club you care about.

At Work

  1. Offer to teach a workshop or course in a subject you don’t yet fully understand
  2. Raise your hand for that hard project that interests you.
  3. Seek to transfer to a division, role, or geography that is more interesting to you.
  4. Look for your next step – the job that will keep challenging and rewarding you in the ways you want – and then actively go after it.


  1. Tackle a new physical challenge – A 10K, a Tough Mudder, a dance competition.
  2. Take a trip to a geography you’re unfamiliar with and where you don’t speak the language.
  3. Sign up for a class in something you currently suck at and that will require a bit of humility to get through – dancing, public speaking sleight of hand magic, martial arts, coding, whatever.
  4. Start a nonprofit or small entrepreneurial venture that lets you develop new skills and make new contributions.

Whatever you do, don’t settle for less than joy. Don’t waste your one precious life on a career that doesn’t fulfill you.

Living a life true to yourself is one of the greatest ways to maximize lifetime joy and fulfillment. Being a Risk Taker is but one of the ways to reach that destination (and one that makes the journey much more fun.)

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