The Joy and Pain of Taking Risks


Very few things in life come without any risk, and most of the really interesting things have a proportionally high risk associated with them. Being a web worker, for example, comes with significant risk, whether you are on your own as a freelancer, or working in a corporate gig where you need to be able to demonstrate that you can be just as effective when working from home.

We have to take some risks if we want to be successful and make our mark on the world in some way. If you don’t believe me, here are a few quotes from people you might recognize:

“Taking risks takes practice, and if we keep doing the same things we already know, in the same way, our willingness to dare to be different atrophies.” — Kathy Sierra
“Life is either a daring adventure or nothing.” — Helen Keller
“Only those who risk going too far can possibly find out how far they can go.” — T.S. Eliot
“I am always doing that which I cannot do, in order that I may learn how to do it.” — Pablo Picasso

I’ve taken my share of risks. Some of those risks have turned into amazing experiences, while we’ll refer to some of the others as great opportunities for learning. Some risks that have turned out very well for me: moving to California to take a job at Intel and letting them move me again to Oregon 6 months later; organizing some large events for the Portland technology community where hundreds of people were counting on us to pull it off’ co-founding a non profit; blogging; speaking at events in front of hundreds of people; and many more. I’ve also learned a few things from some of the risks that didn’t pan out as well: not every online community can be saved; the best technological solution doesn’t always win no matter how much you wanted it to succeed; and some projects just need to killed swiftly before they die a long, slow and painful death.

The key to taking risks is to keep things in balance without swinging too far toward either extreme. Don’t jump into something that involves a serious risk without at least taking some time to do a little research and think about whether you are doing the right thing. However, you don’t want to make the mistake of swinging too far toward the other extreme of  over-analyzing every possible outcome and missing the opportunity.

If you aren’t already a natural risk taker, here are some tips to get you started.

  1. Find some work that takes you outside of your comfort zone that involves both some risk and a nice reward, but that won’t leave you bankrupt or dead if it doesn’t work out. In other words, start with some small risks and work your way up.
  2. Do just enough research to make a smart decision about the opportunity. Don’t just jump in and do something stupid without at least taking a quick look at what you might land in after the jump, but don’t spend forever analyzing it, either.
  3. Ultimately, just do it. Try something and see if it works.
  4. If you didn’t have a wild success the first time around, learn from your mistakes, go back to step one and try again.
  5. If you were successful, go back to step one and try again with something a little bigger.

I try to make sure that I’m always doing something that feels at least a little uncomfortable. It is way too easy to coast along in life, but coasting is boring and not much fun. I’d rather take a chance and do something incredible (or fail miserably) and learn something new in the process.

How do you take risks?

Image by Flickr user lumaxart used under Creative Commons.


Pierre Khawand

Very insightful and what I appreciated most is that you put it in 5 Actionable steps, and recognized that this is an iterative process.

Angela Connor

This post really speaks to me, Dawn. I just accepted a new job as Social Media Manager at a great communications agency in Raleigh and while I am beyond excited about it, it is somewhat of a risk. I take risks by leaving my comfort zone. And when I do it I am always glad I did. Sometimes it isn’t obvious that the decision was right. When I left Florida to move to Raleigh it was a huge risk. And the man who hired me left three days after I arrived. But I took that lemon and made super-sweet lemonade. Risk-takers know how to adapt to their environments and make decisions they can stand behind, or even nix, when needed. Good post!
Angela Connor

Shankar Saikia


I remember watching the 1991 Texas-Miami football game at the New Years Day Cotton Bowl. I watched the game on TV still remember the Texas QB Peter Gardere’s shaking legs as he was taking snaps and getting beat. Texas lost 46 – 3, and I’ll never forget Peter Gardere getting beaten up on the football game (not literally, but with pass rushes, hits and sacks etc.).

Whenever I think of risk I think of a quarterback on a losing football team, of the responsibilities and burdens that rest on the shoulders of that QB. You know you are taking a risk when you feel some fear, you feel the trembling of your heart, and yet you have the responsibility to make things work. It’s an interesting conundrum: it’s a great feeling because of the potential rewards and it’s a horrible feeling because of the potential downside.

I know the feeling because I’ve been on my own for 28 months. There’s nothing glamorous about being in a risky situation – what keeps me going are the potential rewards as well as the fun of the chase. Every now and then I think of the shakes!

Ralph Leon

One way I take risks is by accepting projects at work that involve another department. I just don’t accept any projects, just projects that I know is out my comfort zone, but I know is doable. I agree with you, balance is key in taking risks. If the positive outcome outweighs the risk or is equally beneficial I will take it. Other wise I don’t bother. This is a great post, especially with the state of our economy. Enjoyed reading.

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