A good friend of mine – someone who has worked with me, served as a mentor, and shaped my career- recently commented that I am afraid to take chances. In my head, I thought that it was precisely because I took chances that I allowed him to influence me the way he had; I accepted new roles and grew into management by saying yes to the challenges he laid out for me.

I responded to this friend by saying that I take chances when the circumstances are suitable for them. One has to question, however, how much of a chance something is when I’m waiting until a situation favours its outcome. (Mathematically, I am still exposing myself to risk if the outcome is not assured. Realistically, I am being fairly conservative.)

When I think about why I behave like this, the temptation is to trace it back to how I was raised. I grew up in a home where both parents were not particularly adventurous; it felt like both of them were highly methodological and intentional with what they did. While in some ways, I had great freedom as a kid (e.g. no formal curfew, limited spending limits), the big decisions were often not mine. I didn’t have much of a say when I was enrolled into Boy Scouts, nor in piano lessons, nor to the high school I attended. In some ways, then, I felt like I was deprived of some of the big opportunities to forge my own path and open myself up to failure.

Perhaps that was done for my “own good” and out of love. (I’d certainly like to believe it was.) But being able to experience, handle, and grow from failure is an essential part of life. At work, despite prevailing pressure to expand quickly and capture as much revenue as possible, I maintain that growth has to be organic and that risk has to be contained. In a business context, there’s the adage to innovate when the cost of failure is low. Not everyone sees it that way and I often get really stressed out because, at the end of the day, it’s often up to the engineers to make good on new business deals. Unless the engineering staff is scaled appropriately to the work, there is a real concern that we’ll fail our existing obligations. But maybe some failure at work is a good thing, too. I can’t always protect people against themselves, so allowing them to experience the consequences for which I think they are singing up may encourage them to reevaluate their perspective. (Does this make me a bad team player?)

The personal trainer I occasionally see often reminds me that he wants me to fail; if I always finished the prescribed number of sets and reps, it meant that I didn’t push myself hard enough (which then reduces growth potential). This all makes physiological sense but it’s still hard for me to come to grips with it. When I don’t hit the numbers, I don’t get 100%, and I feel bad about it. Maybe it’s because I was born to two somewhat stereotypical Asian parents who indoctrinated a higher-than-usual value in marks and success that pervaded the rest of my life.

Recently, I have found myself consciously letting go of some of the control I exercise over my personal life. (That means I’m still in control, right?) Inspired by a friend of mine who embarked on a “Year of Risk” last year (which saw her move from Australia to New York with her husband, get a pixie cut, throw down in rap-offs, engage more strangers, and the like), I have started to open myself up more to both uncertainty and failure. At the heart of it, I realized (again) that life on earth is finite and, by limiting myself to what I know and to what I can control, I run the real risk of missing out on joy. Debbie Millman writes: “If you take away uncertainty, you take away motivation. Wanting to exceed your grasp is the nature of the human condition. There’s no magic to getting what we already know we can get.” How great is that?

2014 is nearly half over, and this is the first post in well over half a year. But it is my hope that this is the first post of many more where I can share about how I’m continuing to grow, failure be damned.