On fear of risk and failure


There was much talk at this year's Nonprofit Technology Conference about failure, the need for us all to more open to and about our mistakes, so others can learn from them. 

Unfortunately, there are obstacles in the way, preventing most of us from embracing this idea.

Supervisor attitudes are key

It's all well and good for those of us on the ground to feel okay about failure, but that's not going to get us very far if our supervisors aren't on the same page. Oftentimes in the nonprofit industry (and other industries), failure isn't treated as an opportunity to learn and grow - it's treated as One More Reason You Don't Deserve This Job. Our aptitude is often measured by how few mistakes we make, rather than by how many things we accomplish. It takes an open-minded supervisor to actively encourage a person to take risks - the kind that stand the chance of propelling the organization to new heights - even if taking those risks means the person will occasionally fall flat on their face.

I'm lucky that my boss has a good attitude about this subject. I talked to Casey about it yesterday, and he said, "Embrace failure and don't be afraid of it....but certainly don't try to fail." And, he would add, when you do fail, learn from it. Don't make the same mistakes over and over.

Escaping the comfort zone

While I'm lucky that I have a good relationship with my supervisor, and that my supervisor is open to the idea of failure as an inevitable and occasional occurrence, I admit that I still probably don't take as many risks as I should. There's a part of me that is very drawn toward maintaining the status quo once I get comfortable with a particular process. 

To that, Niccolò Machiavelli says:

"All courses of action are risky, so prudence is not in avoiding danger (it's impossible), but calculating risk and acting decisively. Make mistakes of ambition and not mistakes of sloth. Develop the strength to do bold things, not the strength to suffer."

In other words, comfort is the enemy of innovation. Risk is necessary, and therefore, occasional failure is an inevitable part of the path to success.

Realistically, how bad could it be if we fail?

And most of the time, our fears of the consequences of our failures may be blown out of proportion. I have yet to sit in a staff meeting where everybody bursts into this song: 

(Sing it with me, now!)

After all, mistakes happen. 

It's important to remember that, as the Sesame Street record told me when I was a kid, everybody makes mistakes. You just may not be noticing them.


We're particularly vulnerable to mistakes and failures when we're trying something for the first time, so we need to forgive ourselves when that happens.


Go forth and try something new today!

So my challenge to you is to figure out what is standing in the way of you taking more risks professionally. If it's management, consider taking lots of small, calculated risks to test things before diving in deep. If it's yourself and your own fears, keep in mind what I've said above, and then again, take lots of little risks before you jump into the deep end of the pool.