I’ve been listening to a lot of podcasts by and about freelancers and entrepreneurs recently. Their way of making a living fascinates and attracts me (even though I can’t spell entrepreneur – that and “bureaucratic” get me every time!), and they have given me loads to reflect on in my own professional life. One of the key takeaways has been the importance of taking risks, even when you’re scared. This is an explicitly integral part of entrepreneurialism, which is helpful, because it means that entrepreneurs tackle head-on something which is actually a pretty important part of all our lives, personally and professionally. It can be hard – leaping off the metaphorical cliff takes guts – but it’s usually worth it. How, though, do you figure out if this is one of those times that will be worth it? And how do you get the guts to do it?

Identify the Fear

So here’s the thing about Fear: she can be irrational and she can be mean. In fact, it’s often hard enough to even notice a risky opportunity when Fear’s around, trying to swiftly sweep great ideas off into a corner, so I understand if putting a risk opportunity squarely on the table for consideration really seems to push Fear’s buttons for you. Thankfully, there are some great ways of sorting this out, the first of which is this: you’ve gotta ask Fear what she’s actually scared of. There’s a lot of kicking and screaming going on, but what is she actually scared will happen? “I promise you,” you could try reassuring Fear “I haven’t made any decisions yet, so tell me, what is it exactly that’s making you feel crazy? Is it fear of rejection or fear of failure? Is it fear of humiliation, fear of not being good enough or fear of ending up alone?” Get some honest answers.

Once you’ve got them, you can look at that fear squarely in the face and ask yourself four questions:

  1. How likely is it that I will be ______________ [your fear goes here]?
  2. By what mechanisms, exactly, is this most likely to happen? (“You’ll look stupid” isn’t good enough. HOW exactly might I look stupid? Is that really something that is normally considered stupid?)
  3. Is there anything I can do to make that outcome less likely?
  4. How bad would it really be if that did happen?

Greatest Gain, Greatest Loss

Once you’ve figured out what Fear is scared of, you can start to evaluate the risk realistically. It’s easy with risky opportunities to think we’ve got more to lose than we have to gain, but in practice this is rarely true. This is where a quick and dirty risk assessment can go a long way. The following chart gives you an idea of what I mean by a quick and dirty risk assessment.

Quick and Dirty Risk Assessment Chart wyldeandfree.com

Each of the columns has to be assessed separately, and then weighed against each other. For example, asking your boss to let you try something new at work might feel risky. She might say no. He might think you’re audacious. But what does a quick and dirty risk assessment show?

coffee with senior staff risk assess wyldeandfree.com

The likelihood of a terrible outcome is almost non-existent, a “bad” outcome is unlikely because even if your boss says no, he or she will probably think well of you for taking initiative, the likelihood of a good outcome is reasonable, and the likelihood of an amazing outcome is possible. You’ve got so little to lose. It’s so obviously worth it.

Some things I’ve learned:

  • The life-is-a-dream outcome happens way more than you’d think. I think Fear make us really bad at evaluating how likely people are to support us when we’re taking exciting and meaningful risks authentically.
  • Often, the most likely negative outcome of risk-taking at work is getting a “no” response to an idea, question or invitation, which, when you think about it, isn’t actually that bad. In fact, it’s more or less equivalent to the outcome of not taking the risk at all. You are left with the feeling of rejection or embarrassment to deal with, but that is usually manageable. The experience can even be re-framed: “I didn’t get this, but it was great practice and now people know I want it. I’m a step closer to my goal.”

Of course, there are times when it isn’t as straightforward as the example above. For example, there are times when the likelihood of a good outcome and a bad outcome are more or less the same. I remember supporting some young people to run a big party in our youth centre. The youth centre was in the middle of an area notorious for gang activity and youth crime, and the young people who would organise and attend the party had been threatened by rival gangs. The whole plan could have gone horribly wrong. The rough and ready risk assessment would have looked more like this:

youth party risk assess wyldeandfree.com

The chances of it going horribly wrong were definitely higher than the chances of it turning into a dream, so why did we do it?

What’s the Payoff?

There are three reasons we did the youth party anyway, and they are worth bearing in mind when considering being brave at work:

  1. There were risks to not doing it too. They weren’t so dramatic or fear-inducing, but we knew they were just as destructive. The young people would believe we didn’t trust them, and they’d be right, our youth programme would stagnate, we wouldn’t develop because any work with this particular group was risky, we’d get stuck in a rut…we’d find ourselves going nowhere.

What might the risks be for you of not taking risks at work?

  1. Sometimes taking a risk is worth it simply for taking the risk, even if it doesn’t go well. In this case, working with our team of young people and staff to do something huge together was a big deal.

Wise and intelligent risk taking can position you as someone people want to work with.

  1. IF, by the skin of our teeth, the youth party went amazingly well, we would have taken huge strides forward in what we were trying to turn the youth centre into.

Sometimes, however slim the possibility of it coming off, the ‘good’ or ‘best’ outcome is worth taking the risk for.

Sometimes, yes, success is a slim possibility, but it might be an even slimmer possibility if you don’t take the risk…and if it comes off, it might be incredibly worth it.

So in the case of the youth party, we put in tons and tons and tons of safeguards, prayed our assess off, and took the risk. The result? It came off without a hitch, it was one of the highlights of the six years I worked there, and I loved (nearly) every moment of that night. (Did I mention I enjoy adrenaline?)

My challenge to you is this: what risks could you take in your work that you might look back on as the highlight of your year? What risks you could you take, however small, that you might look back on as a turning point?

Image by Pixabay user Heike Georg