When was the last time you failed at something big?

We’ve heard the rhetoric many times before. Lawyers are risk adverse, we don’t make good entrepreneurs, we’re not good in business.

And it’s true. Most lawyers are overly cautious. It’s in our nature.

But without risk, there is no reward. As Robert Kennedy put it, “Only those who dare to fail greatly can ever achieve greatly.”

Fear of failure is the biggest obstacle to our success. But this fear is often unreasonable.

What holds us back is that we tend to overestimate the cost of failure. We imagine dire consequences and worst case scenarios that are greatly unrealistic in their scope and very unlikely to occur. (Researchers have found that eight-five percent of what we worry about never happens.)

We also underestimate the potential rewards of our actions. One good idea or relationship can make us rich.

It comes down to this: If you want to be more successful, you’ve got to try new things and take more risks.

If you try something and it doesn’t work, you learn from it. As Napoleon Hill tells us, “Every adversity, every failure, every heartache carries with it the seed of an equal or greater benefit.”

Okay, take more risks. Got it. But how?

I think we start by taking small risks more frequently. We get in the habit of regularly trying new things, things that might not work but which have limited downside.

We get used to the experience of failing often, but on a small scale.

As we see that most things work out most of the time, and that when they don’t we easily recover, we eventually take bigger risks.

In other words, we learn how to take risks by taking risks.

Start by changing the way you look at the ideas that cross your path. Instead of rejecting many of them automatically, as we both know you do, collect them and put them on a list called “maybe”.

Then, once a week or so, choose something on that list and try it. If it doesn’t work, if you hate it, if someone you report to says you can’t do that anymore, you will have learned something and you can try something else.

And whenever you feel the tug of fear that seeks to hold you back, remember what Mark Twain said: “My life has been filled with calamities, some of which actually happened.”