A friend of mine is really good at getting free things. Whether it’s an extra drink at the bar, a new product to try and tweet about, or a fun perk for her growing company, she always seems to have people offering to give her things for absolutely nothing (or at least for a significantly discounted rate). Not only has it gotten her lots of cool stuff, it’s gotten her far in the world of entrepreneurship.

I remember once asking her how she got so good at this, and she explained that she started practicing by going up to food trucks toward the end of the day and asking if she could have some of their leftover food for free. No reason, no excuse—just because she wanted it.

This might sound crazy—and many times she did get turned down—but sometimes she didn’t, leaving her with a delicious plate of food that she never would have had if she hadn’t asked.

But she wasn’t just doing it for the free food.

She was doing it to condition herself against letting the nagging thought of “but what if they say no?” stop her from trying. She was doing it to remind herself that, even if they did say “no,” she was no worse off, just at the same place she started. And she was doing it so that the next time she had to make big, scary, actually important asks, she didn’t let the fear of failure hold her back.

So, how can you develop the same gumption in your career (and life)?

The folks behind Failure Games think they can help you challenge yourself in little ways—like my friend did—to slowly grow a resistance to the fear of putting yourself out there and failing. Once you download the free app, you are given a daily challenge that you have 24 hours to complete and give photographic evidence of. These can be anything from giving $1 to a total stranger to grabbing a meal with a friend and ordering for each other—all designed to put you in slightly uncomfortable, out-of-the-ordinary situations and pushing yourself to do them anyway.

But even without the app, you can start to challenge yourself and grow your ability to push past fear. Next time you find yourself thinking, “nah, that’ll never work,” or “there’s no way they’ll agree to that,” try to push yourself to ask anyway. Sure, you might fail—but you might not, and you’ll never know if you don’t try.


Photo of person in parachute courtesy of Shutterstock.