This post on doing things you love even if you’re not good at it prompted discussion — or at least people asking me about doing things that feel scary or are hard. For most people, the challenges are internal.
Most people aren’t risking health and safety doing something like climbing Everest — they’re thinking of trying out for that senior position, singing karaoke, going to a gym for the first time, or asking that guy or girl out. Their risking losing social standing — aka embarrassing themselves.

Why people don’t try new things

Their biggest fears are based on beliefs of imagined futures. People don’t predict the future effectively, all the more when projecting fearfully, so they tend to project worst case scenarios. Even if they are climbing Everest, there’s a community there that will do its best to help them in life-threatening situations. If you’re doing something less life threatening than climbing Everest, your risks are probably more about embarrassment than safety. Even swimming across the Hudson River isn’t that risky, even if you don’t know the current or boat traffic.
If the risk is mostly in belief and perception, you can act on it. Only you can, and you’ve changed many beliefs many times in your life, so you’re experienced at it. My preferred way to pass a barrier, objection, or block is not to overpower it with brute force — impressive and macho as it sounds — but to lower the barrier. I prefer success to trying hard and lowering barriers has brought me more success than pushing hard against them. Besides, if you push hard on a barrier and don’t overcome it, you tend to reinforce it, even if it’s a belief you have all the power to change.

How I motivate trying new things

The first time I do something I like, I set low standards for myself. I want to motivate doing new things first, doing them well second. Sometimes I just want to learn I don’t want to do it again if I don’t enjoy it. My judging myself is usually the biggest obstacle.
What’s the value in doing things for the first time? Nothing inherently, but as much as I’ve done amazing things, I doubt I’ve scratched the surface of amazingness. I’m curious and my sense of what I’d enjoy or learn from has served me well. That self-knowledge and experience — I presume yours is similar — tells me trying new things my gut tells me I’d enjoy or learn from will benefit me.
The difference between doing nothing and doing something tends to be greater than between doing something at all and doing it well. Besides things tend to be more enjoyable when I don’t feel I’m being judged, even by myself. The more I reward I get from something, the more I want to do it again. The more I do it again, the better I get at it.
Besides, other people seem to recognize and value when you try something new, no matter how badly you do it. People seem to value people expanding their horizons than doing great at something they’ve never done before. In other words, our fears are overblown. They keep us from embarrassment but also reward.
Every case is unique, but I believe finding things you love is the best way to get great at them, and one of the best ways to find those things is to have low standards the first time.
So set your sights low enough to pursue that promotion and see how it goes. Sing that karaoke song however out of tune. Go to the gym even if you’re the least coordinated person there. Get out on the dance floor. Ask that guy or girl out. I bet you’ll succeed at senior management, singing, exercising, and relationships faster and have more fun in the process with low standards at the start than any other way.