The real downside is often tiny

We are extremely risk-averse, especially in modern society when we are so protected and stable. But things like fear-setting or defining the worst possible thing that could happen can be helpful because usually the worst outcome is not that bad. We are just a little too attached to and afraid of losing some money, losing a friend, or searching for a new job.

It's worth asking yourself, "What's the worst that could happen?", and genuinely answering it. The fear of losing your friend that leads you to avoid bringing up problems with them lessens when you remember that you'll actually be totally fine if you lose them. It feels like we need things to stay like they are, but these terrible things we imagine do happen and we almost always persevere. (And most of the time the bad things don't happen anyway).

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TLDR:

Right now you are fine. Every worry you had before now that ended up happening told you you wouldn't be. But you're okay. Our fears make things seem like they'll truly permanently harm us, but almost nothing does. You have truly overcome every single terrible thing that's happened to you to make it to this point.

Define your fears to overcome them. On the other side of fear is nothing.

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References:

The Almanack of Naval Ravikant

Realize that in modern society, the downside risk is not that large. Even personal bankruptcy can wipe the debts clean in good ecosystems. I’m most familiar with Silicon Valley, but generally, people will forgive failures as long as you were honest and made a high-integrity effort. -- Eric Jorgenson, The Almanack of Naval Ravikant: A Guide to Wealth and Happiness, loc. 482-84