There’s something strangely masochistic about confronting your fears. There’s enjoyment in bravery, sure—but also in the pleasant discovery that often, your fears are worse to anticipate than to actually experience. Accepting the inevitability of pain doesn’t prevent anything bad from happening, but it does give you something to bite on.

These are four fears that have come true for me. Maybe they won’t for you, or maybe you are scared of different things entirely. This exercise can help you create your own list: What are you freaking out about? Write it down. Following that, write down the worst thing that could happen. What would happen then? OK. What would happen after that? Keep answering yourself, as realistically as possible, until you reach the end. Given that you’re reading this from a computer / iPhone screen, I’m guessing that the end won’t be too morbid. So grit your teeth and let’s rip off the bandaid together.

1. You are not going to be taken seriously.

Yeah, sorry. Especially if you aren’t doing something explicitly clear, like selling a product that people can easily equate value with and understand. Oh, and being female and ‘sweet’ won’t help your chances. If you’re doing something creative, or anything to do with the internet, you’re going to encounter people who think your thing on the side is cute, or a hobby (what’s worse?). This is amplified when you’re in a situation outside of your social circle, and people ask ‘what do you do?’

The guts of this fear is not so much in what other people think. It’s a reflection of your own self-doubt. Some people are going to think you are a confused, delusional, idealistic type. And you have to be cool with that. You have to be quietly confident enough to not need others’ approval. With this in mind: you can never over-value the people who do support and listen to you, responding as if you are doing something important. When you are surviving on recycled self-affirmation, their encouragement is like fresh oxygen. Let them know.

Work on communicating what you do in a clear, succinct way, (even if you are still figuring it out yourself) for your own benefit. Being able to articulate what you are doing helps you form and distill your ideas. As Courtney says, saying it out loud makes it real. But do not waste your time waiting for others to validate what you are doing. Also: relax. You don’t want to be the person who takes their project so seriously they need to spend 5 hours describing it in detail, ensuring everyone understands it’s unique greatness and potential. Be cool. People who over-prove themselves are exhausting.

2. There will be a better version of your idea by somebody else.

This is a hard one to swallow, because your idea is special, right? There’s plenty of room for everyone until everyone is doing what you’re doing and then it’s all GET OUT OF MY ROOM. Resign to the fact that there is absolutely nothing you can do about this. Every second you spend looking at that other person’s shiny thing / scrolling through their million-follower Instagram / reading about their VC investment is one less second that you are spending on making your own thing better. The success of others is only terrifying if you decide it is. Keep your head down, and worry about the things you can control.

3. You are going to get rejected.

There is no way around this one. Let it sink in for a minute, because if this bothers you, you should get out of the game. Perhaps you’re a lucky one and rejection will only happens a handful of times. Or, you’re like the rest of us, and it will happen frequently. If you’re putting yourself out there, really going for it, your chance of rejection is higher. Of course, your chance of succeeding is also higher. For every wonderful person who believes in what you are doing, there will be 10 others who have said no, not emailed you back, said, ‘oh how nice, no.’

Sometimes you will take it in your stride and congratulate your nonchalant, thick-skinned self. Other times you will lie in bed at 3 in the afternoon with the sheet up to your chin questioning everything in your entire life. You have a choice here. You can say: this is when most people would quit. Or: this is when an invincible beast would suck it up and keep going. Up to you.

4. You will totally embarrass yourself.

The how and why will be your own glorious doing, but it will happen. You will say something stupid. Be misunderstood. Jump in too fast. If you’re creating your own path, messing up is part of the territory. You have to be willing to sacrifice your pride for the sake of your venture. This is not about you and your ego. This is about doing whatever it takes to get your thing out into the world. Your mission should be bigger than you are.

Resilience is the antidote to embarrassment. There’s also something liberating about forsaking a bit of pride. Not in the completely-shameless-what-is-wrong-with-you kind of way: you need to hone your skills at being tactfully fearless. This sounds like something out of Entrepreneur Magazine, but all it really means is to find the sweet spot between bold and gracious. Which is something you learn from messing up. And while you can’t prevent mistakes, you better be good at making up for them.

Amy Woodside


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