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Dear Amy,

I would love to know your thoughts on being brave and believing in yourself. All of the women you feature seem so open to fear and failure, so unafraid. It’s inspiring but also makes me self-assess and think: what am I so scared of? I know that bravery comes in different forms, and that fear is natural, but when it’s stopping me from creating, then what should I do? How do you hush the voice within that tells you that you suck?

Yours truly,
R.

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Dear R.,

In 9th grade I had a creative writing teacher who told the class not to write about love. The next week she read us a poem about love that one of our classmates had written in defiance, called: You Told Us Not to Write About Love. It was a really good poem. The teacher was delighted with the irony, but all this taught me was that you can break the rules, but only if you can swing a good outcome.

I see examples of this everywhere. Like the woman who pursues a writing career and is regarded as courageous and inspiring if she gets a multi-million dollar book deal, but if she fails is called idealistic and irresponsible. Even worse, called ‘lucky’ when she does succeed. Or a male who leaves his high-paying corporate job, couch-surfs and spends all of his (and his parents’) money while developing an app that everyone says is stupid, then ends up selling it to Google and is celebrated on the cover of Fortune Magazine. I read these articles and think, what about the people whose shitty life chapters aren’t absolved by a happy ending? Of course, what I’m really worried about is my life. That I’m going to get stuck in the trying-really-hard-and-risking-everything part and not come out the other side. Just like how you read about these women who look like they’ve overcome so much and think: how will I ever do what I want with my life if fear is stopping me from even starting?

There are so many articles and endless advice about how failure is part of success, that fear is healthy, that it’s a sign you’re doing something right. This is all true. But then I think, am I messing up the right way? Instead of learning how to improve this site’s SEO and figuring out how to get people to come to our events, all I really want to know is, am I making the right mistakes? And while I’m worrying about the fact that I’m worrying about the wrong things, I do this:

Keep moving.

You can try to ignore the voice that says you suck, or scream over it with positive affirmations, but this doesn’t work for me. What does work is staying busy. I tackle small things and by doing one thing means I have to do the next thing. I focus on what I have to do instead of what I have to worry about. Fear festers when you stay still, but it doesn’t like being forgotten about when you are busy doing other things. Even if you are just pretending to forget about it. Start moving and stop worrying.

Learn to live with it.

When OKREAL was just an idea, I was so worried that no one would let me interview them for a website that didn’t exist. Some people didn’t, but some people did. Then I was scared that no one would come to my site once it launched. It didn’t end up on the homepage of a monolith website and get a million hits overnight, but people started coming. Then I was scared that no one would come to my first event, but when they did, I was scared that they wouldn’t enjoy it. And now I am scared that I need to keep growing, and mostly that I will get in my own way. I’m scared that I’m writing this while lying in the sun in New Zealand, because if I’m not working every night until 3AM in New York City and surviving off ramen while growing my business, I can’t be serious about it, right? Fear does not go away, it evolves. Sometimes your fears will come true. And then you will get over it and be scared of something else.

You get to choose what you’re scared of.

You mention bravery comes in many different forms. People might say I am brave because I am choosing to launch a startup instead of working full-time. But one of the reasons I’m in this position is because I am afraid of working for somebody else. Just thinking about it gives me anxiety. For me, bravery is a nice way of saying I was too scared of doing one thing, so I was backed into a corner of doing another. There are fears that come with working for someone else, and there are fears that come with working for yourself. You get to decide what you’re most scared of, and what you’re willing to sacrifice. OKREAL might not work out, but I am more scared of regret than I am of being poor and making a fool out of myself.

Do things before you’re ready to do them.

I used to waste so much time over-preparing. Like perfecting my pitch before I scheduled a call, coming up with an answer for every potential question, safety-netting myself against every possible situation. I had a nice collection of excuses to keep me in my safe place, too. And then I looked around and saw everyone getting on with shit, and became more afraid of being left in the dust than having my media kit ready before I scheduled a meeting. If you spend your time getting hung up on the details of how everything is supposed to pan out, you will never get anywhere. And you will annoy the hell out of everyone while you talk about this thing you’re going to do one day, but why you can’t do it just yet, but as soon as this other thing works out, you’ll be able to start. You need to have enough humility to iterate and learn as you go. Claudia Batten likens this to kayaking:

You know you are getting in the kayak and heading downstream, but exactly the twists and turns, how you will navigate through the rapids, is something you need to be in the moment for. Planning in advance is the basic element but not the whole. We know how to plan and it’s comfortable—but we risk getting caught in trying to make something perfect and never doing.

Prepare enough so that you don’t look like an idiot, and then schedule the call. Buy the ticket. Book the trip. It’s amazing what you can figure out when you don’t have a choice.

LOL.

When you ask yourself: ‘What am I so afraid of?’ what is it, exactly? If it’s about creating, I’m guessing that it’s the same as what everyone else is afraid of: I’m going to look like an idiot, I’m not capable, people will criticize me, no-one will care, I don’t want to take on too much, I’ll spend all of my time and money on something that has no guarantees. I’ve talked about writing a list of the worst things that could happen, and then what would happen, and so on. But if rationale doesn’t work, I try humor. I tell myself to lighten up, to get over myself. Am I really going to spend my short time on earth worrying that someone might not like a website I made? That some random person won’t agree with something I wrote? Or stay working somewhere I hate because I’m too scared to see what might happen if I try and do what I really want? We are here for the most minuscule flash, for who knows what reason, and we get to choose how we spend our tiny slice of time. There is nothing like a mortality reminder to realize that you’re being ridiculous.

I’m glad I’ve finished writing this response. I kept putting it off because I was scared I didn’t know how to answer it properly. Because much like writing about love, writing about fear is so universal it’s hard to say anything original. You might become an embarrassing cliché, or you might become a good example for how things work out when you take a risk.

Love,
Amy

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