It starts with just a single thought.

It might be a question: “Can I really do that?” It might be a self-imposed assumption: “Well, this is what I should be doing.” Or, it might be a secret confession: “But…I don’t know how.”

As soon as your brain has formulated itself around that microscopic idea, you’re in trouble. No matter how much you tell yourself it’s not true, or insist (rationally), that you ought to simply brush it aside, it’s stuck. When and where it’ll turn up next is just a game of chance. A roll of the dice.

From then on out, everything around you seems to confirm this irrational fear. All those little things that you tell yourself you don’t see only validate its existence: Your raison d’être. And so, what starts as a question slowly morphs into a half-truth, and then, like a snowball rolling down a hill, it grows bigger and bigger. Until one morning when you wake up and realize with horror that you’ve fulfilled that perverted destiny of what you’ve been afraid of all along: You aren’t good enough.

“Have you heard of impostor syndrome?” I ask, sniffling over my cup of coffee with my new companion, a 75-year-old former lawyer who happened to sit herself down at my table by happenstance.

“I know the word, impostor…” she tells me. I wave her off and explain.

“Yeah, that’s the basic idea. It’s this new thing people are talking about these days. In a sense, it describes the feeling of being put in a situation where you feel marginalized or isolated from everyone else, so much so that you wonder if you even deserve to be there at all. You might feel it if you’re the only woman in a group, for instance. Or maybe, if you’re the youngest person…” My voice trails off as my mind starts whizzing around me. I try to fend off tears and stay focused when she jumps in unexpectedly.

“Or the oldest,” she replies back.I recognize immediately that she understands what I’m talking about. And I’m grateful for it.

“I mean, maybe you felt that way, back when you were in law school. How many women were in your graduating class?” I ask her.

“Five,” she says.

“Out of how many?”

“150.”

“Shit.”

I take another sip of coffee. She goes on.

“Back then,” she tells me. “The thing they used to say to women lawyers was, ‘Well now…how does it feel to be taking the spot of a man at this firm?’”

“That’s terrible,” I say. She shakes her head.

“It’s not as bad as what I used to say in return.”

“What was that?”

“I’m sorry.”

She says it plainly, apologetically, even now. As she does, I can see it still affects her today to admit this. “I would say, ‘I know, you’re right, and I’m sorry to take their place.’”

Whoa.

We were a pretty unlikely pairing: Young girl going through a downward spiral of her own talking with an older woman still regretting and wondering “what if?” about her own career. After a few minutes, it was pretty clear that neither one of us was doing the other any favors. So, after a few minutes more, she left.

“I’ll be thinking of you in my thoughts today,” she said.

“Thanks for sharing your story with me,” I reply.

Fake it until you make it

It’s exhausting, keeping up with the perception that you know what you’re doing.

When you look at your own resume and think to yourself, “Huh. Well that’s a great sounding bio,” you know you haven’t fully internalized it yet. It’s easy to list out titles like trophies. It’s harder to own it.

I’m typically the type of person who only likes to talk about projects once I’m about 90% sure that I’ll get it done. Or, better yet, after I’ve already succeeded. It’s a smaller risk, of course. The potential of blowing everything up and failing is pretty low.

There’s a stat I read once, that men are more likely to apply for jobs if they only meet 6 out of 10 criteria, whereas women typically won’t apply unless they meet 10 out of 10. While I certainly can’t speak on behalf of all women, I personally feel like this example is part of the same problem.

I’ve noticed that I was acting similarly in meetings. In a debate or conversation, I’d rarely interject with a comment or question of my own unless I was at least 90% sure that it would “sound smart.” Others around me, I observed, were much freer in their commentary, perhaps more comfortable at a lower confidence threshold. I decided to commit to pushing my 90% confidence down to 80% and then maybe try for 70% and so on. But it’s a hard habit to break.

With most jobs in my life, I felt like I’d had some “practice” at doing the thing before formally claiming the job title. This is a pretty classic startup conundrum. You want the promotion? Great. Prove you know how to do the job, then we’ll give you the title.

Joining a non-profit board is not quite like that. You’re brought on partly for what you’ve done, but unlike a job title, inheriting a board title doesn’t really mean anything…yet.

“Whoa, you’re on the board of a new charter school?!” people would exclaim. “What are you doing?”

“Um, nothing…yet.” I’d reply.

“So what do you have to do?”

“I need to sort of figure that out. Let me get back to you.”

This confuses people. It also confuses me. I think they are expecting some loftier proclamation, some bravado, maybe a personal sales pitch. But more often than not, while I’m excellent at pitching the school, the mission, and the vision, I’m doing a terrible job of selling my own right to be a part of the project.

And meanwhile, I’m sitting here asking myself, “What should I be doing? How do I know, for real?” But while I’m stuck in this inner existential debate, one fact rings loud and clear: I’m wasting precious time in the waiting.

You are not alone

“You know how they say willpower is a muscle?” I ask, over a glass of wine with a friend, later that same day.

“Uh huh…” she says.

“Right. Well, with willpower, they say that the more temptations you have, the more things you have to say ‘no’ to, the lower your tolerance is, and then you snap. It hasn’t been talked about as much, but I think there’s a depletion effect to ‘self-promotion’ too. As in, the more you ‘fake it until you make it,’ the more it catches up with you, and the more likely you are to snap at the slightest sign of failure.”

“I can relate to that,” she admits.

“Why did I burst into tears while talking to this 75-year-old woman who just happened to sit down next to me? There is literally no good reason.”

“It’s okay, it happens to everyone.” (Does it, though? Really?)

“I’m just feeling really emotionally vulnerable right now,” I confess. “My threshold of tolerance has been obliterated. That’s why, all of the sudden, I just decided to unload all of my fears and worries onto that poor, unassuming woman who sat down at my table for coffee. I felt so bad for leaving that with all of my drama. In the end, though, we each triggered each other so much that she knew we couldn’t keep talking to me.” I sigh and take a sip of wine, then shrug my shoulders.

“You’re doing a great job. You know that, right?” she reassures me.

I take a minute before responding. “I know that logically,” I finally admit. “But emotionally, I can’t always keep up.”

This, in a nutshell, is the heart of it all. The core of what keeps us awake at night — this cohort of over-achievers who can’t stand to associate with any amount of mediocrity. The paralyzing degree of inaction that results from the fear of fucking up. It’s a dangerous thing, the spiral. If you can’t keep your wits about you, it will control you.

A few beats pass before she speaks up again.

“I’m glad you texted,” she continues. “The truth is that I was spiraling myself yesterday and didn’t reach out to anyone else. This is a good reminder that it’s okay to do so.”

Paying it forward

Not twenty minutes later, and I’m back home in my apartment, curled up on the couch with my cat, and my phone buzzes. It’s a new connection, someone hoping to move into the startup sector. I told her I’d chat today, even though I haven’t felt up to it. I wonder I’ll encourage or discourage her from getting into the tech industry.

In the end, I take the call.

“I’ve noticed that, even though I’m coming from a different industry, there might be a lot in common with the work I’ve done and the kind of things needed in the startup sector,” she tells me.

I’m equally impressed and jealous of her self-awareness and perceptiveness in this way. On a good day, the “in between” folks are my favorite ones to speak with because the conversations are never the same, their words not totally scripted. There’s something powerful and exciting about translating skills from one domain to another. It feels more authentic. Honest. Candid.

“This is really my first conversation to explore what else I might be looking for.”

And I recognize all at once that it’s not only my turn, but my imperative to pay it forward. I know I need to ignore whatever questions I’ve been asking myself and to just focus on answers, if only for this thirty-minute phone call.

So, I tell her what I know. How I got into this industry, the job I had before, the one I have now. And along the way, as I’m convincing this new person to trust me with the information I’m about to provide, I realize that I’m also rebuilding trust in myself, trust to step into the shoes of the person I’m telling her that I’ve become.

“I was feeling pretty bad about losing out on this one interview I had,” she says. “And then I had one other conversations, but the salary expectations felt so out of whack. They asked me back for another interview and I wasn’t sure if I should do it, but then a friend sent me your blog post. You know, the one about how candidates are interviewing companies, too? And then I realized, wait, I do have a say in this. So I’m going to really look for what makes sense for me.”

Fuck. I’m momentarily frozen. Here’s this person I’ve never met — quoting me back to myself at a point in my life when I’m already feeling pretty raw myself. If only she knew the day I had, I think. And even though she’s looking to me for advice, what she doesn’t know is that I’m the one getting a big payoff for offering it to her in the first place.

There and back again

Spirals go up just as much as they go down.

You might spiral down, but you can also spiral right back up. As soon as you tell yourself you’ve hit rock bottom — as soon as you’ve let that lowest low thought tap onto your conscious thought — it’s all up from there.

From then on out, everything around you seems to confirm this newfound acceptance. All those little things that you tell yourself you don’t see only validate its existence: Your raison d’être. And so, what started as a question slowly morphs into a half-truth, and then, like a snowball rolling down a hill, it grows bigger and bigger. Until one morning when you wake up and realize with astonishment that you’ve fulfilled that surreal destiny that you meant to be all along: You are good enough.

Originally published at Dry Erase.