'Am I Setting Myself Up For Failure?'

You'd better be.

New York Street with Moon (1925) by Georgia O’Keeffe

Dear Polly,

My question is simple: What would you tell someone who is about to enter a new decade?

I turn the big 3-0 in a week and a half, and though I thought I would be able to process this with minimal drama, I find myself spiraling. I know that 30 is still young (though if you want to emphasize that point, god, by all means). Most of my friends are a year or two older, and I'm extremely close with my sister who is six years older, so I in no way think you turn 30 and somehow fall off the face of the earth.

Yet there is a distinct sense of panic. My twenties weren't that great, or at least they weren't what I expected, and I think I feel scared about getting crushed by my expectations again.

I thought my twenties would be full of amazing friend groups and sparkly nights out and a big city on the East Coast and the fancy job to match. I thought I would be fabulously dressed all the time and finally learn how to walk in heels and look and feel like a supermodel. I thought I would find my person somewhere along the way.

Instead, my twenties kind of felt like a long slog, an uphill climb that wasn’t that fun most of the time and pretty lonely. I ended up in the South, far from my East Coast ambitions and my closest friends. I've never had a fancy job, and you could probably count my "sparkly nights out" on one hand. My dream of turning heads everywhere I go is long dead, as I've learned to accept I just want to be in casual, comfy clothes literally all the time. And finally, true love has proved elusive, though I managed to date a couple guys who either cheated on me or wouldn't commit.

I try not to minimize the very real progress I’ve still made, how I slowly figured my shit out, working hard to upgrade every few years to a better-fitting job or a nicer apartment, even if it all looked pretty lame from the outside. I've grown more into myself and realized what truly matters to me. I’m in therapy now and starting to unravel my lifelong perfectionism, the way my anxiety disorder can make things seem particularly bleak and my low self-esteem can complicate my relationships with men. It’s helping, though progress is slow and not always consistent.

In my thirties, I want to find my person more than anything, and yet online dating makes it feel like I’m trying to build a rocket ship to the fucking moon. If I could somehow find him, I know I would probably want a family. And yet my married friends who are 33 or 34 are constantly telling me about their fertility struggles and how they may have waited too long and how their chances are slimming by the second, especially if they want more than one kid. I do the math for myself and feel overwhelmed by how I'm already behind, how I'm so far even from the starting gate.

In my most fearful and low moments I imagine turning 40 and... nothing having happened. My life will be small. My life will still be the same as it is now. I know you can’t make guarantees to me, Polly. Maybe I will end up 40 and alone. But is there any advice you have for me? How do I expect the best — that my thirties could be incredible, a time when things that are important to me come together — without setting myself up for failure?

29 And Feeling… Not Fine

Dear 29AFNF,

Go ahead and set yourself up for failure.

Your thirties are all about taking risks that could fail. But you know what? Your whole life will be like that. It’s not age specific.

**Daring to pursue your truest desires always includes setting yourself up for failure.**

Does this require confidence? No. Does it require becoming an adventurous, bold person who isn’t ashamed of herself overnight? No. Does it require moving to a different city? No. Does it require staying in the same place, keeping your head down, and slowly building a life? Nope.

Do you need to find love in order to feel secure and also achieve your dreams? Definitely not. Do you need to give up on love in order to be joyful? Nope.

All you need right now is to set yourself up for failure. Tee off from the worst spot with the jankiest club. Die on the ugliest hill. Dive after two birds in the bush, miss them, then watch the bird that was just in your hand fly away. Piss into every wind.

And when you fail? Say to yourself THIS IS WHAT IT’S LIKE TO REALLY LIVE, MOTHERFUCKER!

Last year I felt like an idiot for moving across the country. Now I own a large yard full of encroaching weeds that I cannot maintain (#failing), my children are still angry at me for moving them away from their friends (#losing), and I’m preoccupied by trying to make sure that the best thing I’ve ever written is actually read by someone, somewhere, instead of being dismissed as “Bitch Hates Husband” before anyone gives it a chance.

I could conclude that this is what I deserve. After all, I’ve spent half a lifetime shrugging in the face of bad luck, growing defensive and dismissive, protecting myself, writing off the whole world, and now, just when I could feel defeated, just when I would normally crawl deeper into my hidey hole and feel sorry for myself?

I’m saying fuck no to that. There are birds outside my window, and a storm is kicking up outside. Today, I’M GOING TO SET MYSELF UP FOR FAILURE! Woohoo!

Why would I do that to myself? Is it because I’m confident, I’ve got some swagger, and I’m not afraid of looking like a complete dumbass? Is it because I am loved and secure? Is it because I’m deluded? Is it because I’m losing my fucking mind?

No. I just know what I value, and I’m going to fight for it, even when I look a little stupid doing it. I’m not going to let my self-conscious nature (still there!) or my fears (sometimes whispering in my ear, even now!) or my easily discouraged soul (picture Eeyore!) stand in the way of living the way I want to live.

It’s not about GETTING SOMEWHERE. It’s about creating a life that’s extra large and messy and full of love. Friends are showered in love, invited into the center of everything. Big dumb parties are quickly organized, even though the food and drinks are merely adequate. Hasty trips out of town are planned on a whim. Bright red lipstick is worn at unusual times.

But that’s not all. When my mom (who just turned 80 yesterday!) starts talking loudly about something that matters to her, I listen. When my husband busts in and wants to discuss uh drivers, nine irons? The information won’t stick to my brain because I can’t force my cells to care about golf, but I do listen to the emotional side of his golf, er, journey. And when my kid wants fake nails, I do not lecture or dismiss her desires, I treat them as legitimate and interesting.

Why? Because I give myself what I need, too, even when it feels a little stupid or selfish to my extremely sexist brain.

And because I know I want to honor the deepest desires of the people around me, even when they seem trivial at first glance.

AND because I realize that I’m setting myself up for failure at all times. My new friends might not like me (it’s happened before!). The party might suck. My mom’s mood could shift and we could get flinty with each other.

Here’s one small, vivid example of #FAILING: When I took my kid to get the fake nails, I was thinking: This is too expensive. She won’t like them once they’re done, causing an emotional meltdown. A nail will fall off a week from now, creating more trouble for me. I will have to drop everything to discuss her nails, a thing I don’t give a shit about that I already spent too much cash on. I am setting myself up for failure here.

All of these things happened. You might say it was all a huge mistake.

And it would be a big mistake IF I DIDN’T KNOW WHAT I BELIEVE IN!

Here’s what I believe: Teenage girls need to experiment with what matters to them, what makes them happy. (Ahem, this is about you, too, 29AFNF, so pay attention!) If something small feels exciting to them, it’s nice to be able to try that small thing, so they know how it feels to try it. Also, daughters need their mothers to have their backs about tiny things sometimes. They need to see another human being get invested in their desires. They need to WITNESS compassion in action, even when they realize deep down that their mom might have mixed feelings about fake nails.

Here’s another example of using your values in the world, even when you know you’ll fail: Yesterday, my two daughters were bickering and dismissing each other’s needs. I said to them, “You two have to dare to be vulnerable with each other even when it’s embarrassing. Instead of insulting each other, you need to say, ‘I want something from you,’ very directly, even when it feels awkward. Because when you practice stating your needs out loud to someone you trust, that’s good for you. I know it’s nearly impossible to do that with new friends and even old friends. That’s why everyone in this family needs to practice it here, where it’s safe, with each other.”

So even though I’m a shitty preoccupied loser who wants people to read her dumb book because she loves her dumb book so much it makes her cry every time she thinks about it? I’m also a mother who stops in her tracks and talks about what matters, even when it makes her kids feel slightly taxed to hear a little psychobabble out of the blue. I knew I would fail! I spoke up anyway.

That’s a lot about me, 29AFNF. I would give you examples from when I was 29 and I started spiraling downward — the risks I took, the controlling man I eventually dumped, the ways I stuck my neck out. But then I’d risk giving you the impression that YOU ONLY HAVE A FEW YEARS TO GET YOUR SHIT TOGETHER AND THEN IT’S ALL OVER FOR YOU.

And that is not it. That’s not it at all. You can dive into dating, freeze your eggs, make a hard and fast plan to try to have a kid by 33 and I would support every single one of these decisions. It’s smart to take fertility into account, for sure!

But here’s the main takeaway: Pursuing your truest desires is A DAILY CHALLENGE THAT LASTS A LIFETIME. I am 51 years old and I fucking CARE about my joy. Nothing is stagnant and settled and dead for me. Life is not about crawling behind glass and staying there forever, once you have ENOUGH.

Living an exuberant life is all about daring to set yourself up for failure, every single goddamn day.

When you move across the country and also when you open your mouth to talk to a teenager? You set yourself up for failure.

And when you install an online dating app? When you show up at a friend’s house feeling frazzled and meet an attractive single person and dare to talk to them?  When you research jobs in a big, exciting city where you might want to live? When you talk to your friends about your deepest desires and dreams? You are setting yourself up for failure.

Make this the year you learn to accept failure. Don’t just accept failure. Invite failure. While you’re at it, imagine people laughing at you – friends and strangers alike. Imagine a huge crowd of naysayers, rolling their eyes at how clueless you are. Imagine potential love partners thinking you’re too bossy, too needy, too tall, too short, too talkative, too shy.

Use your imagination to create a hostile world inside your mind. Because guess what? THAT WORLD IS RIGHT OUTSIDE YOUR DOOR. You cannot live in a fantasy world if you want to be happy. You need to live in reality - at least part of the time!

It’s more fun to live in reality anyway! Because you realize what’s happening around you. You can recognize that people are skeptical sometimes, and you KNOW that IT JUST DOESN’T MATTER.

PEOPLE WILL MISUNDERSTAND YOU. THEY WILL REJECT YOU. AND THAT’S COMPLETELY OKAY.

You know what you want more than love, 29AFNF? You want to become more daring. I hear that in every word of your letter. You want to live a more daring life. Your only problem right now is that you want to take big risks but also guarantee that you’ll succeed at everything, dodge trouble, protect yourself from heartbreak, win all the prizes! And that’s not possible.

So you’re not taking any risks at all.

You must do the opposite of what you’re doing right now. You mention your looks. This is an indication that you’re dissatisfied. Change a thing or two, to boost your confidence. Indulge yourself a little. Attractiveness is a value of yours. You care about aesthetics. You can love comfort and also love beauty! Do not succumb to idiotic binaries! Identify what you value and stand up for it.

You mention love and children. These things are extremely important to you. Make love a priority and accept that this prioritization will come with heartache, frustration, devastation, even. Here’s what it SHOULD NOT come with: The message that not finding love means that you’re unlovable. No!

Looking for love, valuing love, every day of your life, whether you’re 22 or 102, includes setting yourself up for failure. LOVE INCLUDES FAILURE, ALWAYS. This is my whole fucking book, man! It’s all in there.

There is nothing wrong with failure. Nothing at all. It’s not a mark on your character. It’s not a thing to be avoided, even. You are a vulnerable, big-hearted, exceptional human being who is still practically an infant at the tender age of 29. You have time.

But I have time, too. That’s another thing I said to my kids yesterday. They were expressing dismay that their peers in our new town have all taken many, many lessons of all kinds, which means they’re way behind on everything. I told them, “If there’s one thing I want for you, it’s the ability to start anything and be very bad at it at any time in your life. If it brings you joy to learn it, to do it, then you fucking do it. You can become a different person who loves different things AT ANY TIME.”

So listen. Write this down and tape it to your wall right now:

I WILL SET MYSELF UP FOR FAILURE.

Now, I know what you’re thinking. You’re thinking you’re not cut out to live this way. You’re thinking that you need things to be perfect or they shouldn’t happen at all. You’re thinking you’re too chicken. So listen to me: You’re wrong. It’s true that you will not become a new person, ever! You will feel fear. You will panic. You will wonder if you’re making a big mistake.

And are you making a big mistake?

I certainly hope so.

Will you keep making big mistakes?

God willing, yes.

And when you screw up, big time, you will thank the good lord for another day of daring, another day of fucking up, another day of everyone laughing at your stupid ass, and rolling their eyes, and protecting themselves from your dumb mistakes, talking shit about your bad choices and making them look foolish and sad to each other, because that’s what makes them feel a little better about what they’re too afraid to try, or say, or do.

They’ll make your choices sound immoral. They’ll make it sound stupid and embarrassing, to tell the truth, to be yourself, to honor your desires.

But you’re the lucky one.

Try to enjoy it.

Polly

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For fuck’s sake, buy my book and read it. And today, take some risks by opening your heart and seeing the needs and desires of the people around you a little more clearly. Thank you for reading and supporting Ask Polly. Sending you LOoooooOOOOVE!!!