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‘I Can’t Stop Comparing Myself to More Successful Writers!’

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I feel stupid even writing this because an integral part of my issue is that I never look to myself for answers, I always have to look to someone else, but here goes: I have crippling self-doubt that manifests itself in seething envy of others. I compare myself constantly to everyone and anyone else, and it causes me a lot of grief.

I’m trying to be a writer and am constantly comparing myself to writers who were hungry to break in at a younger age. Writers who are published now, struggling but excited, hip to the scene, comfortable, confident.

I am envious of smart people, people who went to grad school at a younger age (I am just starting to apply now and I feel old and insecure).

I am financially unstable and constantly compare myself to people who got out of school and pursued careers that now allow them to comfortably have things like nice apartments and furniture they care about and health insurance and yoga-studio memberships. I know these things will not fix it, but I can’t help but want the lives they represent.

I pursued, aggressively and stubbornly, a freelance position I no longer care for that is difficult to transition out of. I did it because it was hard to get in and I wanted to prove that I could. Well, I did. Now, I’m stuck and almost 30 and petrified that I won’t ever be able to recover the years I lost doing stupid things instead of focusing on something that could have brought me closer to where I wish I were now. I KNOW this is petty, I know this is silly, but it feels inescapable …

I feel like I made this massive mistake when I left undergrad and just started fucking around while other people were doing internships and building contacts and studying abroad.

I want to know how I can stop comparing myself to others and learn a little bit of self-love, patience, and respect for my journey.


In My Way

Dear In My Way,

At first, I read your pseudonym not as “In My (Own) Way” (see also: Sabotaging Myself, Blocking My Own Path) but as “In My Way” as in “I did it my way!” (see also: Frank Sinatra feeling himself, big time).

What would Sinatra think if he visited the Americana in Glendale, California, that outdoor mall a few miles from where I live, and he encountered an enormous water fountain gyrating and swirling to the strains of his signature tune? What would he think, sitting on the side of that fountain, being lightly misted by strange water-spraying arms that tilt and spiral as soulfully as Ginger Rogers, but also look a little like the haunted brooms that chase Mickey Mouse in Fantasia? I’ll bet he would get a slow, sinking feeling in the pit of his stomach that all of those glorious nights drinking and singing and playing poker and chasing broads with Sammy Davis Jr. and Dean Martin would boil down to this: a repetitive, warbling background for indifferent consumers trudging zombielike from the Sephora to the Top Shop to the Apple Store.

Nothing lasts, not even for the legends. From a certain angle, everything is empty and broken and nothing adds up. You work for years — to break through, to be seen, to be noticed, to be listed on some 30 Under 30 list — but you’re always late. Why are you late? Because you’re blocking your own path, of course. Because you lack the courage or the gumption. Because there’s something deeply wrong with you. While those talented Under 30 list members are cruising through their MFAs in Iowa, while those Under 40s are publishing their third, fourth, fifth novels and being celebrated at the book festival’s gala dinner, you’re delivering your pointless witticisms to a crowd of retirees in the “Lesser Known Nonfiction Flunkies” tent. You introduce yourself to someone at the cocktail party and they don’t care, no one cares. Or at least no one cares until you bump into that one writer whose book you reviewed not all that compassionately, and the writer is pissed, and you think, “Get a real editor next time,” but you say, “I haven’t reviewed a book in so long,” as if that makes up for anything. Who are you to judge? What makes you so great, anyway? You imagine that writer, reading your work and thinking, This is shit, shit, shit, overrated shit!

But chances are that writer isn’t reading your work at all. This is the beauty and the horror of being a writer — or trying to be anything, really: You can feel important or unimportant. No one cares. No one is watching. You can have fun or you can suffer. No one is grading you. No one is invested. You can proclaim yourself ahead of schedule, or you can spend your whole life telling yourself that you’re running behind. No one is there to measure. You can suspect that you’re insecure and outdated, long-winded and short-sighted, high-strung and lowbrow. Or you can conclude that you’re charismatic, a teensy bit talented, never boring, and reasonably worthy. You have choices. You are the decider. Because the truth is, no one else gives a flying fuck.

What are you doing right now? Are you really running late? Or are you doing it your way — your unique, slow, strange, panicked, bewildered, besieged, bewitching way?

How do you stop comparing yourself to others? You do it the same way you stop smoking: You just quit. You resolve to remove your insecure judgments from every equation. Instead, you observe from a distance. You reach for your compassion. And when you observe through the lens of compassion, you notice that the people with the nice apartments secretly hate their jobs, and the fast-zombies with graduate degrees secretly hate themselves, and the hip-to-the-scene writers secretly hate each other. These sound like judgments, of course, but through a compassionate lens, they’re just benign observations. All humans have their unique struggles.

So this is a major shift. Instead of going out into the world guided by your fear and your insecurity, you open your eyes and you calm yourself down and you pay attention. And you also pay attention to how much attention you’re already paying, to everything, all of the time. You pay attention because you are a writer. This is what you do. Your comparisons are just you, opening your eyes and then translating what you see using your insecurities as a lens. You are translating with your assumption, born out of your competitive parents or your competitive high school or your competitive college or your competitive soul (these exist — some souls are truly cutthroat!), that SOMEONE IS WATCHING AND MEASURING.

Take a minute and imagine this judge, watching and measuring. “She’s late,” the Judge in the Sky proclaims. “She has made many mistakes. She is ALMOST 30.” The crowd gasps, then giggles at how old, how late! “She is not special. She will not win prizes. They will not take her photograph, wearing something muted, hair up, serious look on her face, for the 30 Writers Under 30 issue of that important literary magazine. They will not invite her to speak or invite her to read or invite her anywhere for any reason at all. She will not read her novels or essays or poems out loud or workshop her plays or sell her screenplays. No water fountains will dance to the strains of her songs. No shoppers will gaze blankly at the new ten-inch iPhone 15 as her lyrics form a blanket of muddled shopping sounds in the background. She has failed. She is nothing and no one, and she has no one but herself to blame.

This week I had lunch with a friend who’s writing a play. She went to grad school right out of college while I was working as a secretary. Now she spends most of her time with her very young kids. She said to me, “It’s hard, because I have to push through all of the noise in my head, that I’m not good enough, that I don’t matter, that it’s way too late, that whatever I write is stupid and it won’t matter anyway.”

“That’s the way it is for me, too,” I told her. “That’s the way it is for everyone.”

“I just feel stupid talking about this with you, fresh from your book tour.”

“It was nice to travel,” I said. “But you and me, we’re exactly the same. You’re a writer and I’m a writer. And any writer who wants to draw clear boundaries between themselves and other writers is living in a very bad place. If you write, you’re a writer, the end. Prizes and distinctions and published books are nothing compared to figuring out how to enjoy the work itself.”

I asked if she was enjoying her work on her play. “I love it,” she said without hesitation.

“Then you’re in the right place,” I told her. “Whether or not you publish a thing, it doesn’t get any better than this.”

It’s not like I don’t have my insecure moments. It’s not like I’m not a snob. It’s not like I don’t read certain books out loud to my husband, in order to laugh at how COMPLETELY FUCKING STUPID they are. It’s not like I don’t have blood running through my veins. And I love writing book reviews, so I will probably write more of them. I love being a snob about quality and not feeling ashamed about that for once in my goddamn life. I love reading and knowing the difference between good stuff and total shit. (I love it! Yes, I do know the difference. It gets more and more obvious the older you get.) You can have a big heart and still care about these differences, and also care about making your own work as good as it can possibly be.

My friend knows the difference between good stuff and shit, too. We like to think that we’re both very good at this. We compare the good stuff to the bad stuff, all day long. We love comparisons. We even have a long history of comparing ourselves to each other. Our souls are pretty cutthroat. We grew up in tumultuous houses. We were sensitive and needy as kids. We turned on each other in high school. We lost touch in college. We came back together when we were your age, almost 30, and we had a lot in common, we realized. We were both arrogant and grandiose and neurotic and pretty disordered. We were both selfish and narcissistic and sometimes not so dependable. But she’d learned more quickly from therapy than I had, and she was the one who taught me to love myself, more than any other friend has before or since, by telling me over and over that it was normal to feel enraged and embarrassed and desperate and sad and ashamed. She would tell me to make some room for those things, at a point when I was trying to stuff big parts of myself under the floorboards. She would walk with me in the hills above Los Angeles and say things like, “Give yourself some time” and “Give yourself some credit” and “Give yourself a break.”

Give yourself a break, In My Way. You are doing this IN YOUR WAY. Celebrate your way. Enjoy your way. Savor your ugly used couch and your shitty freelance gig and your uncomfortable, awkward, never-hip-to-the-scene friends. But most of all, stop seeing the world through the lens of your fears. Invite your fears into the center of your life and address them, instead. What if you are nothing and no one? What if everyone else is ahead? What if a mean judge is watching from a throne in outer space? What if you are deemed inadequate, unimportant, tardy, tedious, middling, overwrought and underdone, insecure and outclassed? Does it really matter?


All that matters is that you enjoy your work. So learn to enjoy it, right now, first and foremost. One day, fountains will dance to your song and it will make you sad. Or fountains will never dance to your song and that will make you sad. You are the author of this moment. You are the center of this day. Stop looking over your shoulder. No one knows anything. No one is ahead or behind. No one is better or worse. You hold all of the answers. Learn to look inside, to hear your heart, to treasure what it tells you, in all of its uneven, fearful, bewildered, bewitching glory. Learn to honor your bizarre, freakish, amazing gifts. Once you do this, you’ll also learn how to honor other people’s gifts instead of fearing and resenting them.

Give yourself some time. Give yourself some credit. Give yourself a break. Do it YOUR way. Celebrate your cutthroat soul, on the page and out in the world, and SAVOR THIS MOTHERFUCKING DAY.


Order Heather Havrilesky’s new book, What If This Were Enough?here. Her advice column will appear here every Wednesday. Got a question? Email

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‘I Can’t Stop Comparing Myself to More Successful Writers!’