A+ Roundtable: Our Favorite Mistakes

Mistakes, like shit, sometimes happen. You don’t mean to do it, but before you know it you’re two feet in already and there’s no turning back. A lot of times we think of mistakes in terms of regret or misfortune, but then there are those lucky miracles that – once it’s all over – you wouldn’t take back even if you could. This week we asked ourselves: What’s a mistake you’re glad you made?


Heather Hogan, Managing Editor

When Stacy and I found a litter of feral kittens on our back slab of concrete almost four years ago, I made the mistake of promising that I would get TNR certified by the ASPCA, trap them, have them spayed/neutered and vaccinated, socialize them, and adopt them out to other families. Because no one has more than two cats, max, especially in New York City. I did all the things I said — except the part about letting them go live with other people. After Stacy and I socialized them, we did adopt out one of them, who’d already become very loved by another couple on our block. Of course we kept the other three. And so yes we do now have four cats. It’s not easy; it’s kind of like running a zoo. But all four of them are so unique and wonderful and they make my heart so warm and full. I’m grateful every day that Stacy knew the mistake I was making and let me do it anyway.


June Gehringer, Writer

I don’t know how to answer this because I’m flawless and have never made a mistake in my entire life. Just kidding. I’m a messy bisexual and I know it.

Deciding to major in writing in college was probably a “mistake”. Everyone around me at the time seemed to think I was making a mistake. Growing up, I was strongly encouraged to pursue a STEM field. When I applied to colleges, I applied as a math major. Just before registration, I had a last-second change of heart. My parents didn’t understand what I was doing or why, but to their credit, they supported me in it anyway. I will probably never have the level of financial security or stability I would have attained if had I become an engineer, but I think I made my peace with that when I decided that I wanted to pursue writing as a career. Through my reading and writing, I have become an immeasurably kinder and more conscientious person. I don’t make much money, but writing has given me the opportunity to travel and build relationships with LGBT people across the country whom I otherwise never would have met. In terms of every conceivable American definition of success under capitalism, deciding to pursue writing was a huge mistake. I think that’s the best kind of mistake to make.


Carrie, Contributor

Having this essay be the first thing I ever published online was, shall we say, a bold choice. In hindsight, do I wish I’d built up a broader catalog first? Probably. Is it weird that some people will solely and forever know me as its author? Yes. Would it be a different piece were I writing it today? Absolutely. But am I sorry I wrote it? No.

Look — that essay, specifically, set me on the path of activism. If we’re being honest, I don’t think any other type of work could have given me that push. It introduced me to the disability internet and vice versa. Without that space, I wouldn’t be where I am now, doing the work I’m meant to do, understanding what I bring to the table and looking toward a more exciting future than I ever thought I had a right to. It blew up my life in the best way. Yes, it does make me squirm sometimes that such an intimate experience is just out there for anyone to find (and they do, and they have, and they will), but I think I needed to go that far to find what I wanted to say and needed to hear.

Also, it’s a great piece. Whatever.


KaeLyn, Writer

I’ve made at least four separate and serious plans to go to grad school that I didn’t complete. The first was applying to MFA programs right out of undergrad. I didn’t really know what I wanted to do after graduation, but everyone including my professors and parents was urging me to apply. I think I honestly didn’t want an MFA, so I applied only to private, super competitive creative writing programs at schools that only took 3-5 students each year. Thankfully, I was rejected by all of them. It meant I couldn’t afford my bills for a bit after college because I had no contingency plan, but it ultimately was better because I really didn’t want an MFA.

A couple years later, after being tired of working two jobs in two different cities and still struggling to keep my bills paid, I went all the way to the point of submitting reference letters for an MPA/MPP program a few hours away. I was ready to hit “send” and sure I’d get in when one of my employers offered me a full-time job. I took that instead and moved to Rochester, NY for the position. I only planned to stay here a few years. That was 12 years ago and I ended up making Rochester my long-term-and-possible-forever home.

About 10 years ago, I actually enrolled part-time in an MPA program in my city. I HATED IT and cut out after completing enough credits to earn a certificate in nonprofit management. A few years after that, I decided I was going to go into public interest law and my parents were so excited and bought me all these LSAT prep books and materials and gave me money to help with the fees. I did a bunch of informational interviews with nonprofit workers who had J.D.s and decided against it. I coincidentally moved into an advocacy job at a legal organization shortly after deciding against law school. Through working at a legal nonprofit, I realized I truly have no interest in litigating and, thus, can’t fathom paying for law school just or funsies.

Finally, a few years ago, I transfered my various MPA program credits into a hodge podge Master of Arts in Liberal Studies degree at a local state college. It’s kind of a random degree, to be honest with you, but it was inexpensive compared to any of my other plans and I did most of the remaining coursework online. :shrug emoji: I have some loans to pay off from the MALS and the failed MPA, but nothing compared to what I would have taken out if I went for the elite MFA or a J.D.

Having an M.A. lets me adjunct some LGBT culture courses at local colleges and gives me a little boost on my resume. I have no regrets about abandoning all my other carefully designed plans to execute the simplest, cheapest one. As Aunt Freckle says, “Sometimes things that are expensive… are worse.”


Alexis, Contributor

I accidentally came out to several people at once through a Creative Writing assignment during the second semester of my senior year of high school. I told my sister and my aunt recently about how some girls made fun of me afterwards, in a way that still confuses me to this day, but I’m still really glad I made this mistake. I’ve always valued being really honest in my writing, because I could rarely be honest anywhere else. When I wrote that story, I just wanted to write something I needed to read. And I did. I just forgot to change the pronouns and didn’t realize the entire class was going to be reading about a lesbian relationship (MY CRUSH WAS IN THE ROOM AND IT WAS SO OBVIOUS THAT THE PIECE WAS  ABOUT HER AND I’M STILL MORTIFIED ABOUT THAT PART). It’s one of my best mistakes. One of my favorite teachers was was reading the piece to herself and taking notes. Her only note at the end was “HOW COULD YOU LET HER DIE LIKE THAT?!”, which: 1) Guides all my writing and 2) Let me know that if no one else in this school was going to stick with me, she was. I learned a lot about the friends I had verses the people who were some kind of good to me just because it was convenient? or for a good laugh? It’s taught me to be as intentional as possible and has saved me a lot of time and heartache. (I’m still learning these lessons, but this is definitely the mistake that started it all.)


Valerie Anne, Writer

Wow have I made a lot of mistakes!! Thinking of one that turned out for the best, as opposed to the ones that haunt me every time I close my eyes, is tough! And I want it to be more interesting than “one time I accidentally ordered my egg and cheese on an everything bagel instead of a plain one and now that’s the only breakfast sandwich I eat” even though that’s also true. Okay, maybe it’s because I have the Sheryl Crow song stuck in my head, but I think I have to go with the more obvious one: the first girl I ever fell in love with was my favorite mistake.

I should say “mistakes” because a series of them were made by both parties over the course of our non-relationship. It was a mistake to let her hold my hand, it was a mistake that I didn’t kiss her when I had the chance. It was a mistake to believe her lies, it was a mistake to wait for her. It was a mistake to answer her texts, and maybe that email was a mistake too. It was a mistake (and a little on the nose) to go see “She’s Just Not That Into You” with her. Even though we both made mistakes by the dozen, my feelings for her were so overwhelming that they were a catalyst for my coming out. The heartbreak I endured made me stronger and smarter, I think. Or maybe it broke me forever, honestly who knows. At the very least, this particular mistake helped me connect to stories that otherwise I might not have understood on the same level. I needed to know that if I accepted the fact that I was a lesbian and came out to myself and eventually others, it didn’t mean I was going to be alone forever. I’m still not entirely convinced I won’t be alone forever, but at least now I know the reason won’t be that I’m queer.


Molly, Writer

There were choices I made at the end of my last relationship that were not great in retrospect — like agreeing to an open relationship when I had no idea what I was doing and knew the other person wasn’t being up and up about it. But now, with a year’s perspective, those are some of the best mistakes I made, because I’m in a much better place now, despite the horribleness that comes with a breakup. It actually was for the best, no matter how much I want to yell at that concept sometimes. At the time, they felt like the only choice I could make, but now I know that’s not true, they were the choices that extended the life of a dying relationship. It’s over, and I don’t have to make choices like that anymore. I can finally breathe.


Rachel, Managing Editor

One of my most charming qualities is how constitutionally allergic I am to admitting I’ve made a mistake at all; thinking even more specifically about a mistake I’m glad I made is difficult! This past year I got a divorce, which is generally understood to be a public declaration that marrying that person was a mistake. During a particularly tense conversation about the details of filing court paperwork for our months-long interstate divorce, my ex told me that getting married had been a mistake. “I don’t regret our relationship, but I do regret getting married,” he said, which was fair considering he was at the moment the one who had to try to navigate finding the clerk’s office in the courthouse and discover whether there was yet another set of papers we needed to fill out that no one had told us about. He apologized for it later, although I guess he didn’t technically take it back.

I’m not sure whether I regret getting married, or think it was a mistake — obviously I didn’t think it was something I wanted to keep doing, and it was bad for me in a lot of ways. At the same time, I’m not sure if I’d be where I am now otherwise, and I’m happy where I am now. I can mourn the things I lost or missed out on over that period of time while still being grateful for what it gave me. There are memories and skills and things about myself that I don’t think I’d have if I hadn’t spent the last six years the way I did. Ultimately it wasn’t right for me and I’m sorry that I hurt someone very badly by leaving and I’m sorry about a lot of it, I guess. Almost everything I was afraid of as a result of leaving that marriage and in some ways the marriage itself came true — I did have to depend on a lot of people in uncomfortable ways (and still do); it is almost impossible to afford living alone as a single person even in the Midwest; I do carry injuries from the whole experience that will maybe stay my entire life; I opened the door to break my own heart in wildly creative ways I’m not sure I could have even imagined. But I’m not sorry it happened. Even if I were, if I did want to take it back, where would I start? The courthouse wedding? When I said yes? When I moved in? When I started buying groceries for his apartment? Any of the hundreds of days before that? When I moved to the same city as him? When I left home? It feels like either all of it was something I regret or none of it was, and well, here I am!


Erin, Writer

I’m glad I moved to a city that I for sure should not have moved to, when I moved to it, and who I moved with. It was a terrible decision financially, professionally, emotionally, spiritually. However! Because things were so awful, and I’m talking everything, it forced me to do all the things that I actually need to do, like end my then-relationship, move to the city I actually wanted to move to, and get serious about mycareer™. Had I not moved there, I think everything else would have taken years and years longer, and what a continued waste that would have been. Or it would have never happened, because I decided to walk into a forest never to been seen again. The city was Nashville, by the way. Sorry, Nashville!


Stef, Vapid Fluff Editor

A cool thing I did was lose my damn mind in 2013, quit my dead-end job and move across the country to Los Angeles with only the barest bones of a job and no idea what the hell I was going to do. I knew my seven-day-a-week job was going nowhere and I was exhausted, then my grandma (my favorite person) died and one day I just… bought a one-way plane ticket. Long story short, I did not succeed. What I DID do was burn through my entire life savings and (at least temporarily) ruin my relationship with my parents. The job I’d planned on fell through, I couldn’t find other meaningful work and I ended up falling in love with someone who lived… back in New York. When I came back, I had an actual nervous breakdown and then my cat and I lived on a very patient friend’s couch for a couple of months while I struggled to figure shit out. It was not my favorite time in my life.

Looking back though, I think I’m still glad I did it; I gave something drastically new a shot, and I met a lot of wonderful people during my short but intense tenure out there. I love LA, but learned I’m not meant to live there. Also, my move back timed out perfectly with getting what turned out to be my dream job, and the career boost I’d been fantasizing about before my move ended up actually happening. Would it have worked out the same if I’d stuck around? I WILL NEVER KNOW.


Vanessa, Community Editor

This question sucks and I hate it, FOR THE RECORD. I’ve been texting Rachel for a solid three weeks complaining about this goddamn question. All my mistakes were terrible and I have awful anxiety so don’t worry, I do replay every single one over and over and over in my head on loop before I go to bed and as soon as I wake up and also whenever I’m slightly bored or vaguely alone, thank you so much for asking! So like, first of all, I don’t want to be prompted to think about my mistakes because I’m already thinking about them pretty much 24/7, and second of all, my favorite mistake? What does that mean?! I hate doing things wrong. I hate not being right. Did you know I’m a Capricorn? I don’t have a mistake that is a favorite, I hate them all equally and wish I could disappear when I think about them!

If I’m being slightly less dramatic (and thus 100% less myself), I can acknowledge that my favorite mistakes have always been relationships with other people. Was it a great idea to fall in love with a shy Leo who was still in love with her ex-girlfriend when I was leaving the country six months later? It was not. Do I think I really nailed it diving into a deep four year monogamous partnership with a Cancer right when I was trying to figure out if non-monogamy was the right lifestyle choice for me? Obviously no. Was it the best idea ever to get attached to a partnered poly Pisces, a workaholic emotionally unavailable Aries, a monogamous Leo who lives in the suburbs and is looking for a wife, and a 24-year-old Scorpio poet who is also looking for a wife during the year I resolved to be single and prioritize my own needs and my work above all else? NO IT WAS A FUCKING TERRIBLE IDEA, I KNOW, I REALLY REALLY HATE MAKING MISTAKES AND I UNDERSTAND I MADE A LOT OF THEM IN THE PURSUIT OF HEALTHY BOUNDARIES OKAY I KNOW. But I like being intimate with other humans. I value partnership and the things I learned in those relationships. I fucking love sex. So those mistakes are my favorite, if you’re forcing me to look at my life that way.

(But if I’m being real I don’t really view those choices and connections as mistakes, because anything I did that I overall don’t regret isn’t really a mistake. And, fucking hell, I am who I am – I will never regret taking a risk for an intimate connection, even as I work on keeping things casual and maintaining healthy boundaries. But! But – for the love of the goddess, if I tell you I have a girlfriend this year, please fucking shake me. Let’s learn from these favorite (not) mistakes, shall we?)

Before you go! Autostraddle runs on the reader support of our AF+ Members. If this article meant something to you today — if it informed you or made you smile or feel seen, will you consider joining AF and supporting the people who make this queer media site possible?

Join AF+!

the team

auto has written 766 articles for us.

25 Comments

  1. Uh, you know how you’re supposed to apply to college, like, while you’re still IN High School? 😬
    Or to make up your mind already about your future ahead of graduation?
    I kind of botched all admission deadlines to the American and British schools I might have gone to because I simply could not make up my mind and realised way too late that my hometown didn’t actually offer the translation course I did mean to apply for finally.(In my defense: Google wasn’t really a thing at the time)
    But then, my final exams went unexpectedly well.
    They asked me about a book I loved and I spent an hour enthusiastically acing the thing. With the unexpected extra points my GPA slipped into an entirely different territory..and I qualified for med school through my country’s lottery system in the fall.
    “So,”I thought,”while I’m figuring out what to do with my life, I might as well learn about it.”
    University is free in Germany, and they’ll even help with living costs, but you’re only allowed to switch majors once.
    I never was able to make up my mind about what it was that I REALLY wanted to do, or where I actually wanted to live,but in lieu of an alternative, I stuck with medicine until I would finally be able to make up my mind.
    I never did.
    Over half of the people I had started college with would drop out eventually, those who wanted to make money or were there for loftier goals almost all did, but me,almost twenty years later, I’m still learning about life.

    • I love this story and the randomness, at times, of life trajectories. Thanks for sharing, amidola!

  2. These are all so intimate and beautiful and I extremely strongly relate to so many of them in varied and unique ways. Thank you, as ever, for sharing and for letting us all see and learn about parts of ourselves, reflected back in you.

  3. Vanessa, I was nodding along enthusiastically through all of yours. Those mistakes need to be made sometimes!

    But I think my only ‘favorite’ mistake is the class I failed my junior year of college. It meant I had to retake it and thus mess up my schedule, and graduate a semester late. But in that extra semester I got to take some great extra classes, had an amazing social group with rugby and met friends who were studying abroad here, and was in my first relationship. That mistake may have cost me $5,000+ in student loans, but I wouldn’t trade it for anything.

  4. I suuuuper relate to the grad school thing. I definitely did the “spend like all my money applying to extremely selective MFA programs right out of undergrad and get rejected by all of them” bit. I later ended up applying to programs in a different field and got into almost all of them. My mistake, though, was accepting a place at a school under circumstances that were basically the worst I could have put myself in? This was several years after undergrad; I was in deep denial about being disabled, and essentially talked myself into every bit of the situation I almost ended up in. I enrolled at a school that was across the country where I knew no one (I’ve never lived outside the state I was born in), in a third-floor walk up with no elevator, in a city that was literally on fire at the time and has BOTH earthquakes and a nearby active volcano when I know that natural disasters are my biggest fear on the planet aside from failure/rejection???

    (It’s Portland; can you tell it’s Portland? love u Portland, but from afar, okay?)

    BUT… two weeks before I was supposed to leave, I had a complete breakdown and realized I couldn’t do it and I needed to address my health problems, aka unmedicated anxiety and an undiagnosed chronic illness! For about two months, I thought *that* was the mistake, the dropping out before I even got there, and I was pretty miserable. As time has gone on, I’ve become increasingly thankful that I didn’t put myself through what could have honestly been the worst decision of my life. I’m now a year into treatment and rebuilding my life, and my anxiety disorder is medicated properly for the first time in my entire existence. I might even get my driver’s license?! Like, if I hadn’t done all of that, I might not have woken up from my denial phase and gotten my diagnosis. I still want to go to grad school, but I’m only looking at local schools because I’m trying to meet myself where I’m at, and now I actually know what I want to do with the degree once I get it. ^_^

  5. I mean, technically, splitting up with my boyfriend of 3 years bc I had a foursome with my female best friend, someone genderfluid and another woman was a mistake.

    …a very enjoyable miss-take though.

    Sometimes mistakes are definitely the way to learn.

    • Pretty sure this is just a humblebrag, but also can’t blame you because that’s certainly a story worth telling. Thank you for sharing with the class.

      • Lol it was actually my first experience with anyone other than one cis het guy, a long time ago.

        I think perhaps I misunderstood when someone said I was missing out on foreplay.

    • This is less of a nomination for a comment award and more of a nomination for some kind of life award. (insert gif of Lorelai Gilmore singing “did you ever know that you’re my hero”)

  6. I relate so hard to Valerie’s entry! While I lost out on a lot of time due to being in the closet because of my first marriage, there’s a lot I learned that I still carry with me (as well as how not to be unfortunately). It was my coming out that ended everything, but I would never have dug deep and embraced my queerness and transess if we hadn’t, so ultimately i’d say it was as happy a mistake I could ever make considering where I am now all these years later.

    Also, I literally just signed up for A+ today so this was such a great first article to get to read! I can’t wait to dig into the archives and see what I’ve been missing!

    • welcome to A+! I feel a tiny bit of relief every time someone says they’ve signed up for it, after hearing from the editors about how tough it is to keep this wonderful ship afloat.

      • Thank you! I wish I could do so much more than this because these editors and this community are treasures and one of the best places I’ve found on the internet to be.

  7. CHILD’S PLAY!! I moved six states away from every person I knew on this Earth with a boy I’d been dating for a year, already *pretty* aware I was gay(he just, he was a very pretty girl of a boy, okay?) With no driver’s license and a job I almost quit to do it. Did we break up months after we got there? Of course. Did I land more less on my motorcycle boot wearing feet? Shockingly also yes. Was I still six states away and never more than working class when my disaster of a family started sinking into the sea with no life-raft-dyke nearby to save them from their own decades old mistakes?? HELL. YES.

  8. If I overthink every life & daily decision, and some turn out badly, are those mistakes? Or just bad choices?

    Without overthinking: I don’t regret any time I got lost in the woods, on a hike, or in a city. I live for scrambling up a leaf-covered hill in the middle of nowhere looking for the maybe-path. Tumbling into a foreign neighborhood and figuring things out from there.

    Is it a mistake if you know you’ll be safe?

  9. “The heartbreak I endured made me stronger and smarter, I think. Or maybe it broke me forever, honestly who knows.” HARD RELATE, VALERIE ANNE.

    I’ve spent the last year dealing with ~some stuff~ so I’ve made a lot of choices driven solely by short term thinking that my friends will tease me about for years to come – I was looking so short term that it’s just now beginning to settle that my “year of mistakes” is part of my life now. I don’t really regret anything that’s happened. There were lots of silly things – last minute flights, secret trips to new cities, being bolder in how I handled career difficulties like asking for credit where it was due and telling men off for talking over me (both of these backfired, zero regrets though), messaging people I’ve not spoken to for years to try and reconnect because LIFE IS SHORT!

    I think basically 2018 was one big, necessary mistake – it was a reaction to spending 3+ years getting very settled with one clear goal in mind, finally meeting that goal, then suddenly and unexpectedly losing so many of the the things that shaped any plans I had beyond that point – I had a clear future, and then I didn’t, so I spent a year letting myself make silly mistakes while I figured out the next step, because I hadn’t been able to do that for so long, and I needed to completely reevaluate what I actually wanted.

    I find it strange knowing that I have to carry all of these choices with me now that I’m beginning to think about the future again, and knowing that the idea people have of me after this last year isn’t an accurate picture of what I’m really like.

    Anyway, thank you all for this roundtable and helping a former-perfectionist-turned-serial-mistake-maker feel less weird about her choices.

  10. “Even if I were, if I did want to take it back, where would I start? The courthouse wedding? When I said yes? When I moved in? When I started buying groceries for his apartment? Any of the hundreds of days before that? When I moved to the same city as him? When I left home? It feels like either all of it was something I regret or none of it was, and well, here I am!” This part is how I feel about my accident, and I’ve never managed to express it as clearly as this. If I take back the accident, which, yes, has caused me a literal lifetime of pain, do i also take back the 6 months of depression building up to it? Do I regret even deciding to move to that city, or going to university? I wouldn’t be the me I am now without the accident, the time in that city, the subsequent dropping out and doing a different degree somewhere else. So even though it’s definitely the worst mistake I’ve ever made, I don’t regret it.

  11. I really relate to Rachel’s, except that I do regret parts of my relationship. I stayed for 8.5 years (from age 18-26) in a relationship with a man who was sometimes supportive and healing but was sometimes abusive and damaging.

    I say now that I learnt a lot from that relationship, and I wouldn’t take that back, but I wish I’d learnt a lot faster. I think if I’d been in that relationship for a year or two it would’ve left some bruises but I’d have been able to look back fondly, but it went on too long and when I look back now I just see my inability to look after myself and prioritise my needs over trying to save him.

    So my actual favourite mistake is getting involved with my now-girlfriend in the last few weeks of that too-long relationship. I kissed her and he was fine with it, but then I slept with her, which he wasn’t fine with. I told him I’d slept with her right after he told me he’d cheated and given me an STD a few weeks before, so I felt pretty vindicated. It didn’t even feel like cheating because she was (is) the real thing and her liking me showed me that I’m likeable and lovable, contrary to what he told me. That was like finally getting rid of the anchor that was holding me to him.

    It was unkind to sleep with her while I was still with him, but it was also exactly what I needed to be able to get out.

Comments are closed.