Dear Younger Self
An all-star collection
“If you could send a letter back in time, what advice would you give your fifteen-year-old self?” a friend asked me.
“At the moment, it feels like no one likes you, especially romantically. But as soon as you graduate from this god-forsaken, dysfunctional high school, guys will come out of the woodwork wanting to date you.”
That was my first thought. But why tell myself this? That stint was a waste of time, whatever confidence boost it provided.
Maybe this: “Forget about dating. Read more and use those big words you’ve been made to feel self-conscious for knowing. Stop making yourself small for other people. It’s ok to be same-sex attracted, by the way. It’s ok to feel desire and to explore it with respectful partners even if no marriage or babies or picket fence lies on the horizon. It’s ok to say no to relationships that don’t meet your standards, no matter whose feelings are hurt and how much they argue against it.”
I wondered what others would say to their younger selves. The women I asked wrestled with mental health, beauty standards, and—like me—setting boundaries. The men worried about authenticity, sex, and money.
“I am less interested in lecturing my 15-year-old self than my 20-year-old self, since the 15-year-old was beholden to her parents and couldn't have followed my main piece of advice, which is: change your last name to something you won't spend your life spelling and pronouncing for people (pronouncing incorrectly, as it turned out.) But, barring that, I would tell her to drop the oboe (by age 15 she was a serious oboist) and take up a string instrument instead, ideally the violin. I would tell her that, unlike the oboe, the violin is an instrument that you can play throughout your life in a relatively low stress way, hiding in the back of a community orchestra or messing around in a folk band or something. I would tell her that mastery of the oboe is a non-transferable skill but even basic competence on the violin would make it easier to learn the guitar, which her older self will yearn to play but never have the time or patience to do so and this will break her heart daily. I'd also say this: learn to ski, because every man you get into a relationship with is going to be a skier and they're always going to resent you at least a little if you don't ski. So, those are the things: play the violin, ski, and start thinking of new last names for when you turn 21. This is probably good advice for anyone.” - Meghan Daum, author of the hilarious The Problem with Everything and other books, founder of the Unspeakeasy
“I think I'd tell myself that attention from boys and men is cheap, that being pretty isn't the most important thing, and that you have to live with yourself, so don't worry so much about what other people think you should be.” - Leslie Elliott, host of The Radical Center podcast
“Everyone is much more concerned with themselves than they are about you!” - Eva Kurilova, Canada's preeminent lesbian, substacker
“Try to relax, Stella, and enjoy yourself more. You’re alright and you’ll be alright.” - Stella O’Malley, psychotherapist, author of When Kids Say They’re Trans and other books, cohost of Gender: A Wider Lens podcast
“Trust your resistance. Looking back, my resistance was ‘right’ about all the important things. And I was trained to second guess / doubt myself.“ - Kristin Renata, producer and host of OurVoices podcast.
“When I was 15, I was preoccupied with figuring out 'who I was,' unaware that my 'identity' would change many times over the course of my life. I had a hard time making and maintaining friendships. The outside world and school was very overwhelming to me. So I spent a lot of time alone, looking inward, highly critical of myself, and constantly trying to figure out what was 'wrong' with me. As a result, I developed very low self-esteem, which led to depression, self-harm, an eating disorder, suicide attempts, many psychiatric inpatient visits, and then a long-term stay in the troubled teen industry. Doctors and therapists told me I had a chemical imbalance in my brain and labeled me “mentally ill.” Those labels really stuck with me, and I continued to make bad decisions out of extremely low self-worth.” - Christina Buttons, independent journalist, substacker
Don’t kill yourself. It gets better, I promise. All you have to do is survive, don’t worry about the rest. - Nina Paley, artist, animator; winner of 35 international film awards
“I would try to convince my 15-year-old self that the most precious asset he will have in life is his relationships with other people. My 15-year-old self will then tell me that his relationships with others are in fine shape! He knows this, he will say, because people are always telling him that he's clever and funny. Middle-aged time-traveler Jon will then reply that just because people put up with you for the jokes and the wry commentary doesn't mean they feel appreciated and respected. The world is full of dicks whom people tolerate because they're entertaining or charismatic, or have some other redeeming feature. It doesn't change their dickishness, so don't be that person. Of course, my 15-year-old self won't listen. But what are you gonna do, right?” - Jonathan Kay, journalist, Editor of Quillette Magazine
“For your entire life, the people around you will try to convince you of the right way to think about things and what to believe. And for a long time, you'll acquiesce, if only to avoid excommunication and to be seen as a "good person." But soon, stifling your thoughts and words will make you sick. You'll eventually summon the courage to say out loud what you actually think, and there will be consequences, but after the heartache will come the greatest freedom you've ever known.” - Ben Appel, journalist, award-winning creative nonfiction writer, substacker, author of the forthcoming Cis White Gay: The Making of a Gender Heretic
“15-year-old Matt, you are a total fucking moron at love, and will remain a total fucking moron at love until you are 25, when you will become merely an idiot at love. Maturity and wisdom regarding romance will not arrive until you are 35, and even then you will still be rather stupid about it. Note that this does not mean you will never have sex, indeed you will have entirely too much passionate, lusty sex during the time that you are a complete and utter dumbass about what you are doing. Here, then, are three words of advice: follow your instinct to date women who are older than yourself, for they can help you grow out of this childish phase; make sure you know the character of the person you are having sex with, so that you never, ever put your dick in someone who is crazy; and wear a condom, you dipshit.” - Matt Osborne, conflict historian, writer, recovering political scientist/internet opinionator, substacker
“My serious piece of advice, if I could give only one, would be "Buy and hold Bitcoin." I would be worth about $80,000,000 today, if I had held on to a stick/flash full of the things that I got from a hacker girlfriend/buddy 12 or so years ago - and it wouldn't be hard to make yourself into Iron Man by giving Past You some stock or crypto tips. But, if we're talking about human, ‘moral’ advice: actually just pursue what YOU want, rather than what you feel you are expected to do. There are some basic ethical limits here, but I would have saved literally years of time spent ‘presenting’ as everything from a tough jock to a proper academic had I just honestly laid out 20 or so personal goals as a young man, gone after them, and kept updating the list every two years or so.” - Wilfred Reilly, political scientist, co-host of Cut the Bull podcast, author of Lies My Liberal Teacher Told Me, Hate Crime Hoax and other books
And lastly, evidence that great minds think alike:
“Buy Bitcoin.” - Colin Wright, evolutionary biologist, Manhattan Institute Fellow, and substacker.