The memo: could one missed message have saved me a lifetime of regret?

I can pinpoint the exact moment my fantasy flickered into life. It was a drizzly spring afternoon in 2019. I had just had an appointment at the eye doctor and found shelter from the rain at a tiny newsstand uptown. It happened to be around the corner from my first job, where I answered phones for a man who oversaw a newspaper, now long out of print. I was many jobs beyond that point, but still always on the phone, this time with my best friend. I wanted to chat with her for a few more minutes before I took the train home. The subject at hand: my college reunion, which was only a few weeks away, and for which I had yet to register.

The prospect of facing my fellow classmates was something I was having a hard time getting excited about. I had a lovely family, but I had recently been fired from my job at a magazine and I was struggling to make it as a freelance writer. As I stood there at that newsstand, my vision still recovering from dilation drops, all I could see was a blurry sea of magazine titles whose editors weren’t banging down my door – or responding to my emails.

My fellow college graduates were now living in exotic-sounding places, establishing what sounded to me like glamorous careers. Two of my former classmates had started a company to do with wind power, and rumour had it they had become gazillionaires overnight. And here I was, in the same city in which I had grown up, waiting to never hear back about my latest pitch on granny pants.

“Don’t you ever feel that you didn’t get the memo?” I asked my friend. “Some magical set of instructions that could have saved us from all our bad choices, and steered us on to the right path?” A set of rules that could have saved us from all the bad haircuts and bad boyfriends that littered our 20s? What if I had received marching orders that had warned me not to share my former therapist’s phone number with my close friend (who would, after a few sessions, realise that she couldn’t stand me and cease to be my close friend)? I really never got the memo.

I asked my social media friends to share their fantasy memos, and the answers poured in, overwhelmingly from women. “If it’s too good to be true, RUN.” “Stop worrying what other people think.” “Get a driver’s licence.” “My memo would have told me that when people suggest you ‘be patient’, they mean: ‘Accept the way things are.’” (The last one is from yours truly.)

I have yet to find a woman who can’t put her finger on what her memo would have told her. These suggestions can be momentous – go to dental school, don’t marry an arrogant fishmonger – or seemingly small: learn about Icelandic sagas, take a right on Classon Avenue on 7 March 2018 at 4.04 pm. The other day, I wandered around my neighbourhood and asked people on the street what their memos would have told them. A construction worker said she wishes a memo had told her to start doing karaoke earlier. “Don’t date a bartender,” deadpanned a neighbour who was sitting on her stoop. The woman who runs my local wine shop would have liked a memo to urge her to stand up for herself when she was younger.

I began to realise just how often they boiled down to a version of what my best friend, the one who was on the phone while I was at the magazine stand, wishes she had received: a memo that advised her to take a break from clambering up some invisible ladder of success and obsessing over her romantic relationships, and instead nurture her friendships with women. “I wish I’d been informed that the patriarchy is a real thing, and that these structures you try to ignore will creep up on you.”

The fantasy of a memo would be less potent if we did not live in a sexist culture. Look at the self-help industry, which preys on women’s insecurities: according to Goodreads , the majority of self-help readers are women, while male authors dominate the genre’s sales. Men are doing just fine in other industries, too. They clog the corridors of Congress and manspread in the House of Commons. The people who dominate the patter on Zoom calls take home more money than their female counterparts.

And let’s not forget the miracle of biology. As Al Pacino and Robert De Niro are here to remind us, a man can have a baby at pretty much any time in his life. Meanwhile, women over the age of 40 fret about job interviews, and dye their hair and get Botox before they meet a potential employer.

According to the Center for American Progress , women’s earnings drop 5.6% below peak mid-career levels by the time they are in their mid- to late-50s, as opposed to men, who see a 2.7% income drop. And according to a London School of Economics report , women make up only 19.4% of the top 1% of earners. We can have it all, as long as we are prepared to smooth out our foreheads and accept a smaller piece of the pie.

No wonder people want specific solutions. Jen Oddo, a New York psychotherapist whose clientele is primarily female, says: “This is a theme that comes up a lot in my client sessions, especially in the last three years, as we try to bounce back from a paralysing pandemic – they ask me what they should do , rather than my thoughts.” She adds: “The idea of having a manual” – or a memo – “is appealing not just because they’ll have the answer, but because they’ll have something to point their finger at and blame if things don’t turn out the way they were hoping. Clients struggling with anxiety, especially, tend to obsess over options and forks in the road. Thinking about every version of what could have been feels safe to them. It gives them something concrete to hold on to, and also something they can’t control. The anxious brain thrives on that.”

Shoshanna Hecht, a life coach whose clientele mostly comprises “high-achieving women” across the world, says many of her clients get promoted only to find that they are in no less pain. “A new level of achievement means a new level of challenge,” she says. “Without the ‘girlboss’ myth guiding them, so many people feel alone.”

I have always held that my memo would have insisted on my youthful self accepting that, beneath my pretentious carapace, there was a goofy soul. I should have joined the college humour magazine. I should have said yes more, and no to the people (OK, men) who wanted me to waste years of my life answering their telephones. It would have told me to take up Beyoncé on her (however disingenuous) suggestion that we go vintage shopping together when I interviewed her in the early 2000s. Perhaps we would now be best friends?

In this game of hindsight hang-ups I am not alone. I can hear another friend, a writer, wince as she shared her answer about what her memo would have told her. When she was in her early 30s, she received an invitation to dinner from a man who knew a friend of hers, and who would be in town from New York for a single night. She had committed to other plans that evening, and told him as much. When she got home from her dinner, she Googled his name and learned that she had blown off a titan of the publishing world.

Jane Rosen, the fiftysomething author of the bestselling novel Nine Women, One Dress, has a similar story. “Once I was young and wandering around the Village and [the actor] Judd Nelson came up to me on the street and asked me to go to an afterparty and I was too scared to say yes. Who knows what could have happened?”

Also, she says: “Wear more sunscreen. And don’t give a crap if somebody doesn’t like me.”

I know another SPF regretter, Mia Levitin, a London-based literary critic. “I wish I had got the memo about sunscreen,” she says. “In my defence, when I was coming of age in New Jersey, we didn’t know better and the self-tans were Donald Trump-orange. In order to get any tan at all, we had to lather ourselves in oil and cut up aluminium foil that we set up under our precious faces. But we thought that death was never going to come for us, let alone that we would get wrinkles.”

The other day I asked my daughter, who is nine, what her memo might have told her. She froze and then gave me that look that generally comes before she tells me I am being “cringe”. This time, though, she merely shrugged and shook her head before walking away. The concept of a memo was idiotic to her.

It should have comforted me to see that she feels so secure in all her life choices, but there was a prick of pain that came with understanding that this curious and strong gymnast and insect-rescuer was still on the other side of memo-mania. Her future is a blank slate, a map of possibility whose shapes have yet to be coloured in. If only I could freeze time. Try as I might to protect her, though, it is inevitable that she will one day find herself wading through regrets and what-ifs, of time she will never get back.

If my magic memo were to fall down from the heavens now, though, I fear it might be too late. Not because my window of opportunity has closed, but because the allure is fading. I am 46 now, and have read enough novels to understand that life has a way of slipping by, and that is what makes it so precious. I am less obsessed than I used to be with scrabbling my way up an organisational chart, or writing a bestseller. My priorities are as follows: I call my friends as often as I can. The other day I took my 73-year-old father to see a Björk DJ set under a bridge in an industrial patch of Brooklyn. And last night I skipped a party to stay home and watch my daughter practise the viola. Her technique was, let’s just say, far from perfect. I could not have appreciated the concert more.

• The Memo, by Lauren Mechling and Rachel Dodes, is out now