I loved getting the newspaper as a kid: we had stacks of them, memories of the home I grew up in a hoarder’s paradise with newsprint in boxes, in the washroom, on the couch. I wasn’t really a news junkie - I didn’t understand politics, economics or current events, and I wasn’t really into sports. All those years, I never spent a second in the sports section, the most time I’ve ever spent consuming something about sports probably watching I, Tonya or Serena Williams’ documentary while on a long-haul flight to wherever that was. So I skimmed the front and skipped the back; my favourite was the fluffy bit in the middle, the stuff that’s never in the headlines. The lifestyle section! Fashion, arts, food, money, horoscopes too.
Enter the syndicated advice column.
Ann Landers, Dear Abby, and well, even Dan Savage, offering my first peek into the complicated and sometimes R-rated world of modern romance. What business did I have reading relationship advice as a preteen? None.
This is “Ann”, technically Esther Lederer (get it? letterer? which name is the real one!?!). Her twin sister, Pauline Phillips was “Abby”. They, of the joint wedding variety, became the most widely read and quoted women in the world, so said Life magazine in 1958.
I’m not sure exactly why, in my journey this year to document my creative influences, that as I started to put fingers to keyboard, the rather undramatic and mundane advice column was the first thing that came to mind. I could’ve started out with something obscure and extremely interesting, scoured the edges of my creative self to kick off with a statement. But I think this says something about me.
The advice column has been ubiquitous for decades now, growing in popularity since its “invention” tied to the uprise of the American dream starting in the 1600s: with new history being made, the question of how do I be in this world was bound to come up, and someone there to answer it.
What I like about the modern internet-age advice column is that they offer perspective, humanity and connection, without a whole lot of sparkle (Salt? Yes, plenty. Sparkle? No.), not even a face except one carefully tuned headshot, and today, not even that, your advice giver sometimes writing under a sugar-laced pseudonym.
Before Reese Witherspoon played her in Wild, Cheryl Strayed was an anonymous advice columnist known by the name Sugar. I read her book Tiny Beautiful Things when Wild came out. It was indeed, full of tiny, beautiful stories, stories to answer questions, stories that had a problem to solve, often ending in poetic phrases that probably should be printed on mugs - no more “But first coffee” or “Live Laugh Love”, but “Clutch onto whatever you love the most when the tires leave the road.” (Dear Sugar #96)
Below, a walkthrough of some my favourite advice columns, starting with Dear Sugar, who I devoured when I was lost, grieving, directionless, and who, in a whim, became the namesake for this newsletter v1.
When I was done writing it, I understood that things happened just as they were meant to. That I couldn’t have written my book before I did. I simply wasn’t capable of doing so, either as a writer or a person. To get to the point I had to get to write my first book, I had to do everything I did in my twenties. I had to write a lot of sentences that never turned into anything and stories that never miraculously formed a novel. I had to read voraciously and compose exhaustive entries in my journals. I had to waste time and grieve my mother and come to terms with my childhood and have stupid and sweet and scandalous sexual relationships and grow up. In short, I had to gain the self-knowledge that Flannery O’Connor mentions in that quote I wrote on my chalkboard. And once I got there I had to make a hard stop at self-knowledge’s first product: humility.
Your assumptions about the lives of others are in direct relation to your naïve pomposity. Many people you believe to be rich are not rich. Many people you think have it easy worked hard for what they got. Many people who seem to be gliding right along have suffered and are suffering. Many people who appear to you to be old and stupidly saddled down with kids and cars and houses were once every bit as hip and pompous as you.
On getting unstuck:
You will never stop loving your daughter. You will never forget her. You will always know her name. But she will always be dead. Nobody can intervene and make that right and nobody will. Nobody can take it back with silence or push it away with words. Nobody will protect you from your suffering. You can’t cry it away or eat it away or starve it away or walk it away or punch it away or even therapy it away. It’s just there, and you have to survive it. You have to endure it. You have to live though it and love it and move on and be better for it and run as far as you can in the direction of your best and happiest dreams across the bridge that was built by your own desire to heal.
The Atlantic describes Ask Polly like this: “You’ve come to expect that there’s going to be some sustenance in there when you open that door, and instead you get entire worlds.” Polly/Heather aka Molly answers questions with clickbait titles packaged so succinctly for the internet that in a string of words, you kind of get it already: “My Life is Pathetic!”, “I Am Rich and Worthless”, “No One Likes the Real Me!”. Except! There is so much more.
In “Am I Too Obessed With My Nemesis?”, a successful entrepreneur cyber-stalks her husband’s ex over several years, describing an internet game of social media cat and mouse, telling us almost the entire story of her life - her husband who hardly figures in this game, her upcoming move to the West Coast, her "more interests than most women” disclaimer - before asking Polly for permission to move on and let go.
In response, Polly starts:
I’ve never been that motivated to succeed in a vacuum. I need success to feel personal and emotional. I can only understand success if it strikes me as a kind of sensual pleasure, something to grip onto, something to savor. Likewise, I never valued money or popularity until I could link it to something visceral:romantic love, or an experience I craved, or the sensation of being secure or adored or admired or respected in a specific place, by a specific person, in a specific way. For years, even these things were impossible to touch because I was sure, at my core, that I wasn’t worthy of any of it. I wasn’t even worthy of imagining it.
I think you have trouble feeling your way forward, too.
Then, I found Ask a Manager.
When quiet and introverted me was thrown into the world of management, HR expert Alison Green accompanied me on my journey. I spent many nights reading page after page of archives, enlightened, amused and schooled in the mysterious art of modern work. At first, it was to answer a question I had myself. But then it became voyeuristic, when in between the expected questions (“Is 8-6 the new 9-5?” and “My coworker keeps bossing me around”), there were some ranging from laugh out loud to cringey to what in the world? See: “I overheard my girlfriend on a work call and am worried she’s a mean boss”, “I think there’s a sex club in my office” and “I have a spider phobia and my boss has a giant spider model”.
A turn from the poetic pragmatism of Sugar and Polly - two saccharine names to soothe the tough love they deliver in long form essay - Ask a Manager columns are often short and straight to the point (sometimes with multiple questions and answers per post, to keep pace with the entire internet’s workplace dramas, I suppose). There are no meandering life stories to drive a point. It’s also one of the rare places on the internet where comments are alive and well, with the average post a hotbed for hundreds of anonymous discussions.
After I recently left my job as a manager, I found new space to become interested in other things, one of them being how we can measure qualitative information through quantitative data and statistics. Enter Dear Mona, data journalist Mona Chalabi’s column at FiveThirtyEight, a website that uses statistical analysis to report on “serious” things like elections, politics, sports and science.
Mona, ironically using her real name, is younger and more Millennial than Sugar or Polly. Her secret sauce is one of the modern permutations of the advice column: cold, hard information rather than soft, poetic intuition. At 32 years old (28 when her column said goodbye in 2015), what her advice lacks in experience, it makes for in facts.
Using data, she’s covered questions on long distance relationships, how often you should change your socks, and job tenure, in a way that reveals the norms and asks you to determine, on your own accord, where you’d like to be on that “normal” or not scale.
Advice columns have evolved in other ways: they can be found in podcasts (Ask a Clean Person), video (most of Youtube), even social media, anyone and everyone now a potential agony aunt or uncle (UK speak for advice columnist, as I recently learned from my Manchester-hailing boss). I have even found a wonderful advice column on one of my favorite fashion websites, Man Repeller’s Ask MR, a place where life, love, Millennialisms and fashion can live happily together.
Everyone is now an expert-in-the-making, but from what I’ve started to discern, advice columnists don’t try to come across as experts as all, but as masters of empathy, inquiry and storytelling.
You probably know someone who gives great advice. They may not be as polished or poetic as The Advice Columnist but I find them in places like Reddit r/relationships, where I can, in any moment, put myself in the shoes of the many women who suspect their partners are cheating, the women who feel stuck and want a way out, and all the people who are in relationships that make no sense to me at all, each comment a mini column of its own, with a upvote and downvote system to surface and rank the best advice to the worst. I saw, through the strange and everyday stories of people on the internet, many times what I myself needed to know and do.
Somewhere in between the front page and the back page, the tweetstorms and the one-to-one human interest stories, the dirty news and the boring news and now the big wide world of the internet of every kind of news, the advice column epitomizes the softer, often denigrated, human side of information.
It’s a really tough balance to strike: to write to one person and to an entire audience, to be both wise enough to challenge and break all kinds of people and all kinds of problems wide open, but also to be “soft” enough to be the helper and not the all-knowing god of everything, even if you are. (If there was a god, I think, like Ariana Grande, that god would be a woman and she might come down to earth as an advice columnist.)
In between the optimization and provocation the noise of the internet begs for, there is safety, wisdom, honesty and empathy, the whole truth of human optimization (doing the best thing) and provocation (saying the hard and ugly things) turned on its head, in public domain spaces formerly dominated by “serious” things and people. We are seeing a gentler, more vulnerable, more personal path to what knowledge means, as all kinds of information coexist in complete disharmony and disarray. In this state, nothing seems more important than helping people get through it all, whether it’s how to work, love, live, be or even clean.
My name is Ana, and I’m documenting my creative influences. I’m currently managing (but not writing) an advice column at work.