Tales of a Midlife Failure
what I'd say if Guy Raz called...
I’m addicted to the How I Built This podcast, where Guy Raz interviews successful entrepreneurs. And while each guest is wildly impressive (billionaires! household names!), I’m listening for the stories of failure, not success.
I tune in to hear the messy, difficult, middle part of each interview: when the aspiring entrepreneur has come up with a brilliant idea, but everyone tells them it’s terrible. The intrepid founder perseveres, driven by an inner resolve and desire to prove their doubters wrong: trying and failing, again and again, sometimes for years, wholeheartedly committed to making their dream a reality.
I love these stories because I relate: as an aspiring professional writer, I find great comfort in knowing that trying and failing is an unavoidable part of the process.
I’m nearly 50, and while I was successful in earlier careers in finance and nonprofits, as a writer, I’m in the humbling start-up stage. My business plan is simple: refine my product (improve my writing through trying and failing) and grow an audience large enough to buy lots of books, pay for subscriptions, and attract advertisers. And, like a nascent tech company, I’m spending a few years doing R&D and burning money.
If Guy Raz called, I would be extremely well-prepared to detail the trying and failing part of my story. Here are some of the highlights (or, um, lowlights)…
The incomplete and abandoned projects:
A blog, “Obsessed with IKEA,” in which I chronicled my, you guessed it, obsession with shopping at the Swedish superstore.
A self-help book, based on the principle of giving up “the shoulds” to become more organized.
A screenplay, “The Wedding Test,” which follows a middle-aged woman caught between her excitement at planning her daughter’s wedding and her disapproval of her daughter’s choice of fiancé.
An advice column, “Ask Dr. Write” where I recommend books to solve specific problems.
A novel, tentatively titled, “Middle-Aged Tennis Ladies.” I think you get the idea…
Another novel, based on the storyline of Four Weddings and a Funeral, following a divorced middle-aged woman finding love and romance at a series of glamorous summer weddings. Working title: “The Icing on the Cake.”
Months figuring out Instagram, trying different ways of posting, from calm scenic videos to talking to the camera (to the great horror of my children).
Countless pitches (all rejected!) to magazines and newspapers, including The Huffington Post, Glamour, Elle, The New York Times, The Cut, Gloria, and Marie Claire.
A searchable, online database cataloging all the books, movies, and TV shows I recommend every week in this newsletter.
A completed book-length memoir (about the midlife crisis which lead to my writing career!) which resulted in the following:
Rejections (some kind and encouraging!) by at least 50 agents and editors, in both the US and Australia.
The writing class during which a teacher questioned the veracity of my life story, telling me I “didn’t look like someone who’d suffered trauma” and suggested I was wasting my time writing about this topic.
And of course, there’s my ongoing writing project, this newsletter.
Each weekly issue is a “try” as I experiment with topics, writing styles, formats, layouts, and graphics with the goal of producing content that helps people live happier, more fulfilling, meaningful, and fun, lives.
I often ask you, the reader, a question, because I want to know more about who you are and what you think. Some topics and questions garner excitement and measurable “success” in the form of page views, shares, likes, and comments; and some…don’t.
While the fails don’t thrill me, each week, I gain more insight into what readers like and how to provide it. Slowly, I’m building an audience, gaining one or two new subscribers each day—from zero when I began, to 1,300 now.
Given my status as a resident in trying/failing land, I think a lot about what “success” means to me.
On How I Built This, each episode typically culminates in the entrepreneur being offered a huge amount of money to sell their business. Their single-minded striving has finally paid off, validated by the many people buying their product, and an enormous windfall!
At that point, some of the founders cash out, having accomplished what they set out to: financial security and the freedom to follow other interests.
But the stories I love most are the entrepreneurs who continue to run their companies because they’ve retained the passion they had at the very beginning.
And that’s something all of us in trying/failing land possess: the drive to make our dream a reality, even though no one is asking us to, plenty of people will discourage us along the way, we have no idea how long it will take, and we’ll try and fail and try again more times than we can count.
“I have not failed. I've just found 10,000 ways that won't work.”
Thomas Edison
📖 The Mysterious Case of the Alperton Angels: I have brilliant writer, cultural critic, and my very own editor/coach,
, to thank for recommending this highly entertaining epistolary-style novel, which follows bestselling true crime author Amanda Bailey as she attempts to revive her career by writing the definitive book on the never-quite-solved case of the “Alperton Angels,” a death-pact cult in a small British town. Told in the form of WhatsApp and text messages, emails, and interview transcripts, the reader is along for the ride as Bailey doggedly works to piece together what really happened - while racing to beat another writer, Oliver, who is chasing the same story. Twists and turns and subplots abound, and almost nothing is as it seems, in this addictive, satisfying mystery.📺 Eric: after watching the first two episodes of this new limited series starring Benedict Cumberbatch, I’m hooked. Set in 1980s NYC, Cumberbatch plays Vincent Anderson, a brilliant but curmudgeonly puppeteer at a children’s television show, very similar to Sesame Street. Vincent is in conflict with everyone in his life, from his wife and wealthy property developer father to his colleagues and his young son, Edgar - who goes missing after walking to school alone for the first time. The show is beautifully filmed and complex, and I’m preparing myself for heartbreak in future episodes as we find out what happened to Edgar, and how Vincent, who seems determined to self-destruct, will cope…
🎧 American Fiction Original Motion Picture Soundtrack: On a rainy day last weekend, I rewatched American Fiction - one of my very favorite movies in recent memory - with Jim, who hadn’t seen it. I had forgotten how perfectly the music in the film complemented the storyline, and when Jim commented on it, we took to Google to find the soundtrack. Having assumed the jazz was predominantly made up of Thelonius Monk classics in a nod to the main character’s name, we were stunned to learn that the score by Laura Karpman is entirely original and was composed specifically to interplay with the dialogue. I’ve been playing it each morning this week, and it’s a lovely mellow way to start the day!
📆 May 2024 Recs // 📖 Books // 📺 TV Shows // 🍿 Movies
In Case You Missed It: The link between gardening and happiness: “It reduces stress, lowers blood pressure, promotes feelings of mastery, accomplishment and competence, higher levels of self-efficacy, self-esteem, and psychological wellbeing.” // My mouth fell open and stayed that way while reading this much-discussed story on “pronatalists” Simone and Malcolm Collins: like Elon Musk, they believe that population decline is currently mankind’s biggest threat and raising extremely large families is an urgent imperative. They also believe in naming their children according to data and that heating their Pennsylvania home is a “pointless indulgence.” // 😂Summer Camp Sign-Up Press Conference // It takes a LOT of energy to carry a baby, specifically “about 50 pints of Ben and Jerry’s Cherry Garcia ice cream” // These are the top 10 US States to work from home // Welcome to the Summer of On-Screen Moms Getting It On // 😂Amazon Echo Silver for seniors “the phone is in your right hand.” //
❤️Plus, two reader comments on appreciating nature during the winter months:
says, “Natural cold plunging weekly in the winter has changed a big part of my perspective.”Ginny added, “Embracing winter is about having the right outerwear —I say this with some authority because I grew up in Buffalo.”
That’s it for me this week! Thank you for reading and see you next Friday! xo Amelia
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I absolutely loved reading this and learning about everything you've tried! It was so vulnerable and I admire you sharing. Plus - it's really encouraging because it just goes to show eventually you'll land on something you love that other people do too (aka this newsletter)! Hadn't heard of Eric but totally gonna try it out!
From what I know of middle age tennis ladies - that is a very very rich subject. I’d buy it on the title alone.