Tales of a Midlife Failure
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 blog and my newsletter.
Each post 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.
Some topics 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
