On the one year anniversary of my accidental entrepreneurship and having my own peanut butter and jelly sandwich
At first, I didn't realize I was going into business for myself. But it's been the best decision I ever made.
This was the day I shed my hair. Two weeks later, I shed my job and started working for myself. I’m incredibly happy with both decisions.
Not long ago, in a breakout room on a Zoom with my friend and business guru Kim Walsh Phillips’ Powerful Professionals coaching group, we were asked to introduce ourselves and say a little about our businesses. When it was my turn, I explained that I’d been a journalist for almost 30 years, but had been running my own independent writing business for less than one.
“What made you decide to go out on your own?” someone asked.
“Honestly,” I answered, “I didn’t realize I was at the time.”
Everybody laughed, including me, but it was the truth. One year ago today, I not only quit a job I’d had for six months that was not a fit, but a 28-year stint as an employee, who worked full time for someone else. I didn’t know I was doing the last part. All I knew was that something had to change. And then everything did.
In the month of February 2022, I am billing significantly more than I did in the same period last year, working for someone else. Of course, I gotta keep hustling in March. But that’s part of the game, and it’s a game whose rules I get to write. It’s so worth it.
I had no idea that my decision to quit was going to cement me, even on shaky little newborn entrepreneurial pony legs, as an independent contractor. By the time I left that position in what was basically corporate communications, which provided me an opportunity to move my family north during a pandemic and buy our house, I fully expected to land a different full-time job any minute now. I’d already been a finalist for one that I ultimately lost because I didn’t want to relocate, and had two more interviews in the hopper.
I’d also had a great run of recent paid side gigs, including some online speaking opportunities and some freelance writing. This would tide me over until the next full-time job happened, I thought. Because I didn’t know anything else, you see. I’d been hanging out with Uncle Sam and FICA and them since I was pulling out flaming meat patties that had fallen into the broiler with tongs at my local Burger King at 15. And since landing my first newspaper job in Miami at the age of 22, I’d been a full-time employee with benefits and vacation. They were crappy benefits at first, but in time, that job begat a second, with better stuff, and then a third with even better.
That third job, at the Palm Beach Post, I had for 18 years until a pandemic, a furlough and the general state of the world drove me north to my native Baltimore. This fourth job, the one I took that bridged the chasm between Florida and Maryland, involved writing but in a different way than I was used to. It wasn’t my skill set and the constant Zoom hours and stress made me a bad employee and a not-great mom.
I’d already considered leaving, thus the job interviews, even though the idea of only being on a job for 6 months terrified me - my average tenure since college had been 7! What did that say about me? I’m a person who sticks to things. I am not a quitter. But then the vacation time I took the week before I officially resigned triggered something within me I hadn’t expected. That was the week that the paperback version of my memoir, Black Widow, was released, and I had some long busy, hectic happy days, including a British interview about the book, a Zoom session with other widows, and the aforementioned class and freelance.
It was exhausting, but thrilling, because I was in my element, talking about the things I was passionate about. It confirmed to me that I was right about my upcoming resignation, and that my next job as an employee was going to encompass those things that I cared about, just like my newspaper career had.
I didn’t get it yet.
So I left my job, explaining that I wasn’t able to both follow my passions and work that job, so the job had to go. I set an alarm at 6:30 every morning to apply for new jobs, and in the meantime hit up my three decades of good contacts for ideas about freelance. (Never burn bridges, kids. It’s dumb and also smoky.) I spent lots of time on the potential employee track with the sample stories and multiple interviews over several days, none of which yielded an actual offer.
The funny thing is, two of the newspaper jobs I didn’t get lead me to my most enduring freelance opportunities, working with editors who like my work and trust my experience, speed and ability to get diverse contacts. I didn’t plan that. It just kept happening. I kept getting freelance jobs! Newspapers, magazines, even some unexpected projects like writing bios for indie musicians and some corporate content. It was challenging, interesting and rewarding. I set the tone, the time and the price. If it didn’t work for me, financially, time-wise or spiritually, I didn’t do it.
It wasn’t until months later, when I was being turned down for yet another full-time gig with a really groovy company that I’d again been a finalist for, that I heard myself say “You know what? It’s OK. I don’t think I want a full-time job anyway.” It was a shock to the person I was talking to, and shocking, but satisfying to me. The minute I said the words, I knew. My life that year hadn’t been without stress - I’d had to tap into savings and there were moments that I panicked and took some gigs that underpaid me because I felt I had to immediately replace my previous income with ANYTHING.
But a year later, I don’t do that anymore. I regularly turn down gigs that are not a fit, either because they don’t meet my fee, or because I just don’t think I’d be good at them. I have chosen to do a few things that don’t pay a lot because of the opportunity to get into new genres of writing and work with great people, but it’s a strategic move, not a desperate one. Mostly, I have found that the time I’m not spending making money for someone else is filled making money for me, on things I love.
For instance, I’m writing a new book. I’m about to leave for the second of two speaking engagements that each paid me about the same amount of cash I made, after taxes, at my old job. If I was working for someone else, I’d never have been able to do that. I was never probably going to make more money than I already was at my last two jobs, and that decision was made by someone else. I don’t have to worry about that anymore.
Are there times when I miss having paid vacation? Sure. And if a really exceptional employer came along with a fulfilling job, great insurance and benefits and a big check along with some flexibility, I might consider it. But I don’t see it. Being my own company has allowed me more than economic possibility - it’s allowed me time. I don’t have to ask permission to leave in the middle of the afternoon and walk my kid home from school every day. No more am I besieged with emails and WhatsApp messages on weekend nights while we’re watching TV. Do I have to send emails on weekends in my own gig? Sure. But on my own time. Because it’s all my time.
There’s a scene at the end of “St. Elmo’s Fire” when Wendy (Mare Winningham) explains to her crush Billy (Rob Lowe) that she’s just made her first peanut butter and jelly sandwich in her own home for the first time in her life, since moving away from her parents’ house. It’s a simple thing, but, as she said, “it was my kitchen, it was my refrigerator, it was my apartment… and it was the BEST peanut butter and jelly sandwich that I have had in my entire life.”
Being on my own is the best peanut butter and jelly sandwich I’ve ever had. Sometimes I wish for more peanut butter. But it’s mine.
I loved reading this. How excellent and inspiring, Leslie!
Well done! You are an inspiration. And a wonderful writer.