Home + Work: A layoff and an Uber driver’s 1099

Photo by Stephen Leonardi.

The day I was laid off from my first and only startup job, I stood crying on the curb at Pike Place Market waiting for my Uber. I didn’t see the let-go coming and, as silly as it may sound, “getting fired” was one of my biggest fears. I had faced another of my biggest fears a few years earlier when cancer took my dad, but I was back to feeling like I had more control over my life than I really did. So, when I was walked out that day, I felt blindsided and humiliated. 

I slid into the backseat of the sedan that pulled up, apologizing for my tears. The driver turned around and assured me, “Oh, this is no big deal! You can drive Uber! I made over one hundred thousand dollars last year.” Somehow, he had his 1099 ready for this moment. He offered it to me. 

“I believe you,” I said, sinking down into my seat and looking out the window as he nodded and put the paper back in his glove compartment. I couldn’t help but smile. Just a little. My Uber driver had made more money than I had in the job that I was so shocked and upset to lose. And, while I had no plans to drive Uber (I don’t really like strangers and I certainly don’t like strangers who have been out drinking), he showed me the limitations of my thinking. 

Over the next six months, I struggled to find a new job. I so badly wanted to be chosen. I wanted a cool job at a cool company that people would gush over. I sat through endless interview loops only to be told no or ghosted completely. 

To add insult to injury, I felt ready to be a mom, but I wasn’t getting pregnant. Just like when my dad got sick, I felt completely out of control. Why wasn’t the world bending to my will? Why wasn’t it easy? Why wasn’t I getting an A on this project? 

I hated feeling less impressive on paper. I hated feeling like I was behind on my goals. I hated feeling like I wasn’t contributing to my life financially. And I really hated collecting unemployment. 

It would take another two years (and that baby I was hoping for) to get brave enough to branch out on my own, to remove the ceiling from my income and my creative potential like my Uber driver had. My life may have looked a lot different had he not offered to show me his 1099 that day at Pike Place. 

I wasn’t ready then. I had some learning about myself to do first. And that learning was painful. 

As anyone who owns a business knows, every day is an exercise in personal development. Every day is a mirror to the healed and unhealed parts of you. I have gone deep with myself, uncovering why I desperately needed to be chosen, why external validation drove my sense of worthiness. I’ve taught myself about money and energetics. I’ve read biographies of people I admire deeply. I’ve watched a lot of sports documentaries on Netflix. There’s just something about high-performing athletes I find so inspiring even though I am far from a high-performing athlete. 

The books, though. I read at least 50 every year. Those have helped me the most. Here, in alphabetical order by title, are a baker’s dozen of the most valuable resources I’ve found in business, creativity and life:

1. Building a StoryBrand by Donald Miller

2. The Creative Act by Rick Rubin

3. Dark Horse by Todd Ros

4. The Everyday Hero Manifesto by Robin Sharma

5. The Game of Life and How To Play It by Florence Scovel Shinn

6. Help, Thanks, Wow by Anne Lamott

7. Outrageous Openness by Tosha Silver

8. Real Magic by Wayne Dyer

9. Shoe Dog by Phil Knight

10. Tiny Beautiful Things by Cheryl Strayed

11. We Should All Be Millionaires by Rachel Rodgers

12. The Year of Magical Thinking by Joan Didion

13. You Can Heal Your Life by Louise Hay

I believe books and stories and messages find us when we’re meant to receive them. I read Tiny Beautiful Things sometime around that Uber driver 1099 time. I’ll leave you with one of the passages I needed then: 

“Nobody’s going to do your life for you. You have to do it yourself, whether you’re rich or poor, out of money or raking it in, the beneficiary of ridiculous fortune or terrible injustice. And you have to do it no matter what is true. No matter what is hard. No matter what unjust, sad, sucky things befall you. Self-pity is a dead-end road. You make the choice to drive down it. It’s up to you to decide to stay parked there or to turn around and drive out.” -Cheryl Strayed

And, you know what else? I believe I was meant to get in that Uber.

— By Whitney Popa

Whitney Popa is a writer, editor and consultant for little companies with big dreams. A born communicator, she connects people through stories. She believes strongly in many things, including expensive sweat suits, offroad vehicles, good books and bad TV. With her two cats, two kids, and one husband, Whitney splits her time between Edmonds and Waterville, WA.

 

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