My goal for 2019 was simple. I wanted to fail more.
Yup, you heard that right. I decided that I would move into 2019 with the intention to fail quickly and often. I didn’t tie specific metrics to it. I didn’t limit the number or scope of the failures. I just wanted to fail more often than I had in past years. Simple, right?
Some reverse psychology I used on myself several years ago inspired the resolution. When I first moved to Portland, Ore., in 2017, I started a job that demanded I do a lot of public speaking. It wasn’t exactly the kind of public speaking that required me to stand in front of large audiences (though, eventually, it did), but I hated public speaking in all its forms, so I felt intimidated even when called to present to small groups of executives or colleagues.
During my first couple months on the job, I remained tight lipped while on conference calls with top-tier executives, afraid I might slip up and say something stupid. I figured not talking at all would be safer than speaking up and saying something dumb. But, as I’m sure you’ve already deduced, not speaking wasn’t a good solution. I needed to lead content on these calls, and I was letting people down by being too afraid to speak up. After a couple months of being silent during these meetings, I gifted myself the freedom to mess up. As a bona fide perfectionist (and I don’t say that in a good way), it seemed crazy. Purposefully mess up? Really? It sounds silly, but it actually worked. Before entering each call, I would tell myself: “Sarah, say something stupid. Go for it. Who cares? Maybe people will laugh. So let them. Laugh with them and move on. It won’t be the end of the world.” And so I began entering each call with the mindset to mess up. My hypothesis was that by giving myself the freedom to “mess up,” I would also be giving myself the freedom to speak up, ask questions, be curious and, ultimately, lead a successful call. Because while being silent kept me safe from making “mistakes,” it also hindered me from performing my job. Of course, speaking up increased the potential that I might say something stupid, but it also made it possible to truly lead a great call. Suddenly, the reward seemed worth the risk of looking dumb.
This logic worked so well that, over time, presenting in front of groups became something I craved. I finally shed my shyness in favor of boldness. And while I still can’t speak to large crowds on stage (still working on that one), I’ve come a long way in being able to speak confidently in other situations.
So now that brings me to the beginning of 2019 when I decided to apply this same logic to, well, my entire life. For all intents and purposes, my life was pretty swell at the beginning of 2019. I lived in Portland, a city I loved. I rented a really cute studio in my favorite part of town, had a solid group of girlfriends and managed a budding freelance writing career.
Even so, I wasn’t living as boldly as I wanted to. For one, I was in an unhappy relationship. I succumbed to the pressure that I think women sometimes face. The pressure that says we need to be in a relationship. The pressure that encourages us to stay in things that don’t make sense for us. The guy was fine, but our values didn’t align. And yet, I was really afraid to leave. And as much as I write and talk about being confident in doing things solo, I was kind of afraid to be alone. OK, I was very afraid to be alone. I’d wake up every morning and think to myself: this relationship isn’t for me. And yet I stayed for the comfort, cuddles and company.
In addition to that, I wasn’t totally getting after it in my freelance career. Not the way I wanted to, at least. Sure, I was being consistent and disciplined, but I wasn’t really getting after it in other ways. I was letting the internal angst I felt about my humdrum relationship distract me. I was engaging in a bit of self sabotage, if you will. My freelance career needed that obsessed, hungry, focused version of me that I knew was buried by doubt—the same doubt I often felt when I first attempted public speaking. I was hungry to make my freelance career viable, but I was so afraid of all the unknowns. Is it possible to have a career in writing? Will I be lonely if I leave my boyfriend? What is the next step? Where do I even start?
And so I ripped a page from my 2017 handbook and applied the advice to my situation: I decided to start failing.
First things first—I ended my relationship. This was the last week of January 2019. I woke up the next day with teary eyes and a lump in my throat. It was “failure” number one, and it was a tough one to swallow. Anyone who has been through a breakup knows that these failures sting and linger longer than you would like them to. Unlike a rejected job application or writing gig, this kind of pain lingers. Still, I ripped off the bandaid and threw it away.
Next up: I signed up for a new workout program. Anything to distract myself from the breakup, right? This decision seems like a simple one, but it kept me sane at a time when I was really trying to overhaul my approach to life. Plus, the workout of choice was new to me, and I was really bad at it in the beginning. The exercises required balance and, though I used to dance, I was a bit rusty. I fell a lot. In front of people. Failure number two: check.
Next: I went hard on freelancing. Really hard. I made lists—long lists—of publications I wanted to write for. Publications that had a mission that aligned with my own. Some of these were big names. Others were small startups. I cared less about the size and more about the purpose. This was going to be a values-driven year. No more bullshitting about what I wanted to stand for. I reached out to people on LinkedIn like it was my job. I hustled for coffee meetings and introductions. I followed up, often. Heck, I even met one client while on a two-week road trip (I showered at a campground beforehand). I created an individual strategy for engaging every new person, and I executed with vigor. And then I played the waiting game. I didn’t hear back from some for months. And others—I didn’t hear back at all. Failure number three, four, five, six … 200.
I got a lot of no’s: ”no” to coffee meetings, “no” to story pitches, “no” to full-time writing gigs. But after months of chasing and embracing the failure, I started getting some “yes’s.” And let me tell you, these “yes’s” really counted. They were from companies, people and publications that I admired.
Now, I’m not going to bore you with the things that finally worked out. I don’t think it’s super helpful to write you a list of what I accomplished, and I’m sure you can find many such lists on the interwebs. What I will say is this: thanks to embracing failure, I accomplished a heck of a lot in 2019. And more importantly, I accomplished things that are really meaningful to me and align well with my vision and values. I tend to fear failure most when it involves something I really care about. For instance, asking out a random, cute guy (or girl) feels a lot less scary than asking out someone you’ve been really crushing on for awhile. It works that way in work, too. I’ve always worked hard, but this past year, I committed to work hard for things I really care about, which required me to push through a lot of fear.
I also applied the logic to other parts of my life, including my personal life. I got some “no’s” in that area, too. And that’s OK. I’m trying to live boldly, while also practicing patience and trusting in the timing of things. Living boldly, to me, isn’t about being pushy. Being pushy still comes from a place of fear. Practicing patience and honing your hustle, on the other hand, are valuable beyond measure.
This experiment also taught me that it’s fine to look dumb and to get rejected. It means you’re trying and that you’re reaching far beyond your comfort zone. If you asked me at the beginning of 2018 whether I was trying as hard as I could to make my freelance career a viable business, I probably would have said “yes.” But after a bit of introspection, I realize how much the fear of rejection—and of stepping out of my comfort zone—got in the way of really trying to make things happen.
So what’s in store for 2020? I really don’t know. I’m not typically a huge fan of resolutions. I goal set regularly, so I don’t fuss with year-long plans. Instead, I set themes. Last year’s theme was failure, and I think I want to continue it in 2020. As far as whether I’ll add a second theme—I’ll make sure to keep you posted.