Chapter 7: An Idiotic Optimist on Failing

98% of the population will die not knowing “Never Going Back” is Fleetwood Mac’s best song. And I’m not saying that because I just discovered this myself. 

It’s currently 6:10 pm on a Tuesday night and I’ve already decided “Gold Dust Woman” is another song most people will never know about.

My point is that my new playlist, “Underrated Top Rated,” is rather poetic. How many of us actually take Mark Twain’s road less traveled? If we did take the underrated, under traveled road, I think most of us would find that road a top rated experience. 

I’ve also been thinking about this in the context of new chapters because I find myself in a new chapter. And with new chapters, the question begging to be asked is, “How did I get here?” What exit did I miss to end up on this less traveled, underrated country road with no lights and no highway in sight? 

Historically, this question probably wouldn’t resonate with most but given the times we are living in, I challenge this. The C word has ripped people’s lives apart. 

One minute I was laughing at bat soup in Israel and literally the next minute I was scrambling to pack a 10 month wardrobe for a flight leaving in five hours.

I had a plan and then poof. My plan was gone. 

My plan to move to NYC was put on hold while the city, you know, went through some things. So I had a lot of time to reflect, and one of my personal breakthroughs was that for someone who loves having a plan, I actually hate them. Nothing ever goes according to plan, it’s exhausting making them and, generally, they’re a waste of time.

When I was 10 I planned to be the youngest woman to win the Academy Award for Best Actress. Jennifer Lawrence beat me to it. When I was 16 I planned to be the first female self-made billionaire. Two words: Kylie. Jenner. When I was 18 I planned to go to NYU so I could easily intern at a music magazine in the city — I was planning to write for Rolling Stone. At 23, with a Communications degree from Michigan, I can say that all of these “plans” (dreams) never happened.

But maybe that’s where our frustration with plans stems from — are plans just dreams dressed in sweatpants? 

I don’t know. But what I do know is that “Big Love” by Fleetwood is being added to “Underrated Top Rated” as we speak and so is “Storms.”

Where was I? Oh, yes, new chapters. Right, so I’m in a new chapter and it’s weird because I kind of feel like I was sleeping for the past six months and now, all of a sudden, I got the last kick like Cobb in Inception. 

One day I was in Cleveland, now I’m in NYC — very much not sleeping. 

Because I’m in a new chapter, I’m in the mode of reflecting on the last one. I would say the past six months, the last 15 really, have been as Kylie Jenner would say, the year of, like, realizing things. 

When you’re on the hamster wheel of life, you lose yourself. Most of us actually don’t even know who we are. 

Especially my generation. The Gen Z cohort. Graduating from college was another chapter that forced reflection; my friends and I discussed it a lot. We spent our whole lives with a general idea of what the future would bring. In kindergarten, we knew we would start big kid school next year. In 4th grade, we knew middle school was looming with 7th grade Bar Mitzvah parties as the social event of the season. Middle school gave rise to high school, high school gave rise to college, and then… Nothing. 

There wasn’t one person I encountered that was happy about graduating college. Which is strange because only a handful of people actually like school. Parties, freedom and financial support from your family aside, I think most people weren’t happy about graduating college because it meant they actually had autonomy over their lives for once. They no longer had the next four year cycle of school to fall back on for their future guidance.

When you have to choose who, what and where you want to be in your life with no absolute plan or social construct guiding you, it can be scary. And for so many people, it is. But so many people end up taking the easy way out. They end up moving to a certain city all of their friends are migrating towards and accepting the first job that offers them employment. Of the people I know, very few of them have taken a risk and chosen otherwise. 

I’m not here to judge, and I’m not saying they are wrong to gravitate towards what they feel is safe and secure. But when a pandemic hits and you’re laid off and forced to move home, are you prepared? 

No. You’re not. Because you spent your whole life on the hamster wheel, running from plan to plan, so not having one is the most terrifying feeling in the world. How do you live without an idea of where or what you’ll be doing tomorrow, next week or next year?

That was a big lesson for me during my last chapter. I feel like I have it down — taking risks, embracing idiotic optimism as my navigator for doing the next right thing — a lesson that’s been labeled and reinforced in my new chapter: work. 

Work, career and job are three words that always sent me running for the hills over the past five years. Not because I didn’t want to do any of the aforementioned, but because I had no idea what I wanted to do. 

On the hamster wheel of life, at least the one I was trapped on, there was a lot of pressure to know what you wanted to do the second you started college. At 18 I was supposed to know who and what I wanted to be — but I didn’t. I thought I did, but I really, truly, didn’t. 

So when my peers would have a 10 year plan set up with impressive internships at Goldman Sachs, HBO or Chanel paving the way, I just found whatever opportunity would take me.

I interned at a magazine in Cleveland when I thought I wanted to be a music writer. I interned at a PR agency in NYC when I realized journalism was a dying field. I interned at a real estate investment trust after deciding that there’s more to life than pitching to journalists who don’t care about your client. And then graduation hit and I realized that PR, journalism and communications were all really not for me. 

But I no longer had the luxury of time. 

Running out of time forced me to take my first big risk. I took a gap year post-college. My last chapter. And it paid off. I thought it would help me figure out my “passion” and give me clarity as to what the next chapter of my life would look like. But what I recently learned at my new job is that finding work you're passionate about is not the way to go. Finding a 9-5 with meaningful work overrides the satisfaction passion brings.

Luckily, I learned a great deal about meaning in my last chapter. What I didn’t learn, and am finding myself currently struggling with, is the upside to failure. 

I’m learning that part of taking risks means failing, and that failure is encouraged. Fail confidently, fail often, but don’t fail and not admit to failing. And on paper, I’m on board. I love it, I’m here for it and I might even get a custom neon sign reminding me of it.

But in practice, failing is extremely uncomfortable for me. I’ve been unfortunate in my lack of failures. Yes, unfortunate. ‍

And it’s hard for me to really be honest with myself, because my euphoric recall is probably more euphoric than most. Maybe I’ve failed more than I’m giving myself credit for - maybe I’m such a risk taker that I’m blind to failure because I see it as just a natural pattern of life. 

It could also be that I don’t understand the definition of failure.

Subconsciously, I perceive failure as a nasty, hairy beast with choppers so sharp there’s no coming out of there alive. But I know cognitively that all great men have failed. They’ve failed so often that they all have quotes on failure: Winston Churchill, Thomas Edison, Albert Einstein, Henry Ford — the list is exhaustive and now that I’m thinking about it, exclusively male. 

My brief stint in Women’s Studies would allow for deep analysis into why I feel like women can’t fail the same way men can, but that’s writing for another day.

For now, I’ll say this: failure is completely subjective. Things can objectively fail, but people cannot. An oven can break and fail to turn on, a car engine can die and fail to run the car, but people can’t fail. We can’t make a mistake and completely break. What we can do is make a mistake and learn from it. But that’s not failure. 

Failure could be defined as missing the mark on your intended goal — oftentimes, though, missing the mark on a goal leads to an outcome greater than the one you set out to achieve. If the outcome isn’t great, then at least the lesson learned is greater. 

My understanding of failure definitely needs fine tuning, which is why I’m fortunate to enter a new chapter where it’s encouraged. 

For now, until I make friends with the big hairy beast, I’ll try to think of him this way: in trusting my gut and following my interests, I’ve always done reasonably well — I’ve never experienced wild success or wild failures — my life has been a progression of stone hopping from experience to experience. Yes, I am an idiotic optimist. I see potential in everything, even when others don’t, which is why I had no qualms about moving to New York in the height of the Gotham era. 

But in hopping from stone to stone, I never felt like I was slipping. I never really fell. Or maybe I did and I just liked the water I slipped into? 

To be a true idiotic optimist, though, I challenge myself to slip into the waters of failure more often; and that means taking bigger leaps across more stones. I need to get comfortable with slipping and falling hard into the water — maybe I’ll still like the water, but even if I don’t, I need to be okay with it and be okay with admitting that it’s a cold, uncomfortable place to be. Because, after all, the earth is 70% water. There’s serious opportunity and potential there for those of us brave enough to take the plunge.‍

Postscript. It’s now Friday morning and after building up “Underrated Top Rated” to six Fleetwood Mac songs, I’ve completely jumped ship to a random discovery station featuring another artist 98% of the population will probably die not knowing about: Hot Chip. Interesting music, largely unremarkable.