Me (center) during my more adventurous days at age 17.

Why I’m Spending 2020 Winging It

I’m doing 12 different challenges throughout the year and blogging about the experience like it’s 2010.

Lily Herman
Nov 30, 2019 · 6 min read

I had a bit of an existential crisis on November 3, 2019.

My roommate and I were watching the New York City marathon and cheering on the 53,000 runners making their way down the course. It was supposed to be a chill activity. You clap, you dance to good early 2010s Top 40 music, you see who’s running in the wackiest costume. What’s not to love?

Most people on the sidelines have #thoughts on the marathon. Some will tell you point blank that they think running a marathon is nuts and they’re never doing it. Others will say it’s a major bucket list item that they’ll tackle it one of these days.

And then there’s me: A person who has a mix of those feelings—and who was supposed to be a marathon finisher years ago.

When I was a senior in high school, I was actually training for a marathon. I was doing the weekly long runs and ran a half marathon two months prior to my race. But through a combination of getting sick in the weeks leading up to the marathon and losing a lot of motivation, I just didn’t run it. I ran another half instead. And eventually, that dream sort of left my brain. It was replaced by stresses of getting into and then getting through college, launching a career, graduating, and becoming A Real Adult™ who pays bills and worries about things like health insurance and yells about how heinous the MTA is. And nowadays, given that my current line of work includes a lot of political writing, it’s easy to get lost in the massive sea of bullshit that our country and our world is going through on what seems like a minute-to-minute basis. Running a marathon feels trivial and unimportant compared to how royally fucked we all are.

So here I was almost a decade later watching people run the race I thought I’d have under my belt by now. Instead, I was tired, out of shape, and had just downed an entire bag of Sour Patch Kids and two Bon & Vivs before barreling down several avenues to watch folks on the course. To say I was going in the opposite direction of my previous marathon goal would be a massive understatement.

Then I started thinking about all of the other dreams I had over the years. When I was eight, I wanted to write a novel. During my senior year of high school, I added a screenplay to that list of creative writing works I was going to eventually crank out. At some point in college I realized I wanted to master the art of cooking since neither of my parents had really taught me anything. In my early twenties, I admitted to myself that I had absolutely no ability to really discern any form of alcohol (when someone refers to a glass of wine as having “woodsy undertones,” I shrug) and wanted to know more about how to make a good cocktail. And I told myself after the 2016 election and with the ongoing rise of anti-Semitism that I’d reconnect with my Jewish identity. The pile of random hopes and dreams and goals went on and on.

Well, here I am years later and none of those things have happened. Sitting on the sidelines of that marathon, I realized why: I’d stopped taking risks and saying yes to things that felt unfamiliar. Nowadays, I eat at the same four restaurants, where I get the same dish at each place every time. I generally hang out with the core crew of friends and acquaintances. I don’t really venture out to anywhere that isn’t a neighborhood I can get to in under 30 minutes.

This isn’t the first time I encountered this problem and tried to do something about it. Back in 2016 during my post-election haze, I decided I was going to mix things up in 2017: I was going to create a list of 12 challenges I wanted to do that year—one for each month—in the hopes of enriching various parts of my life.

But much like my goal of running a marathon and any number of my other dreams, I just…didn’t do it. I didn’t even finish writing the initial 12-challenge list and it never came to fruition.

In the midst of my existential crisis on the side of the New York City marathon, I thought about that list for the first time in three years. And suddenly, something clicked: I wanted to do it this time. I wanted to start checking some of those goals off.

Thus, my list of the 12 different challenges for the year was born. I present to you: Winging It 2020.

  • January: Visit at least 10 museums.
  • February: Cook 20 different dishes in one month, culminating in an honest-to-God dinner party.
  • March: Check out 5 different Jewish experiences.
  • April: Book a spontaneous trip where a flight must be taken and see 3 sights.
  • May: Get 7 friends to tell me the most non-touristy things you “have to” do in NYC.
  • June: Run a marathon.
  • July: Take bartending class and hold a cocktail party.
  • August: Go on 5 first dates set up by friends.
  • September: Try 5 forms of wellness/self-care treatments.
  • October: Go to 3 different major sporting events.
  • November: Participate in NaNoWriMo.
  • December: Take up a new hobby.

Of course, there’s some irony in calling this series “Winging It” given that many of these challenges take quite a bit of planning. For example, I’m currently working through a 26-week marathon training plan in preparation for the June race. I have to sign up for this bartending class months in advance. Trying to figure out how to see so many museums as cheaply as possible requires some research to know when the deals are.

But as we all know, even the best laid plans go awry. For example, something will inevitably go wrong with my marathon—I’ll cramp up, I’ll hit the runner’s wall around mile 20, or my body will not deal well with the elevation despite never having altitude sickness in my life. (Oh yeah, did I mention that this marathon I’m running in June is in…Utah? Starting at an elevation of 6,000 feet?) And that’s where you’ve just got become the embodiment of the shrug emoji and take it in stride. That’s where you wing it.

There’s another important element to taking on this year. I think part of the issue from the first time I’d considered coming up with 12 challenges is that I thought about it as being this very solitary endeavor that I’d shoulder alone. It was about self-reflection! Self-discovery! Self-reliance!

Eh, now that I’m a couple years older, I realize that’s bullshit, not to mention incredibly lonely and boring. I’m doing things a little differently this time around: I’m taking a lot of friends along with me.

As soon as I started telling people in my life what I was up to, the offers to join and the resources flew in. I convinced three friends and half of the co-workers at one of my editorial gigs to run the marathon with me (again, IN UTAH). Another friend already offered to take me to some sort of group she’s a part of for my month of Jewish rediscovery. (The way she described it honestly made it sound a little new age-y, but I’m here for a good story.) Unsurprisingly, people are already requesting invites to the dinner party I’m throwing. And folks tweeted endless museum suggestions for January’s challenge. It’s gonna be a fun year.

And why blog it? Well, I write for a living, so it makes sense. I also need a certain level of accountability here, so I figure this will help. And ironically, despite writing for a living, I’ve always been bad at keeping journals and have long regretted it; there’ve been so many moments in my life I wish I could look back on and read how I felt at those times. So hey, why not start now?

And I’m not just looking for suggestions from friends; if you have anything to add, feel free to comment below, tweet me, or send me an email.

Anyway, let’s do this. Let’s wing it.


I’m Lily Herman, a writer, editor, and digital strategist. You can learn more about my 2020 Winging It challenge here, and follow me on Twitter, Instagram, and Facebook. Feel free to email me with any suggestions for my year of winging it.

A blog about a woman spending 2020 doing all the shit she wanted to but didn’t.

Lily Herman

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Winging It
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