100 Days Unbored: What I Learned By Challenging Myself to Try 1 New Thing Every Day

Ever since I was a kid, I’ve had a frustrating relationship to boredom.

When I was young, minor fits of boredom would set in and drive me suddenly-stir-crazy. “I’m so boredddddd,” I would complain to anyone within earshot, usually my mom. I would resort to opening our family’s designated “junk drawer” and pulling out a combination of paper clips, thumbtacks, and elastic bands — whatever was available — to try to “invent” something.

All I could ever come up with was a little thumbtack slingshot thingy. It wasn’t very impressive.

My fits of boredom were never solved by my haphazard junk drawer inventions, and I didn’t outgrow this relationship to boredom as I grew older, either.

In my early twenties, especially when I was living in Washington D.C. and looking for work during the onset of the Great Recession (after my White House internship — have you and I ever talked about that?), I felt the same, sudden pangs of boredom ripple through my body. I would describe them as deep angst, anxiousness, and restlessness. I responded to them with a need to urgently escape from wherever I was feeling “cooped up” at the moment.

Sometimes, I’d escape for as little as a breath of fresh air or a walk, and that was enough.

Sometimes, I’d go to the grocery store, just because.

At other times, I’d get in my car and literally drive in one direction until I felt the boredom fever subside.

Then, I’d just turn around and head home.

Today, pangs of boredom don’t attack me quite as hard or quite as dramatically. Usually, I can sense when they’re coming. Usually, my daily practices of self-care and exercise and creativity — blended with a habit of leaving my home to get out and be around people every day — is enough to keep the boredom bug at bay.

But, earlier this spring — as the seasons shifted and I felt so ready for the expansive, open summer months and long, bright days to arrive — the boredom bug did come back. And strong.

“I’m so boreddddddd,” I started saying to whoever was in earshot, this time, usually just to myself.

I was tired, though, of hearing my lifelong “bored” story. I was tired of feeling bored, and I was tired of complaining about boredom. At the very least, I was tired of reciting the same old language to express the same old feeling.

So, in May, I decided to commit to doing something about it.

Never one for hard-lined daily habits or multi-day “challenges” — I’ve always pushed back against industrialized approaches to “productivity” or achievement — I decided this spring that I would, in fact, put myself through my own 100-day challenge.

The big goal, I told myself, was to go for 100 days without complaining about boredom. I didn’t want to feel the need to use the language or to tell that old, stale, predictable story.

To counteract my propensity to get bored, I would challenge myself to do one new thing — or, at the very least, one non-routine, non-habitual, or unfamiliar thing — every day, for 100 days. That number felt big and significant — like a true commitment to change — but the daily deed still felt manageable enough to sustain over time.

I began to call my personal experiment, “100 Days Unbored.”

Last Wednesday, I marked Day 100 of the challenge.

Today, I’d like to share a bit of what I’ve learned.

100 Days Unbored: What I Did

Before you give me too much credit for doing one “new” or “non-routine” thing per day for 100 days, you need to know that my 100-day challenge did not consist of doing 100 brand new things that I had never done or tried before.

I did not intend from the beginning for this to be studded with “wow” moments of adventure that would impress on social media, and I actually didn’t intend to even write about my 100 Days Unbored challenge when I began it.

My 100 Days Unbored project was simply about challenging a personal narrative that I had grown tired of hearing myself recite — “I’m bored” — and doing something small, incremental, and sustainable about it every day, in step with my needs and obligations in everyday life, and to see what happened next.

Here’s the list of what I did:

Day 1: Birdwatch and walk at Sachuest Nature Refuge, Newport
Day 2: Collect litter while walking my favorite park trails
Day 3: Gift a loaf of sourdough bread to a friend
Day 4: Clean and fix what I thought was a broken iPhone charging port
Day 5: Record my first podcast in-studio for a day
Day 6: Go for a run on Providence Blackstone Boulevard
Day 7: Start to read a new book of Mary Oliver collected poems
Day 8: Have my first fresh lobster roll of the summer
Day 9: Joining a dating app
Day 10: Attend an open house
Day 11: Detail and clean my car
Day 12: See comedian Michelle Wolfe’s stand-up in Providence
Day 13: Bring a book (not the computer) to the coffee shop
Day 14: Go on a first date
Day 15: Try a dairy-free diet for a day
Day 16: Submit my new podcast’s trailer episode for publication
Day 17: Meet someone new
Day 18: Attend a friend’s live webinar
Day 19: Go to the movies with friends
Day 20: Go for a hike on a Saturday morning
Day 21: Cook homemade falafel from scratch
Day 22: Create a latte budget
Day 23: Take a solo sunset walk on Narragansett beach
Day 24: Take work offline and to the park
Day 25: Spend time over a friend’s house
Day 26: Upgrade to a queen-size bed
Day 27: Do various home fix-up projects
Day 28: Go on an artist’s date to the RISD Museum / Providence Flea
Day 29: Have a long phone call with a friend (instead of watching Netflix)
Day 30: Make a pumpernickel rye loaf from scratch
Day 31: Deep clean my entire apartment
Day 32: Make traditional French “coq au vin” for the first time
Day 33: Impromptu coffee and walk on Main Street with neighbor Ashley
Day 34: Start a new audiobook on neuroscience
Day 35: Attend a family cookout
Day 36: Coffee and morning walk in town with friends and their babies
Day 37: Go bowling
Day 38: Go out to lunch with a male(!) friend
Day 39: Start Ho’oponopono, a Hawaiian forgiveness practice
Day 40: Host a small dinner party
Day 41: Review legal contracts with dad
Day 42: Bake a sourdough loaf for family dinner
Day 43: First visit to the beach and swim in the ocean
Day 44: Bake a new pizza recipe
Day 45: Learn the kettlebell high snatch
Day 46: “Cook in” and watch Fourth of July fireworks from my balcony
Day 47: Hike Mount Monadnock in New Hampshire
Day 48: Homemade baby back BBQ ribs
Day 49: Yoga on the beach
Day 50: Start, double prove and bake a sourdough loaf (in the same day)
Day 51: Make popcorn and rent a movie at home
Day 52: Dinner at a friend’s house
Day 53: Host a thank you dinner for local clients in Providence
Day 54: Watch a new movie instead of Netflix reruns
Day 55: Go to mini golf
Day 56: Don’t open the computer for the day
Day 57: Order a standing mixer for future baking adventures
Day 58: Watch the full moonrise from the beach
Day 59: Cook from a new recipe (seared lemon coconut chicken)
Day 60: Meet a friend’s new baby
Day 61: Bake homemade croissants!
Day 63: Start reading another a new book
Day 62: Sew and repair my broken hat (instead of throwing it out)
Day 64: Deadlift 380 pounds (trap bar) to beat my prior personal best, 325lbs, from 12 years ago
Day 65: Have a scheduled cardiac MRI
Day 66: Breakfast with a friend who’s visiting from out of town
Day 67: Try a new restaurant
Day 68: Go to a wake for a distant relative
Day 69: Have an Aha! moment
Day 70: Take my little cousins to the park
Day 71: Permanently delete my Facebook account
Day 72: Explore Pawtuxet Village
Day 73: Work on book proposal revisions
Day 74: Attend an open mic night
Day 75: Replace the key fob battery
Day 76: Use homegrown lemongrass, Thai basil, and Thai peppers to cook a Thai basil chicken recipe
Day 77: First, first-date in a while and visit Point Tavern on Wickenden Street
Day 78: Meet a former client for lunch at their new community workspace in Boston
Day 79: Watch 1989 cult flick Roadhouse for the first time
Day 80: Try out Bayberry Beer Hall for dinner and drinks
Day 81: Lead class at the gym for the instructor
Day 82: Take myself stand-up paddleboarding on a whim
Day 83: Cook homemade turkey burgers (red onion parmesan) and balsamic roasted veggies
Day 84: Start re-reading the book, Iron John
Day 85: Bake my first scones, sourdough peach
Day 86: Kettlebell swing 36kg as a new personal best
Day 87: Grab a lobster roll for dinner on the Narragansett sea wall
Day 88: Walk the new PVD river pedestrian bridge
Day 89: Try a new earthy red wine with dinner (instead of a familiar rosé)
Day 90: Bake French-style Madeleines for the first time
Day 91: Write and schedule a newsletter in one sitting
Day 92: Start to workout 4+ days per week
Day 93: Taco night at Coral’s
Day 94: Attend the August Main Street Stroll
Day 95: Pizza party dinner with the cousins
Day 96: No bread for a day
Day 97: Grocery shop at a different Whole Foods
Day 98: Go out to a new oyster bar on the water for dinner
Day 99: Increase my flat bar bench press by 25lbs (150lbs to 175lbs) in 1 week
Day 100: Impromptu hammam visit / spa day / self-care afternoon

As you can see, my project didn’t involve many crazy things like going skinny skydiving from the Goodyear blimp, or really extremely experimenting on myself to learn about and showcase pressing social issues as one might by being homeless for a day (though, major kudos to those who have and do).

My 100-day challenge consisted largely of getting myself out of my comfort zone; to face even remedial tasks and deeds that, while small to outside eyes, were objects of what I had been avoiding; and, altogether, to not simply resort to familiar, habitual, routine choices and decisions — even with regard to daily meal choices — that I might ultimately feel bored by.

Many of my 100 days were simple efforts to try new cooking and baking recipes for the first time (and kind of often) to venturing out to new cafes and restaurants in the area with friends (can you tell I like to eat?), to going on new hikes in New England, to joining an online dating app to meet new people, and starting to read new books, and even starting a podcast (which I had been thinking of doing for years, previously).

The challenge of my 100-day challenge was ultimately, I now realize, to reside within an ongoing and active meditation about what I considered to be “boring” — and thus, to discover what I considered to be a solution to my own definition of “boredom.”

What I never considered beforehand was how this 100-day meditation would challenge me to understand and redefine my lifelong “boredom” story, for good.

And that redefinition really became clear on Day 69, when I had an “Aha!” moment so significant that the realization itself became my “new thing of the day. In fact, it completely changed my understanding of my relationship to the word “boredom” that I’ve had throughout my life.

After more than two months of residing within my 100-day challenge, I suddenly realized that, despite my using the word “bored” for my whole life, that “boredom” was never actually the precise story that I was expressing my own frustration with.

Whenever I had said, “I’m boredddddddddd,” I wasn’t really expressing frustration with a lack of stimulus or entertainment, or, as the English Oxford Dictionary defines boredom, “feeling weary because one is unoccupied or lacks interest in one’s current activity.”

I suddenly realized on Day 69 that the story I was trying to express all along was frustration with feeling “complacent,” “disconnected,” or “disengaged” from meaningful, significant or fulfilling life experiences in my life.

Whenever I had said I was “bored,” I was not only acknowledging that feeling complacent and disengaged from life bothered me, the complaint also implied that I must have felt some fundamental sense of personal responsibility for letting myself get and stay complacent.

That’s why I always tried to respond to boredom by inventing nonsense from the junk drawer or getting in the car to drive nowhere if it meant feeling like I was actively in the world, if even indirectly around people.

I always said, “I’m bored,” but I meant, “I’m frustrated by my passivity and willingness to remain in this feeling of complacency or disengagement from the life I want to live.”

*Cue head-explode-emoji.*

How I Began to Rethink Boredom

The etymology of the word “bored,” which we use in our everyday language to describe feeling unstimulated, uninterested, or unengaged from a particular activity, actually means hollowed out or emptied, as in, to “bore” a hole into.

That means the original meaning of the description, “I’m bored,” literally means, “I feel hollow or empty.”

I can think of no better description of my own use of the word “bored” throughout my life.

Even though I thought I was always referring to stimulus, entertainment, or adding “more” of something into my life, the feeling I was always describing was a sense of hollowness or emptiness — for me, a gaping void that left me feeling disengaged from life itself, and disconnected from people and experiences.

Which brings me to the last point that I want to leave you with today: overwhelm.

When I last wrote you, we discussed how the “age of overwhelm” in which we live is adding untold amounts of pressure onto the most precious commodities that we possess as humans: our time, our attention spans, and our energy.

As noisy iPhones, attention-baiting apps, and addictive-by-design social media consume what little space we possess on a given day (once all our needs and duties are fulfilled), we’re more likely than ever to feel increasingly overwhelmed, stretched thin, or stuck in “survival mode” day in and day out.

In the age of normative anxiety and stress in which we’re now living, it can feel tempting to reflexively add “more” to your plate, your expectations, or your daily To-Dos, to experience more fullness and less hollowness or boredom in your life.

For me, I would never have been able to pull off my 100 Days Unbored challenge if not for first eliminating what I increasingly consider to be superfluous distractions from the life I want to be living — even small, unconscious habits like flipping on Netflix at home or opening Instagram and scrolling forever.

Instead, I replaced these small but hollowing habits with one daily decision or action or choice every day that made me feel more full.

Now, whenever I feel hollow or empty or “bored” — which, as my “Aha!” moment taught me, actually means I am feeling frustrated with my own acceptance of complacency, instead of engaging more deeply with people and experiences I desire in my life — I know that all I need to do is take one small action to feel more full, fulfilled, or satiated.

To you, dear reader, I ask this:

Would you willfully exchange one small habit that makes you feel hollow or unwhole for one small deed or decision per day — a new pizza recipe, an impromptu walk with your neighbor on Main Street, or signing up for a dating app — if it means possibly feeling more fulfilled, more full, or like more of an engaged participant in the great dance of life?

If so, please, consider it.

Your time is so valuable. Your space deserves more than to be stretched thin to the point of snapping. The tools in your pocket deserve clamping down upon, and given no further allowance to clamp down upon your mind, your feelings, your emotions.

Your attention span is the most precious resource that we possess.

With it, we possess the power of autonomy, of personal freedom, and the ability to express our lives as completely and honestly as possible.actively

Reclaim your space.

Do not be bored or “hollowed out” any longer.

Embrace your time, your space, your attention, your energy — even a few precious moments of it — by feeling more full, more whole, more complete.

Yours in unboredom,

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