The 365 Day Challenge

I did it. Today is day 365. I find myself looking back at the year and reflecting on all the things I’ve done and all I can think is, “thank god it’s over”. Honestly, it was not easy at times. The year long journey has been both insanely rewarding and mildly stressful. But I accomplished everything I wanted and more. I experienced things I never thought I’d do, stretched my comfort zone, pushed boundaries, and even changed a few of my everyday behaviors. But there are a lot of things I didn’t get to. Thankfully, I have the rest of my life to do them.

Let me first explain why I started the 365 day challenge, what I set out to do, and what I actually did. In this post I’ll talk about the best, the worst, and most exciting days of the journey. I’ll touch upon what I learned, and best of all, what my friends liked most out of all the individual challenges.

Why I did it

The reason I started this challenge was to overcome the monotonous daily routine I was bound to. I felt I was living Groundhog Day, except Bill Murray was doing way cooler shit. As for me, I commuted an hour into the city, worked, took the same route home, went to the gym, then binged Netflix until I fell asleep. The cycle would repeat every day. Day after day. Something wasn’t quite right with the way I was living.

My solution was to do something different each day. It could be as simple as trying a new coffee shop or as massive as traveling to Italy. Throughout the challenge, I found I enjoyed doing things I’ve never done before. However, my goal wasn’t to do something new each day, it just had to be different enough to break my everyday routine.

If you haven’t been following, check out my #365daychallenge on Instagram

What I learned

There’s an entire world worth exploring, you just need time or money
One of my big concerns was running out of things to do. I quickly realized there is no shortage of stuff to do. There are no excuses. All you need are one of two things: time or money and an open mind.


Regret is a non-existent feeling
Stepping out of your comfort zone is scary. I couldn’t help but feel anxiety before and during several challenges. Hanging out at a bar alone, sleeping outside in the deep woods of VT, rollerblading the gay pride parade, and getting a pedicure were not exactly easy for me. But afterwards, all those experiences were awesome and worth doing. I look back to learn I don’t regret a single day or challenge.


Try it, you just might like it
I hated cooking. Seriously hated it. I wasn’t good at it, I never like waiting for homemade food, and I couldn’t distinguish differences in quality. At the end of 365 days I found myself making homemade pasta and sauce, and enjoying it. This rang true for meditation, tea, and tons of other stuff I found myself enjoying.


Once a day isn’t enough for true appreciation
I quickly realized doing something for one day left me wanting more. One day doesn’t provide enough time to fully immerse and learn everything. In fact, I lacked true appreciation for many of the things I was doing. Take for example day meditating on the beach. Sure, it was fun, but it wasn’t even 1% of what I could do with more time. Most days I was left wondering what the other 99% is about. In the case of mediation, I incorporated Headspace into my weekly routine.


Say yes. After all, it’s more fun with friends
Shooting a gun, rock climbing, drinking pear brandy, chopping down a tree, skateboarding, and watching a drive through movie are among the things friends encouraged me to do. They were all a blast.


You learn more acting like a tourist
Every state, city, and neighborhood offers an opportunity to discover something new. Chicago, Philly, Boston, Portland, and Florida led to some of the more enlightening experiences. Every day was different because I let it be. I researched locally and took part in the most touristy of attractions. Eating a chicago dog, visiting a great lake, running the Rocky steps, and eating the original Philly cheesesteak remain highlights of the trips.


Go big
The more you plan, the better the experience. Italy was incredible. Seeing and experiencing the Sistine Chapel, David, and touring the Colosseum were among the highlights of my year. It was a big trip will the longest lasting memories.


Don’t be yourself
I did a lot of things I never pictured myself doing. Growing a man bun, making a gingerbread house, rocking a mustache, playing board games, and baking. I even found myself abstaining from beer as I drank only Tuscan wine for a week straight.
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You don’t have to like everything
Yea, some stuff sucked. I ate a flower and hot chili pops, helped friends move, and attended an annual homeowners meeting.


What I had the most fun doing

  • Urban snowboarding
  • Tour the Colosseum
  • Rock climbing
  • See Michelangelo’s David
  • Participate in a painting class
  • Rollerblade the gay pride parade
  • Join a meditation session
  • Give blood
  • See Creation of Adam at the Sistine Chapel
  • Get a pedicure
  • Pick up basketball
  • Go Kart racing
  • Go to the NY auto show
  • Attend Doughnut Fest
  • Make homemade pasta
  • Sleep under the stars
  • See a Great Lake
  • Donate to charity
  • Shoot a gun
  • Get a drawing of myself in Times Square
  • Go skateboarding
  • Sport the man bun
  • Take a picture with the bean
  • Reenact a famous movie scene
  • A night at the drive in theater
  • Use a payphone
  • Visit the world’s largest selection of beer
  • Polar bear plunge into the ocean

What you loved most, based on total likes

  • Become a father (102 likes)
  • Create life (76 likes)
  • Drink breast milk (72 likes)
  • Bond (70 likes)
  • Change your first diaper (58 likes)
  • Capture the moment, maternity photos (55 likes)
  • Carry on tradition (50 likes)

What you love most, that wasn’t baby related

  • Explore Venice (47 likes)
  • Drink wine in Tuscany – no beer for 6 days (40 likes)
  • Party with the stars – Madame Tussauds (40 likes)
  • Cut your hair (38 likes)
  • Skateboard (38 likes)
  • Explore something larger than life (37 likes)
  • Grow a mustache (34 likes)
  • Advertise in Times Square (33 likes)
  • Get a watch (31 likes)
  • Get a pedicure (30 likes)
  • Throw your parents a retirement party (28 likes)

In the end, the experience was truly amazing. While I’m happy to wake up tomorrow and do nothing, I’m looking forward to 2017, where I’ll carry on the spirit of the 365 day challenge as part of a new way of life.

If you haven’t been following, check out my #365daychallenge on Instagram

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