#377 - 30 Day Challenges

10 minute read

In late 2013 I watched a TED Talk that changed my life. Attributing a life change to a TED Talk feels somewhat embarrassing in 2019, but it happened to me. The video (in the header of this post) is Matt Cutts’ talk on incorporating 30 Day Challenges into your life. It’s short and provides context for everything I’m about to talk about - so I recommend watching it before proceeding.

Quick List of All Challenges I’ve Done

  1. Digital Minimalism
  2. Active Time Tracking
  3. Embrace Boredom
  4. Aaron Information Management
  5. Whole30
  6. Stop Snoozing Weekdays
  7. Heal the Fingers
  8. No Zero
  9. Scheduled Life
  10. Learn to be a Dad
  11. Explore New Places
  12. No Passive Entertainment
  13. Monotasking
  14. Blue Apron
  15. AM Workouts
  16. Bullet Journal
  17. Bucket List Movies
  18. BACK to Health
  19. Complete Android Beginner Nanodegree
  20. Costco Food Challenge
  21. Sketching Faces
  22. Stop Nailbiting
  23. Establish Honeywell Workflow
  24. No Screens after 10PM
  25. Sweat 5 Days/week
  26. Study Every Day
  27. “Healthy Life” (eat, run, stretch, lift)
  28. Life Tracker Rewrite
  29. Don’t Eat Out
  30. No Phone During Conversations
  31. Before Work Exercise Routine
  32. Move to New Apartment
  33. No TV, No Videogames
  34. Workout Workflow Redux
  35. Living on a Budget
  36. The Incredible Bulk
  37. Yes Man
  38. No Reddit/Social Media
  39. Drop Windows, Pick Up Linux
  40. Use GoPro Every Day
  41. Enjoy Wedding and Honeymoon
  42. Run 50 Miles
  43. Write Every Day
  44. Read 5 Books
  45. Paleo + Crossfit
  46. The Swollening

That list is in descending chronological order. “The Swollening” (which was called “The October Project” at the time) took place in October 2013, about 6 months after the TED Talk was published. If you were obsessive or weird mathematical savant, you might have already figured out that there have been 72 months between then and now, and my list up there only goes to 46. That means that 25 of those months I did not run a 30 Day Challenge. Of those 24 months, 2 times I just failed so miserably at achieving my goal that I didn’t even feel it was worth writing down (e.g. “eat a Paleo diet” but then I ate pizza for dinner on day 1), the other 22 months came in chunks, where my system of 30 Day Challenges was put on hold to do some other, related thing. I held the “No Zero” challenge for 10 months straight, before accepting it as a Standard Operating Procedure & moving on with new Challenges. For all of 2016 I did a complicated, multi-faceted New Year’s Resolution, rather than 12 individual 30 Day Challenges. As I’ll get to later, I don’t recommend that sort of all-at-once approach. My point here is just that I’ve been doing this stuff for a while.

I have thought of myself as an amateur writer, amateur self-tracker, and amateur in the world of N=1 experiments, but that’s changed. By no means am I a professional any of those things… but I have given myself permission to feel qualified to talk about them with interested parties. I’ll have to keep that little self-realization in mind if I ever meet an interested party. Anyway, back to it.

Challenge Selection Analysis

Most of my 46 challenges lump into a few main categories:

  • Exercise - e.g. Run 50 Miles, Try CrossFit
  • Diet - e.g. Don’t Eat Out, Paleo, Whole30, The Incredible Bulk, Blue Apron
  • Productivity - e.g. Bullet Journal, Active Time Tracking, Write Every Day, Study Every Day, Digital Minimalism, and others

That list isn’t exhaustive.

Some of my favorite challenges don’t fall into any of those categories. For example: “Yes Man” in which I said yes to every opportunity presented to me for a month. Or the “Only new places” challenge, in which I did not go to any restaurant, gas station, grocery store, or other business - unless it was my first time in that place.

Challenges I Found to be the Most Worthwhile

Blue Apron

The Blue Apron Challenge was great not because it’s the best food service in the world and we continue to use it to this day. It’s not and we don’t. It was great because it was an awesome learning experience. We learned that we had the capacity to cook fancy things using our own kitchen. We learned new cooking techniques. We learned how to incorporate vegetables into meals and that doing so was actually a good addition.

Before Work Workout

This challenge was so nice I did it twice. It takes discipline to follow through on, but when you start the day with the discipline to get out of bed and into the gym, everything else that day is just a bit easier. Also, it feels incredible to have accomplished something worthwhile by 7:30AM. Plus it’s the best way to ensure you actually work out 5 days a week. If you wait until after work to sneak in a workout, exercise will get preempted by life.

Yes Man

This challenge came about after re-reading the book Yes Man by Danny Wallace. For a month I took away my ability to choose whether or not I wanted to do something - I just did it. Relieving myself of the ability to choose not to do something weirdly made me much more content to do things like “hey can you do the dishes?” It wasn’t “sigh, yes.” I just started doing them. It made me truly realize that what you’re doing is less important than your attitude about what you’re doing. They key to this challenge, though, is not to let people know you’re doing it.

Paleo & CrossFit

This wasn’t the first challenge, but it was the first one that I decided to go all-in on. We joined a CrossFit gym for a month, and ate a (modified) Paleo diet. I learned a LOT during this month. For one thing, I realized how effective CrossFit is at wearing me out. Also that I felt better when I ate less garbage. These habits didn’t truly stick, though.


I hestitate to mention this, because it’s so similar to the above - but Whole30 really introduced a long-term change in our diet. If you don’t know what Whole30 is, just think of it as a (quite strict) more-strict-than-paleo-but-paleo-like diet. I lost 15 pounds in a month, and haven’t really gained any of that weight back. We don’t keep bread in the house any more. We don’t keep cereals. We don’t keep chips or other snacks.

Digital Minimalism

This is my most recent challenge - and came with some habit changes that I think are likely to stick. I really enjoyed this challenge.

I turned my phone to Do Not Disturb for the whole month. It rang if someone in my contacts called me, and alarms worked as normal - but other than that it was silent. No notifications for texts. None for “Scam Likely” callers. I’ve subsequently just turned off notifications for every app that isn’t my phone or my Ring Video Doorbell. Also - I uninstalled Reddit, and only went there twice during the month. Once because I wanted to hear what Reddit was saying about Marvel losing Spider-man, and once because I was bored and too tired to be productive. The great thing is, I didn’t miss it. Rather than defaulting to low-quality information binges, I just spent that time working on personal projects. I got much more done… and that’s a much more rewarding and satisfying use of time than browsing /r/all.

Then, while working these personal projects, I would get way more done due to the lack of distraction. There’s a reason this website looks different today than it did 30 days ago.

This is what intentionality feels like. It feels good.

Challenges at which I Failed Miserably and Unexpectedly

No Screens After 10pm

Turns out I’m addicted to screens. I didn’t really figure out in advance what I was going to do instead. Then I found myself just sitting around. Then I thought of stuff I could be working on, but required my phone or computer. On day 2 or 3 I said screw it.

“Healthy Life”

This challenge was never defined. I was the quintessential loser who wanted to “turn it all around for the New Years!” but had zero follow-through on deciding what that meant. I wanted to swallow the world with this one, and wound up doing nothing at all.

Run 50 Miles

Turns out running extended periods caused my lower back to flare up. After day 3, I was in near constant back pain. I thought doing the “barefoot”-style running (running on your toes) would help prevent that. It didn’t. That’s what I learned from that.

30 Day Challenge Design Tips

If you’re interested in trying something like this for yourself, and I highly recommend it to everyone, here are some pro-tips.

  • Don’t be overly ambitious. This means you should aim to change one thing - and only change it to an extent that its reasonable to accomplish without sacrificing other things in your life.
  • Don’t be vague. What specific behavior are you going to do. When are you going to do it. How are you going to do it. How will you know when you’ve done it.
  • If your goal is to remove a habit, try replacing it with something instead. This isn’t specific to 30 Day Challenges, but given that so many 30 Day Challenges involve habit change, it’s something to keep in mind.
  • Do stuff you’re interested in. If you’re thinking about doing something, don’t Google “Good 30 Day Challenge Ideas”. I’m guilty of having done that when I felt uninspired, and guess what - I failed every time. If you’re truly out of ideas, see the Top 5 below.

Closing Thoughts

30 Day Challenges are a habit I’m really glad I’ve adopted. They’re a great way to learn about yourself, the world, and life in general. They mark the passage of time. They make you grow as a person. If you’re doing them, though, maybe don’t talk about it all the time. I took to just writing to strangers on the internet about them rather than boring my friends about them.

Top 5: Recommended Starting Challenges

  1. Start the day by drinking a full glass of ice water. Notice how much it wakes you up. Notice how forcing yourself to prepare enough the night before to have the glass by your bed ready for the morning makes for a nice little routine.
  2. Say “Yes” to every opportunity that comes up. Notice how what you do changes. Notice how how you feel about what you do changes.
  3. Put your phone on Do Not Disturb. Notice how much easier it is to ignore it. Notice how many more periods of uninterrupted quality time you get thinking, working, or with friends or family
  4. Track your time, or food, or money, whichever thing you think you could be managing better. You don’t have to change anything about it. Just write down what you’re doing with it. Analyze when you’re finished. That which gets measured, gets managed.
  5. Just do whatever you’re passionate about. If you want it, you’re much more likely to stick with it.


An expert is a man who has made all the mistakes which can be made in a narrow field.
- Niels Bohr

He had a self help podcast on speaker, and a mouthful of gummies so big he couldn’t close his mouth. I wonder if he’s just weird or losing his s%%%.
- Josh