Creative and Crazy Monthly Challenge Ideas To Inspire You

The first challenge between you and succeeding at a monthly challenge?

Coming up with a good challenge idea.

You don’t want to bite off more than you can chew and end up failing. But you also don’t want something so easy it doesn’t do you much good. And you probably don’t want to do something boring or commonplace that doesn’t stand out in your memory.

You want a story. A mini victory! An adventure that squeezes into your schedule and makes a lasting impact on your comfort zone.

For that, you’ve got to be creative.

Here are a bunch of monthly challenge ideas to get the cyclones swirling in your brainstorm.


taco dinner party
Invite 30 different people for dinner parties, drinks, coffees, workouts, or whatever over 30 days.

Monthly Challenges for Your Relationships

The Butterfly Net

Organize get-togethers with 30 different people in 30 days. Arrange some one-on-ones, host a dinner party or two, and/or try a 2-hour cocktail party.

The Gratefiller-Upper

Tell your partner something different about them you’re grateful for every day. Sounds simple, and it is, but this had such huge benefits on Kim and my relationship that we’ve kept it up and are at over 2,000 days and counting.

The Ferrazzi

Named in honor of the author of Never Eat Alone, line up lunches with someone for every day of the month.

The Long-Lost and Found

Reach out to 30 old friends who you’ve lost touch with. Update them on your life and ask about theirs. I did this in November 2021. Not only did it make me feel good, but the people who responded were also happy to hear from me out of the blue.

A Ruff Month

Foster a dog for 30 days.

Mr./Ms. Generous

Give someone a gift every day or allocate a budget of, say, $500 to buy surprise presents for people throughout the month. See my gift-giving tips for some ideas.

The Re-Courting

Pretend you and your spouse are back in the days when you first met: Go out on dates; Exchange flirty messages and even love letters; Sleep in different rooms; Try conversation starters; Hold each other’s hand when going for walks; Surprise each other with gifts.

Something to Consider:

Make It More Fun

No booze, no sugar, meditating, jogging every morning, or reading 30 pages of a book every evening are fine monthly challenges.

But they’re also kind of bland. So to make your 30 days hit harder, ask yourself:

How can I make it 10 percent more fun?

  • Cut out all added sugar and replace it with a different exotic fruit every evening.
  • Find friends to read the same book(s) as you and host a book club celebration at the end of the month.
  • Jog to a different café in your city every day.
  • Try 30 different guided meditations.
  • Replace booze with herbal teas and try to find your favorite flavor.

I just pulled these ideas out of the air. You can do better, and have more fun with your monthly challenge, if you give it some more thought.


Me taping my mouth to force myself to nose breath at night
I taped my mouth at night as part of my Nostril Opener challenge.

Monthly Challenges for Your Physical Health

Half-a-Million March

Go for 500,000 steps in 30 days. That’s an average of 16,667 steps a day.

The Bummer

No resting your butt on a chair or couch at home all month.

Breathe and Flow-vember

Follow the free 28-day series from my favorite YouTube yoga channel. Or, for an easier challenge, brush your body like you brush your teeth every day with a simple daily mobility routine.

The 50 Meal-er

Limit yourself to 50 meals in 30 days.

The Home Cookout

Eat only food you prepare yourself.

The Nostril Opener

Re-condition yourself to breathe through your nose instead of your mouth. I had a surprisingly fun time with this challenge in 2020, and it’s had even more surprising benefits.

Super Pantathlon

A month-long version of my go-to “pant-athlon” HIIT workout format. Pick 5 exercises and a target number of reps you want to do for each, then try to get them all done in a month. An advanced example may be 1,500 burpees, 100 kilometers jogging, 500 pull-ups, 10,000 rope jumps, and 3,000 pushups.


Selfie of me walking without listening to podcasts
Challenge yourself to take nothing (except maybe a camera for selfies and a newborn baby) on daily walks.

Monthly Challenges for Your Mental Health

The Wander-full

Go for a device-free “empty pocket walk” every day to let your mind wander as you wander around. This won the Kaizen Award for Best Monthly Challenge in my 2021 Unrutty Awards.

The Cold Snap

Turn off your home’s hot water tank. A reader named Patrick told me he’s kept at it for two years, adding, “This thing alone has changed my life in so many ways.”

The Breeze

Spend at least two hours a day outside.

The Mind Alterer

No alcohol, and in its place do different things that alter your mind’s state: cold exposure, heat exposure, exercise, meditation, marijuana, gratitude journaling, breathing exercises, etcetera.

The Pep Self-Talk

Say aloud a different positive thing you believe about yourself every day.

For a bonus, film these self-affirmations and compile them to make a pump-up highlight reel.

Feel Like Trash

Pick up litter every day, filling a big garbage bag by the end of the month.

Operation Sliver Removal

Spend the month dealing with all the little things that annoy you: Replace your phone battery; replace burnt-out light bulbs; grease noisy hinges; get your bike tuned up; tidy your garage; get a spare set of keys cut; say that thing that’s been on your mind for ages.

Delight Finding

Find something every day that delights you and write it down. I came across this idea from this delightful Happiness Lab podcast episode: Laurie Gets a Fun-tervention (Part One).

Bored Straight

Spend 30 minutes a day doing something incredibly boring, like watching a clock tick.


Me questioning whether to listen to podcasts or not
Break up with your earbuds for a month to rest your ears and listen to your own thoughts.

Monthly Challenges for Your Information Diet

The Net Creator

Spend more time creating stuff than consuming. So if you want to watch a two-hour movie, you have to offset that with at least two hours of building, writing, or painting something.

Good News!

No news is good news, right? Avoid all news for the month. Related to one of the thought experiments that convinced me to mostly quit the news, how long will you spend catching up with everything at the end of the month? So why not limit your news consumption to that much every month?

The Unbelievable Month

Shift your beliefs about as many things as possible during the month. For more on this, see how to be more open-minded and keep an open mind.

2006 Wasn’t So Bad

Named after the year before the first iPhone came out, put your SIM card into an old-school cell phone.

Intermittent Internet Fasting

Intermittent fasting for the internet. Consider the classic 16:8 protocol, where you’d have it for an 8-hour window of every day, then not at all for the other 16.

Un Bon Mois

Only consume content—books, shows, movies—from France. Or do this for any country or language you’re interested in.

The Podfast

Don’t listen to any podcasts for a month. My consumption was out of control, so this challenge benefited me big time in 2021.

LOL-a-palooza

Do something that makes you laugh every day: Go to comedy shows; listen to humorous podcasts; drop in on an improv class; watch funny movies.

A research project

Pick a topic to study for the whole month. Read a couple of books, go through many articles, watch YouTube videos, listen to podcasts, and talk to experts on it. Then collect your learnings into some sort of research report or video. I’ve done this before on topics like changing people’s minds, the science of taste, gift-giving, and personality.

Something to Consider:

Have Someone Else Choose For You

The advice you don’t want to hear is usually the advice you need.

Oliver Burkeman

We tend to challenge ourselves in ways that strengthen our strengths:

  • Fit people tend to choose monthly challenges that make them even fitter.
  • Social butterflies choose 30-day challenges to better flap their extraverted wings (and their mouths).
  • Disciplined people choose challenges that enable them to be extra strict in their behavior.

But, for the greatest bang for your buck, you’re better off challenging your greatest weakness. And it’s probably something so buried in your psyche you’re too scared to dig it up.

To overcome this, if you really want a monthly challenge that’ll improve your life, do this:

Ask people who know you well and want the best for you to go through this list and choose for you!


Spend time among fans to acquire a taste for that food
My licorice-loving dad and wife helped me get over my aversion to black licorice in a month.

Monthly Challenges for Your Flexibility

The Yuck-to-Yum

Pick a food you dislike and reapply the tricks I researched and applied to successfully teach myself to like black licorice.

The Waste Away

Sandy from Rugs By Roo told me at a picnic that challenging her family to generate no waste was so rewarding she’s planning on making it an annual tradition.

The Idea Machine Greaser

Come up with 10 ideas a day. See this FAQ from James Altucher for more.

The Smorgasbord

Go the whole month without eating the same food twice. Make it extra difficult by not eating the same ingredient twice.

Very Firsty

Do something you’ve never done before every day.

2.5-Year-Plan

Come up with 30 monthly challenges you’d like to do, and schedule one for each of the next 30 months.

On a (Dice) Roll

Number these monthly challenges, then use a random number generator to select one each day.


Keeping Track of everything you do cover image of Chris lifelogging with clock in foreground
Challenging myself to keep a log of everything I do has been my most impactful challenge so far.

Monthly Challenges for Your Self

The 30-Day Redirect

This is a 30-day challenge I led 35 people through in April 2021. Try it on your own by spending a week on each of the four steps I outline for filling out your “GPS” (general personal strategy).

The Handbrake Loosener

Hone in on a self-limiting identity and release it by strengthening an empowering identity that is incompatible with your self-limiting one. Read the story of how I did this for my “unsocial” identity, plus a bunch more examples.

The Method Actor

Find an identity of yours that’s holding you back, and spend the month doing your best Daniel Day Lewis impression, acting like you’re someone who doesn’t identify that way at all.

The World Class-ifier

Study and train to be in the top 0.1% of the world at something obscure, like my friend Cam did for the Settlers of Catan board game.

Morning Pages

As soon as you wake up, scribble whatever comes to mind for 15 to 20 minutes. A reader inspired me to try this in August. I’ve found it such a good way to warm up my brain and come up with ideas that I’m still doing it.

Time to Count

Keep track of how you spend your time like an accountant tracks spending. I experimented with this “lifelogging” as I call it in 2015 and haven’t stopped. I recommend everyone try it for at least a month.

The Humbler

Find an opportunity to say “I was wrong” every day.

Homework for Life

This is what Matthew Dicks calls the exercise of taking five minutes to write down a story from every day. He elaborates in his excellent book, Storyworthy, and in this video:

Something to Consider:

Narrow Down Your Options

My philosophy is that “getting out of your comfort zone” isn’t the smartest approach.

What’s better?

Make your comfort zone as fit, flexible, and capable as possible. So don’t look at your comfort zone as a circle, but as a body to train.

For your monthly challenge, you’ll want to improve some area of this comfort zone—the weakest, most likely, unless you want to be a specialist.

So I suggest you start narrowing down your choices by picking the area you want to work on, then coming up with monthly challenge ideas for it.

New and improved comfort zone diagram
  • 🦵 Your leg muscles are your relationships. Without them, you go nowhere. And super strong ones can help you jump and sprint. But they take hard work and time, so we tend to spend less effort on them than we should. Or we do frilly, cosmetic “toning” exercises rather than heavy lifting.
  • 💪 Your arm muscles are your career and finances. Men, especially, tend to sweat over bulging biceps. But why? Just for show. Practically, most of us need to do enough so that this part of our comfort zones doesn’t become so feeble it holds back our overall performance.
  • 🎽 Your core muscles make up your “self”—your sense of identity, values, and purpose. Everyone wants a six-pack, but dinky introspective exercises like crunches and planks won’t cut it. Life athletes with the most impressive cores do compound exercises that work the whole body of their comfort zone. This develops a strong core as a bi-product.
  • 🍽 Your diet is what you learn. Even the healthiest information diet won’t do you any good if you don’t move. Conversely, no amount of hard work will overcome consumption of pure junk.
  • 🏃‍♀️ Your cardio is your commitment. The harder and longer you work at something, the easier it’ll make things and the more energy it’ll give you.
  • 🧘‍♂️ Your flexibility is your openness to trying new things. It doesn’t always feel practical or like “hard work,” but you’ll get stiff, brittle, and sore if you ignore it.
  • 🦴 Your backbone is your health. When you’re young, it’s perfectly fine, but the longer you mistreat it and ignore it, the sooner it will cause you pain, limit you, and make you completely miserable.
Hanging out with Valencia expats
Challenge yourself to actively network with people in your industry, like me here with fellow online creators Tomas and Isabella.

Monthly Challenges for Your Career and Finances

The Side Hustle Sprint

Challenge yourself to somehow make $300 from something completely separate from your current career. I’m challenging Kim to do this for her blog, FeedMyFriends.com. Can she consult for corporate gatherings? Help people organize dinner parties? Sell PDF guides?

The Pocket Tightener

Spend 50 or 75 percent on non-housing expenses than you usually do. Consider pairing this with a challenge to add fun and/or rewarding and cheap activities in their place: boxed macaroni dinner party, hiking, fasting, etcetera.

A Grand Month

Withdraw $1,000 cash and limit yourself to only spending that for the month.

Designing My Life

Challenge yourself to do every exercise in the practical book on making a living you love, Designing Your Life.

The Networkout

Spend at least 30 minutes every workday expanding and strengthening your professional network.

The Pipe Cleaner

Write 1,000 words every day. At first, your words will trickle out slowly and be full of junk, but the more you run through this challenge, the clearer your thoughts will flow. This article by Nathan Barry inspires you on the career benefits of doing this.


Want to Make Your Monthly Challenge a Success?

Don’t Jump Into It Willy-Nilly

A monthly challenge gone wrong can do just as much damage as a successful one.

So whatever you challenge yourself, use the extra energy and willpower you have at the beginning of the month to follow these steps that minimize your odds of failing later on:

Join a Month of Discomfort

Periodically, I lead a cohort of monthly challengers. Everyone does their own challenge, but we have a group online community, each person is assigned an accountability buddy, and I help you implement some structure and sprinkle on a bit of fun.

See here for more info:


Want Two New Challenges Every Month?

If you're the type of person who's willing to experiment with different approaches in pursuit of a more extraordinary life, you'll look forward to my "Consider This" newsletter.

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If you're the type of person who's willing to experiment with different approaches in pursuit of a more extraordinary life, you'll look forward to my "Consider This" newsletter.

Every 14 days, you'll get a new idea that has improved my life in some way and may do the same for yours. 

Each email is short, fun, and free. Over 5,000 subscribe.

0 spam. Unsubscribe any time.

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