How to Succeed at Whatever 30-Day Challenge You Choose

When you succeed at a 30-day challenge:

  • Your comfort zone expands ever-so-slightly into your true potential.
  • You “act your way to a new way of thinking,” proving yourself as a self-motivated, self-helping “type of person.”
  • You slow down time because the 30-day challenge serves as an anchor for memories to latch onto.
  • You earn the right to humbly brag about your accomplishment on social media.

Fantastic, right?

Yes. But here’s the problem:

An unsuccessful 30-day challenge can have the opposite results:

  • Your comfort zone’s walls shrink inward and reinforce in self-defense.
  • You “act your way into thinking” that you’re a loser who can’t even complete a simple 30-day challenge.
  • Your ego erases it from your memory to protect your feeble identity.
  • You have to post a cute photo of your dog on social media instead.

So when you take on a 30-day challenge, try not to fail.


Here are six maybe less-obvious steps to try following to make that happen.

Step 1: Take on an “easy” challenge.

Comfort zone expanding into potential after a 30-day challenge
Highly sophisticated diagram of what a successful 30-day challenge does to your comfort zone.

If you don’t watch foreign movies because you hate reading subtitles, you probably shouldn’t challenge yourself to read 50 pages of a book a day for a month

And if you grunt with effort standing up from the toilet, it’s probably not a good idea to challenge yourself to 100 air squats for 30 straight days.

I mean, you can try.

And you’ll probably feel like a badass for the first few days. “Look at me! I’m self-helping myself!”

But your overzealousness screws over your future self. When Future You hits a wall later in the month and realizes you’ve bitten off more than they can chew, they will be in pickle:

  1. Power through with this miserable, too-hard 30-day challenge you got them into, or,
  2. Give up and feeling like a sack of crap because of it.

How do you avoid such a pickly predicament?

Pick something that you could feasibly do for 365 straight days, then see if you can do it for thirty.

Step 2: Be positively pessimistic.

Holding up phone showing the cover image of a remarkable 30-day challenge transformation
Step 2.3: Don’t blindly believe 30-day challenge results on blogs, YouTube, or Instagram.

2.1 Don’t expect to get new habit out of it.

In this study that every blog post on habit creation is obliged to reference, but that I only read the abstract of, it took between 18 and 254 days, with an average of 66, for participants to turn a new daily activity into a habit. The more difficult the activity was perceived, the longer it took.

So what does that mean for you and your 30-day challenge?

Pick something you don’t perceive to be too hard. (See again, Strategy 1.)

This will give you a better shot of forming a habit in just 30 days.

Odds are you’re not going to engrain a new habit in 30 days.

So rather than expect to develop a new habit, expect to simply learn something new about yourself, expand your comfort zone ever so slightly, and create some memories.

Be wary of trusting claims bloggers back by linking to some study.

2.2 Don’t expect your 30-day challenge to be a non-stop adventure.

Taking on a 30-day challenge is like starting a new relationship.

The first day or two feel exciting, but the novelty wears off fast. Then it feels like a chore—maybe even pointless. Your life will feel the same, except now with an added burden of this challenge that your past self thought was a good idea.

(Kim, if you’re reading this, please disregard this analogy. Our marriage is special.)

2.3 Definitely don’t believe YouTube, blogs, or Instagram.

Any content creator’s testimonial, story, or before-and-after photo is guaranteed to be exaggerated to justify their own efforts and to suck in an audience.

For similar reasons, don’t believe your friends if they rave to you about so-and-so 30-day challenge they did.

2.4 Do expect the start of something potentially life-changing.

Look at your 30-day challenge like you’re planting a seed.

To start, you have to get your hands dirty to break fresh ground and till the soil. Then, if you’re diligent, you might see a tiny little bud break through by the end of the month. But it will only bear fruit or flowers much later if, and only if, you keep giving it attention.

P.S. If you like this analogy, you’ll love my post on daily habits.

Step 3: Make the right time for it.

doing a daily mobility routine is the same as brushing your teeth
Kim remembers to do her daily mobility by doing it after (or simultaneously to) brushing her teeth.

3.1 Remove and replace.

If you expect to “find the time” to do your challenge every day, expect to fail.

Make the time.

Ask yourself this:

What’s something I currently spend a chunk of every day on that I can carve out to clear up space for my 30-day challenge’s activity?

For example, in April, my challenge was to do 30-or-more-minute “empty pocket walks” every day. To free up that time, I’ve banned myself from reading email newsletters.

If you’re astute, you may already have realized this gives me a two-in-one 30-day challenge. Bonus!

3.2 Tie it to a trigger.

The best way to remember to do your 30-day challenge activity every day is to append it onto a habit you already have.

Do it at the same time as an existing habit.

If you intend to do mobility every day, remove the pillows from you couch so you do it while you watch TV every evening. Or rather than take your phone with you to the toilet, use that time to do your challenge of daily gratitude.

Or do it after an existing habit.

When you wake up in the morning, reach for your book rather than your phone for 15 minutes of reading. Or put a notepad in your bathroom so that after you brush your teeth in the evening, you remember to write down your story of the day.

Step 4: Set some rules.

Kim celebrating with two big beers
One rule to consider: How will you celebrate after?

4.1 What happens if you miss a day?

Plan in advance for the possibility that, for whatever reason, you miss a day of your 30-day challenge.

Bake it into your challenge.

Give yourself one or two “free days” to use at your discretion.

Or set a penalty.

For example, if you’re on a no-riding-the-elevator challenge but feel obliged to ride up with your boss one day, your penalty could be having to go up and down your office’s stairs ten times. Or if you slip up on your challenge to not nag your partner for 30 days, make up for it by giving them a 20-minute massage.

4.2 How will you celebrate?

Taking a page from The Power of Moments by Chip and Dan Health (and one of my rules for living a meaningful life), look at the day you complete your 30-day challenge like a scene in the movie of your life. Then ask yourself:

How can I elevate this moment to make it extra memorable?

For example, if you’re completing a 333,333-steps-in-a-month challenge, make your last steps to get to your favorite bar or restaurant where you’ll meet a couple of friends to spend $333 to celebrate.

(N.B. Inviting other people to your celebration scene has the added bonus of putting more pressure on you to deliver.)

Step 5: Post it up.

30-day challenge tracking calendar posted on fridge

Fork out a few bucks on a physical calendar, put it up somewhere where you can’t miss seeing it every day, then ceremoniously cross off every successful day with a bright red marker.

It might sound childish, but it helps:

  • The small investment of time and money to buy a calendar and find a place to put it up makes you feel more committed.
  • Crossing off each day is surprisingly pleasurable.
  • The dopamine dose you get from anticipating that feeling will motivate you to keep it up.

Step 6: Formally commit.

Me holding my letter to my future self that I wrote
Writing to a letter to your future self seals your commitment and is fun for Future Your to read.

This final tip for making your 30-day challenge a success is the most important because it brings together all of the previous ones:

6.1 Write a commitment letter to your 30-day-from-now self.

As hokey-pokey as you probably think it sounds, writing it down makes it real. It also forces you to collect your thoughts into something sensible and actionable. This dramatically increases the likelihood you succeed at your 30-day challenge.

In your letter to your glorious post-challenge self, try to include:

  • Why are you doing it? What do you positively pessimistically expect to get out of your challenge? (Step 2.)
  • Who for? Who is counting on you to succeed? Your older future self, for sure. Maybe your friends, parents, kids, colleagues, or spouse, too?
  • What actions? What exactly are you going to do in this challenge. Be specific.
  • When will you work on it and what will it replace? (Step 3.)  
  • Why might you fail? What excuses might you invent sometime in the coming month for not delivering your commitment? Preempt them by writing them down.
  • What are the rules? (Step 4.)
  • How will you feel? A month from now, how will your future self feel if you succeed at your 30-day challenge?

6.2 Send this letter to someone.

Send your letter to someone you know.

If you’re doing your 30-day challenge with someone else (obviously a good idea, if possible), you could exchange letters with them. Or you could send it to someone who you know will encourage you to keep it up.

Or, if you’re shy or embarrassed, send it to your future self. offers this service for free. Alternatively, you can use Gmail’s snooze function to have your letter appear in your inbox at the end of your 30 days.

Step 7: Disregard Steps 1-to-6 at your own peril.

Me questioning this post's steps for succeeding at a 30-day challenge

“I don’t need no silly letter, rules, or pre-arranged time for my 30-day challenge. I’ll just do it.”

– Everyone who ultimately fails at 30-day challenges.

If you think it’s overkill to go through the previous six steps to a successful 30-day challenge, that’s fair.

It’s entirely possible to get it done without any of them. I’ve done it before. Many people do.

But many more people fail that way, too.

Like most things—but not slot machines or pyramid schemes—you get what you put into it. If you put careful thought into what you’re doing, who you’re doing it for, why, when, and how, your challenge will be less of a challenge to get through.

Then, not only will you have something to brag about on social media, you might even make a lasting impact on your life.

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