The 30-Day Challenge Anti-Failure System

This 13-step research- and experience-backed system will dramatically increase your odds of succeeding at your 30-day challenge.


“We don’t rise to the level of our goals, we fall to the level of our systems.”

James Clear

Imagine you’re standing on a ledge 30 feet above the cold ocean, holding the end of a rope, and thinking of making a Tarzan-esque swing onto another platform.

That’s what a 30-day challenge is like.

If you succeed, you’ll earn a rush of accomplishment that will stoke you for more.

But if you fail, you’re in for a rapid fall, painful smash, and self-loathing climb just to get back to where you started to try again—if you can muster up the courage.

Given such high stakes, you’d be nuts to approach a 30-day challenge with a kamikaze, “Here goes nothing!” adrenaline-full-but-brain-less leap of faith. Better to set yourself up for success.

Here’s a system to follow.

I’ve compiled it from 30-day challenge experience and dozens of books on building habits, motivation, and the weird ways our brains our wired. It’s worked for me and will work for you.

1. Make a PACT.

PACT has kicked SMART off the pedestal as the gold-standard acronym for goal-setting in personal development. Because rather than being about where you want to go, it’s about how and why you want to move in that direction.

  • Purpose: How does this 30-day challenge fit into your longer-term life goals?
  • Actionable: Is it within your own control and not dependent on outside forces?
  • Continuous: Are the actions simple and repeatable?
  • Trackable: Can you easily mark whether or not you’ve completed the actions?
Chris in the middle of a fun HIIT workout called a Pantathlon
“I get to go outside and work out every day this month. Lucky me!”

2. Relish the opportunity.

Make your 30-day challenge more appealing to your brain by looking at it as something you get to do instead of something you have to do.

Even if your challenge is “no _____ for 30 days,” look at it from a positive perspective. For instance:

  • ❌ “I can’t eat sugar” → ✅ “I get to eat all sorts of delicious fruit.”
  • ❌ “I can’t drink alcohol/caffeine.” → ✅ “I’m lucky to have so many delicious non-alcoholic and caffeine-free drinks to try.”
  • ❌ “I’m abstaining from the news.” → ✅ “I get to dive into an incredible library of non-fiction books and articles.”

3. Make it seem super doable.

“We need to believe we can succeed before we are able to succeed.”

Dan Lieberman and Michael Long, The Molecule of More

Give yourself better odds.

“To aim at results that cannot be achieved—or that can be only under the most unlikely circumstances—is not being ambitious; it is being foolish.”

Peter Drucker, Managing Oneself

Before making the plunge into your 30-day challenge, ask yourself:

On a scale of 1 to 10, how likely are you to succeed?

If your answer isn’t a 9 or a 10, what do you need to change to get there?

Take it easy.

“Sometimes when I consider what tremendous consequences come from little things. I am tempted to think there are no little things.”

Bruce Barton, quoted in The 7 Habits of Highly Effective People

Beware overzealously believing all your energy and momentum from Day 1 of your 30-day challenge will carry on throughout.

That’s like sprinting at the beginning of a marathon.

To set a fail-proof pace, it’s worth asking yourself, What could I have no problem doing for 365 days straight? Then shoot for 30.

Holding up phone showing the cover image of a remarkable 30-day challenge transformation
Before-and-after photos like this are complete BS.

4. Lower your expectations.

“The things that create success in the long run don’t look like they’re having any impact at all in the short run.”

Jeff Olson, The Slight Edge

Don’t expect to build a new habit.

A University College of London study found 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 that’s another argument for taking it easy.

Don’t expect non-stop adventure.

A 30-day challenge is like most long-term relationships.

You’ll feel on top of the world early on, but that novelty fades away fast. Then it starts to get tedious. You’ll feel like you’re going nowhere and like the challenge is weighing you down.

But, as long as you made the right choice initially, it’s worth persevering.

Don’t expect a brag-worthy before-and-after.

All those inspiring before-and-after shots in Youtube thumbnails, blog post feature images, and fawning testimonials are cherry-picked and exaggerated.

And even if some are legit, the odds those changes stick are about as dismal as The Biggest Losers‘ chances of keeping off all the weight they lost.

We’ll get into how to improve your before-and-after perspective further down.

Spend time among fans to acquire a taste for that food
I involved my black licorice-loving dad and wife in my challenge to acquire its taste.

5. Loosen up a little.

The greatest threat to success is not failure but boredom.

James Clear

How can you make your 30-day challenge 10% more fun?

This makes your challenge more memorable, less of a slog, and maybe even something you look forward to every day.

  • Invite friends to join you on some days?
  • Make a playlist to accompany you on your challenge?
  • Add some quirky reward for accomplishing each action?
  • Give your challenge a fun name?
  • Take on a superhero-esque alter ego when thinking of and performing your challenge?

According to Katy Milkman, an added bonus of that last suggestion is it depersonalizes things, which makes the challenge less about your identity and motivates you more.

6. Recruit others.

Obviously, doing your 30-day challenge alongside someone else gives you extra accountability and support.

And even if everyone you know is too wussy to join your challenge, they can at least provide you encouragement and social pressure from the bleachers.

Month of discomfort calendar

Up for a monthly challenge with extra accountability, structure, motivation, community, and fun?

Join the next cohort of The Month of Discomfort.

7. Free up the time.

Trying to squeeze your 30-day challenge into your already busy schedule is a recipe for failure. So ask yourself:

What will I remove from my current schedule to free up the time for my 30-day challenge’s activity?

For example, when I challenged myself to daily “empty pocket walks,” I banned myself from reading email newsletters.

By removing and replacing in this way, you actually give yourself two 30-day challenges for the price of one. Bonus!

doing a daily mobility routine is the same as brushing your teeth
Kim using her existing tooth-brushing habit as a cue to brush her body with daily mobility.

8. Tie it to a trigger.

“Trigger” is habit-nerd speak for the cue reminding you it’s time to get to work.

Interlace your actions with an existing habit.

If you intend to do mobility every day, put the pillows from your couch in storage and get it done 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.

Tie your actions onto an existing habit.

When you wake up, reach for your book rather than your phone for 15 minutes of reading or morning pages. 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.

9. Clear the runway.

“A good change leader never thinks, “Why are these people acting so badly? They must be bad people.” A change leader thinks, “How can I set up a situation that brings out the good in these people?”

Chip and Dan Heath, Switch

Take the quote above and apply it to yourself:

How can you make it as easy as possible to perform your desired actions? And how can you minimize obstacles and temptations?

  • If you’re pod-fasting, delete the podcast app on your phone.
  • If you’re challenging yourself to get outside first thing in the morning, put your coffee maker on the patio.
  • If you want to have only cold showers, turn off your hot water tank.

10. Contingency plan.

Here’s a quote from ultramarathoner Dick Collins: Decide before the race the conditions that will cause you to stop and drop out. You don’t want to be out there saying, ‘Well gee, my leg hurts, I’m a little dehydrated, I’m sleepy, I’m tired, and it’s cold and windy.’ And talk yourself into quitting. If you are making a decision based on how you feel at that moment, you will probably make the wrong decision.

Seth Godin, The Dip

Mentally commit to a plan of action for when, inevitably, the going gets tough.

As my favorite non-fiction brothers, Chip and Dan Heath, write in The Power of Moments, this substantially increases the likelihood you’ll overcome the issue.

Some examples:

  • If you’re doing 10,000 steps a day, what will you do if the weather’s miserable or you get a blister?
  • If you’re avoiding sugar, how will you respond when your wife orders a $20 dessert at the restaurant and only has one bite before saying, “This is too rich for me. I’m full”?
  • If you’re taping your nose at night to stop your mouth breathing, what if you catch a cold and have a runny nose?

What happens if you miss a day?

Bake it into your challenge.

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

Assign a penalty.

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.

Last Ditch 30-Day Challenge Rescue Strategy

If the devil on your shoulder’s whispers are getting too powerful to ignore, speak up:

Say aloud what you’re tempted to do and the consequences.

“I’m trying to avoid reading any news for a month, but my sister just told me Tom and Gisele are separating and I need to know all the salacious details! But doing so will ruin my news-less streak and make me feel like a failure tomorrow.”

If you can’t get yourself to say it, try writing it down.

How to write a letter to your future self cover image of me starting my letter
Write your plan in a letter to your future self.

11. Put it on paper.

Document your plan.

Include your answers to the questions from all the steps in this system:

  • Why are you doing this 30-day challenge?
  • What exactly are the actions you’ll take?
  • When will you perform them?
  • What are your reasonably low expectations?
  • Why might you fail, and what’s your contingency plan?
  • How are you feeling going into the challenge?

This dramatically increases your odds of success at your 30-day challenge because it makes it real, forces you to synthesize your thoughts and plans, and serves as a commitment device.

Record your present.

Your memory can’t be trusted.

Carol Tavris and Elliot Aronson will convince you of this, as they did me, if you read Mistakes Were Made (but Not By Me).

So add as much detail as possible about your present state going into your challenge.

  • What dissatisfaction compelled you to take on your 30-day challenge?
  • How are you feeling?
  • What are you worried about?
  • Where are you writing your letter?
  • What else has been going on recently in your life?

And take a photo that you can look at to rekindle these memories.

Why bother?

The better you can capture your current status, the better you’ll be able to appreciate your gains from your 30-day challenge. This will motivate you to continue pushing yourself in the future.

30-day challenge tracking calendar posted on fridge

12. Mark your progress.

This may seem childish, but it helps:

Buy, print, or make your own month calendar with empty boxes, put it somewhere you can’t miss seeing, then ceremoniously check off every successful day.

Make your check marks as soon as possible after completing your desired action. This ties the dopamine reward you get from doing so with the activity that caused it.

Kim celebrating with two big beers
This is maybe not the best way to celebrate an alcohol-free month.

13. Make it momentous.

Look at the day you complete your 30-day challenge like a scene in the movie about your life’s story. Then ask yourself:

How can you elevate this moment?

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 few friends to spend $333 to celebrate.

This gives you:

  • Something to look forward to as you slog through your challenge.
  • Another few percent of fun.
  • A fond memory.

Being intentional about your celebration also increases your odds of taking on 30-day challenges in the future by using the “Peak-End Theory” to your advantage. Chip and Dan Heath explain it with this Mickey Mouse example in The Power of Moments:

“Even if the average of the moments you have on a trip to Disney World is just 6.5, if your peak was a 9 and the last moment of the day was a 9 too, you’ll remember the day as a 9 instead of a 6.5.”


Want help implementing these steps in your next 30-day challenge?

Then consider getting on the waiting list for the next Month of Discomfort:

Month of discomfort calendar

Up for a monthly challenge with extra accountability, structure, motivation, community, and fun?

Join the next cohort of The Month of Discomfort.

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