Here are my thoughts on why Challenges work:

1.They hold space for new things in your otherwise-crowded world/life/calendar/day/mind. Life is very, very full before you try to add in a new habit or project. Formulating your aspirations into Challenges holds a new space in your mind and your calendar for the things you want to do. It also forces you to prioritize, and decide what you won’t be doing for that time frame. That allows for decathexis to happen, where you recoup the time, energy or money you were spending on something less important so you can flow that toward your new habit or project or way of being.  

Challenges also usually involve some level of tracking and accountability, and are often also (naturally or formally) social, all of which increase the probability of your actually doing the activity at hand compared with the likelihood you’d do it without the Challenge.

2. They build momentum and habits by focusing your energy on actions you can control, vs. outcomes that are outsized or out of your control. Challenges set you up to experience significant momentum and progress toward a project or change that matters to you. If you want to write a book, setting a Challenge that says you’ll write for 2 hours a day will automatically trigger some progress and mental momentum, because you know that if you just do that over and over again, for six months, chances are very good you’ll have at least a rough draft in place when you’re done.

3. They chunk big transformations down into doable daily practices. I love to make lots of big life changes at once, but the data shows that massive behavior changes just don’t stick for most people. A Challenge to cut out sugar and alcohol for 30 days is vastly more likely to create lasting change than a nebulous “Lose 50 pounds” goal. Instead of “write a book,” Challenge yourself to write something—anything—every day for 30 days, and watch what happens.

4. They create a standard and provide structure. Without the rules of a Challenge, your goals can be structureless and just hard to put a mental frame around. It’s the difference between “start doing kettlebell swings” and “do 10,000 swings in the month of June.” Having some standard to get to, whether it’s a word count you’ll write or just a number of days for which you’ll do a thing, sparks that tiniest bit of competitiveness and energy.

5. But that standard is personal. You are the boss of yourself in a Challenge. Whether you create it yourself or you take on a Challenge someone else is running, you decided to take it on. And you have infinite authority to tweak the terms of a Challenge in order to make it work for you. You can start it a week later than everyone else. You can do it for 10 days instead of 30. You can do 3 days/week instead of 7. Or you can do 7 instead of 3. A Challenge is a competition, but it’s only between you and you.

If you experience fear at the prospect of certain Challenges, I would give you two pieces of advice. One: You should do it. That fear is a sign you’re onto something. Things will get very interesting if you proceed. Two: Take the Challenge, but be gentle and easy with yourself. There’s no extra credit for perfection. You already did yourself a big mazel by taking the first step. Don’t turn the tone of this experience from growth to self-critique, harshness or perfectionism.

6. The flexibility of the standards makes Challenges fun.  From philosopher James Carse:

“There are at least two kinds of games: finite and infinite. A finite game is a game that has fixed rules and boundaries, that is played for the purpose of winning and thereby ending the game.

An infinite game has no fixed rules or boundaries. In an infinite game you play with the boundaries and the purpose is to continue the game.

Finite players are serious; infinite gamers are playful.” 

In a Challenge, you get to choose whether to be finite or infinite. (Hint: choose infinite.)

7. They are hard, fast and fun. Have you ever taken a Bikram yoga class? They’re fond of pushing people to hold hard postures with the encouragement that “you can do anything for 30 seconds!” I feel that way about Challenges. Even when they’re super hard, they are also generally fast. You can do anything for 30 days. Or 90 days. Or even 6 months.

The fact that you go into a Challenge knowing the time frame is finite often allows you to tap into those deep stores of energy and discipline that are hard to access when you’re more vaguely trying to build a new habit or practice. And the fact that you know you’ll have made significant progress by the end of the Challenge, if you go hard enough, allows you to tap into even deeper internal resources.

And you always have the option of continuing the practice, or some portion of it, after the Challenge is over. But having an upfront start and stop date just makes it easier to wrap your head around doing something hard for that time frame, versus telling yourself you have to start a new thing and do it For All The Days Of Your Life.

8. Challenges leave successful transformation in their wake, regardless of whether you have a technically “perfect score” . The first time I did a writing Challenge, I wrote for maybe 12 of the 30 days. And honestly, I was happy I did that much, and saw it as 12 days more than I’d written the month before. During that 12 days, I also made a ton of progress in getting clear on a book project I wanted to work on, and some big business decisions I needed to make.

Two months later, I came back around and wrote every day for 6 months. And I still have a near-religious daily writing practice, plus the confidence to tap into the creative flow I know I have access to anytime I have a major book project or writing project I want to bust out.

To my mind, that initial writing Challenge was an extremely successful Challenge, even though I did less than half of what I’d signed on to do.

When you do what you committed to do during a Challenge, you’ll leave the Challenge feeling tired, and stretched but also expanded, because you’ve proven to yourself that you can do things harder or more consistently than you ever have before. But even when you don’t have a “perfect” Challenge, you’ll often find success in the form of personal breakthroughs, a-ha moments, momentum, new habits, mindset shifts, emotional healing or even just lots of words on the Page you didn’t have on the Page before.

More from James Carse: “You can do what you do seriously, because you must do it, because you must survive to the end, and you are afraid of dying or failing or other consequences. Or, you can do everything you do playfully, always knowing you have a choice, having no need to survive the way you are, allowing every element of the play to transform you, taking pleasure in every surprise you meet. Those are the differences between finite and infinite players.” Challenges position your personal growth, habits and your life, really, as infinite play; they position you as the infinite player, and real healing and progress as the prize. Game on.

P.S.: I issued a 30 Day Writing Challenge for Conscious Leaders a few weeks back, and over 150 brilliant souls signed up! I decided to take the Challenge right along with them, and it’s been a profound journey for many of us. Most people are journaling or free-writing every day, privately. But I wrote this post on Day 17 of the Challenge. I’ll be doing another writing Challenge in January; click here to get on the list for the January Challenge.