When it comes to starting new habits, we often start with a “challenge”: 30 days of meditation, Dry January, losing ten pounds before your wedding, giving up coffee for Lent, National Novel Writing Month, Whole30.

I love a “challenge.” They can be fun. They can be a useful experiment, to show us what life is like if we quit eating dairy, write 1,667 words every day for a month, etc.

But sometimes we use a challenge to try to jump-start a habit, and for that, they often don’t work. A friend once told me, “My sister and I did a 30-day yoga challenge, and it was great. I was doing so much yoga, I loved it! But I haven’t done yoga since.” She felt frustrated, because the reason she’d done the challenge was to solidify the habit of doing yoga.

One reason for this challenge of “challenges?” The danger of the finish line. To learn more about the problem of the finish line, and how to avoid falling into that trap, read here.

Another reason for this challenge of “challenges?” The gap between what we can do for the short term and we can do for the long term.

With the short period and intense focus of a “challenge”—thirty days, Lent, November, countdown to a big event, etc.—we can maintain behaviors or activities that aren’t realistic for the long run.

And that means that during “challenge” month, we aren’t working to establish the habits that we can sustain in the future.

My friend successfully did a 30-day yoga challenge, but when it was over, she stopped, because she hadn’t thought about how to keep going to days 31, 65, or 5008. She didn’t consider key questions such as:

• “Going forward, I don’t want to do yoga every single day. How many days a week is the right number for me?”
• “Going forward, I won’t be doing this challenge with my sister. As an Obliger, how will I get the outer accountability that I need?”
• “It’s easy to track how often I’m doing yoga when I’m doing it every day. How will I monitor my yoga practice when I’m doing it some days?”
  
  

To maintain a habit, we need to figure out, “What’s manageable, what’s realistic for me to maintain indefinitely?” And that can be a hard, messy question to answer. The “challenge” may help to answer it, but often doesn’t provide an actual answer.

Sometimes, too, the “challenge” sets such a high bar that adjusting the behavior for ordinary life can feel like a compromise or failure. “I’m slacking off, I’m only doing three days of yoga each week.” So we give up a habit rather than dial back.

Also, “challenges” are often all-or-nothing: yoga every day; no sugar for a month. But often, going forward, people don’t want to live all-or-nothing.

To be sure, some people do like all-or-nothing. At least with some habits.

For example, me. I love all-or-nothing! I love the freedom from decision fatigue—no decisions, no will-power needed.

That’s why I love the “don’t break the chain” approach. (If you also like this approach, check out the Happier app and the Don’t Break the Chain Habit Tracker.) For me, it’s often easier to do something every day (write, visit the Metropolitan Museum, exercise) than to do it some days.

That’s also why I often use the Strategy of Abstaining. For Abstainers like me, it’s easier to have none than to have some. Because I have such a strong sweet tooth, I quit sugar entirely. Having no sugar is easy for me; having a little sugar is very hard.

But unlike me, most people don’t want to quit sugar entirely, or do yoga every day for the rest of their lives, so they need to figure out what they do want. Quitting sugar for a month, or doing a 30-day yoga challenge, doesn’t answer that question.

And even I don’t use the all-or-nothing approach with most of my habits. It’s not practical.

We need to think carefully about how, when, where, why, and with whom we’ll keep the habit going forward. What’s realistic? What’s manageable? What tools might make it easier? There are 21 strategies we can use to make or break our habits, and we need to figure out which ones to deploy.

The good news: it’s often easier to build a habit than you might expect, but you have to do it in the way that’s right for you. It’s crucial to reflect deeply on yourself, so you can set up the habit in the way that’s right for you.

We can also help energize ourselves to keep a habit by looking for milestones.

One appeal of the “challenge” is that we have a clear finish line in sight, and we can pace ourselves to hit that goal, and we can justifiably celebrate when we hit it. “I did thirty days of yoga! I kept up my streak! I did it!” It feels great to hit the finish line.

But actually, we want to eat healthfully forever. We want to exercise regularly forever. We want to read every day forever.

Without the reassuring limit of a “challenge,” without the end in sight, keeping a habit can feel overwhelming. “Am I committing to doing yoga forever?” Well…yes. And that can be intimidating.

So instead of sprinting toward the finish line, it’s helpful to think of milestones. “Thirty days of yoga” is a wonderful milestone, and it’s just one of many milestones that you will pass in a lifetime of yoga.

Hitting a milestone gives us a sense of progress. It reminds of how far we’ve come, and that we want to continue, with a good habit.

For suggestions about ways to observe and celebrate milestones, read here.

As we think about the design of a habit, we need to consider, “How will I chug past milestone after milestone? How can I keep up this habit for the long term?” That may mean lowering the bar of a habit. Instead of aiming to “Go for a run every day,” the aim becomes “Go for a run or walk five days a week.”

The modest habit that we keep is better than the ambitious habit we don’t keep. It’s better to do yoga four times a week forever than to do yoga seven days a week never.

It’s all those old sayings: Don’t let the perfect be the enemy of the good. Don’t get it perfect, get it going. Many things worth doing are worth doing badly.

What milestones have you identified, to help you keep going with a good habit? Do you find “challenges” to be useful—and have they ever helped you jump-start a habit?