When I was writing Better Than Before, my book about how to make or break our habits, one thing took me a long time to realize: the danger of finish lines.

Setting a finish line does indeed help people reach a specific goal, but although it’s widely assumed to help habit-formation, a finish line can actually undermine habits.

A finish line marks a stopping point, and once we stop, we must start over, and starting over is harder than starting.

This problem comes up often with “challenges”—a 30-day yoga challenge, Dry January, losing ten pounds before your wedding, giving up coffee for Lent, National Novel Writing Month, Buy Nothing, Whole30, etc.

It feels new and exciting to push through the challenge period, and usually that challenge period is short enough to muscle through. But then—you hit the finish line! Congratulations! And…then what?

The more dramatic the goal, the more decisive the end—and often, the more effort required to start over. By providing a specific goal, a temporary motivation, and requiring a new “start” once reached, a challenge may interfere with habit-formation.

Also, once we decide that we’ve achieved success, we tend to stop moving forward.

To be sure, sometimes a challenge is meant as an experiment, to learn how a certain habit feels or to achieve a specific goal. “If I stop drinking, will I feel better?” “If I write for thirty days in a row, will I get a creative break-through?” “If I don’t buy anything for a month, can I make myself more aware of my spending?”

That’s valuable, but that’s different from doing a challenge as a way to jump-start a habit—which is often what we want to do, when we undertake a “challenge.”

We start on Day One, we end on Day 30—and we do a great job of celebrating beginnings and endings. But the hard truth about a good habit is that usually, once we start, we don’t want to end. We want to eat healthfully forever. We want to exercise regularly forever. We want to read every day forever. And that can feel intimidating.

To avoid the problem of finish lines, and to energize ourselves to work toward a habit that we can keep “forever,” it can help to celebrate milestones.

Instead of sprinting toward the finish line, we chug past milestone after milestone. “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.

Some suggestions for celebrating milestones:

• Beautiful tools make work a joy, so if you can afford it, mark a milestone by buying yourself a wonderful new tool to use in that activity. Cooking regularly? Splurge on some great knives. Running every day? Upgrade your shoes. Note: choose a tool related to the good habit! Not an unrelated reward! External rewards are very, very tricky to use. And speaking of rewards…
• Note the rewards of keeping the good habit. Now that you’ve been exercising regularly, maybe you’re sleeping better, or you’re less restless during Zoom meetings, or you have more energy. Revel in these good feelings, in these benefits! Really take note of why this habit makes you happier, healthier, more productive, or more creative. (A One-Sentence Journal can be a good way to note and track these kinds of benefits.) This reward is very useful for habit formation.
• Claim that new identity! “I’m a podcaster,” “I’m a photographer.” For Rebels, in particular, claiming a new identity can be a very powerful strategy: “I’m an artist,” “I’m a nature-lover.”
• Keep track of all you’ve accomplished. Hitting a milestone can remind you of all you’ve done and give you energy to keep going. (A Don’t Break the Chain Habit Tracker might be useful.) Remember, you’re aiming at progress, not perfection. Give yourself credit, allow yourself to take satisfaction on what you’ve done. And to do that…
• Identify milestones to celebrate. For instance:
  • Celebrate anniversaries. Recently, I’ve been trying to pay more attention to significant anniversaries—for instance, I just realized that the 5th year anniversary of The Four Tendencies is coming up or that we’ll record the 400th episode of the Happier with Gretchen Rubin podcast later this year.
  • Look back to see how far you’ve come. I did a fun exercise with my high-intensity weight-training instructor. When I hit my ten-year anniversary (see above), he got out my old records, and put the weights at the setting used for my very first session. With high-intensity weight training, I always work on the outer limits of my strength, so it never feels easier. But when he set the weights to where they’d been when I struggled on that first day, I realized how much stronger I’d become.
  • Look for imaginative milestones. I heard about an app that tracks your running and translates it into distances: “You’ve run from New York City to Cincinnati!” And I think I remember that the old StairMaster would say something like “You’ve run up the Empire State Building.” So fun.

But remember, we’re hitting milestones, not finish lines. Hitting a milestone isn’t a reason to take a break—that’s the moral licensing loophole.

Hitting a milestone is a reminder of how far we’ve come, and how far we want to go, with a good habit.

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?