Challenge Yourself to Success

Through my years of pursuing personal growth, I’ve encountered numerous ways to set goals, to start new habits, and to be a better version of yourself. And I’ve learned a new approach to self-improvement: the 66-day challenge.

What I like about it is that it’s simple — one step at a time. And, you have a set time frame to work in. You can do the challenge with others or alone. You can have a support and/or accountability team. This is a challenge of your own making, and that tickles my sense of independence and desire for accomplishment on my terms.

The 66-day challenge is a great tool — weapon, maybe — for your success.

You have your dream, a goal to strive for. You go after it to be the best you can be at it. That takes time and practice. You count it out 66 days at a time, like metered steps to move you along. Even getting better at the first step of your growth and progress toward your goal makes you better.

What I mean by that is that if you want to be the best calligrapher in the world, you may decide to make your first 66-day challenge be learning how to draw a line. Along the way, you decide you want to learn how to make ink, so that becomes your next 66-day challenge. Then you want to learn how to change the width of your lines, so there is your next 66-day challenge, an idea that came to you during your second 66-day challenge. On you grow.

This is more than “learning” how to do something. It’s perfecting what you know. It’s creating a habit of working on your craft. It’s getting comfortable with being uncomfortable.

You could decide to get into the best health shape of your life; what would you start your challenge with? Would you start with food, movement, strength, weight, or maybe flexibility? Any of those would be great, and your inner voice will guide you as to which is your first challenge.

Or maybe your dream is to be the best sitar player. How about the best writer? Maybe you want to be the best gardener. What first step would you make your 66-day challenge? There are so many dreams! There are so many 66-day challenge options!

The 66-day challenge is taking action toward your dream, deciding what step to take to get you closer to your dream. And then you work that step, getting better and better at it every day for 66 days. You practice, you push yourself outside your comfort zone, you repeat.

You may fail some days, but the next day you pick right up again and keep going. The idea is to always seek to do it better this time than the last. If you fall off course, pick yourself back up, brush yourself off, look at the mistake and figure out what you need to learn from it, and go again. You learn from your mistakes and failures as much as from your successes. You grow from your mistakes and failures, and from your triumphs.

During the course of your 66-day challenge, your inner-knowing will tell you what your next challenge is going to be. That knowing comes out of the progress you make toward your goal. You can’t know ahead of time what the next important step is for you to take until you are in a challenge. You may think you know what you want to do next, but that’s based on where you are now, not where you’ll be then. Trust the inner-knowing to guide you.

It’s more fun doing a challenge with someone else. You have a built-in accountability partner that way. You have someone to give you support and encouragement, someone who knows what you are going through. That person can bounce ideas around with you about what you’re learning, how to approach the challenge better or differently, and even help you brush yourself off when you fail. Plus, you learn things that help you by being an accountability partner for them.

One secret is to not let the lack of a partner keep you from stepping into a 66-day challenge. You could have an accountability partner who is either doing their own challenge or someone who isn’t but has your best interest at heart.

What’s important is to have dreams, take action to reach them, and always apply your best effort to everything you do. Challenge yourself to success.

4 thoughts on “Challenge Yourself to Success”

  1. Good article Kit and I hope readers do undertake a 66-day challenge of their own. One point you left out is that research has clearly shown that if something new to you is adopted as faithfully as possible for 66 days, after that time it’s actually harder to stop doing it than it is to continue. So you want to make healthier choices with food, it’s comforting to know that once you do it for 66 days in a row, you’ll just naturally keep doing it. The emotional rollercoaster of ups and downs when you try something for a short while and then go back to your old ways will cease. 66 days and you’ve got something new in your life you want for yourself!

    • Ah, yes. The Magic of 66 days in creating a new habit is to smooth the way to a better way and to show you how good things can be. The Magic of 66 days in learning or polishing a skill is that you push yourself to new heights and successes.

      I see the 66-day challenge having a 2-fold purpose: to learn a new skill and to learn/cement a new habit. Sometimes the two purposes are the same, and sometimes they are different. I can quit sugar, an eating habit, for 66 days. I can practice my Origin Story, a new skill, for 66 days — and solidify the habit of improving my speaking skills.

      Thanks for your note, Pat. Happy challenge to you!

  2. My take on the Challenge is that it’s more about setting good habits. The 66 days is based on psychological studies, but it’s simplified, perhaps overly so.

    Researchers from University College London researched how long it took to establish a new habit (and in their study, it related to eating, drinking, or some other specific activity). The range of time it took to achieve “automaticity” was very wide: 18 to >200 days. But the average time was …66 days. Some of the gurus have simplified it to “it takes 66 days to create a new habit,” which isn’t really the point of the study. My take on that point is, you have to understand what it takes for you to establish a new habit (“automaticity”) so you don’t give up too soon.

    Stanford University human behavior researcher B.J. Fogg’s studies gives more guidance, which echoes advice I’ve heard you give: “baby steps” (as you put it). That is, shoot for changes that are “too big” (and what’s too big depends on the person) and it’s highly likely you’ll fail. The more you fail, the more discouraged you get. Thus: take on a small new challenge that you’re very likely to achieve. That gives you success that you then build on by taking on another, slightly greater challenge. And then another, and another, and….

    So the real question comes down to, what’s the magic formula to both push yourself and have a good chance at success to build yourself up the fastest? Well, as it happens I talked about just that on my podcast a few weeks ago, Failure is Not Optional: “the late Harvard researcher David McClelland found that when you set stretch goals for yourself that have a 50-70 percent chance of success, you’re more likely than not to achieve the goal, which gives you confidence to stretch even further.”

    And then repeat!

    • I like the idea that the magic formula is to create the one-two punch of (1) good habits that (2) push/stretch you toward your success.

      I had a client several years ago who knew she couldn’t add exercise to her health regime because she’d failed with an exercise program so many times before. I challenged her to walk to her mailbox daily — a 2-minute round-trip walk; she accepted. The following week I asked how that two minutes went. Her response at first startled then pleased me: “Two minutes was a stupid amount of time to walk. So I walked five minutes instead. I’m loving it!” She quickly extended her five-minute walks to 10 then 20-minute walks. She started losing weight, her joints hurt less, and she was proud of her improving health. She went from not exercising at all to pushing herself beyond my 2-minute challenge walk — and won.

      That’s one way to use a 66-Day Challenge.


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