How to Commit to a 365-Day Challenge

One way to pick a good 365-day challenge is to think about what would permanently transform your relationship with some aspect of life if you live that one year of your life a bit differently.

Even though you’re just doing some specific action or behavior each day, keeping that up for a full year will change you, often in ways you don’t expect. When you complete even one 365-day challenge, your life will never be the same again. Even if you only do one of these in your entire life, it changes you forever. You won’t be the same person on Day 365 that you were on Day 1. You also won’t be the same person on Day 3650, even if you stopped after 365.

Doing a 365-day exercise challenge in 1997 permanently changed my relationship with exercise. This year’s daily blogging challenge permanently changed my relationship with creative expressiveness and writing from inspiration.

You also gain a lifetime memory that no one can take away from you. If you do anything daily for a year, you’ll always be the person who followed through and didn’t quit. That’s a powerful reference experience you can always lean on in future years. It changes your self-concept.

I’ve only run one marathon in my life, 20 years ago. That one achievement permanently changed my relationship with running, exercise, and my own sense of potential. Every 365-day challenge is at least as transformational.

It takes a pretty strong why to commit to a 365-day challenge and complete it. Knowing that the payoff goes well beyond that year, even if you stop after a year, is good framing to finish the full year. It’s helpful to know that you’ll still be reaping benefits from the exploration 10 years later, 20 years later, and beyond. It’s not just about that one year.

This realization also makes the cost of quitting exceptionally high – too high to even consider once you’ve invested beyond a certain point. One bad decision during one moment of weakness, and you’re killing off decades’ worth of benefits. You’re doling out an extremely harsh punishment on your future self, which is dreadfully cruel – a lifetime of regret, always wondering how your life might be different if only you’d followed through. Even 20 years later, you’ll still look back and regret the moment you quit. So there is no quitting; that just isn’t an option.

I like to frame the challenge in such a way that the pain of quitting is so real to me that there’s no way I’ll ever seriously consider it after I’ve begun – unless I feel that the challenge has become unsafe like there’s a significant health risk from continuing.

I also like to think of a 365-day challenge as a gift to my future self. It’s rooted in compassion, caring, and hopefulness. I want my future self to have an even better life than I do now. I want him to have knowledge and experience that I currently lack. I want him to have amazing memories that I don’t yet possess. I want him to be happier and healthier. I want him to enjoy positive relationships.

This framing goes back 30 years to when I was 19 years old, sitting in jail for a few days after being arrested for a felony. My life was a mess at the time. While I was in that cell, cycling through boredom, fear, and regret, I realized that my future did not have to be like this. I was in that cell because of my past decisions. A long chain of bad decisions going back for about 18 months had led me there. I was just experiencing the consequences of causes that I’d set in motion over an extended period of time. I accepted that I was going to have to deal with the consequences of those old decisions for a while longer and that it wasn’t realistic to expect that I could turn everything around immediately. But I could turn my life around eventually by making different decisions, and that gave me hope.

Regardless of how awful my short-term outlook was, I could always be hopeful about the future if I keep leaning towards decisions that would set up my future self for a better life. So I began making different decisions, starting while in jail, and that really did change my life forever, making each decade better than the one before. I’ve been feeling happier and more appreciative as I age. The alignment between what I want, what I’m capable of, and what I’m experiencing keeps increasing.

The core of a a 365-day challenge is hope. By committing to such a challenge, you are making your hopes and dreams for the future a lot more solid and real. You’re turning hoping into doing, experiencing, enjoying, and appreciation. Always know that when you pick a good 365-day challenge and complete it, you’re going to appreciate that accomplishment for the rest of your life. You’ll be forever grateful to your past self for following through.

Can you tune into this flow of gratitude and appreciation, flowing backwards in time from your future self, streaming into your heart right now? Can you receive the energetic thank you from your future self if you listen for it? Can you also unwrap the please do this within that thank you?

If a 365-day challenge is purely on a mental level, the why isn’t there. Keep working on the framing until it burrows into your timeless soul.

A good challenge chooses me. It courts me. It teases me. It seduces me. Initially I may try to reject it or shake it off, but the idea persists till it persuades me to finally say yes. It takes time for me to fully surrender to the idea. It’s not an immediate yes. It takes a while for all parts of me to get onboard. I may even dance with the idea for years before I finally commit to it.

Before I’m really able to say yes to such a challenge, I reach the point of realizing that I cannot in good conscience say no to it. Another way of stating this is: My heart and spirit always says yes to it before my mind is fully on board. My heart and spirit say, “We have to do this.”

My mind then goes through stages of saying: “No, not this year. It’s too big of a commitment,” then “Maybe there’s a way… those are some nice benefits,” followed by, “Heart and spirit, you guys are evil! Can’t you just let this go? Why does it have to be now?” and finally, “Alright, fuck it! I surrender. I’m in. Let’s do this.”

Technically I’ve already completed my 365-day blogging challenge since I started on December 24, 2019, and 2020 is a 366-day leap year, but I always intended to blog through the end of 2020, and it’s a breezy coast to the December 31st finish line from here.

I’ve never done back-to-back one-year challenges, but I’m going to do that this time with a 365-day raw foods challenge for 2021, starting on January 1st and going through December 31st, 2021. So as one challenge ends, another begins.

This is also in addition to lots of 30-day challenges that I do with other Conscious Growth Club members. We start a new one on the first of each month, each time with a different theme like productivity, fitness, sleep optimization, decluttering, skill building, etc. I don’t do all of those, but I probably do about half of them each year as well.

I remember when I used to see 30-day challenges as a huge deal, like an enormous weight to lift. But once you’ve done a 365-day challenge, the 30 days ones seem so much lighter – no big deal at all.

For 2021 I’m doing a one-year raw foods challenge, meaning that I’m going to make eating raw vegan food my baseline diet for the year. I want to know what it’s like to be a raw foodist for a solid year, experiencing this lifestyle through all four seasons.

I know that my future will be permanently different if I do a one-year deep dive into raw foods. Even if I don’t continue beyond that year, that year will benefit my future self in many other ways. So it’s not a discipline challenge. It’s a gift. The framing of this challenge is rooted in hope and gratitude.

I have less than 4 months left to go in my 40s since I turn 50 in April 2021. My 40s have been the best decade of my life thus far, thanks in large part to personal growth investments made during my 20s and 30s that keep paying dividends (such as going vegan when I was 25 years old and beginning a wonderful relationship with Rachelle when I was 38).

I want the next decade of my life to be my best ever. The setup for this includes planting seeds for better health, relationships, happiness, creative flow, and more while still in my 40s. One of those gifts is to give my future self a cleaner and healthier body and mind who knows what it’s like to be a raw foodist for a solid year. I want my 50s to be the healthiest and most physically, mentally, and emotionally vibrant decade of my life.

I share this much detail, so you can better understand the depth of framing that goes into a 365-day challenge. When you extend the roots of your why deeply enough, you can feel certain that you’re going to finish the year without quitting. And then you can truly experience that year as a gift as you live through it.