5 Lessons in Motivation: What I Learned About How People Keep Themselves Going to Start a New Thing

Throughout the month of September, I ran a 30-day habit-building activity called the Back to Self Challenge.

The truth is — I was keen to get back into a habit myself: Writing. And after 34 years, I know myself well enough to know that I’m more motivated to get a thing done if I think people are either paying attention or playing along. So I sent out a Tweet, asking basically: I need to rebuild a habit over 30 days. Who’s in?

I got 20 responses, ranging from people wanting to get back into daily meditation, walks, exercises, or creative pursuits. I made it clear that each of us should come up with a small, easily scoped task that you could realistically do every single day.

To get us going, I set up a basic leaderboard and email community. I sent daily reminder emails asking people to check in and tell us, every day: “Did you do the thing? Yes or no?” Then on Sept 1, we got to work.

About halfway through the month, I realized that when it comes to motivation, one size doesn’t fit all. The Challenge was clearly working for some people and not at all for others. Since we’ve completed month one of the challenge, I spent some time this weekend digging into the results from this micro-community of 30 days of habit rebuilding. Here’s what I learned.

The Bell Curve of Motivation

Call me idealistic, but I really thought more people were going to hit their goal 100% of the time. But in the end only 3 of the 20 people managed to do “their thing” every single day for 30 days. (I wasn’t even one of them!)

Here’s how the first month netted out:

  • Never Started: 3 people signed up, declared their Challenge Project and never once checked in
  • Feeble Attempt: 4 people did their thing a handful of times
  • 50% Success: 8 people did their thing about half the time
  • 85–90% Success: 4 people did their thing 20 or more days
  • 100% Success: 3 people (only 15% of the group) managed to do their thing every single day

In other words, what we had was a classic bell curve of motivation. Shown another way:

The bell curve of motivation — here’s how the month shook out for our Back to Self Challenge in September

I felt a little better when I noticed that things were shaking out like a classic bell curve. But I was curious as to what else I could do in future months to help people hit their goals and feel good about their new habits.

  1. Habits need to be simple.
    I’m talking, dead simple. The people with the most success had the tightest, cleaned, most incremental goals they could come up with. James Clear calls these “atomic habits” and wrote an entire book about how you can change your life by stacking up these little habits, bit by bit. In retrospect, I shouldn’t have let people enter the challenge with “compound habits” — things like, “I want to read and write for 20 minutes a day.” A few days in, it became pretty clear that doing two things became tougher than one, and those people were a lot more likely to drop out. We also had some “blurry habits” — things that read more like goals (things like: “I want to learn a new language” or “I want to get fit”). While I absolutely love the aspirational nature of goals, without the tactical, bite-sized scoping down into a habit (ie: “I will spend 10 minutes a day on Duolingo” or “I will do 15 minutes of yoga on my lunch break”) it was much harder to make incremental progress from one day to the next.
  2. You might need a different foundational habit than you think.
    Much like a lot of leadership and management coaching, the presenting problem in habit-building or goal-setting isn’t always the most pressing one to address. At least not right away. A week or two in, I noticed that a couple of people in the Challenge seemed to be having trouble checking in and getting their thing done. I reached out to a few of them and what I learned was, when they finally put themselves in the hot seat to get started, they realized there was something else that mattered more. One person’s initial goal had been to read and write every day for 20 minutes each. After a brief conversation, we uncovered that what they really needed was to make more time to sleep. We reset the goal as something more basic: Get at least 6 hours of sleep each night. Someone else had scoped a habit around an ambitious, new pursuit but ultimately learned they were so distracted with their job search that they needed more time to dedicate on that front. Their habit changed, too: Send one cold email a day. I think it’s important to be honest with ourselves and maximize the way we can set ourselves up for success — and a bit part of that is recognizing that sometimes we strike out a bit on what we think we need. That’s okay, too. It’s just part of the process.
  3. The most driven individuals came with a plan to win.
    I caught up with the three people who hit their goals 100% of the time to understand a bit more about how they succeeded. One note right off the bat was that their habits were clearly scoped and they mentally scripted a plan for now just the what but the how and the when. This specificity made it easier to fall into a habit for real. Interestingly, this group not only wanted to win themselves, but they wanted everyone else to win along with them. They were also the most active in terms of reaching out to me 1-on-1, passing along feedback, and even sending ideas or motivational notes back to the main group.

    I also noticed that, for whatever reason, this challenge really lit a fire from within for them. These Back to Self “Streakers” group refused to miss a day — no matter if they wanted to do the thing or if they felt like doing the thing. Honestly sometimes I wondered if there was also a shadow side to this “can’t fail” mindset. One individual told me how her husband would find her up late at night, refusing to go to bed until she finished “her thing.” “Isn’t it good enough by now?” he’d ask, trying to coax her to let it go for the day. “It’s not good enough. I can’t mail this in.” Regardless, this kind of internalization went a bit deeper than many others in the challenge. They came with a plan, and they won.
  4. We don’t need to do a thing every day in order for it to become a habit.
    There’s a sort of ingrained mantra among many of us that grew up in the “gold star” period of parenting: 100% or bust. We don’t just want an A grade; we want to prove total subject matter mastery with an A++. But this can be a pretty destructive line of thinking when it comes to trying to start something new. Because new things are hard, and nobody hits 100%’s right out of the park. But I noticed this was happening a lot in the Back to Self Challenge. After a few days of not doing the thing, people started rationalizing themselves out of finishing out the month. They’d change their priorities, explain away why they couldn’t fit it in anymore, or just quietly…leave. Almost as if it was better to not do it at all then to admit failure by not hitting that 100% target.

    But the reality is, when it comes to habit-building, even doing something 50% of the time is pretty damn great. Meditating every other day, or getting out for a walk a few times a week, is still a hell of a lot better than not doing anything at all. After talking this over with a therapist who’s coached a lot of people through motivational habit-building, her suggestion was to reframe the goals for month two: Give people a chance to choose how many days a week they want to aim toward achieving that goal, and benchmark them against that. In other words: This isn’t about hitting our goal 100% of the time. It’s about hitting it until it feels good for you. We need to give ourselves a little bit of grace.
  5. After the initial enthusiasm of “getting started” wears off, there is a “dip.”
    There’s another great habit-building activity going on right now called Inktober, which gives artists a daily prompt every day throughout the month of October. A Back to Selfer alerted me to this Instagram post giving their one million followers a few pieces of advice to succeed in the challenge. Notably, they call out “the dip” effect — that period of time when things get hard, when you realize how much work is involved to keep finding the time to do the thing, and you feel like you want to stop. Like a lot of things in psychology, giving a thing a name makes it easier to understand. By calling this out upfront, helped to manage expectations with their participants.

    Admittedly, I wasn’t prepared for “the dip” with my community in September. And we lost a lot of people when things got tough. This month I’m preparing a couple of additional scaffolds in place to help people get through it — including the inclusion of a “motivational mentor” for those middle weeks of the challenge.
Beware the Dip. Via https://www.instagram.com/p/CUdVhgbBuT-/

Based on all of this, I made a few changes to the Back to Self Challenge for October. Most notably:

  • Everyone gets daily reminders, but the leaderboard is based around whether or not you hit your weekly target (in other words, don’t aim for 100% — aim for the habit cadence that works right for you)
  • Creating some scaffolds in place for weeks 2 and 3 to help people get the “the dip” where things really get tough (still figuring out what this will include, but I’m looking into 1-on-1 peer motivation as one element)
  • No compound habits in your Challenge Project (I’m reaching out to folks who include more than 1 habit to encourage them to scope it down and focus on one main priority this month)

It’s been really fun to pick up a side project in learning more about why and how we’re motivated, and I’m excited to keep running this Challenge for as long as I have a cohort interesting in setting out to “do a thing” with me. We’ll see how things go this month.

Originally published at Dry Erase.

VP @ BolsterTalent, alum of @USV, @StackOverflow and @NorthwesternU, board member at @CompSci_High and @NUalumni, co-founder of #BeyondCodingNYC