How to Make Your Habits Work for You and Not Against You.

Jake Wilder
10 min readFeb 1, 2020

The Epic Battle of the Fat Guy versus the Skinny Guy.

“The diminutive chains of habit,” the English writer Samuel Johnson said, “are seldom heavy enough to be felt, till they are too strong to be broken.” Indeed, we frequently fall victim to inertia, with studies showing that we spend more than 40% of our time mindlessly following habit.

Which begs the question, are these habits working for us, or against us?

And if you’re like most people, me especially, it’s not a good ratio. The majority of our habits aren’t helpful. While I want to eat healthy, save money, and be productive each day, my default behaviors often run counter to each of these goals.

An Economist would say that I’m acting dynamically inconsistent — wanting one thing yet acting differently. The rest of us just recognize it for what it is — a war of opposing personalities.

Lazy Jake versus Productive Jake

Lazy Jake scored the victory today. Productive Jake had been doing well. He was waking up early, exercising, getting things done at work. Yet this morning, when that alarm went off, Productive Jake didn’t get up.

Instead, Lazy Jake hit the snooze. Then he hit it again. And once more for good measure, sacrificing any chance to start the day with some exercise.

When was the last time you decided to change your behavior for the better? Maybe go on a diet, or improve your focus at work, or stop listening to political hate-mongering. Whatever it was, it likely created that familiar war between your inner personalities — the fat guy versus the skinny guy, the productive girl versus the lazy girl, or the ever-popular responsible saver versus the guy who makes it rain at a weekday strip club lunch buffet.

We make a decision to change and it’s easy to start out strong. The skinny guy’s in charge. He’s throwing out our junk food and loading up the fridge with kale. Still full of motivation, the skinny guy puts us on an exercise routine and suddenly that triathlon doesn’t seem so far-fetched.

But the fat guy is crafty. He lies in wait, patiently biding his time. Because soon there’s a rough day at work. And instead of having that superfood smoothie, he suggests that we treat ourselves to our favorite Chinese food. I mean, c’mon, one day won’t make a difference.

And suddenly the fat guy is back in charge, and all of his bad behaviors are back with him.

The world is designed to reward the fat guy. It’s designed to help the lazy girl. It makes it very easy to adopt these behaviors. It’s much easier to eat fast food, distract yourself through social media, or buy whatever fad strikes you in the moment. As the comedian Stephen Wright once joked, “hard work pays off in the future, but laziness pays off right now.”

You know this. I’m not telling you anything new. And yet that knowledge, in and of itself, is not enough to drive a change.

Many smokers, drinkers, and overeaters fully recognize the damaging consequences of their behavior, yet continue. Indeed, many of them actually pay third parties to help them avoid these behaviors that they know to be poor choices.

So while GI Joe may have been right and knowing is actually half the battle, that other half is the killer. If knowledge were the answer, there’d be no fat people, no smokers, and we’d all be saving enough for retirement. To quote Derek Sivers, “if information was the answer, we’d all be billionaires with perfect abs.”

No one ever mastered anything from looking at an infographic. It’s only in applying that knowledge that we can make a difference. Which comes down to two things: aligning your identity and setting yourself up for success.

Align Your Identity to the Behavior

“A person’s identity is like a pattern drawn on a tightly stretched parchment. Touch just one part of it, just one allegiance, and the whole person will react, the whole drum will sound,” wrote Amim Maalouf in his contemplation of the soul. And indeed, we hold our identities dear, often transforming our behaviors and to conform in support of that picture we hold so dear.

In many ways, this is deeply tragic. People ignore new ideas, reinforce their own echo chambers, and refuse to listen to relevant witnesses during an Impeachment trial. But we can also use it to our advantage. If our identity can drive certain behaviors, why not make sure it’s encouraging those behaviors that we actually want?

Habit guru James Clear gives the example of offering two people a cigarette. One says, no thanks, I’m trying to quit smoking. The other says, no thanks, I’m not a smoker. Which do you think will have an easier time of adhering to their plan of not smoking? One is trying to avoid a behavior that conflicts with the person he sees himself to be. The other is in alignment. And it’s much easier to take — and sustain! — an action that aligns to our identity.

It could be something as simple as using some self-control in the grocery store. Whenever I’m in the checkout line, and happen to look over and see the candy shelf, Fat Jake offers some encouragement to grab a Snickers or two. I need to remind myself that the store puts this stuff here to take advantage of people with no self-control. Then I ask myself whether I’m the type of person who falls prey to cheap grocery store nudges. Nice try Fat Jake, but not this time.

With elections upcoming this year, there will no doubt be a push to get people out to vote. And while it’s great to emphasize the importance of voting in convincing people to show up, one simple action tends to have a significant impact — just ask them. As studies found, if you ask people on the day before the election, whether they’re going to vote, you can increase the likelihood that they will by as much as 25%. It turns out, committing to a behavior helps reinforce it as part of the way that we see ourselves.

Just as we can influence peoples’ behavior by asking them what they intend to do, we can further affect it by asking them how they plan to do it. If someone asked you whether you were going to eat less junk food tomorrow, it would have some impact. But if you responded with a plan for how you’re going to bring a healthy snack to avoid those office doughnuts tomorrow morning, you’re more likely to follow through.

Ask yourself — What kind of person do you want to be? And what would that person do each day? Recognize the specific behaviors that support the

If I want to be the best father in the world, what behaviors would a great father do? He’d be present with his kids. He’d be patient and understanding when they struggle. And he’d be a great role model in everything he does.

If I want to be a leader that prioritizes peoples’ growth and development, how would I exemplify that each day? I’d take the time to give meaningful feedback. I’d prioritize asking questions so people can develop solutions that are unique to them. And I’d make sure I’m offering positive encouragement to help people develop their strengths.

Each identity has cascading effects. If you’re the type of person who’s disciplined enough to get up and exercise each day, you’re less likely to stop and eat fast food for lunch. If you’re someone who takes pride in maintaining technical credibility at work, you’re less likely to accept deficient performance in other areas of your life as well.

What kind of person are you? And what would that person do each day to demonstrate it?

Stop Making Things so Difficult on Yourself

The reason that Fat Jake and Lazy Jake win so much is because the deck is stacked in their favor. Short-term consequences are tremendously motivating and their behaviors offer those in spades. So if we want to beat them, we just need to be more motivated, right? I mean, if we want it badly enough, we’ll power through the difficulties and put that fat guy and lazy girl in their place, right?

Maybe at first. But here’s the thing with willpower and motivation — they’re like my friend from Long Island.

He’s a good guy. A lot of fun to have around. But highly unreliable.

If you need a hand building a deck, or taking down a tree, or getting bailed out of jail, he’s nowhere to be found. If, on the other hand, you need someone to hang out by the pool, eat your food, and drink your beer for you, he’s there.

You can’t count on him, especially when you might actually need him.

Motivation and willpower are the same. They always seem to be lacking precisely when we need them the most. On those difficult days, when we’re run down and need that extra boost to help us do what deep down we know is the right thing, we reach into that motivation tank…and nothing. It’s gone. No motivation. No willpower. And the fat guy’s back in charge.

Motivation isn’t enough. Willpower isn’t enough. Instead, we need to better set ourselves up for success. And stop putting ourselves in situations where we need to rely on force of will to do what’s right.

If there’s chocolate cake in the house, I’ll eat it. The same goes for pineapple ice cream, any type of cheesecake, or raspberry pie. If they’re in the house, Fat Jake is in control. Skinny Jake has but two options, he can seize on a moment of intense motivation and throw them all in the trash (incredibly unlikely based on past history). Or he can make sure that I don’t buy them in the first place.

The behavioral economist George Loewenstein called this the “hot-cold empathy gap.” When in a cold state (buying groceries), we don’t realize how much our behavior will be influenced when we’re under the influence of a hot state (in the presence of chocolate cake).

When Odysseus was sailing near the Sirens and their irresistible songs, he had his crew fill their ears with wax to make sure they wouldn’t fall victim to their irresistible songs. He also had his crew tie him to the mast so he could listen without submitting to the temptation. He took proactive steps while in a cold state to make sure that he couldn’t act irrationally while in a hot state.

Thwarting our bad habits follows the same prescription. Fat Jake and Lazy Jake have one critical weakness — they’re lazy! So if we can make it a little more difficult to do poor behaviors, and a little easier to do better ones, we can even those odds a bit.

In order to make sure I put away my phone in the evening, my Wi-Fi is set to turn off at 11pm. I could always go turn it back on, but it adds a pause and some friction into the process. People who get rid of their credit cards and auto-pay apps routinely spend less money. It’s one thing to scan an app and another thing to hand over six dollars for a cup of coffee. And to help make sure I drive continued progress at work, I frequently commit my team to arbitrary deadlines. That last one doesn’t always make me the most popular person — but we do get a lot done.

Relying on willpower and motivation is a losing strategy. Like my Long Island friend, you can’t count on them when it counts. Instead, we need to recognize that in our cold moments, when we’re not under the pressure of the moment, we need to take steps to make it easier on ourselves. Don’t buy the chocolate cake. Put your phone in another room. Sign yourself up and pre-pay for that Jazzercise class. As habits researcher Wendy Wood wrote in Good Habits, Bad Habits,

“Self-control is simple when you understand that it involves putting yourself in the right situations to develop the right habits.”

Never Stop Developing

So, how long does it take to correct these habits? How long should it take us turn around this behavior — banish that lazy girl, send the fat guy packing, and replace them both with their more productive counterparts?

I’ve heard everything from 21 days to 66 days to the oddly specific 14.7 weeks. And while it’s nice to have the reassurance of some magic number, I think it’s much better to say that we just don’t know. And that’s a good thing.

For one, regardless of the number of self-help columns that preach it, repetition does not create habits. It’s often correlated with habit formation because — surprise! — that’s what tends to define a habit. For us to continue a behavior, we have to believe that we’re getting a benefit out of it.

Two, who wants to think about enduring a negative practice? If I told you that you were going to be miserable for the next 66 days and then maybe, on day 67, a new habit would form and it’ll be easy, what would you do? In all likelihood, you’d just procrastinate from starting at all.

But mainly, because improving our behaviors is a continuous process. Too often people miss a day or two and then feel as if they’re back at zero. They use that as an excuse to revert for another week before starting again fresh next month. But one misstep shouldn’t be a license to keep sliding. Our behaviors aren’t so fragile that they need us to be perfect.

Instead, take a moment, remind yourself of what type of person you want to be, and focus on setting yourself up to be successful in those behaviors. Use it as an opportunity to strengthen your system. And never stop improving.

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Jake Wilder

I don’t know where I’m going. But at least I know how to get there.