How to Build Habits that Stick: Small Wins Make a Big Difference

Megan Bannister
Megan Bannister / Published January 13, 2015

New Year’s resolutions are essentially made to be broken. Or so your annual habits would have you believe.

Sure, it’s easy to start off the new year at the gym, feeling great on the first day of your caffeine detox before heading home to eat a Whole 30-inspired breakfast and get a jump start on that mythical Inbox Zero. But like clockwork—usually somewhere around today's date—reality strikes.

You wake up late and skip the gym. A massive headache sets in and you cave to the pull of the afternoon coffee break. You’re tempted into enjoying a slice of Jerry’s birthday cake by some well-meaning co-workers. And that’s it—it’s been nice knowing you, New Year’s resolutions.

But it’s alright, because you’re not alone. Toby Stubblebine, the co-founder and CEO of goal-setting app, has been right there with you. He’s learned that when it comes down to it, it’s not about willpower or determination at all. Reaching your goals is actually about momentum and belief.

So we asked Stubblebine to share a few easy steps to get you in the right mindset to still make your 2015 goal a success. Whether it’s running a marathon or simply drinking more water, here’s what it takes to get you off the couch, stay hydrated and keep you moving toward those goals sooner rather than later.

Tony Stubblebine Aims to Unlock the Genius in You

Tony Stubblebine is a web and mobile app that combines coaching, community and data to help you be the best version of yourself. Whether you want to lose weight, take up meditation or learn office chair yoga, provides step-by-step guidance to help you achieve your goals.

In 2011, when Stubblebine started (then called Lift) with backing from Twitter co-founders Evan Williams and Biz Stone, he says they were interested in exploring human potential. “It felt like everything we knew about successful people is that they got to where they were by how they worked, how they practiced and what supported them along the way," he says. "No one is born a genius, you become one.”

So they started helping people find their genius. And over the past few years, millions have, including Stubblebine himself. Right now he’s working toward 19 goals on, ranging from drinking more water and eating more vegetables to bike riding and learning more about weight training.

Once referred to by Forbes as “the most affordable self-help product ever created,” currently boasts a four-and-a-half star App Store rating to show for its commitment to helping users change habits and achieve goals. app

“A lot of people have a really naive conception of human psychology that is essentially you get the carrot or the stick—either you’ll get rewarded or you’ll get punished. But (what) I’ve seen is that people are a lot more complicated than that, partly because they have so much going on," says Stubblebine.

"Goals don’t happen in isolation. When we see people who are succeeding, more than anything, it’s because they have a positive reinforcement loop."

The company recently made their name change—from Lift to—to focus more heavily on the coaching aspect of goal setting. For $15 per week, you can hire one of’s roughly 700 registered coaches who specialize in more than 1,400 different goals, ranging from decluttering your life to running your first marathon.

"Goals don’t happen in isolation. When we see people who are succeeding, more than anything, it’s because they have a positive reinforcement loop."- Tony Stubblebine, co-founder

Whereas traditional coaching has been conducted face-to-face, Stubblebine says he believes is one of the first companies to truly take advantage of the move toward digital. Sure, coaches Skype or FaceTime with their clients, but when it comes down to it, they’re still chatting face-to-face.

“Instead of a weekly, hour-long session, we break that interaction into short texts every day. Through texting with your coach you can get more immediate help when you need it and don’t lose contact," he says. "There’s actually a lot more emphasis on you taking action rather than just talking about the challenges you’re facing.”

Users also can work toward their goals using’s free model which provides reminders and a community of other users working toward similar goals. Stubblebine likens the shift to to how a founder might feel about building a company that helps people remember to floss versus one that’s helping users tackle a triathlon. free plan

“We knew people were capable of working on much harder goals so we decided to bring in more support in the form of a personal coach in the app who is dedicated to your specific goal.”

The Psychology of Habit Change

When it comes to transforming New Year’s resolutions into lasting habits, the first step is setting the right mindset to succeed.

While more than 88,000 users have chosen "Meditation" as a goal on, Stubblebine says there’s more to learn from the trend than an interest in finding some zen. It’s about setting yourself up for success.

To achieve a meditation mindset, it’s important to get in the practice of starting small. For example,’s Guide to Meditation recommends starting off with one- to five-minute sessions, providing the following graph to back up their recommendation.


It may seem too easy or overly simplistic at first, but from watching novice meditators, Stubblebine has noticed a pattern: often the users who meditated in sessions shorter than five minutes were more accepting when their mind wandered. Those who attempted to meditate for 20 minutes right out of the gate instead often felt that they weren’t succeeding.

What he’s learned from these two groups of people—those who find success and those who don't—is that what you really have is not a difference in skill or determination but a difference in belief system.

“The people failing go in with the expectation that they’ll meditate and their mind will go completely clear and calm. The second (their mind) wanders they say, ‘Well, it failed. I can never meditate.’ It’s like they’ll fail 100 percent of the time because their expectation is different. They had framed the experience so they have to eventually fail.

“Meditation is actually noticing when your mind wanders and bringing it back to a point of focus. The people who succeed have the right expectation and the people failing have the wrong expectation, but they’re both doing the exact same things.”

"The people who succeed have the right expectation and the people failing have the wrong expectation, but they’re both doing the exact same things."

In the end, it’s not that successful people achieve perfect meditation every time they practice, but rather that they have the expectation that failure and success aren’t mutually exclusive.

Don’t Let Red Vines be Your Demise

Red Vines

Let’s take a hypothetical New Year’s resolution: Maybe you’re like Stubblebine and strive to give up sugar. Now that’s not to say that sweets can’t be a periodic indulgence, but if and when they are, it should always be a part of your plan. Where Stubblebine has seen the greatest hurdle for goal setters is in a lack of situational planning.

"The idea is that when you get into a certain situation, you already know what you want to do. I don’t want to go out to dinner, have the dessert menu show up and not have a plan," Stubblebine says.

In his case, that plan is to order tea or cheese in place of a sugary dessert. "Without having thought ahead of time, we tend to stick to old habits," he says.

It may seem daunting to sit down and evaluate all of the times and situations where you might be tempted to break a resolution or deviate from a goal, but when the time comes, Stubblebine doesn’t want to have to ad lib.

“If it’s a big enough change, it’s a habit you’ll probably maintain at some level for years. We think of no sugar as a habit all on its own, but it’s also made up of dozens of small habits.

"We think of no sugar as a habit all on its own, but it’s also made up of dozens of small habits."

“When you go to the movies, what do you order? Popcorn or those ice cream dots? You might be on a three-month streak of no sugar and think you’ve nailed it, then walk up to concession stand and your old movie theater habit of ordering Red Vines takes over," says Stubblebine.

“Those are all separate habits you have to break or replace individually to truly achieve a no sugar goal. It may not occur that often and could take years before you’ve ruled out all of them. But that’s why I believe in pre-planning."

Another example: Stubblebine’s birthday is in April and instead of waiting until that temptation arises, he’s already planning ahead.

“Now is the time for me to decide if I’m going to have birthday cake, not on April 30 when someone passes me a slice of cake. Because I’m not going to be making a good decision then in that moment.”

Focus on Building Momentum—Even if it’s Slow at First

So you have a plan in place and know what you’ll do when the ice cream truck comes rolling down your street. Now it’s time to take those manageable pieces and start building something bigger.

“The people who succeed typically have a momentum and belief change. Those who succeed start very small. Beginning very small means they can actually get it done tomorrow and the next day and the next day and that builds momentum. Once they have that, it grows into something bigger.”

"Beginning very small means they can actually get it done tomorrow and the next day and the next day and that builds momentum."

Back to Stubblebine’s goal to kick sugar: “If you’re trying to give up sweets, there are probably 10 times during the day where you’ll be tempted to have sweets.”

When it comes to resisting those temptations, your success hinges not on resisting completely but on planning for a given array of situations and knowing what you’ll do when each of them arise.

“The second group of people take this goal and say, ‘I’m going to completely avoid sugar’ and they make it to 4 p.m., screw up and that’s it. Their New Year’s resolution is done for the entire year.

“The people who succeed say, ‘Ok, I made it to 4 p.m. today, I’m going to try to make it to 4 p.m. tomorrow.’ Then after they’ve done that for a week, maybe they try to make it to 6 p.m. They just keep pushing and don’t settle for complete success or complete failure. They’re always looking at ways to build on some success to continue the momentum.”

"The people who succeed say, 'Ok, I made it to 4 p.m. today, I’m going to try to make it to 4 p.m. tomorrow.'"

Once you’ve established some momentum, Stubblebine says it becomes easier to operate in the mindset of success.

“A person with momentum from that routine can’t help think of themselves as someone who doesn’t eat sweets even though they’re consistently failing in the evening. They’re still focused on succeeding during the day.”

Forget 66 days. Or Even 21. Just Make it to Nine.

Earlier this month, New York magazine published an article warning that your New Year’s resolutions might not transform into lasting habits until March, citing a 2009 study that argues it takes, on average, 66 days for a new habit to form.

And though Stubblebine doesn’t dispute that it might take that long to develop a habit, you have a “roughly zero percent chance of ever breaking,” he says the team sees more value in celebrating milestones when it comes to long-term goals.

“When we’re talking about a new habit, it’s the milestones that are going to matter more to you. The first time you do something is a huge achievement because it’s not really about habit but about ability.”

"When we’re talking about a new habit, it’s the milestones that are going to matter more to you."

For instance, the first time you go to the gym after joining is a milestone because you previously didn’t have the ability to do so as a non-member.

“We also measured success on a day-to-day basis and saw it got a lot easier around day nine. There’s a huge drop-off the first couple of days, and at day nine, 90 percent made it to the next day. That was consistent over and over for every day after. It’s most important to keep (that fact) in mind, especially after that initial milestone where there might be a period where you have to white knuckle it for awhile.”

Get into a Growth Mindset

Within its own team, practices what it preaches.

“We’re really about self improvement. It doesn’t have to be changing a habit but some way improving. Everyone in the company has a budget they’re given for self improvement projects and we have weekly retrospectives where we talk about how you improved this week.”

Lately, Stubblebine has been focused on triathlons. For another team member, it’s marathons. And for another, learning to play the guitar.

And no, it’s not that’s six team members are all super-human, goal achievers. Stubblebine says they just approach everything with a growth mindset.

He points to the findings of Carol Dweck, a professor of psychology at Stanford University, who argues that people either approach life with a fixed mindset or growth mindset. According to Dweck, a fixed mindset assumes intelligence and ability is static, while a growth mindset embraces challenges and sees failure as a potential for improvement.

Dweck writes in her book, "Mindset: The New Psychology of Success":

Why waste time proving over and over how great you are, when you could be getting better? Why hide deficiencies instead of overcoming them? Why look for friends or partners who will just shore up your self-esteem instead of ones who will also challenge you to grow? And why seek out the tried and true, instead of experiences that will stretch you? The passion for stretching yourself and sticking to it, even (or especially) when it’s not going well, is the hallmark of the growth mindset. This is the mindset that allows people to thrive during some of the most challenging times in their lives.

For the team, and their users, that mindset is what Stubblebine says makes tackling those bigger goals manageable. “Basically, you can train people to have a growth mindset and that’s what we try to do. We talk about growth in a way that makes it feel like it’s achievable and possible.”

Because when you break it down, it is.

Credits: Runner photo courtesy Thomas Hawk. Red Vines photo courtesy arbyreed on Flickr.

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