Struggling to form good habits? Happiness expert Gretchen Rubin shares strategies that can help you stick to a new routine

Gretchen Rubin has built a career studying what makes people happy — and, in her research, has learned that many times, the path to a happier life is all about forming good habits.

The former lawyer turned author has penned four bestsellers — The Four Tendencies, Better Than Before, The Happiness Project and Happier at Home — in which she test drive strategies for living a more fulfilling, manageable and overall happier life. Yet Rubin's conclusions are not one-size-fits-all. For the writer, the key step in finding the life strategies that work best for you begins with first getting to know yourself, and specifically identifying your "tendency" towards meeting expectations.

Rubin, who created the wellness company The Happiness Project, just released more tools to help people with habit formation: a series of journals, designed to track aims and habits but also to get to know oneself a little bit better.

With the school year fast approaching and many parents and students starting a new routine, Yahoo Life spoke to Rubin about the fundamentals of habit formation, how knowing your tendency can help you succeed in sticking to good habits and why a "clean slate" can be so important.

What is the biggest obstacle most people face when it comes to creating a new habit and sticking to it?

The biggest obstacle is that people don't think about themselves. They try to cram themselves into what someone else says is the best way, or the right way, instead of saying "What works for me? When have I succeeded in the past? People are saying I should get up and exercise in the morning, but I find I have more energy at night, so I should do that." We all want to be told what the answer is, but whenever I think of tools or strategies, I like to look at what every person might need. Something might be super successful for one person, but no tool works in every hand.

There are theories that you can keep a habit if you stick to it for a specific number of days. What are your thoughts on that?

I think it's a really catchy idea, that if I could just perform a habit for a certain number of days, it would take hold. However, if you have a doughnut with your morning coffee three days in a row, you'll find that habit is locked in — but if you go for a run three mornings in a row, that might not be enough. I will say, for most people, the more consistently you do something and the more frequently you do it the more effortless it will be, and that's what we all want with habits. I created the "don't break the chain" journals because, for a lot of people, that's really helpful. They want to keep up a habit. The more consistently people keep a habit [intentionally], the more effortless it becomes [later].

Can you talk about your Four Tendencies framework and how knowing which category you fall into can help with habit formation?

The Four Tendencies has to do with how you meet expectations, like a work deadline or your own desire to meet a New Year's resolution. Depending on how you respond to outer and inner, whether you meet or resist them, determines your tendency.

Upholder meets expectations. They meet New Year's resolutions without much fuss, and their inner expectations are just as important as other people’s expectations for them. Their motto is, "Discipline is my freedom."

Questioners question all expectations. They'll do something if they think it makes sense. They make everything an inner expectation. If it meets their inner standard, they'll do it no problem, and if it fails, they’ll push back. They’re looking for reasons and justifications. They don’t like anything arbitrary, irrational or inefficient. Their motto is, "I'll comply if you convince me why."

Obligers readily meet outer expectations but struggle to meet inner expectations, so the secret for them is to create outer accountability, even for inner expectations. So, if you want to read more, join a book group. Exercise with a trainer, or a friend who will be annoyed if you don’t show up. For some obligers, a journal can help, but for others, it's not enough. There's a lot of variation amongst obligers. Their motto is “You can count on me, and I'm counting on you to count on me."

Rebels resist all expectations, inner and outer alike. They want to do things in their own way, on their own time. They can do anything they choose to do, but if you ask or tell them to do something, they'll likely resist. They often won't do things like take a pottery class every Saturday at 10 am, because they'll say, "I don’t know what I’m going to want to do Saturday." However, sometimes rebels love a challenge, like "You think I can’t run a marathon in 2021? Watch me do it." Their motto is, "You can't make me and neither can I."

In terms of how you think about your tendency, you can see how different tools would be helpful to different tendencies. Just to talk about accountability generally, obligers have to have outer accountability to meet inner expectations — that's what they need. You need to find structures of accountability. But rebels, they hate the feeling of someone looking over their shoulder. They're doing something because it's their identity, and someone checking in on them can turn them off.

Can different tendencies succeed by using the same tool or strategy for habit change?

People can use the same tool in different ways. Like my "don't break the chain" journal. You get why upholders would like that, because they like gold stars and checking things off a list. Questioners like efficiency and "hacking" themselves — they like data and metrics. Obligers — and not all because for some it's not enough accountability — might check off a task in a journal and send a picture of it to a friend, to say "I did it today, did you do it today?" Other people might just feel accountable to their future selves. Rebels, meanwhile, love a challenge. Someone thinks they can't do something, so they want to prove it.

What is the strategy of pairing, and how can it help people stick to habits?

Pairing is great. It tends to really stick because you pair something you need to do with something you really want to do. I'm not a natural exerciser, and when I was in college, my version of this was I could only take a shower on days when I exercised. You can go a day without showering, maybe two, but you really want to shower. Podcasts are big for this. People will find a podcast they love and say they can only listen to it when they're on a walk, for example. My sister is like this with The Real Housewives — she lets herself watch it only when she’s on the treadmill. It makes the habit so much stronger because one-half of the pair is so compelling. It also makes people enjoy it more because there is one aspect they are really excited about.

Is there a specific time when it's best to start a new habit?

The best time to start a new habit is now, but for many people, there are auspicious times. In my framework, there's the strategy of the "clean slate," which is when you're starting something new. That can be you started a new job, or just moved or are starting a new school routine. Your old habits are wiped away, so new habits can come in. There are also auspicious times like a birthday or anniversary.

When you look at people who start new habits, many do it on a Monday. Is there something special about Mondays? No, but it’s how some people's minds work.

It's just not good to say, "I'm going to start January 1, so it doesn't matter what I do in the meantime." You want your auspicious beginning to happen pretty quick.

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