36 Lessons I’ve Learned About Habits

I’ve learned these lessons the hard way.

I struggled to quit smoking in the early 2000s, failing seven times before finally succeeding in late 2005. I struggled with exercise habits, with changing my horrible eating habits, with waking earlier and being more productive and getting out of debt and simplifying my life.

I failed a lot, and still do. It was through those failures that these hard-fought lessons emerged, and so I don’t resent any of the failures. I recommend this attitude.

I’ve taught habits to thousands of people, in addition to changing dozens of my own. Teaching what I’ve learned to others taught me even more.

And still I’m learning. That’s the fun part.

Changing habits is one of the most fundamental skills you can learn, because it allows you to reshape your life. To reshape who you are. That’s truly transformational.

I share these lessons not as Commandments from On High, but as things you might try, in your journey of change and learning. Try them one or two at a time, so you’re not overwhelmed. Come back to this list after you’ve done that.

I hope they help.

1. When you make a small change, your ‘normal’ adjusts. Imagine that you’re used to a whole set of conditions — if you deviate from those conditions very much, you will be uncomfortable. Going to live in a foreign country where you don’t speak the language, don’t know anyone, aren’t used to the food, don’t understand the customs, don’t have the same kind of home you’re used to … this can be very difficult. But if you make one tiny change, it’s not very uncomfortable. And after a month or two, you adapt to this tiny change, and it becomes part of the conditions that you’re used to. Your new normal. Changing your life in small steps like this, one small change at a time, is much easier and much more likely to succeed than making multiple huge changes all at once. Gradually change your normal.
2. Small changes are easier to start. A big change not only requires your mental commitment, but more time and effort. If you already have your time tied up in other things, you’ll find it difficult to find the time to start your new habit. You might do it once or twice (go to the gym for an hour) but that habit is dead before it starts unless you put in an extraordinary effort. A small change — just a few pushups in the morning, for example — is much easier to get started. You could start it right now, in the middle of reading this article. Making it easy to start a habit means you’re more likely to actually do it.
3. Small changes are easier to sustain. If you start a big change (go to the gym for 30 minutes every day!), you might actually be able to start it with all the enthusiasm you have in the beginning. But that enthusiasm wanes, depending on energy and sleep levels, what else is going on in your life, disruptions in routine, etc. And eventually you’ll probably fail. But if you make the habit very small when you start, you are much much more likely to sustain it for longer. It’s easier to keep a small thing going than a big one. And keeping it going is what matters.
4. Habits are tied to triggers. When the trigger happens, the habit follows, if it’s been ingrained strongly as a habit. For example, for some people, when they arrive at work, they immediately turn on their computer. And then maybe immediately do another habit after that. The habit-trigger bond is strengthened from lots of repetitions.
5. Habits with variable or multiple triggers are harder. If you want to meditate every morning after waking and drinking your customary glass of water (for example), it’s much easier to create a habit like this with one daily trigger … as opposed to a habit that requires either 1) variable triggers, like not reacting angrily when someone criticizes you (you don’t know when that trigger will happen), or 2) several different kinds of triggers, such as smoking which might be triggered by stress or other people smoking or drinking alcohol or coffee, etc.
6. Learn to do easier types of habits first. If you try to do hard types of habits (like ones with variable or multiple triggers, or ones that you dislike or find very difficult), and you’re not skilled at creating habits, you’re much less likely to succeed. I highly recommend doing easy habits first, ones that only require a couple minutes a day, are tied to a single daily trigger, and that you enjoy and find easy. What’s the point of trying to form an easy habit? Well, you might find it harder than you think, but also, you’re building your habit skills, and most importantly, you’re building trust in yourself.
7. Build trust in yourself. What I lacked before I got better at changing habits was trust that I would stick to a habit. Why? Because I’d failed so often before, allowing myself to break promises to myself because it was easier than sticking to the promises. It’s like if another person constantly lies to you — you don’t trust that person anymore. The same is true of your promises to yourself. And the solution is the same — to build trust slowly, with small promises and small victories. This takes time. But it’s arguably the most important thing you can do.
8. Incremental changes add up to huge changes. This might seem to make sense on the surface, but I don’t think most people feel its truth in their gut. We all want all the changes we want, right now. We can’t possibly make ourselves give up a few of those changes for awhile, to focus on one, because then we wouldn’t get what we want, right now. I’ve seen this so many times — people want to make 10 changes at once, and can’t choose just one to focus on. But doing lots of changes at once, or big changes, means you are less likely to succeed. But if you stick with small changes, you’ll see some powerful long-term change. Try making small changes to your diet and activity levels — after a year, you’ll be way fitter than before. Try learning something a little at a time — if you can make it a habit and stick with it, you’ll be way better at it in six months. This is what I’ve seen in my life, and it’s been dramatic in scope.
9. It doesn’t matter which change you focus on first. We’re not in it for the short game, we’re in it for the long game. It can be hard to figure out which change to make right now, because that means giving up lots of other important changes. And I’ve seen people agonize over which change to make first, because they think the order matters. Sure, maybe it would be optimal to learn to meditate first, before making eating changes, but you know what’s not optimal? Making no changes. Over the long term, if you pick one small change at a time, you’ll have all the important habits formed. So honestly, just pick the one you feel like doing the most — the one that you’ll enjoy most.
10. Energy and sleep levels matter a lot. I wrote about this recently, but if you are sleep-deprived, you’ll be tired and have little energy to focus on habit changes. That’s fine when your enthusiasm for your new habit is high, but the moment things get even a little difficult, you’ll skip the habit because you don’t have the willpower to push yourself through a little discomfort. Sleep matters.
11. Dealing with disruptions in routine is a learned skill. One of the most common causes of habit failure is disruption in routine — taking a trip, having a big work project that requires you to work late, having visitors, having a cold. These kinds of things change your normal routines, which do a couple things to the habit you’re forming: 1) the trigger might not happen (if you’re sick you might not get up and shower, for example, if showering is your trigger), and 2) you might get so busy/tired that you don’t have time/energy to do the habit. So how do you deal with this obstacle? Anticipate it. Know that it will happen (yes, everyone’s routine gets disrupted). Plan to either take a break while you’re traveling (for example), or have a new trigger while your old one is temporarily disrupted. This kind of anticipation and planning is a skill that you can learn, and this skill makes you better at creating new habits.
12. Think ahead to avoid foreseeable obstacles. Other than disruptions to your routine, there are other things you can anticipate. For example, if you’re changing your eating habit (say, no sugar) and you’re going to a restaurant with friends or a birthday party, what will you eat? What will your strategy be if there’s sugar (which there will be)? If you forget about it and wait until it happens, you’ll be unprepared and less likely to stick to your habit. How and where will you work out when you travel? Anticipate and prepare.
13. Watch your self-talk. We all talk to ourselves. It’s just not always obvious, because the self-talk happens in the back of our heads, unnoticed most of the time. That’s normal, but when the self-talk is negative, it can absolutely ruin a habit change. If your self-talk is a series of things like, “This is too hard, I can’t do this, why am I making myself suffer, it’s OK to cheat, it’s OK to quit, this is too hard, I hate this” … you need to either catch it, or you’ll likely fail. You have to become aware of what you’re saying to yourself, and recognize that it’s not true. Then tell yourself things that are positive. This is a key habit skill.
14. Get good at watching but not acting on urges. When you see the urge to smoke, or eat a whole bag of Doritos, or not meditate, or procrastinate, or not go on your morning run … you can pause and watch it but not act on that urge. The urge usually goes unnoticed, and you just act on it. But you can watch it, and not act. You can give yourself a choice. At the moment you’re watching, dig deep and remember your powerful motivations.
15. Have powerful motivations. It’s easy to say, “Sure, I’d love to learn to program!” It sounds nice. But something that sounds nice isn’t going to stick when things get a little hard. You need to have a very strong motivation — wanting to have better health so you won’t suffer as much, wanting to create a good life for your kids, wanting to help people in need. Looking good is not a good motivator, but feeling strong and empowered is. Write your motivation down. Remind yourself of it when things get hard.
16. Use accountability to engineer positive & negative feedback loops. Feedback loops help steer you to doing a habit long enough for it to be ingrained as a habit … or they help steer you away from a habit. Sugar and drugs have feedback loops that are good for forming habits (you get pleasure from doing the habit, suffer if you don’t), while exercise often has the wrong feedback loops (it’s hard to do the habit, enjoyable to watch TV and skip the habit). However, we can re-engineer the feedback loops, and accountability is one of the best ways of doing that. If you’re going to meet a friend at 6am to go on a run, you’d feel really bad if you missed the run, and feel good about going on the run with your friend and enjoying the conversation. Boom. New feedback loop. Same thing when you blog about your habit to an audience, or join an accountability team.
17. Challenges work really well. Short-term challenges of 2-6 weeks can be really motivating. Maybe it’s a challenge between two people (you and a friend), or a group challenge. It’s a form of accountability that’s fun and, again, revises the feedback loop in a good way. Examples of challenges: no sugar for a month, work out every day for 21 days, stick to a diet for 6 weeks, etc.
18. Exceptions lead to more exceptions. It’s really easy to justify not doing your new habit (or doing an old habit you’re trying to quit) by saying, “Just one time won’t hurt.” Except that it will, because now you think it’s OK to make exceptions. And now you don’t really trust yourself to stick to your promise to yourself. It’s much more effective to not make exceptions — catch yourself if you’re thinking about it and trying to justify it, and remember your motivations. When I quit smoking, I told myself Not One Puff Ever (NOPE).
19. The habit is the reward — it’s not a chore. Adding external rewards can be a useful way to have good feedback for doing the habit, but the best possible reward is internal. The reward is doing the habit. Then you get the reward immediately, not later. For example, if you think exercise sucks, you’re getting bad feedback as you do the habit — you won’t stick to it for long. But if you can find ways to enjoy the exercise (do it with a friend, see the enjoyable aspects of exercise, play a sport that you love, go on a hike with awesome views, etc.) then you’re getting positive feedback as you do the habit. Change your thinking — the habit is lovely, a reward in and of itself, a way to care for yourself. Do not think of it as a chore you need to get done, or you’ll avoid it.
20. Lots of habits at once means you’ll probably fail. Go ahead and try an experiment: do 5 new habits at once. See how many you’re successful with. Then try one habit only, and see how long you stick to that. In my experiments, one habit is much more successful than two at a time, and exponentially more successful than 5-10 habits at once.
21. Recognize when you’re getting distracted. In the beginning, we can get very focused on a new habit, and have lots of energy to put into it. But other things can come up and we might find a new shiny toy to get excited about … and soon the old habit change is falling to the wayside. This has happened to me many times. Now, I’m not saying a habit needs to take up all your mindspace and free time. That’s not healthy either. But you should be able to focus on it for a small amount of time each day, and still enjoy it and look forward to it. If that’s falling away, re-examine your motivation and priorities, and either drop the habit or re-focus.
22. A blog is an amazing tool. As I said, accountability makes a huge difference in your habit’s feedback loops. Blogging is a great way to get accountability. And as you’re sharing what you’ve been doing and what you’re learning, you are forced to reflect on your habit, which makes what you learn about the habit and yourself a much deeper experience.
23. Failure is a learning tool. You will fail in your habit attempts — that’s a given. But instead of seeing it as a failure of you as a person (it’s not), see it as a way to learn about yourself and habit change. Each person is different — what works for me won’t necessarily work for you. And you won’t know until you try it and fail. When you fail, you learn something new, and that helps you get better.
24. How you deal with failure is key. When many people fail, they feel bad about themselves and give up. This is why they have such a hard time changing habits. If instead they got back up and tried again, perhaps with an adjustment to their method (some new accountability, for example), they’d obviously have a much higher chance of success. The people who succeed at habits aren’t people who never fail — they’re people who keep going after they fail.
25. Adjust or die. On a related note, habit change is about learning to adjust. New job? That will change things, so you’ll need to adjust your habit. Missed a few days? Figure out what’s going wrong and adjust. Habit isn’t enjoyable? Find a new way to make it enjoyable. Self-talk sabotaging your habit change? Focus on becoming aware of your self-talk so you can solve that problem. Adjust, adjust, adjust.
26. Enlist support. Who will you turn to when things get hard? When you need encouragement? When you fail? Have a support buddy — I had one when I was quitting smoking, and I’ve used it other times as well. If you start out without support, and fail, that’s OK — adjust by finding someone to help you. That might be your spouse or best friend or parent or sibling or co-worker. Or maybe you find a support group online. It makes a big difference.
27. You limit yourself. Lots of times I suggest people give up something like cheese or sugar or beer, at least for a little while. They respond: “I could never give up my cheese!” (or meat, or sweets, etc.) Well, that’s true if you believe it. However, I’ve learned that we often think we can’t do something when really we can. I recently talked to someone who was absolutely sure she couldn’t give up baked goods. She limits herself with this belief. We all do to some extent — but if you can examine your beliefs and be willing to test them out, you’ll often find out they’re not true.
28. Set up your environment for success. If you’re going to give up sweets, get rid of all the sweets in your house. Ask your spouse to support you by not making or buying sweets for a little while. Tell friends you’re not eating sweets and ask them to support you. Yes, this can require others to make adjustments, but if you ask nicely for their help, often they’ll be glad to support you. But the point is, find ways to create an environment where you’re likely to succeed. Create accountability, reminders, support, a lack of temptations and distractions, etc.
29. Just lace up your shoes & get out the door. Reduce the barrier to starting the habit. If I need to go for a run, often I’ll think about how hard it is, how long it will take, how cold it will be, etc., and I’ll psyche myself out and not do it. But when my rule is, “Just lace up my shoes and get out the door”, that’s so easy it’s hard to say no. That’s my bar. As easy as possible. Once I’m out the door, I’m invariably glad I started and things go well. For meditating, just get your butt on the cushion. For writing, just open up your writing program and write a sentence.
30. Define your breaks. If you’re going to be traveling and know that you can’t stick to your habit, for example, set the dates of your habit break in advance, rather than letting it slide and then thinking that you’ve failed. And have the date when you’re going to get back on track, and set a reminder so you don’t forget. This will keep a planned event from completely derailing your habit change.
31. Habits are situational. A habit is tied to a trigger, but really, the trigger is an environment. So if your trigger is your morning shower, that’s great, but it’s not the shower itself. The trigger is taking the shower in your home, getting out, seeing a something in your bathroom that somehow triggers the impulse to go and meditate (or whatever your habit is). So if you take a shower in a different bathroom in your house, or in a hotel, the trigger doesn’t happen. The same is true if you got a phone call as you got out of the shower, or your wife comes and gives you a hug, both disrupting the trigger. Anyway, there’s not much you can do with this info, as you can’t control all the things in your environment, but being aware of subtle environmental changes that affect your habit can help you to understand what’s going on.
32. Learn to cope in other ways. Often your bad habits are ways of coping with a real need — like needing to cope with stress or bad feelings about yourself or a fight with a loved one. The need to cope with these things won’t go away, and so bad habit becomes a crutch. You can find other ways of coping that are healthier, so you don’t need the crutch anymore. Read more.
33. Be kind to yourself. You will fail, and you can be hard on yourself and feel guilty and think that you’re crap. That won’t help at all. Being kind to yourself is a good habit skill, if you pair it with an adjustment that allows you to improve your habit method. To be kind to yourself: remind yourself of how hard it is to be happy, and that you’re struggling to find happiness despite things that cause you stress and frustration and anger and irritation and disappointment. This is hard. Have empathy with yourself. Be understanding and compassionate. It will help you as you adjust and try again.
34. Perfect is the enemy. Often people strive for perfection, but this stands in the way of progress. Progress is much more important than perfection. If you find yourself not starting a habit because you want the perfect circumstances, or not meditating because you want the perfect time or space, or not writing because you want the perfect tool, or not being happy because you haven’t been perfect with your habit — drop your expectations and just do the habit.
35. A workout partner works wonders. For exercise, the most effect method for me is to have a workout partner. That’s true whether I’m going to the gym, taking a Crossfit or yoga class, going for a run or hike. When I don’t have a workout partner, my frequency can often drop. This concept can be applied to any habit that you’re struggling with.
36. Habit changes are tools for self-learning. Habit changes aren’t just ways to add a new thing to your life. They’re tools for learning about yourself. Through habit change, you learn about what motivates you, about self-talk and rationalization, about urges, about internal vs. external rewards, about weaknesses and kindness, about progress and empowerment. You can learn more about yourself through a few months of habit change than you have in the last decade, if you pay attention. And in that way, habit change is an extremely rewarding process, regardless of the outcome.