Stop lying to your dentist: a guide on how to pick up flossing and other habits

Having a routine is about making the boring mundane tasks automatic, so that you can invest your creative thinking time on the stuff you really need to. Morning routines are particularly important to set you free to do what you need for the rest (or most of the rest) of the day.
checklist morning routine healthy habits matheus silveira
My morning routine checklist for the last two weeks


I started using checklists for my daily tasks some years ago. I did it so I wouldn’t have to rely on my memory to remember everything. I tried to use to do it for a while in 2012, but the site didn’t work well on mobile at the time, and I dropped it after some months. This recent “streak” of tracking my daily tasks using a checklist began at the end of last August.

In the beginning, I just made a list of every one of my daily actions, including things like going to the bathroom, or drinking water. Then I refined the process by taking some unnecessary actions out of it (I was always a heavy water drinker, and tracking my trips to the bathroom wasn’t exactly achieving any goals).

Now my list for the morning looks a little bit like this:

morning routine checklist havewematt matheus silveira

When I finish all of it, I get to my work-related tasks for the day. In the evening, I do some of the house chores (dishes, laundry, mail, trash) if nobody else has done it. At the end of the day, I do some personal tasks, like taking a magnesium pill, brushing my teeth again and showering again.

Some of the actions on my list are weekly tasks. Examples are preparing my schedule for the week, changing the sheets on my bed and taking my body measurements. Those also have a place in my checklist, in the back of the page. Also in the back of the page, there’s a list of things that I need to take when I go to the gym or when I play soccer with my friends. That way, I’m never stuck thinking if I’ve forgotten anything.

“We are what we repeatedly do. Excellence, then, is not an act, but a habit.”

– Aristotle

My approach is similar to the so-called Seinfeld strategy. Jerry Seinfeld had a big calendar on a wall and marked a big X in each day he wrote new jokes (so that he could see when you did it or not). That way, when he accumulated a lot of Xs, he’d be much less inclined to break the chain. If I have a lot of Xs in a certain activity on my checklist, but then I don’t do it for a day, I get furious that I’ve broken that streak.

Now you’re saying: “This is interesting, but it only helps me track the habits I already practice every day. It’s pretty hard for me to pick up new habits, man! Help me out!”. Don’t worry. I’ve got your back.

How I Finally Built the Habit of Flossing Every Day

I was never a big flosser. I was one of those guys that, if I were very disciplined, I could endure flossing for a week, tops, before a dentist appointment. It all changed when I got introduced to the notion of the habit loop, presented by Charles Duhigg in his 2012 book The Power of Habit.

The habit loop consists of three elements for habit formation:

  • a cue (trigger), something that makes you remember to practice the habit that day. It could be anything, like waking up, getting out of the shower, looking yourself in the mirror, hearing an alarm on your phone, etc.
  • the habit (routine) itself: this is the part where you perform the action that represents the habit you want to build. It could be something like flossing, eating a salad, meditating, etc.
  • a reward, something that makes you feel good by having practiced the habit. It could be the outcome of the action you just did (like feeling relaxed by having meditated). Or it could be just a treat (like eating a small chocolate cookie after having made your bed).

habit loop Charles duhigg trigger cue routine reward

When I discovered the idea of the habit loop, a lot of people used flossing as an example. It was something I always felt guilty for not doing. So I decided to try it again.

In the beginning, I flossed, in the evening, while watching something on my computer, trying to count how many teeth were left. I can’t tell you how many times I lost the count and had to start again. I did that for a day or two, then I got bored/annoyed and stopped doing it.

First lesson: I had to see myself doing it, because counting sucked, and, if I were in front of the mirror, I could just see what was left. Then I did that for a while, but, again, I stopped doing it.

Lesson number two for me was that I wasn’t going to be able to pick up a habit at the end of the day, when I was usually tired and sleepy. So I had to put flossing just after the second time I would brush my teeth, after having coffee/breakfast. That’s when I finally picked up the habit of flossing.

These ideas are usually referred to as “set and setting” in the literature of psychedelic drug experiences. David McRaney used them in the video below (one of my favorites) to describe how to manage procrastination. Both concepts can also be useful when we talk about changing a habit or forming a new one. “Set”, in this case, refers to the mindset of the person trying to pick up a new habit. In my case, it wasn’t going to happen if I were sleepy. “Setting” refers to the physical and social environment in which you’re trying to pick up a habit. In the case of getting me to start flossing, it was enough just to change the part of the house where I was doing it. Another personal example would be that, when I was in college, I couldn’t stop talking and laughing with my friends (even at the library), so I had to start studying alone.

Flossing is an automatic habit for me now. Recently, I’ve changed it to right after I brush my teeth when I wake up, so it’s the second thing I do every morning. I did that because, sometimes, after waking up, I brushed my teeth and went straight downstairs to have some coffee. Then I would stay there reading an article, watching television or listening to some podcast (wasting my time, usually). Then I decided that it was best for me if I just did every single thing that I could upstairs before going downstairs for coffee. So now I brush my teeth, floss, make my bed and, only then, I go down the stairs to have breakfast.

Now, this is how this habit loop looks for me:

  • Trigger: when I finish brushing my teeth in the morning
  • Habit: flossing
  • Reward: just the fact that I got it done has been enough for me

If none of this is enough to make you pick up a new habit, try what BJ Fogg advises in his Tiny Habits program: take baby steps (in our example, start by flossing just one tooth). Breaking habits into micro steps was not necessary for me with flossing. But it was with my reading. Now I make sure that I read at least a paragraph of some article I’m studying at the time whenever I can, so that I don’t get stuck. Changing something gets easier if you turn it into a game, but you have to make it a game you can win.

Summing up what I’ve learned about habits

  1. Habit loop: If you want your habit to stick, decide on a good trigger and, if necessary, a reward for yourself.
  2. Set and setting: Find the most comfortable way of performing your habit. Don’t try to pick up a new habit while you’re tired/sleepy. Put all the new habits you’re trying to pick up in the beginning of the day, or when you’re most inclined to do it.
  3. Baby steps: If your habit looks too big for you to feel comfortable dealing with it, break it into micro steps that you could do quickly and easily.

Tools that I use

The most important tool that I use for automating my personal daily habits checklist is a boring Excel spreadsheet. I list in it all my tasks for the next two weeks (so that the Seinfeld effect builds up with time during those 14 days). But I like to print it, so I can feel the joy of marking those Xs.

I use a black/blue pen (I just pick it randomly from my pencil case) to mark the Xs as I do a determined task. I also use a pink highlighter pen to fill the squares of tasks I didn’t complete that day. Recently, I’ve started to write with a red pen the number of tasks I missed in a given day, at the end of the spreadsheet. I hope that builds some pressure on me to start being more effective.

Finishing Thoughts

During the next weeks, we are going to explore how to pick up habits related to nutrition and work productivity. I am going to tell you about how to read faster, how to avoid getting bored with work and how to eat vegetables for good.

But, for now, tell me in the comments what is your morning routine (or daily routine) like? Do you have any more tips on forming habits? Let me know!

PS: if you need help with picking up a specific habit, reach me on Twitter or by e-mail on the Contact page, and I’ll help you change things for the best.