home

Iterate Your Habits

The thing about habits is some—perhaps most—aren’t meant to last forever. We often hold on to them far past their expiration. When they are no longer healthy, helpful, or what we actually want from ourselves. Why? Because humans are creatures of habit. We need something to ground us. They are shortcuts allowing us to spend time on more important things: swiping right on Tinder, binge watching Netflix after work, etc.

I joke, but something I’ve been thinking about more and more lately is iterating upon my habits. Taking a fresh look at habits I practice and evaluating if they still provide meaningful value. Or if I’m just doing them because I’ve always done them. They might have made complete sense until they became involuntary parts of my day. I’m not the same person I was a year ago, why should I do the same habits?

Admittedly, it’s really tough to change these things, especially the deep, enduring ones. But you totally can. First, experiment. If you want to break your college habit of staying up, simply make a change for a week. Really commit to yourself for seven days to go to sleep early. Then decide if you want to continue. If you miss it, you can always revert and go back.

I did something similar for my excessive phone use.

I wanted to own my own time and not get constantly interrupted by my phone so I gradually took three steps. The first iteration was turning off all notifications except for Messages.app and Phone.app. Next, I scheduled Do Not Disturb from 10p to 6p (nearly the whole day). This allowed me to be more intentional about when I used my phone and why.

The more extreme—and third—step was removing all social apps (Snapchat, Insta, Twitter) and Gmail. I got rid of Facebook in college and it was a huge productivity boost. Twitter was the hardest to remove because I get a lot of value from it. But I realized that my mobile use of Twitter (and email) was almost always about undirected consumption—it was dead time in read-only mode.

Removing Snapchat supplied plenty of FOMO initially, since it’s my only means of communication with some friends. After a week without it, all the fear subsided. In total, this whole experiment took over two weeks. It was anxiety inducing. I actually cried a little. Just for a couple minutes. I wanted to quit.

Lot’s of people say they really want to break habits or create new ones, but they start off with high hopes and even higher expectations. This habit stuff is hard work. Experimenting helps set more realistic expectations, boosting your confidence in the short term and giving you a chance to succeed in the long term.

Along with experimenting, another great way to make progress is through small chunks of consistent effort—think slow and steady wins the race. It’s achievable. If you want to get in shape, you’re almost better off doing any type of exercise as long as you do it consistently. Rather than spend tons of time crafting the perfect workout, only to dread doing it. Show up everyday and try.

Witnessing small chunks of consistent effort from the outside is extremely dangerous. It actually looks effortless. This is true for professional athletes, startup founders, or really anyone performing at a high level. It appears these people achieved overnight successes. Likely what they did was a combination of consistently work hard and experiment until they found what worked for them.

There’s a lot of conflicting research about habits (you can only replace, not break them) and lot’s of opinions floating around the Internet (including mine). No one knows your habits better than you though. Make a list with as many as you can think of. Meditate on it. What is part of you that you want to discard? What do you want to do that you aren’t doing right now?

I find myself asking these questions every once in a while helps me stay more present. These habits are ones I iterate and opt in to.


There are many other great ways to change habits, like adding/removing triggers. I only present my favorites.

Thanks to Himanshu Sahay for reading drafts of this.


Thanks for reading! Join 70+ others subscribed to my once-a-month newsletter.