How Your Daily Routine Can Turn Into Your Biggest Enemy

Ryan Holiday Instagram

Routine and ritual are everything, including, if you’re not careful, a dangerous weakness.

A few weeks ago, I got a letter—yes, an actual letter—from an NCAA player who will probably go pro. His question was a simple one: Like many basketball players he was big on pregame rituals and routines, but he was worried that these patterns made him vulnerable to being disrupted. What if the team plane was late and he had to rush his usual warmup? What if his headphones were dead or he forgot to pack his gameday socks?

Would his competitive edge—the comfort and confidence he took from these practices—suddenly turn into a liability?

This is a perfectly reasonable concern. Because while rituals can be a source of strength to an athlete or a writer, they can also be a form of fragility. Take Russell Westbrook, who is famous for his pregame routine, which begins three hours before a game. It starts with him warming up exactly three hours before tipoff. Then one hour before the game, Westbrook visits the arena chapel. Then he eats the same peanut butter and jelly sandwich (buttered wheat bread, toasted, strawberry jelly, Skippy peanut butter, cut diagonally). At exactly 6 minutes and 17 seconds before the game starts, he begins the team’s final warm up drill. He has a particular pair of shoes for games, for practice, for road games. Since high school, he’s done the same thing after shooting a free throw, walking backwards past the three point line and then walking back to take the next shot. At the practice facility, he has a specific parking space, and he likes to shoot on Practice Court 3. He calls his parents at the same time every day. And on and on.

The point is, while this process is likely very calming and reassuring in an entirely chaotic and emotional game, it also reads like a recipe for how one might throw someone off their game. A teammate vying for Westbrook’s playing time, a competitor who will stop at nothing, or just Murphy’s Law could all wreak havoc on that system and get inside his head. All it takes is “accidentally” parking in the wrong spot, or the right insult right before a free throw to send the whole thing sideways. And what if the trainer is sick and can’t make the sandwich? Or what if the arena chapel is closed due to a leaky ceiling?

Any routine junkie can tell you what happens when your routine gets messed up: Your thoughts race. You get frustrated. You feel what is almost like withdrawals. I can’t do this. This isn’t right. Something bad is going to happen. You doubt yourself. Then all of a sudden you aren’t getting warmed up or falling into the zone as easily as you usually do.

This problem is compounded the more successful you get or the more you specialize in a certain feild, because you get used to and feel entitled to have things your way. People enable this dependence because they want you to be your best, which makes it all the more frustrating and surprising if the script is suddenly deviated from.

I came face to face with this reality with the birth of my son in 2016. A few months before he was born I was profiled for the New York Times, and as part of the article, the reporter had me walk her through my fairly extensive set of morning and daily routines (what time I got up, how I journaled, where I sat, what my workout was, etc). She remarked that it would be interesting to see how this would all hold up with a newborn. Confidently, I told her nothing would change.

Ugh.

But of course she was right—because kids are, if anything—wrecking balls for the carefully built order of our lives.

The first couple months of his life, I struggled. It actually wasn’t the lack of sleep that was the problem. It was the unpredictability of that lack of sleep. Some mornings I was up at 5am. Some at 10am. Sometimes there was a baby I was supposed to quietly take care of while my wife slept, other times we were all up, other times it was just me while they slept. Was he napping at 2pm or not at all? Did I need to get home early for his dinner and bath or was the whole schedule blown apart by something that happened earlier in the day?

All of a sudden quiet time every morning, not checking email, going for a long run or swim in the afternoon, writing from 8-12am every day—this was not possible. At least not possible to do in the same way in the same order each day.

I experienced something similar years before when my career took off. I was used to working at home and then suddenly I was on the road a lot. Lot of flights. Living out of suitcases. Meetings and events that I had to go to. But early on I could compensate for this by spacing the trips out, setting up camp in each city for a few days and approximating some version of my normal routine there. As the trips increased and I got older, this became less tenable (even more so after accumulating a wife and a kid), and my reliance on my capital-R Routine became a weakness. A couple days on the road would completely set me back. It would also make me frustrated—even though I had chosen to say yes to these opportunities.

In both cases, my cherished routines either crumbled or were blown apart. But I still had to do my job (writing) and if anything, the stakes were higher than before. Which meant I’ve spent a lot of time thinking routine ever since.

What I’ve come up with might not seem that profound but the impact has been enormous for me: It’s not about having a routine. It’s about having routines.

I no longer have a writing routine or a morning routine. I have several. I have a routine when I get up early on the farm (We go for a walk, then I write until breakfast, and then resume writing). I have a routine for when I am on the road (run or exercise early, slot writing/work in as the top priority between whatever the scheduled events for the day are). I don’t have one shirt I wear each time I give a talk, I have a set of 3-4 that I choose from. Depending on what city I am in and what time of year, I have different mornings and plans that I’ll do. When I fly, I either read, answer old emails from starred folder, or sleep. I don’t eat before I perform, but if I do, I eat the same thing. If I get interrupted and can’t journal the way I want for a morning or two, so be it—but I’ll make sure I quickly resume my old habit. And on and on.

Depending on circumstances, I have strategic flexibility. I’m not winging it, but I am not such a creature of habit that I am flustered when disrupted (or can I really even be disrupted since I am indifferent to Plan A, B, C, D, E). Think about musical scales—the notes themselves are fixed but they can be played in a limitless amount of combination. This allows the musician to improvise while still maintaining a base they can return to and derive confidence and comfort in. That’s how you want to be with your routine. Not so rigid that you can’t respond to the moment, not so free that you can do everything in the moment.

There is a line from the Super Bowl-winning coach Bill Walsh about how most individuals are like water, they naturally seek out lower ground. By that he meant that without discipline or order, we are not our best selves. Ultimately, this is what routine is about: creating practices and habits and rules that force us to be better.

Without a routine of any kind, Resistance is given too much room to operate. Doubt, chaos, laziness—if you give them an inch, they’ll take a mile. Routines are essential in that battle.

In creative or athletic or entrepreneurial fields, the uncertainty and stress of the endeavor makes us crave simplicity and dependability. When Russell Westbrook was asked the reasons behind his many specific, very detailed practices, he replied, “No particular reason. I just do it.” Actually there is a reason. The reason is reassurance. As a player, Westbrook is emotional, chaotic, intense. The game he plays is random, difficult and overwhelming. Doing the same things the same way at the same time, creates comfort and order as well as superior performance.

We can get addicted to that. In fact, it may actually take more discipline to be moderate in your discipline than to be insane about it. There is an interesting Michael Lewis article about the NFL kicker Adam Vinatieri who actually works at making sure he doesn’t wear the same socks twice or having too many rituals because of how easily this can descend into superstition and thus psyching oneself off. But without this work, we end up beating on ourselves for falling short.

It’s better to remember Marcus Aurelius’s line…

“When jarred, unavoidably, by circumstance, revert at once to yourself, and don’t lose the rhythm more than you can help. You’ll have a better group of harmony if you keep ongoing back to it.”

In a way, this is what I’ve worked on most with my routines lately. Can I purposely disrupt them? What happens if I change things up? Am I still me? Am I still able to do what I do well? I want to be sure that the tail is not wagging the dog, that I am in control of the routine and not the other way around. Because the last thing you want to do is become ossified and unable to handle change.

Because life is change. Murphy’s Law is real, and you will drive yourself insane thinking you can simply outwill or white knuckle your way through the inevitable tendency for things to go exactly the way you’d rather they not go.

Discipline is a form of freedom, but left unchecked becomes a form of tyranny. So the key is the ability to rotate from routine to routine, discipline to discipline, according to the needs of the day and the moment.

Otherwise you’re not only going to be miserable…you’re an easy opponent to defeat.

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