The Anti-Routine Routine

I have never been one to appreciate the power of routines.

I don’t like doing things the same way, every day. I don’t like showing up at the same place to work, 5 days in a row. When I go for a walk or a run, I don’t like going back the same way that I came, and I specifically don’t like it when routines from other groups of people interfere with my own preferences.

Of course what I’m describing in itself is a routine. A somewhat chaotic routine, but a routine nonetheless.

As a fractional worker in COVID times, I’ve spent an inordinate amount of time working independently for the past three or four years. So by now, I have a pretty good sense of what things I default to doing on days when I don’t have a schedule. What I’ve noticed is, even in the anti-pattern of a regular, 9-5 job, I have slowly but surely carved out habit loops of how I work that work for me.

For instance, right now I have four possible places where I tend to do work: A one-person office downtown, a coworking space uptown, “flex” days where I jump in and out of offices all around town, and work from home days, where I stay at my apartment. I have habit loops for all of these work modes. 

For my three most usual spots (my downtown office, my uptown coworking space, and my apartment), I have multiple preferred routes for getting to and from all of these places. I have 2-3 different coffee shop circuits for each location. I have the “usual” spots where I go for a quick lunch, and I have the “treat yourself” spots where I go for a more luxurious meal. I have the go-to store I go to when I’m bored and need some external stimulus, the go-to park for when I need to see a little green, the go-to happy hour hang. I even have a preferred route for a midday walk that I like to take after a particularly energizing meeting where I need to clear my head.

All of this is routine.

In fact, I even have a routine for when I don’t have a routine. The sort of “find fun new places as you go” serendipity mode, if you will. I turn on this mode whenever I visit a new office, a different part of town, or in the case of my present mode, visiting a different country to work for awhile. While I like to think this is me being in spontaneous mode, I basically always do the same things in this mode too. I find a nice coffee shop with fast wifi, in a neighborhood with cute women’s clothing boutiques, preferably with some not-too-stuff art galleries nearby. 

While it is somewhat annoying to acknowledge that alas, even the power of routines have bested such an “anti-routine” person, it is telling to me how much we as humans rely upon familiar patterns to help us make sense of the world. I will admit that my 3x/week walks around Madison Square Park, exactly I complete my first “deep work” session in the morning, and either coinciding with or preceding my second coffee of the day, have helped my brain process many work cycles and “stack overflows” in my brain, so to speak.

It’s a pretty special thing to be able to figure out, slowly, iteratively, and over many years, your preferred patterns of peak work output. Most of us rely upon a single employer to define routine for us, one that might include all-hands meetings at a time inconvenient for you, or mandatory in-office days that add friction to your preferred habit loop of work. While this is a very useful way of knowing some of the broad strokes of your personal preferences (ie: do you prefer meetings in the mornings or the afternoons?), you obviously don’t get nearly as much autonomy to arrive at your own day-to-day nuances. 

I think a lot of this is changing as we enter an era of work where more of us operate independently, remotely, and across multiple projects at once. I also think this iterative process of discovering how you essentially “program yourself” to perform, to speak, requires quite a bit of patience to get right.

What I've come to understand is that routines aren’t necessarily about following a script—they’re about finding the rhythm that works for you, even if it’s unconventional.

So, whether you're a few years into your career or just beginning to explore fractional work, take a moment to consider: What are the unconscious routines shaping your day? And how might tweaking them help you thrive in your work?