My Relationship Status with Time

When starting my career break, I put a lot of pressure on myself to make the experience impactful. The prevailing wisdom for me as I exited was to “keep busy” and I took that to heart – developing a plan that “should” get me ready to return to work in 3-4 months.

My goal was to deconstruct and rebuild my relationship with work. The starting point was developing healthier habits, and I began piling on new routines – gym, meditation, reading, writing – to get me to a better physical, mental and emotional place all at once. Eventually, though, this got me into trouble. I started to rush through these habits so I could fit anything else into my day, and rushing produced a great deal of stress.

One day, I was marching home from the gym, thinking about how quickly I had to rush through my ‘healthy habits’ so I could meet someone for lunch… when something in me stopped me in my tracks. I stood still on the sidewalk, feeling the warm, sunny day I had been ignoring and taking stock of how tense my body was, how agitated my mind was. It was a small wake-up call at the time, but honestly it now feels like a movie moment!

I had left work to address a healthier lifestyle, and I ended up tense and stressed on that sidewalk. What happened!? With the benefit of distance, I now see that part of the struggle was how I related to time itself, which is worth unpacking further.

Finding the Right Schedule

Paul Graham introduced me to the concepts of manager vs. maker schedules. The former parses out one’s calendar into regimented blocks while the latter creates large swaths of unstructured time in pursuit of a project. When these two types of schedules interact, there is no real compromise; the structured calendar approach can wreak havoc on both output and morale of makers.

I have had experience with both types of schedules. As a Chief of Staff, I clung to my manager schedule to survive a significant volume of work, relying on teammates to build many of the solutions themselves. I did not feel empowered by my schedule to create much myself. But in a previous chapter in Singapore, I sometimes had entire days without meetings, and the luxury of having unstructured time enabled me to invent new projects and programs at work, as well as spoken word poems & a one-man show outside work.

Coming back to that sunny sidewalk… I had thus far approached my career break using a manager schedule. This is not intrinsically bad, but I realized that a maker mindset was more valuable for the ends I was seeking. I wanted to be more deliberate in inviting space for discovery and deep thought, for unlearning and deprogramming.

Deadlines Are a Human Invention

Do I know how long something REALLY takes to do?

Two years ago, I learned about Destin and the backward bicycle. Destin knew how to cycle, but that was put to the test when he was given a different bike: if he turned the handlebars one way, the front wheel would turn in the opposite direction. Destin thought he would figure out how to ride it pretty quickly, but one (hilarious) video later, he revealed to us that it took him eight whole months to unlearn and relearn how to ride the backwards bike.

Could Destin have done this faster? Perhaps. But even if he shaved a few months off, it was a far cry from his (and mine, I’ll admit) expectation that he would figure it out in a few days or weeks. After spending decades immersed in one world view, the path to unlearn and relearn something can be soberingly long, much longer than I would expect, or than I would hope for.?

Creating deadlines can be useful in many situations, but I had no basis to guide my expectation (3-4 months to be “work-ready”) as accurate. Moreover, I used my self-imposed deadline to pack in activities to speed up the process, without allowing time for any of these activities to actually take hold; akin to layering on more coats of paint before previous coats had dried.?

Once I acknowledged that I was inventing my own stress, the path forward became clear. My deadlines were moveable, and I relieved myself of the burden of expectations over how long it should take for me to be ‘a new and improved Neil.’ As Seth Godin put it, “‘As soon as possible’ is a trap if you focus on soon instead of possible.’”

Looking Ahead

But why the spontaneous impulse to cast everything aside and bask in the rays of sunshine? This popular Hollywood trope speaks to our hard-wired desire to live in the present tense, to “smell the roses” and feel connected to our immediate surroundings.

When I recall a memory or make plans, I am living in the past or future respectively, not the present. Both nostalgia and planning serve important purposes in my life, but I’d prefer to only visit those realms, not live in them. Maybe that’s why a primal urge in my body rescued me from wallowing in the stress of what’s to come, and returned me to the here and now.

As I move through my current job hunt, I similarly find myself recalling past projects to prepare for interviews, and spending lots of time waiting and hoping for a fruitful future to arrive. But I have no firm knowledge of when that future will arrive – many job seekers wait for a long time!?

In the meantime, I don’t have to be defined by waiting. I aim to continue truly living in the present tense, building off the hard-won wisdom of a career break that may not have always felt sunny, but was certainly timely.

In addition to those cited above, I credit ideas from Jenny Odell and Oliver Burkeman for influencing my writing in this piece.