I Tracked My Time For a Week. It Was A Spectacular Failure.

Why it happened, and how I fixed it.

I Tracked My Time For a Week. It Was A Spectacular Failure.
Photo by Morgan Housel / Unsplash

I have a problem.

I don't know where my time goes.

I never miss client deadlines, but I struggle to hold myself accountable when nobody is watching. Time disappears, things don't get done; life slips away.

Peter Drucker, The Effective Executive, suggests we reclaim time by tracking it. "If you can't measure it, you can't improve it," his famous refrain, echoes Rule 1 of the transformative budgeting software YNAB: give every dollar a job; give every second a job, in this case.

I’ve failed at time-tracking many times before. I’ve used both automatic time tracking apps, and apps that require you to enter a block of time against a project. They were either too high friction, or invisible.

When I automated my tracking, it happened in the background and I forgot about it. (On days where I did remember, the idea of reviewing 14 hours of my workday and ensuring they're assigned correctly still sends me running for the hills.)

With the inverse, high friction approach, I was fatigued after a few hours. I was training a muscle that doesn’t exist. I had no endurance.

With these two factors in mind, I decided logging hours in my journal was the optimal, elegant, solution.

After a day, I was encouraged. After a week, I was lost.

The habit had not taken well.


Part One: Why I Failed

Being mindful of unmindful time is a contradiction in terms. By definition: if I’m distracted and disassociated, I’m not tracking time. I started out well, but I’d zone out and miss an hour.

This kicked off a shame spiral.

I didn’t want to resume tracking because my log wasn’t Perfect™ — a complete failure. Instead of dusting off and trying again, I packed up and quit; I told myself I’d be better the next day.

The first day, I lost focus and stopped tracking at about 2 PM, then again at 5 PM-11:30 PM. The next day 2 PM. Then 10:15 AM.

Until I stopped tracking altogether.

This manual logging failed for three reasons:

  1. There was too much friction.
  2. It wasn’t rewarding.
  3. I depleted myself over time.

There was too much friction.

I was tracking every activity to the minute. My perfectionism was waiting for me to make a mistake. See, it said when I finally missed 5 minutes, I knew you couldn’t do it. The first day, I had enough willpower to resist, and picked up the log again in the afternoon. But I didn’t have enough gas in the tank the next day.

My takeaway: Tracking every minute is outside my current ability. As I develop this muscle, it’s more effective to track “focused” time; or as Cal Newport calls it in Deep Work the lead indicator — hours spent in focus.

It wasn’t rewarding.

Tracking unfocused time is depressing. You’re rubbing your face in your own failures. Compounded by the fact I wasn’t celebrating my wins. I didn’t tie my output to a scoreboard. I saw a completed log, but there was no sense of accomplishment.

My take-away: I needed to aim for a specific amount of focus each day, and I needed to find a way to make it both visual and rewarding.

I depleted myself over time.

The first night, in a euphoric state, I worked long past my bedtime. This sapped the next day’s energy. I called it a shame spiral earlier, because, like an aircraft that spirals to the ground in fog, it’s gradual and unnoticed. You only noticed it’s happened once it’s too late to course-correct.

I was withdrawing energy but wasn’t topping it up. By easing up on self-care, I sewed the seeds of the next day’s failure. In tandem with the aforementioned lack of rewards, I wasn’t re-energizing my chemistry.

My take-away: I needed to build in redundancies for those moments where I couldn’t trust myself; I also needed to prioritize self-care.


Photo by Elena Koycheva / Unsplash

Part Two: My New Solution

Elsewhere in Deep Work, Cal Newport uses a scoreboard to track hours of focus. I loved this idea, but I couldn’t visualize his creation. By accident, I noticed a tool I’d installed on my computer, Session, had scoring features built-in.

(Note: Session is Mac only for now. It's included as part of your subscription if you’re an active Setapp user.)

Although marketed as a Pomodoro tracker, it has numerous advantages over other apps in the space; like the ability to customize your session length each time.

Most apps use a fixed interval, breaking focus into 45-minute chunks. This doesn’t work for me. My days are too varied. Some things, like writing, take more (or less) time and a strict interval is counter-productive. With Session, I can customize the length of time. In doing so, the goal becomes hours of focus, not periods of focus.

In other words, I'm incentivized to chase the lead metric, hours of focus, instead of the lag metric, time that isn't being used well. Better signal, less noise.

A screenshot of my Session daily report.

Here’s what else I love about it, and how it solves the problems I listed in part one:

  1. It gives a daily/weekly/monthly “scoreboard” of time spent in focus.
  2. It’s a pleasure to use.
  3. It pushes to, and syncs with, my calendar.
  4. It encourages you to set a goal and reflect on your work.

The results so far have been excellent.