Progressive Productivity

Published June 02, 2019

After leaving my last position I had spent some time living off a schedule and had become accustomed to a leaky bucket of time. The only thing I had on my plate was to train, teach design, and build Jupiter but then I added school. Yikes.

What came out of this was a productivity training program based on the tenets of progressive overload. It’s been working so I hope this is helpful for you to plug any leaky buckets you may have.


I had to adjust RescueTime1 before I started. There’s a baked-in assumption within the tool’s design: everyone wants to be measured on productivity so it tracks all your time and asks you to set up boundaried work hours as a sort-of solution to creating boundaries.

This is measured by a productivity score:

Screenshot of RescueTime's producitivty score

Not a fan of this for a few reasons:

  1. Tracking all your time means measuring time you’re not working (i.e. enjoying your life). Non-actionable information is noise.
  2. The productivity score fosters feelings of guilt and pressure which I consider mentally unhealthy and have theories on how it affects self-efficacy.2

For a few months I let RescueTime run and track every activity on my computer (didn’t install it on my phone). After amassing enough data, I went through everything and asked RescueTime to ignore everything which wasn’t work related.

After a few months I had a semi-accurate work tracker. No noise, no guilt.


My program consisted of four-week ‘levels’ which were measured in weekly sprints. Weekly goals had to be met consistently met for four straight weeks before adding another level of difficulty.

This process allows me to build on strong habits without overwhelming myself. The goal here is sustainability.3 My first on-monitor sticky note looked like this:

Productivity Goal
  1. [ x ] 25 hrs deep work
  2. [ ] 25 hrs deep work
  3. [ ] 25 hrs deep work
  1. [ x ][ x ][ x ][ x ]
  2. [ x ][ x ][ ][ ]
  3. [ ][ ][ ][ ]

When a week was done, I marked it off. After four weeks, the whole level was marked off. If I didn’t reach the weekly goal, I stayed at the same week until I did.

The initial goals were designed to be easy4 so I could get into a rhythm and routine. After the first three levels, I started to further refine what was considered work, prioritizing Jupiter.

New sticky note looked like this:

Productivity Goal
  1. [ x ] 25 hrs, sans Slack
  2. [ ] 25 hrs, sans meetings
  3. [ ] 25 hrs, sans studying
  1. [ x ][ x ][ x ][ x ]
  2. [ ][ ][ ][ ]
  3. [ ][ ][ ][ ]

From here, RescueTime was asked to ignore more activities: Slack, any sort of meetings on Hangouts or Slack, and my studying.5 Once that was completed I ramped up on time:

Productivity Goal
  1. [ x ] 30 hrs, deep work
  2. [ x ] 32.5 hrs, deep work
  3. [ x ] 35 hrs, deep work
  1. [ x ][ x ][ x ][ x ]
  2. [ x ][ x ][ x ][ x ]
  3. [ x ][ x ][ x ][ x ]

The plan was realized months ago and I’ve since remained at the last stage. I’m currently focused on other time design related assignments but will likely revisit this to further define what ‘working time’ entails. It can be difficult as a founder to pin this down.


Something this schedule doesn’t accommodate for is vacation. This is by design and may change in the future: I don’t have any because it was designed so I would be relaxed.

I work very inconsistent hours–sometimes eight to ten hours at once, sometimes a few hours with breaks in-between. This schedule keeps me well-rested and I tend to overwork my hours anyway. At the end of the month, if I work past my goal hours I decide if I want to ‘bank it’ to accrue holiday time.6 Sometimes I don’t bank it at all.

At the stage the company is in, I want to consistently be putting in hours. While I am absent some days I haven’t really taken time off for quite awhile now.


I’m the most productive and calmest I’ve been in my career. I consider this of critical importance for my team: I handle operations, marketing, and design. Allowing for founder burn-out would be reckless and irresponsible.

One day Jupiter will require me to break this to put in more hours and when that day comes, I won’t be running on empty. Ready to go.

1 Check out RescueTime.

2 More on this next week.

3 This also happens to be the reason why most people fail at their fitness goals: they try to change their lives overnight.

4 I've defined work as deep work which isn't all that easy. But, from the outside, looking at the hours I'm sure people get the impression that I don't work at all.

5 'Studying' is a term for the reading I do for Jupiter. My role occasionally requires dipping into a couple of books here and there to round out my perspective. I consider that necessary for my work yet outside of the boundaries of practical activities.

6 'Holiday time' is defined to me as: time away without my computer.