Quit While You’re On Top

Caleb Jolliffe
2 min readMar 6, 2024

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I’ve been employing a controversial strategy to strengthen my deep work sessions. When I notice my flow state has gone on “too long”, I quit while I’m on top of things. I shut my laptop down for the night and switch over to analog activities. There’s a few reasons for this:

  1. It mitigates risk of burnout since I’m no longer overworking myself.
  2. I’m excited for my next work session.
  3. My subconscious is able to ruminate on unsolved problems.

I use a simple framework to easily go from deep work to rest, and back to deep work: Hemingway Bridges.

I start each bridge entry with the date and a simple reflection: “Today, I…” I often add a quick note about what I was proud of during my work session, then dive deeper into what I worked on. Next, I set up what my next work session will look like. I store all my analog notes and journal entries in my Bullet Journal. To maintain consistency, I outline my next session using the Bullet Journal indicators. When I’m satisfied with my tasks, I immediately put them in that day’s entry.

A recent Friday bridge entry looked like this (redacted for privacy):

HEMINGWAY BRIDGE — [DATE]
Today I made a lot of progress on [PROJECT]. I’m really proud of where I got to, and I’m excited to keep working on it on Monday. I got the [TASK] completed, although I do want to make some adjustments to the structure. Today was mostly about getting functionality going, which I did! I’m so proud of myself for figuring out [MASSIVE, ANNOYING PROBLEM].

I’ll be continuing to reference [RESOURCE] next week, and pulling from [DETAIL] to make the changes that I want to see. This way, [PROJECT] should [FUNCTION] better since I’ll be using primarily [TOOL] to build the [PROJECT].

I will continue working through [PROJECT BACKLOG] on Monday, starting with the tweaks to [TASK]. By refactoring the [TASK] code to the new structure, I anticipate it becoming easier and faster to complete [REMAINING TASKS] within a week or two.

On Monday, I will:
- Use [RESOURCE] to refactor [TASK] code
- Tweak [TASK] as described in [PROJECT BACKLOG]
- Use [RESOURCE] to begin developing [NEXT TASK]

Using Hemingway Bridges has allowed me to cut down on the time needed to complete certain types of tasks. Where I used to run myself in circles to solve problems, I now find it much easier to come back with fresh eyes.

If you’ve never tried this method for yourself, I encourage you to try it for yourself this week.

Further reading:

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Caleb Jolliffe

An independent designer building ridiculously simple Internet tools.