The joy of going down rabbit holes

25 March 2022

reading time:  minutes

“You waste years by not being able to waste hours” – Amos Tversky

When I started working as a lawyer, I liked the idea of time recording.

In fact, before I started practising law, I had been experimenting with recording how I spent my personal time.

Way before Fitbits and smartphones (and children), I felt a spiritual affinity with “the quantified self” movement. I kept spreadsheets, recording all sort of metrics. Among other things, I thought that recording how I used my time would be a good way of determining whether I was spending the time I had on this planet in a way that aligned with my values and priorities.

Alternatively, recording my time would reveal my actual values and priorities, in a “know thyself” kind of way that introspection might have missed. In other words, it would give me insight into my “aliefs” about what was important, and not just my expressed “beliefs”.

After a few years, however, time recording became a burden. It wasn’t because of billing expectations – the firm where I spent most of my legal career was very reasonable when it came to billing, and they also had some innovative approaches to billing that made time less of a factor compared to value to our clients. (Don’t get me started on the idea of “anchored fees”, which is an idea that I came up with and am very proud of.)

Time recording became a burden because I felt like I had to account for every minute of my time. It made it feel like any time that wasn’t productive (ie, billable or at least allocated to a specific task), was time wasted.

By recording my time in six-minute units, it felt like I couldn’t go down rabbit holes. I couldn’t stare at the ceiling and let my mind wander.

I wasn’t being discouraged from going down rabbit holes in any explicit way. But the system of time recording had this effect. It was systemic.

This is one of the reasons I charge all clients of my own business a fixed rate. It means I don’t have to record my own time. I can focus on quality rather than efficiency. It takes as long it takes.

There are other benefits, as well. It means that I can chat with clients as many times as necessary, for as long as necessary, and they don’t feel a need to be watching the clock. It takes as long as it takes.

In the scheme of things, however, I believe this approach encourages efficiency from a longer-term perspective. When you charge time, you’re incentivised to “mow the lawn with scissors”. There’s actually a disincentive to be efficient, by developing systems and automating repetitive tasks.

If you charge a fixed fee, on the other hand, that is based primarily on value, you’re encouraged to be as efficient as possible.

More importantly, however, I’ve now structured my business and life so I have more time and flexibility to go down rabbit holes.

There are two valuable aspects to this. The first is that it’s how I like to think. I like meandering and tinkering with ideas. I understand that some people don’t (you do you!). It’s how I want to live.

On a more pragmatic level, however, I think rabbit holes are where the real value is, at least for me. On a day to day basis, rabbit holes are wildly inefficient. But it’s also where you discover treasure.

I’m making a bet on myself: when I look back on my professional life, my belief is that the big wins will come from going down rabbit holes.

I may be wrong. But at least I’m enjoying the journey.

The counterargument…


creativity, flexibility, journey, rabbit holes, time

About the author 

Sonnie Bailey

Sonnie likes telling people that he’s a former Olympic power walker, a lion tamer, or a popular author of erotic, supernatural, mystery novellas. Sometimes he says he was in a band that opened for Robbie Williams. None of these are true.

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