Illustrated by Violet Jinqi Wang

The secret sleep lives of remote workers and freelancers

Designing your schedule for ultimate productivity

Olivia Barrow
6 min readApr 25, 2018

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By Olivia Barrow

When I quit my job, I envisioned lots of mid-day trips to the climbing gym, sleeping in, and staying up til 2 a.m. finishing an urgent project for a client.

Now, almost two years into my freelance journey, my schedule looks an awful lot like it did when I worked corporate. I try to get up before 7 and catch a bus by 7:30 to get to my coworking space by 8. I usually stay until 4:30 or 5, but sometimes I ask my girlfriend to bring leftovers to the office and so that we can camp out until 9. Very rarely do I take off time during the day for fun or exercise. It just doesn’t make sense when my clients are most likely to be available between 9 and 5, and only a few of my friends are free during those hours to hang out.

I wondered if other freelancers and remote workers’ experiences matched mine, or if they were more similar to what I’d pictured. To find out, I interviewed a dozen freelancers and remote workers from the entrepreneurial community in Madison.

Depending on the kind of freelance work or remote situation you have, you may not truly own your own schedule. But most of the people I interviewed did have full control of their schedules.

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