If I had a dime for every time someone said “That must be nice!” when I explained that I do most of my writing work on my own schedule, from home…

I’d have, uh, a lot of dimes.

As any freelancer will tell you, working from home is not exactly the pajamas-wearing, fatty-food-scarfing utopia it is cracked up to be. It is true that you may, occasionally, find yourself in Oreo-dusted yoga pants at 3 PM on a Tuesday. It is also true that freelancing’s self-driven schedule – PARTICULARLY if you work from home – can lead to frustration, sloth, procrastination, stress, inertia, isolation, and even despair.

… how ‘bout THEM dimes?

Fortunately, there’s a relatively simple tool that makes freelancing flexibly from home bearable (and even preferable)! And that is: setting routines.

I know, I know. Listen, I am the biggest rule-resistant free spirit alive. Nothing makes me want to do something more than being told I CANNOT do it. As a kid, I hated the structures enforced by standardized schooling; to this day, the sound of mechanized school bells make me shudder.

With ALL THAT BEING SAID, establishing a “soft” routine has really helped me be productive – even in pajamas.

One of the problems with having no routine whatsoever is that “work” time tends to bleed into “play” time and vice-versa. Now, some of that flexibility is nice – I truly enjoy being able to take a nap or mess around with paints during the day – but the problem is when you can’t switch off; when you find yourself working at 1, 2, 3 AM not because you want to, but because you’re a certified workaholic.

Making routines is a good way to set internal boundaries for yourself.

Some people thrive under a hard-edged routine; they like to work from 10-12 every Monday, take a break, etc. Now, as I have explained, I am not that person – I chafe under inflexible rules. Instead, I set “soft” routines for myself during the day.

For instance, I set three goals for myself before noon – I can do them in whatever order I want. Some routines are purely play or enjoyment-based; for instance, I wake up every morning and make myself breakfast, then often devote half an hour to reading random articles on the Internet. It’s a nice warm-up for my brain, and ensures I eat something – but because they’re both positive routines, I don’t feel hemmed in.

The nicest thing about making routines? They’re YOURS, and nobody else’s! Don’t feel like you need to follow conventional rules or mores; experiment and see what works for you. Build space in your days for things that really matter to you, including building new skills or exploring hobbies.

If you want to spend half an hour each day puttering around in your hot pepper garden, heck, build in that time. If you want to learn to juggle, make time for that! Devote time to play and creativity; it’s just as essential to your happiness as more “formal” activities.


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Creating routines – yes, including soft ones - helps form a skeleton to hang the muscle of your work upon. It helps you achieve long-term goals, and calms the kind of restless panic that can set in when you’re floating around, jellyfish-like, from project to project.

And if you find that your routines aren’t working for you (or worse, are boring you or making you feel stale), CHANGE them! Nothing is better for you than building a little structure, experimenting with it, and then shaking it up…

And yes, you can stay in pajamas.

Kate Hamill lives and works in New York City, where she consumes an inordinate amount of Sriracha daily. You can catch up with her on Twitter at @katerone.