Working From Home Really Prepared Me For Unemployment

Feet Up 30 Rock

Until recently, I’ve worked a steady freelance writing job entirely from home. Mostly from my couch, occasionally from my bed, and on a nice days from my hammock. That situation was wonderful and I wish all my former coworkers the best. It allowed me to spend lots of time with my wife and daughter, sleep late, save on gas, but perhaps most importantly; it’s really prepared me for unemployment now that the freelance gig in question is over.

I’ve never really been unemployed before. Under-employed, for sure, but like a serial monogamist, I’ve more or less moved seamlessly from job to job throughout my adult life. But now that I’m without regular employment as I pursue other opportunities in writing and comedy (I’m available and my rates are reasonable) I find that the past few years have pretty well prepared me for this exciting new chapter in my life.

For example;

I’ve built up an impressive collection of pajama pants and bathrobes

Early on in my work-from-home career I heard the advice that it helps to still “get dressed for work”. I ignored this advice, and have spent the majority of the last few years in a collection of a dozen or so pairs of soft, comfortable pajama pants. I regret nothing.

Get comfy, everyone. But of course it’s also important to know any time you’re going further than your mailbox you have to put on big boy pants.

Get to know your local baristas

Even when I was working from home, sometimes you just have to get out. A few times a week I visit local coffee shops to get some work done, get out of the house, and have an excuse to put on big boy pants. To avoid becoming “guy who is always at the same coffee shop” I try to rotate through my few suburban options. This situation became tense when a barista from one Starbucks I go to saw me at the other Starbucks I go to and asked what I was doing there. I had no answer. I stared dumbly at her until she walked away, confused.

I’ve seen her several times since, but we’ve never spoken of this incident.

Day drink, but like… responsibly

Drinking at work is generally frowned upon, but when you’re working from your couch group chatting with your editor who is working from a bar for the day the rules are a little more flexible. Still, excess is excess and you can’t overdo it. Learning the proper proportions for an Irish coffee  and cutting yourself off before you start slurring your typewritten words is a useful skill for the home worker and the unemployed alike.

Be productive while still burning through an entire season of 30 Rock in a day

“Hey Glen have you seen the new episode of–”


Being able to get work done while mostly ignoring the TV in the background is a great skill for the work-at-home set, but it also comes in handy while writing resumes or pulling writing samples together.

Oh that Liz Lemon. What kind of hijinks will she get into next?

Being a “self-starter”

Getting work of any kind done without someone looking over your shoulder can be a challenge, so getting used to being able to work on your own steam comes in handy whether it’s for a job or just writing cover letters (or posts on your humor blog.)

Knowing when to stop typing and go outside

Sometimes you can feel like a weird troll person who never leaves the house, so sometimes you just have to put down the laptop and go outside. For example, I could probably keep going here, but I’m going to go for a run.

Have a great day, everybody.