Working from home: Hard mode.

In 2006, although I had to check the math several times to make sure, it turned out I didn’t have to go to work anymore — I could pay the bills working from home as an independent contractor. I wouldn’t be able to afford much else, mind you — I was living in San Francisco, after all — but I had a library card, and I was living a block from Ocean Beach, and Hulu existed by then. I couldn’t imagine I’d really need much else. So I did it: I made the jump to working from home, full-time.

That was a fantastic decision, for me. Mostly. Eventually.

I had a lot of friends that were already living the freelancer lifestyle, so I was lucky to avoid some of the initial pitfalls of working from home. I already knew how important setting my own schedule (and sticking to it) was, regarding deadlines. My budgets have always overestimated expenses and underestimate income, so I was pretty confident I wasn’t setting myself up to financially fail, at least. And I had a small but supportive network of online peers to check in with if any complicated questions came up.

The first year working from home, from a professional point of view, could not have gone better.

The second year working from home, things were going so well that I decided that time is a social construct, and wasn’t essential to getting my tasks done.

That… was a poor life choice.

My work was still fine — I’m good at deadlines (even impossible ones), and there was no slacking when it came to picking things up or turning things in. But the rest of my life… gets a little blurry for a few years. Clocks and calendars stopped being important. I set up alerts for deadlines and rent checks, but all my other bills automagically paid themselves. I slept when I was tired, and put on pants when I needed to go to the store. I scheduled grocery delivery of bulk items to cut down on necessary pants time. I ate when I remembered to, or when the tiny Asian grandma that lived across from me would knock on my door with a bowl full of deliciousness and, I think, to make sure I was still alive.

My office and my living room were the same room, because of SF square footage, so the only time I wasn’t at work was when I was shower, sleeping, or walking through the dead quiet Outer Sunset to buy cigarettes. But I’d worked the graveyard shift for so many years that I was used to a very quiet world, and it also wasn’t much of a change only really being conscious at work. And I’m so very rarely lonely (only child syndrome) that I certainly didn’t notice how isolated I’d become.

I could keep describing those years to you, but the truth is they were boring. They were perfectly fine — I was financially stable, I had enough free time to catch up on a lot of old TV series in the second monitor in my office living room, I visited with friends when they came into town, and I always took the day off on my birthday so I at least noticed the years passing — but really, when folks ask how I liked living in the Bay Area, I can’t say much more than “well, I miss the foghorns.”

(I do miss the foghorns. And I’d like to make it back out to the ocean, someday.)

In 2010, I moved to Portland. And I was still pretty boring, for the first few months. But for what I was paying for a 1br apartment in SF, I could afford a 3br house, here — and so suddenly my living room wasn’t my office, anymore. Which meant when I wanted to sit on the couch, I had to leave work. I ended up buying a TV in the spring, and then I had to go shopping for something to put it on. Which meant I had to put on pants and actually walk around my neighborhood for more than the half hour it took to walk to the corner market.

It took me a while to find a decent TV stand (and I ended up buying one online, anyway), but I did end up going to a diner with pretty delicious fries more than once. And I’m not even sure how it happened, but one day I walked into the restaurant and the waitress said, “Where have you been? We haven’t seen you in days.”

I’d been, I dunno, working maybe. I was so surprised that an offline human was paying attention to my (lack of) schedule that I probably just stared at her until she took pity on me and brought some coffee. But I started making sure to let no more than two days pass between getting lunch at the diner. If time is a social construct, I’d been pulled back into being social.

That was a very good life choice.

I didn’t even notice regaining a schedule any more than I’d noticed losing one. I just started eating at a regular time several times a week, and then eventually nearly every day. I made friends and made plans for weekly dinners around their more rigid schedules. I got tired of looking at my empty back yard and got some bees and a dog, both of which required paying closer attention to the time of day and year. And as I got a handle on my new, actual schedule, I realized how much more time I had than I’d thought, all those years when I was ignoring time and just did stuff to the tune of deadline alerts.

I started volunteering at the local elementary school twice a week during the school year, and taking advantage of our ridiculously long days in the Summer. I adopted a second dog because the first one didn’t completely wear me out every day. I got to know lots of folks in my neighborhood, not just my immediate neighbors. And a few years ago I realized my life is so good, I’m not even sure how it happened. I wouldn’t trade it for just about anything.

But a side-effect of realizing — now that I’m not anymore — how socially isolated I was for many years, is that I’ve begun to realize how professionally isolated I still very much am. My life is genuinely so awesome that I’m frankly a little wary about wanting anything more, but I mentioned I was an only child, right? There’s just one more tiny little thing that would be pretty neat: when folks find out what I do for a living, it would be so awesome if some of them actually understood my answer. And of course that does happen, online, which is a very real part of my life… but still. I find myself wanting to make eye-contact with folks that understand trying to explain what you do to your parents, or that making your own schedule doesn’t mean you’re always free when everyone else is, or can laugh about how my dogs accidentally cured my carpal tunnel issues by making me take regular breaks.

I’m not willing to trade what I’ve got for an office job to make that easy, though. Instead, I’m going to have to figure out some way of meeting a whole bunch of folks working non-traditional jobs, or approaching traditional jobs in non-traditional ways, and then I’m going to have to practice my still relatively newly-rediscovered social skills on them and possibly make new friends.

…that seems doable, right?

After all, I’m going to XOXO 2015 in three days. And I’ve already met so many of the other amazing folks that are going to be there online, that I should be able to manage eye-contact at the least, and maybe even maintain a few friendships after it’s over. Totally doable.

Wish me luck.