But working for yourself from home is not without its challenges. I tell people who ask me about it (with dreams in their head and longing in their eyes) that it’s not for everyone.

You have to be self-motivated. Nobody is checking to make sure you’re at your desk, doing whatever it is you’re supposed to be doing to earn a living. You have to forget there’s a TV a few feet away, a refrigerator full of food, rooms that need cleaning, a novel begging to be read, or an Internet full of time-wasting at your fingertips.

You have to deal with the insecurity of not being sure of your next paycheck. Or the one after that or the one after that.

You have to find all the jobs, pay all the taxes, buy all the supplies, and make all the coffee. You have to be your own cheerleader — attaboys are hard to come by. The very best you can hope for is that they’ll call you again next time.

Working solo means usually being alone. No one’s around the water cooler to rejoice over the big win, lament over the big loss, or dish about what so-and-so said when you-know-who told him about you-know-what. Lunchtime is no different from any other time. There’s never any birthday cake at 4:00 in the conference room. It’s isolating. You have to have the temperament to deal with that. And no, everyone else is not checking e-mail all day long. Your computer is your lifeline in so many ways, but it’s not always attached at the other end.

And, there will be other obstacles you didn’t anticipate. For example, it’s hard to write when you can’t see what you’re writing.

And it’s hard to type when you can’t move your arm.

And yes, you may end up wearing your bathrobe for an embarrassingly long time.

I’m just saying. Just so you know.

Nothing is really work unless you would rather be doing something else. 
                                                ~ James Matthew Barrie

In those days, I used to track billable time religiously — a by-product of working for the most anal firm on the planet for four years. As if totalling and recording it every day and week would somehow make it increase. Today, I’m much more lax in my tallying — but I still have the same Day-Timer and still manage my time and my projects the same way I did on Day 1 (although my penmanship has deteriorated drastically).

I always tell people this is the longest I’ve worked anywhere. Four years was my “as long as I can stand it” threshold in four previous jobs (one lasted only 2 years, another 3). And while I would be making more money had I stayed in a “real job,” and I still miss the security of a steady paycheck, and the isolation can be hard to take (coworkers were always the best part of working anywhere), I wouldn’t have traded the past 9 years of freedom for anything.

There is so much more to life than money. Living at a more leisurely pace for one. My days no longer revolve around my job, the alarm clock, the commuting weather, what the heck I’m going to say in this year’s performance review, or how Joe So-and-So is going to re-write what I’ve spent hours writing. Sure, I’m still a slave to my clients (who sometimes rewrite what I do, but a lot less frequently than my bosses did), still have to do projects I don’t like, and still have to get out there and prove myself every day. I always fret about money and when the next check’s going to arrive.

But, just as Ginger could do everything Fred could do, backwards and in high heels, I can do everything an “on-the-job” writer does, in slippers and while also doing the laundry, paying bills, cleaning the house, cuddling the cat, and enjoying a midday walk on a sunny day. That makes up for a lot of financial insecurity.

Still, I worry about the future. Will clients accept a 60-year-old freelancer? A 70-year-old? Is there a “Welcome to Wal-Mart” or “Would you like to Biggee Size that?” in my elderly future? More and more, it seems that way, and the prospects are frightening. (After all, I’ve never worked retail or food service. Talk about old dog, new tricks.) Maybe I should start now — take a part-time job just so I can learn the ropes?

Such are the uncertainties a middle-age free agent contemplates. Maybe not so different from what a middle-age corporate slave contemplates — but with a little less money in the bank, a little more job (and self) satisfaction, and a lot more likelihood I can look back and say it was all worth it.

How we spend our days is, of course, how we spend our lives.
                                          ~ Annie Dillard, The Writing Life