I’ve covered some of this before, but I still get asked about it occasionally by readers and friends. “How do you do it?” I hear, with “it” being living my life without a boss, a steady job, or company-subsidized healthcare? Some of it is work, some of it is luck, a lot of it, once the work is found, is actually pretty awesome. The bottom line for you folks in a hurry: you need to work with your network to let them know what you do and what sort of work you’re seeking; you need to live within your means; and you need to learn to enjoy a new balance between self-discipline and freedom. If you have more time, read on.

Looking for work

The full-time-employment environment is different because on steady jobs–unless you’re a CEO–someone else is usually assigning you work and telling you when and how to do it. Negotiating deadlines isn’t too common. You might dislike your boss or company, but you (usually) don’t doubt when you come into work that they will have work for you to do.

This is the part that scares people the most when they think about “Escape from Cubicle Nation” because when you’re on your own, you’re responsible for finding and assigning yourself work. Truth be told, during my first two years, it scared me, too. It required seeking work with friends and talking to a friend who was a professional coach and who could help me focus on what type of customer and what type of work I should seek. I also had to work out what I would charge.

Luck actually saved me in the nick of time, but part of that “luck” involved working within my network because someone in my network found and hired me. I got my first job out of Disney via my network and I stopped knocking the notion. In fact, I’ll pause here and refer you to my networking entries here to give you some idea of what I mean by networking now as opposed to what I thought it was in my twenties and didn’t need it.

Bottom line: If you’re going out on your own, you need to establish and maintain a wide, diverse, and active network of friends, coworkers, customers, etc., whom you can tell about what sort of work you do and what sorts of work you’re seeking. You never know where your next job might be coming from; on the plus side, you never know where could come from.

Living within your means

Steady jobs make budgeting a lot easier, because you usually have a good idea of how much you’re going to make every week/month and so can budget accordingly. I actually have this with my primary client right now, but such was and will not always be the case.

Before you leave Corporate Job X, it helps to have paying work out of the starting gate, meaning that you have one or more customers lined up the first day you’re no longer working for someone else. Having money in savings built up to cover you while you’re looking for work (not a job–specific tasks/problems you can fix) is also a good idea. And sock away “extra” money–dollars that exceed your basic needs plus a bit for fun–again, to keep replenishing your rainy-day fund. You will face feast-and-famine waves, and you will need to be smart about setting and sticking to a budget.

Managing your independence

Steady jobs can make things a little too easy for you: regular paychecks, health insurance plans, 401(k), subsidized Social Security payments, paid vacations, etc. On the other hand, you often don’t have as many choices about how those things are provided. Before you leave the relative safety of someone else’s employ, be aware and respectful of the differences.

This is the biggest change for the individual who’s spent their career expecting someone else to manage your time. It is also the greatest joy because you have an unbelievable amount of freedom to set your own work hours and decide how to spend your time. (My favorite perk of freelancing? Setting my own hours, grocery shopping at 10 a.m. on a Tuesday, and being able to have a leisurely lunch with my father on a semi-regular basis.) The flip side of this freedom is responsibility. All of the bill-paying, marketing, insurance-seeking, and of course the actual work are up to you. You need to be self-disciplined enough to work without someone standing over you or dragging you into meetings for status updates on a weekly basis.

If you find that you need that sort of structure, that isn’t necessarily a bad thing. I was a corporate guy for…hmmmmm…22 years and pretty comfortable as a team player until I decided to make the leap. And all the skills I learned doing work and watching others supervise or lead me (there is a difference) eventually gave me the confidence to believe I could do that for myself. And I know that if the freelance work dries up at some point, there are several organizations I could return to and resume my life as a worker bee in someone else’s hive. But I’ve learned to enjoy the freedom and autonomy that come from freelancing, so I would probably work harder to keep the work coming into Heroic Technical Writing rather than helping work go into someone else’s business. You might find that freedom worth fighting for as well.