Ann writes:

“I’m in the beginning stages of trying to go out on my own. But there are two big chains around my neck.

I’m currently employed at a small agency as a director-level specialist, with more than 15 years in my field.

I’ve a had a few stealth meetings with outside clients to develop projects of my own, but with a full-time job, getting out to see clients is a problem.

To free up more time, I tried to persuade the agency to put me on a three-day, part-time schedule. But they’re not interested, mainly because they would have to hire an assistant to pick up the slack.

I feel compelled to stay with the job for now, so I can keep my health insurance (we’re a family of four). But my quality of life isn’t what I want, and I’m incredibly motivated to get out RIGHT NOW.

It feels odd asking a total stranger for advice, but any thoughts on what to do about the job thing, and the insurance thing?”


Now that I think of it, the most irritating and the most useful advice I’ve received came from strangers, who weren’t worried about my tender sensibilities.


“If you truly wanted to do it, you would be doing it already.”

Or this one:

“Six months from now, will you be explaining why you couldn’t make the break? Or explaining how you did it?”

Enough of that irritating advice.

Transitioning out of a full-time job is always a bitch — no matter how you do it.

The conventional advice is to put aside six months of living expenses in the bank. Then you can go freelance with nary a care. Trouble is, that usually translates into perennially planning to go freelance, but never quite doing it. Most of the freelancers I know, including me, were a lot less disciplined. (See this post: Plan less, Succeed Sooner.)

The other option is to keep doing freelance projects nights and weekends, until you have so many clients and so much work, quitting your job is a no-brainer.

But clients who hire moonlighters or weekenders don’t make the best long-term clients. And sometimes you can’t get work without being available during business hours.

Oddly enough, what makes things simpler is getting fired. It eliminates all the cogitating and mulling and inertia. You have to get cracking immediately. It gives you a laser focus on generating paying assignments. It gives you the stones to start calling and writing people. You won’t be endlessly tinkering with your web site or your business cards. It also scares the hell out of you, and can ruin your digestion for two months or so.

In your case, consider this.

Give your boss the official two weeks’ notice. Tell them you’re going out on your own, and that’s that.

“But I don’t want to leave you stranded, so if you can’t find a replacement right away, I’m willing to handle any critical issues or projects that come up — strictly on an hourly or per diem basis, as an outside contractor — just to ease the transition.”

Of course, the agency may be able to replace you in about three days at half your old salary. Which would show how ‘secure’ that stupid job was anyway.

Or, you may end up picking up some convenient assignments from your old agency until they find a new captive employee. That will ease your cash flow while you’re developing new clients.

Or, the agency may find that it’s actually better to sub-contract your old job. No benefits, no overhead, no paying for busywork, no commitments. Just pay as you go. They may like the arrangement. You have a steady client. For a while.

In the meantime, you are ceaselessly talking to as many new people as you can. And you are getting so good at what you do, that clients cannot resist you.

Oh, the health insurance thing.

There is no fix for this, except to buy your own.

Nowadays, it is much easier to do. But it is a damn monthly expense, especially with a family. I’ve been paying that damn thing since forever, and I curse every check I write. (It hurts far less than actually having a job, however.)

What to buy? My strategy, which may be dead wrong, is to opt for higher copays, higher deductibles. You pay more for a strep throat visit or a sprained wrist, but the insurance costs less. You have to pay that damn insurance bill every month or they cancel you. But you have much more leeway with those bills from an X-ray lab or surgi-center. I shouldn’t be talking about this. Ask someone more qualified than me.

Once you get rolling, figure that covering your damn health insurance will take about two or three work days per month.

My freelance friend Gerry mentally catalogues his project fees as, “two and a half mortgages. Or, “week at beach”, or “car payment”, “four electric bills”, “dinner at diner.”