how to quit job and then freelance for the department?

December 5, 2006 7:33 PM

I love my 9-5 editing job, but as a certain hobby becomes viable as a (very small) part-time job, I need a much more flexible schedule. How can I quit while guaranteeing that my fellow editors then hire me as their writers?

It's looking harder and harder to keep my job while pursuing the new opportunities that are opening up, and pursuing them is really important and exciting to me. As is, I'm stretching the minor flexibility of my job to its limits. On the other hand, my department is always in need of writers and has plenty of work to keep any writer busy. I think my writing is respected by my boss and coworkers, and I would imagine that it would be a big plus that I already know exactly what they're looking for. And I'd have fun doing it.

The trouble is that I want to have my schedule open as early as possible in the near year, and I don't have enough in savings to quit my job that soon unless I know I'll be able to get income by writing for the department. Is there any good way to explain my situation to my boss, suggest that I'd like to write for X upcoming project, see what she thinks, and hopefully get an informal agreement? Or any good way to subtly feel her out? Or is it a bad idea to discuss quitting with a boss when you might actually stay depending on how the conversation goes?

I could also have a similar conversation with my fellow editors to see if they'd be into the idea. They're the ones who'd actually be hiring me. But I'd feel more secure if my boss (the head of the department) were in on the plan before I gave notice.

posted by nevers to work & money (7 comments total)

I don't have enough in savings to quit my job that soon unless... Red flag, maybe?

Is it a bad idea to discuss quitting with a boss when you might actually stay depending on how the conversation goes? Yes.

Have you done any paid writing projects for this department yet? Perhaps you should do a few and see how it goes (make no mention of wanting to quit and write exclusively). You think you'd be perfect for the job, you think they'd love your work, you think it'd be fun. I would test those theories before quitting your job.
posted by ThePinkSuperhero at 8:17 PM on December 5, 2006 [1 favorite has favorites]

I left full-time work to become a freelance writer (and then a consultant) about 10 years ago. However, I had money in the bank.

You said, "I don't have enough in savings to quit my job that soon unless I know I'll be able to get income by writing for the department. "

I run a website dedicated to consulting and I have a fairly lengthy series of articles on finance for consultants. Why? Because so many people get themselves into hot water with their finances. And that's not because consulting is a bad thing to do. It's just that you have to be prepared.

Can you stick out this job for another year? I know you say you're getting more job offers. Could you stick it out for another 6 months? 3 months? Pick an end date.

Cut back your finances dramatically.

Pay down any debt you have.

Sock away money until you have enough to cover six months of rent, food and bills.

Shop your resume around. Get a side job before you quit your current job.

Network. Make sure people know you want to freelance.

Get all your marketing in place before you quit. Business cards, logo, etc. You want to look professional.

If you've got all that in place, go for it. I'm thrilled with my consulting business.
posted by acoutu at 11:15 PM on December 5, 2006 [3 favorites has favorites]

Unfortunately, freelancing for my department while I'm employed here isn't allowed.

My current plan is already to cut back finances dramatically, continue to work here for 6 more months while networking/marketing, then leave once I have 6 months rent, food, and expenses. I have no debt and I already have a side job (not enough to live off, but enough to provide some guaranteed income to tide me over).

The reason I've posed this specific question is that there are some opportunities I really want to participate in from February to May, and I don't think I can do them while employed here full time, and if only I could be certain I could freelance for this department, I would be all set. It's such a perfect possibility that I really want there to be some way to make it happen.
posted by nevers at 5:37 AM on December 6, 2006

I doubt anyone here is going to be able to tell you that things will work out perfectly, unless they are your boss. I personally can't imagine you'd be allowed to quit one department and start working in a different capacity for another, but that's just me.
posted by ThePinkSuperhero at 7:04 AM on December 6, 2006 [1 favorite has favorites]

Could you take vacation days that would give you the time needed for the freelance opportunities you want to pursue? Could you go part time while you build your writing income?

I know a few freelance writers who make pretty good livings -- one makes twice what I do in a conventional job. But for their first couple of years as freelancers, they barely made enough to get by and probably would have gone hungry without savings or spouses to cover them. It takes time to build relationships and contacts and to develop the administrative skills to operate like a business.
posted by croutonsupafreak at 7:04 AM on December 6, 2006

I don't know how large the company is and I am not a tax advisor (IANATA?) but a company that I used to work for had to halt the practice of hiring back former employees as contractors for some reason related to the IRS. It used to be a fairly common practice at a company I used to work for to quit your 9 to 5 job, go freelance and make a fairly comfortable living selling back your services as a contractor. Went on for years. Then, in 2000, they weren't allowed to do it anymore. Anyone who wanted to be a contractor for the company could not be hired back as an individual. Many of us ended up cutting a deal with a contracting agency who billed the company for us and we went on working as before, but there was red tape involved and it was a hassle. If I remember correctly, our work for that specific company could only represent a percentage of the total work that we did because of IRS guidelines.

You might want to check into the company's independent contractor policy before you cut those ties to a steady paycheck.
posted by jeanmari at 1:11 PM on December 6, 2006

I gotta say, I was not so helped by the answers to this question. But I did I pull it off. I quit first, and asked about freelance writing second. But I quit in such a way and at such a time that it made a lot of sense for everyone involved to have me do the writing. And I quit at a time when I had zero debt, a small amt of savings, and other options to explore if the writing thing didn't work out. All in all not the safest way to quit a job, but so far so good, and SO liberating.
posted by nevers at 7:10 PM on April 8, 2007