How to decide whether to transition from self-employment back to a job

December 20, 2019 8:55 AM

I've been self-employed for fifteen years, but now have the opportunity to move into employment in a related field. How should I decide whether or not to do this? Have you made such a shift, and how did you decide whether or not to do it?

Let's say I work in widget services, where the widget is an intellectual activity. I've been (mostly) happily freelancing for 15 years, since I started in the field. Work is fairly easy to come by, I have repeat clients, I'm good at what I do, I've been elected to the board of the Widget Service Providers Association, I teach widget services at graduate level, it's all pretty good. The work gives me the flexibility to work around my son's school and extracurricular activities (I'm female, married to a man who is in full-time employment, our son is under 10).

A job has come up in a similar-but-not-the-same type of widget services, making good use of my skillset, but in the local branch of a huge national organization whose mission I strongly support. I was not thinking of applying for jobs, in general, but saw this one and it seems such a strikingly good fit for me that I am halfway through an application and I've visited the department for an informal talk about the role.

If you've been in a similar situation, how did you go about deciding what to do? My thoughts at the moment: I'd lose some flexibility (but the people there seemed to arrange work around their kids pretty effectively, and this role can be part-time); the money would be as good as I make now, more reliable, and I wouldn't have to pay for all my own training; there would be the possibility of progression, which I don't really have in my self-employed role (I'm 41 and would essentially be doing the same task repeatedly until I retire); I could continue to do a little widget services on the side, if the employer was OK about this.

tl;dr I'm happily freelance, with a few doubts. Should I jump ship and opt for a regular paycheck?

posted by anonymous to Work & Money (8 answers total)

Do you want to leave the house at 7:30 am every single business day, be gone until about 6 pm every single business day, and spend all that time inside the same building? Do you want to do your grocery shopping at the same time as nearly everyone else?

The pro of regular employment is the lack of stress around cash-flow (that is, until you start wondering if you're going to get fired or have to quit because you can't stand the internal politics or something). If you're not feeling stressed out about money, I'd say you have a good thing going where you are now.

You've probably already thought of this, but could you advance by bringing on an assistant and taking on more work?
posted by slidell at 9:11 AM on December 20, 2019 [3 favorites]

i personally wouldn't do it. i was freelancing happily, but then circumstances changed dramatically, and i was forced to go back to traditional employment. IT SUCKS. if you like being your own boss, don't have trouble finding clients and getting them to pay, and have the health insurance situation in hand, i cannot think of a compelling reason to going back to working for someone else. if a month of no income (for sickness, client bailing, whatever) wouldn't ruin you, i say stick with freelancing. especially for the flexibility it gives you for your child, which is NOT AT ALL guaranteed in the rat race.
posted by misanthropicsarah at 9:52 AM on December 20, 2019 [4 favorites]

I chose to leave self-employment and go back to working for other people about 6 years ago. I made the initial jump mostly because I was tired of doing all the business-owner “stuff”, and at first it was just really nice to not think about the bigger picture. Now that I’ve been in it a while though, the best thing for me is that I’ve been able to make some sideways career shifts in ways I never would have considered an option, and my work is a lot more interesting as a result. I know someone who made the same decision I did around the same time for similar reasons, and he’s now back to working for himself - which is always an option I’ve kept open in the back of my head for myself as well.
posted by okayokayigive at 10:28 AM on December 20, 2019 [1 favorite]

I did this twice. The first time to a dot-com just before the dot-com crash, and then again a couple of years later. As you suggest, freedom of time and schedule are a big thing. I think that a proper freelancer (as opposed to a faux freelancer, i.e. working through an agency of some description) can earn more and have more free time. There is a lot of time lost in conventional employment, if only what is spent around the water cooler/coffee pot. There is also a welcome bit of prestige in being the outside expert. The inside expert gets no respect.

My freelancing days were also marked by annual anguish over health insurance. It seemed like what appeared to be a good solution always turned sour in a small number of years for whatever reason putting us back into the market.

The second time was when I was 57. It became the best job I ever had but that was largely because I was the head of a small department and there no real prospect of either advancement or competition from a peer. Very relaxing. So it depends a lot on the nature of the full time job that's on offer. I would not have wanted to get back into a big corporate rat race. Freelance is also a rat race, but I was coping with that, as you apparently are too.
posted by SemiSalt at 11:18 AM on December 20, 2019 [2 favorites]

I think you should go for it, unless you lose a lot of steam in your freelance business from existing widget customers. You're not signing up for a lifetime of service, you can work hard, mold your role, learn some new skills, make some connections, then step back out into the world in a couple years.

That's assuming you wouldn't have a long commute and the culture seems like a good fit. Freelancing and working from home is a great privilege and sometimes you don't know what you've got til it's gone.
posted by BlackLeotardFront at 4:41 PM on December 20, 2019 [2 favorites]

The question here is what the upside of taking the job would be. The upside of freelancing is clear, and it sounds like the usual downsides of freelancing are not a huge problem for you (rustling up new business, health insurance, irregular payment). And the downsides of being an employee are pretty implicit in your post--less freedom, especially around your son's schedule.

But I can imagine a ton of upsides to taking the job. Mostly around contact with peers and potential mentors (or even mentees, since mentoring can really hone your skills), networking, learning new angles and new thought processes that you might not have learned otherwise. Basically outside stimulation. Even if you only do it for 3 or 4 years, it could be a shot in the arm to your skills and network.

I would worry about the flexibility a bit, but as someone who works part time myself, if the job can be done part time, you can probably make it work fairly painlessly. If you can work a schedule that has room for after school activities, teacher conferences, and doctor's appointments, you'll probably be fine. I worked 4 days a week with Wednesdays off, scheduled everything I could on a Wednesday, and got off work in time to pick my son up two days a week. So I could shuttle him around three days a week and he would go to afterschool care or a friend's house the other two days. It worked out very easily, partly because my workplace was very relaxed about things like working from home if the kid is sick or there's a snow day.

The only way I'd say no is if the commute was super long, if you really value working in your pajamas all day, and/or if you are very much an introvert and having to deal with people every day sounds like more of a hassle than a benefit.
posted by gideonfrog at 5:02 PM on December 20, 2019

I recently switched from semi-freelance 100% remote to a normal office job after 6 years at that particular job and about 10 total working like that. I was pretty nervous but in the end it turned out that our office hours are extremely flexible and people work from home all the time, so I don't really feel a dramatic difference. The biggest difference is that it's much less stressful to finally just have a solid reliable paycheck that isn't adversely impacted by the whims of clients or dependent on me to chase down invoices, etc. Paid vacation as a concept is amazing after so long.
posted by feloniousmonk at 5:04 PM on December 20, 2019

9-5 can be hard to adjust to if you're used to more flexibility but true part-time would have more of that flexibility and sounds pretty appealing in a relaxed setting. If you child is close to 10 there are less appointments and sick-days so it shouldn't be too bad, but there might be adjustment if you and your husband have more of the same time constraints.

I would seriously consider it and make sure they don't put in any non-compete clauses in your contract so you can freelance on the side and easily continue working if you choose to leave.
posted by lafemma at 5:28 AM on December 21, 2019 [1 favorite]