Last fall I got a part-time job doing some freelance technical writing for a small software company that’s based here in Raleigh. I enjoyed the work that I did for them, and I was excited for some of the projects that they had coming up. However, they’ve had some major employee turnover in the last month or so, and now it seems that things like “have our freelance writer produce more documentation about our awesome software” and “pay our freelance writer’s invoices” have gotten pushed to the back burner. It sucks, but what can you do?

So, new year, new opportunities. I decided to start looking for another job. Obviously I’d prefer to work from home, but I’m not opposed to an office job either. I started sending out resumes, but I figured that it would take a long time to find something that would be a good match for me. And suddenly this week, I’ve come across two different jobs that both sound really good, both companies seem very interested in me, and I’m not sure which one sounds better.

Job A: Entirely work from home, and while it’s in the IT industry, it’s a side that I have absolutely no experience with, but it sounds like it would be a LOT of fun to me. And even though it’s work-from-home, it would involve a lot of talking on the phone, so I’d still get that need for adult interaction fulfilled, and not feel all isolated and hermit-like (which I know is a downfall of a lot of work-from-home jobs). However, the pay is just so-so – it would be more than enough to cover daycare expenses and still have some money left over, which I guess is the main goal.

Job B: It’s an office job, but it’s straight up technical writing, which is what I’m used to. (And I really enjoy technical writing, so that’s not a bad thing.) It would challenge me, which I love. And the salary would be… well, a lot more than the Job A, that’s for sure. It’d probably be enough to bump us into another tax bracket.

Now keep in mind, I don’t have hard offers for either of these jobs, I’m just in the early stages of interviewing with them. But, how do I choose between two seemingly great opportunities? Do I go for the work-from-home job, and take a chance on my gut instinct that’s telling me this would be a good fit for me? Or do I stick with the side of the industry that I know, and accept that security (and ok, the money) in exchange for having to commute to an office every day? Is it all about the dollah-dollah bills? Or is job flexibility the key to happiness?

How would you choose?