How do I know when to leave a good job?
June 1, 2012 7:49 PM   Subscribe

I'm a software developer in my early 30s, working in the defense industry. I'm pretty happy with my job, but wondering if I should move on. I would be looking to move to the San Francisco area. My question is, how do I know when to leave a pretty good job?

I know people do this all the time, but I'm pretty risk averse (too much), so I'm having a hard time calibrating my thinking. Also, because the majority of my career has been during this awful economy, I feel squirmy and guilty when I think about leaving a job I've been so grateful to have at all.

Reasons I'm thinking about leaving include:
  • I moved to a city where I still know no one. Although I like it here in a lot of ways, I've discovered I don't really enjoy seasons (especially the winter one), and it's not very diverse. I miss my family, who now all live in N. Calif. My parents are getting older, etc, etc.
  • I'm afraid I'll get pigeonholed into my industry if I stay much longer.
  • I've gotten great experience working on a fascinating piece of software. After many years though, I'd like to try something new. I'd like more breadth, but there's no doubt I have to find it somewhere else.
  • It might be nice to work with more people my own age. I'm the youngest (by a lot) in my department and always have been. I'm also the only woman on my team. I know there aren't a lot of women in software, but anyone more than just me would be an improvement.
  • There are some bubbling issues in our team that are uncomfortable, and management is aware and not making any of the necessary decisions to stop it. There's definitely a lack of leadership that's making me a bit cynical. I still enjoy going to work, but for the past year there's been an undercurrent of "I need to get out of here before this thing blows!" which dampens my enthusiasm. If I leave before does blow, I can keep my good relationships with the involved parties.
  • This is probably silly, but I really would like to be able to throw away (maybe burn?) my slacks and wear jeans to work.
Reasons I'm hesitating:
  • I like most of my co-workers. We've been working together for a long time and and we're a lot like family (including being a bit dysfunctional, I guess).
  • In spite of the problems within our team, our managers are basically good people and stand up for us.
  • We generally have good working hours. We do a 9/80 schedule and crunchtime is not too frequent. We had a bad year once where we were putting in a scary amount of hours for a long time, and it was hard on me. I don't mind if I know there's an end in sight and it won't be constant, but I have this idea that this might be the relentless norm in software and I worry... Trading in a 9/80 for what might end up being a 9/90+ feels like giving up massive amounts of PTO.
  • The company produces a product that I am fond of--I like that, even though I'm just support staff to the real engineers.
  • Even by awkward geek standards, I don't socialize very well, so I worry about how well I would fit in at a more normal company.
  • The pension??
Sorry for the "Anonymous Question" novel. I'd be so grateful for any insight from people who have already been down this road... throwaway email:
posted by anonymous to Work & Money (9 answers total) 12 users marked this as a favorite
A suggestion to consider: to be more excited about your job, go do something great outside of it. I'm not sure what 9/80 and 9/90+ mean, so I don't know if extensive side projects are actually feasible for you right now, but I definitely agree with the blog author that working on a side project is a good way to get the attention of SF bay area recruiters.
posted by tantivy at 8:32 PM on June 1, 2012 [2 favorites]

There is certainly a lot of demand for strong software engineers in the Bay Area and NYC. I would be shocked if you didn't find a job. It certainly can't hurt to interview.

One tradeoff of note is that, if you have any interest in childrearing, affording the common American amount of space for that is much more difficult in the Bay Area than anywhere with winter that isn't NYC.
posted by akgerber at 8:39 PM on June 1, 2012

Based on everything you have said in this post, then the time to start looking for a new job is now. The time to leave your job is when you find another job you are excited about. If you look, and don't find anything exciting, then no problem, you already have a job! You have nothing to lose by looking.
posted by Joh at 8:44 PM on June 1, 2012 [1 favorite]

The salable advantage you have is in understanding the discipline defense work creates. You will be very well suited to coding or verifying FAA-compliant software per DO-178. It is by no means a trivial matter to get coders willing to work at that level of documentation. Most whine and bitch and claim their code is self-documenting. If you are the exception and you are willing to do the leg-work that DO requires, you have a long and healthy career ahead of you. There isn't all that much FAA-compliant SW work in Northern California, but with a few tweaks you can turn that into GMP-compliant coding for medical equipment companies.
posted by jet_silver at 9:00 PM on June 1, 2012

I think you should go for it! It isn't easy to transition from defense contracting to mainstream software, but I think it will work in your favor that you're young and female. You won't have the set working hours you get at a contractor (there will be 80-hour weeks sometimes). Also, you won't be able to own a home. On the other hand, you'll have way more job opportunities, get paid more, and be working on dynamic interesting projects in a competitive environment.

tantivy: 9/80 means 80 working hours in 9 business days, then every other Friday off. It is the standard schedule at Lockheed. And yes, they have to fill out time sheets, have set start/end times, etc.
posted by miyabo at 9:29 PM on June 1, 2012

I left a very comfortable job at Akamai in January and took a job at Evernote. I had many of the same reservations that you do. Will I like the new people as much as the old people? Will the hours be excruciating? What about stock in a private company when imcurrently get salable stock? What about the health benefits?

But I was bored of the product I was working on, I had been there for years and wanted a change. Evernote was more exciting, more up-and-coming, and I felt like I could have more of an influence.

I have been completely happy with the change. Oh, and I still own a home and haven't yet worked a week longer than 50 hours.

So go, look, interview. Don't leave until you're excited about something new, but don't hold on to your current job even after you find the right opportunity simply out of fear. You will be scared to make the switch even when you should - you'll know because you'll be conflicted, instead of thinking "eh, that's no better than my current job." there's *always* an uncertainty that comes with these changes that makes them difficult.
posted by tylerkaraszewski at 10:16 PM on June 1, 2012

When I get restless, I go out and apply and sort of...feel out my wild oats rather than sow them. It's good to get a feeling for how much you actually want to get out of your job, how much you could actually be making, and what kind of work environments are out there. Applying is not a commitment on either part. Talk, see what's out there, and maybe you realize you like your job and want to stay there, or maybe you want to get serious about looking. Worst case, assuming you're not a dick and THEY'RE not dicks, you make some contacts in the field and maybe you interview again somewhere down the line or they wind up somewhere else and remember you when you apply there and, hey presto, foot in the door.

One thing I'll say is a lot of the San Francisco software culture, startups especially, are very nerd-jocky about how long they stay and how late they work and how they're never home. If that sort of thing is important of you, make sure to feel it out. Some places will say they really care about work-life balance, then say "Oh, actually, we work mandatory 10 hour days, ha, you didn't buy that work-life balance crap?" (True conversation I had). But there are those that do truly care and treat people well and a lot of the bigger companies are run by and for grownups with families and lives that expect people to have families and lives.

If you can swing the time off and trip, maybe set up a bunch of interviews and go out there for a week or so? Figure out roughly where you'd live and try to live whatever lifestyle you'd see yourself envisioning out there. For example, during one of my tenures, I was totally going to live in Berkeley and be cool and take BART in every day and...and after one day of doing it to get into town for interviews, I decided no, that was not the area for me. The area for me was Pacifica/Daly City, which adjusted some of my priorities and where I'd want to work location-wise and look apartmentwise.
posted by Ghostride The Whip at 11:29 PM on June 1, 2012

I'm always about moving onward and upward, your reasons for going are better than your reasons for staying, IMHO.

I also think that everyone should live in San Francisco when they're young. It really has an expiration date on it, so hie yourself out there, pronto!

Plan on taking a week vacation in the near future and use your folk's address for your resumes (for some reason, a local number works better for employers). Get a "voice mail box in the sky" from ATT/Pacific Bell. This should run you about $8 per month. It's a local phone number that rings straight to voice mail. Another option is to get a "burner" with a 415 area code. Either will work.

Your skills are probably great for another, similar position, but with a new piece of software.

I absolutely do not regret any move I've ever made, no matter how wacky it was at the time. That includes Florida, Pittsburgh, Nashville or Atlanta.
posted by Ruthless Bunny at 10:48 AM on June 2, 2012

even though I'm just support staff to the real engineers.

I had this on my list of reasons for leaving because it limited my advancement potential since management would rather promote engineers with domain knowledge over developers. As much as I enjoy working with engineers, I've had more career success working in places where the majority of the office was computer, software, and IT folks.

I'm also the only woman on my team. I know there aren't a lot of women in software, but anyone more than just me would be an improvement.

I've been on a lot of development teams over the years and there was a peak in the late 90s to early 2000s where I worked on teams with with 3 or 4 women developers among a larger group of men. We all scattered to different companies and I'm back to being the only female developer. That said, I have worked with lots of women in tech who've been project managers, domain experts, quality assurance testers, and database administrators. So, we're out there, possibly even down the hall or on another floor. If you find a software company that has well rounded teams of developers, testers, graphic artists, dba's, and project managers, then you might find a few more women in the mix.
posted by hoppytoad at 11:19 AM on June 2, 2012

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