I Want Less Money and No Power!

July 7, 2015 12:56 PM

I was a software developer for the first 10 years of my career (1998-2008) before going into management. I'm now an executive at a Fortune 500 company with a high-stress job overseeing 250+ engineers layered within four levels of management under me. It's a great job - I'm incredibly lucky to have it - but I need help planning my exit. I want to be a software developer again.

The timeline for this transition is 18-24 months away so I have some time. I have great credentials (a CS degree from an Ivy League school) and previously wrote lots of clever and efficient code in a variety of languages (Java, C#, HTML, CSS, etc). I've been exposed to and understand all the fundamentals of professional software development including a variety of development methodologies (Agile Scrum, etc) and the importance of DevOps, CI, etc. I'm proficient in cloud technologies (Amazon AWS and Azure), etc. My detailed skills are way out of date, though, and I'm not sure how to jump-start myself back into being an effective software developer. I would definitely fail any soft of coding test if I took it today.

Also - I've held EVP/SVP and C-Level positions for the past five years at various companies. I know if I were interviewing me for a software developer position, I would be immediately suspicious and toss the resume. I'm worried about this holding me back and am curious if I should modify my experience or minimize the titles I carried. I'm also concerned about the salary conversation... I'm looking at a serious paycut (in the neighborhood of 60-75% reduction) and can't imagine how that conversation is going to go.

Specific questions:

1) One of the things I've considered doing is leaving my executive job and doing one of the 3-6 month coding boot camps that are available in multiple cities in the US. Are these things as good as their marketing material?

2) Can I get where I need to be by dedicating a few hours a day to online coding tutorials and self-help?

3) Any suggestions about the salary and over-qualified title situation?

4) Am I crazy? Have others done this? My family thinks I'm bonkers.

5) One of my priorities for this transition is to be able to work remotely/from the road so I can live wherever I want to. I assume this won't be possible at the executive level and will be much more attainable as an individually contributing software developer. Is this true?

Thank you.

posted by anonymous to Work & Money (15 answers total)

How comfortable would you feel contracting? I think it would look a lot more like a step towards something (rather than away from something) if you decided to strike out on your own, as an independent contractor who wants a lot of flexibility in his days.
posted by xingcat at 1:14 PM on July 7, 2015 [7 favorites]

If you can dedicate a few hours a day outside your day job, I think you should build your own app or web app -- use it as both a way to brush up and a way to make sure you really want to do it again before taking any bigger steps.

"I was a programmer for 10 yrs, then a manager for 7 years and I forgot how to program, but look I just did a 3-month boot camp" is a much less compelling story than "I was a programmer for 10 yrs and so good they kept promoting me and I'm no longer as deep in the weeds, but I've always been coding on the side and I'm still on top of it, for example here's my current side project..." (even if the latter is a slight exaggeration)
posted by neat graffitist at 1:24 PM on July 7, 2015 [14 favorites]

I would do the following:

1) Do side projects/teach yourself some of the software needed.
2) Go to a smaller tech firm or startup. They will need your help if you tell them you primarily need to code that would be fine also.

The three month bootcamp you can do it...but I don't think it will boost your chances...I could definitely see a story of "I missed coding and developing and after going through the bootcamp realized how much more I want to be in it"
posted by The1andonly at 1:32 PM on July 7, 2015

Someone with your background does not need a bootcamp. You need to brush up on some skills and, perhaps at least as importantly, demonstrate your seriousness about this change. The best way to do this is to learn about some modern technologies you find interesting, and use them to build personal project(s) that can be a portfolio for you when interviewing.

Take a look at hackernews for a few days and keep an eye on the non-commercial projects that get posted to get an idea of what impresses and intrigues you.
posted by caek at 1:34 PM on July 7, 2015 [1 favorite]

With the CS degree and solid experience writing code, it seems to me online tutorials and some daily/weekly personal study time would be more than adequate.

I don't think a boot camp is likely to add a lot of value from a strict domain knowledge standpoint. It might provide social reinforcement of your focus if you need that. It's possibly useful in a pinch if you decide to do a total resume reboot, but I think you can come up with a better story than that, maybe something like neat graffitist suggests.

If you want to be unconstrained geographically and don't mind some customer-facing conversation, personal consulting/contracting seems like a pretty good move, and one you have a great resume for. You don't even have to tell anyone you're the developer.

And if you have any product ideas you've been thinking about, it sounds to me like the next two years would be a great time to work on one w/o telling anyone, brushing up your coding skills, and then turning it into a small personal software business when it's time to go. If it fails, it's still a really good resume point that works as a transition back into building things personally vs managing a team.
posted by weston at 1:34 PM on July 7, 2015

1) I have a number of friends who have done these boot camps (specifically App Academy, Hack Reactor) but typically coming from a place of less programming experience. Their experience is pretty darn positive so far and they are happily employed in the Bay Area. There is a great selection bias at play, so it's hard to be sure that the boot camps are responsible, but they seem pretty good if you're ready to spare the money and dedicate the time. I suspect they would be even better for you since you have existing general programming experience and probably just want to learn practical things about working with modern technology. If in doubt I'd contact the people running the camps and talk to them.

2) Assuming you were a decent programmer before and you're a pretty self-motivated guy you should absolutely be able to catch up on anything with a few hours a day of practice.

3) I would make sure you have a side project or two that you wrote recently to establish that you still care to program. Additionally, I would try to get in touch with people at a company you wanted to join directly and make your case to someone who cares, instead of putting your resume into the big HR trash can, but you knew that.

4) Seems reasonable to me if you're pretty sure that the money difference won't be a big quality of life change for you and your family. Solving problems by programming is fun.

5) It's definitely true that working remotely is possible if you're a reasonably skilled programmer. In my experience, you will have more luck finding companies that explicitly advertise remote work instead of just applying anywhere and then trying to negotiate.
posted by value of information at 1:35 PM on July 7, 2015 [1 favorite]

I can only speak to #4. I very recently took a "step back" in my career from a high-stress supervisory position to doing what I really love in the same field. The job hunt took many months and I got a lot of "but you are so overqualified" comments for the interviews that actually called to speak with me rather than assume I didn't understand the step back. I was fortunate enough to get my salary matched (but was considering an offer that cut my salary in half), so the step is really in a lesser title but OMG I am so much happier not having the minute-to-minute stress of managing a large staff and the work itself being stressful. I would have welcomed the pay cut if necessary just to have that impact on my quality of life, attention to my family, ability to leave the job at the job, etc. I used to carry a work cell phone that rang constantly with nothing but problems, and all that is gone now and I could not be happier in my decision. The title means nothing to me -- but that's me -- and I'm still in the same field so I can always pursue it in the future if I desire.

I was honest throughout the interview process -- I've been there and done that and believe it has made me a more seasoned professional, but I am looking for quality of life and want to return to what I really love doing (and am really good at) so that I can be the best employee in this position.
posted by archimago at 1:49 PM on July 7, 2015 [4 favorites]

No to 1, yes to 2. I think if I was interviewing you I'd want to know why you want to get back into coding to decide if you were crazy or not (or more importantly, whether you would be likely to quit and go back to management and more money). If you can answer that question for yourself I think you will find places that will believe you.
posted by crocomancer at 1:50 PM on July 7, 2015

Have you considered starting your own agency? You'd have a ton of flexibility, time to brush up on your skills, and already have the weight of your leadership experience and domain knowledge to leverage new clients. The clients don't need to know who's building the the stuff, so you can lead in the development and also hire great contract talent to work with you (as needed) while not having to deal with the overheard of a corporate or company environment.
posted by homesickness at 2:26 PM on July 7, 2015 [3 favorites]

I'm a happy bootcamp grad and I would get $200 if I referred you to the bootcamp I went to, but I don't think it's a good idea for you. Work on some side projects in a language you haven't used before. Do some coding interview questions in a language that you're already comfortable in. Come on, implement me FizzBuzz in a language you already know. You can do that.

I think the best way for you to find a job is going to be through your network: through people you can be honest with and who will know that you're not a crazy person and that you are being thoughtful. Also make sure you have some current work to show people (the above mentioned side projects). Maybe start attending meetups, depending on how big of a thing that is in your area.

I feel like the 100%-remote work thing might be the biggest sticking point. Definitely look for companies where remote work is a way of life - they are set up to integrate people into the life of the company remotely. Being the one remote person on the team seems much more difficult to me than being one person on an all-remote team.
posted by mskyle at 2:26 PM on July 7, 2015

Definitely look for companies where remote work is a way of life - they are set up to integrate people into the life of the company remotely. Being the one remote person on the team seems much more difficult to me than being one person on an all-remote team.

Yes. Been there, done that, it sucked. Working remotely for a company that knows how to have remote workers is awesome. But being the only remote worker, an "exception" because they really wanted me, and I didn't want to move, was one of the worst career decisions I've ever made. Obviously every situation is different, but it's something to keep in mind.
posted by primethyme at 3:15 PM on July 7, 2015 [3 favorites]

Hey anonymous, I've got some direct experiences with your situation, especially questions #3 and #4. I don't want to go into details here - too easily identifiable. Memail me or have a mod send/post a sock puppet email address.
posted by kovacs at 6:11 PM on July 7, 2015

Lots of good advice above. The main thing I have to add, as someone who has interviewed programmer candidates, is that they absolutely *will* ask about the move "down." I personally understand some reasons a person might want to do that. Most great programmers eventually find themselves elevated to positions where they no longer get to do what they really loved, management isn't the end-all be-all for everyone.

But, the way it looks to a hiring manager is... "something happened" that made this guy not a fit for his old job. Was it...
* he lost his job or he knows he's going to lose it? If that's the case he'll take anything that comes up now and keep looking
* he's transitioning in some way? Like... maybe he wants to move to "my town" and is going to take any foothold so he has time to figure out the ideal spot?
* is his resume really true? (I'm rarely suspicious on this count, because lying about being a VP is not the usual way into a programming job, *however* lots of people who aren't qualified to be programmers don't know that.

All of the above are warning signs that indicate "this guy is not gonna stay here."

People do NOT like to hire people who aren't going to stay. Hiring someone is a pain in the ass, you want them to stay.

So mostly what I'm trying to get at is, you need to be ready for this, and you will need to make sure they are convinced you want the job they're offering - as is.

I've seen more than one guy in your spot hired and they were good employees. Some of them stayed, some left, that's just the breaks. Best of luck to you.
posted by RustyBrooks at 7:42 PM on July 7, 2015 [1 favorite]

Another vote for you're not crazy. In regards to #4, I've been in a similar position, but now I work in a (stress-free!) completely different job & industry than how I came up. My route was obviously different than yours would be: I slowly took positions I was qualified for for less pay/ less power/ less stress until I found the right level/ fit for me. Doing it this way also made the questions less awkward (re: pay, etc.). Best of luck to you.
posted by Laura in Canada at 6:13 AM on July 8, 2015

I haven't gone through the whole thread, but I think a boot camp would be a complete waste of time for you. You're already qualified. You're just a little rusty.

You want to make clear what you're doing in a cover letter. Answer their questions before they even ask. Spend time on this, because it's going to get you in the door.
1. Talk about how much you love technology and software development, that you no longer have an opportunity to do it and that you miss it.
2. Emphasize that you have steady work and have no need to leave, but that this is a choice. Mention that you'd be happy to provide references.
3. Mention that you understand that there may be a pay differential and that it's worth it because of #1 above. Also mention that this is a long-term decision.
4. Talk about your technical skills and experience. Skip right over the C-level stuff. It isn't important.

I agree with the other posters that a portfolio project or two is a really good idea.
posted by cnc at 9:10 AM on July 8, 2015 [2 favorites]