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CTO or GTFO: Does Stepping Down from the C-Suite == Failure?


As some of you know, I quit my job recently. I started there as a senior developer 6 years ago, and left as CTO, with stops along the way as Director of Technology and VP of Technology. Now I find myself faced with a choice. Do I try to find another CTO gig, or go back to my roots in development?

As a CTO, I didn’t write nearly as much code in the past year and a half as I had the years prior. In fact, I felt so rusty that I spent my Christmas vacation away from work writing a new FOSS IT Asset Management system (called Snipe IT, available on GitHub, if you need such a thing) just to get my hands dirty with some code again. Much to my relief, most of it came back to me quickly, despite the fact that  I was using a framework I’d never used before. In a week and a half, I had a working alpha that people in the community were using and contributing to. It felt great.

While a CTO doesn’t always have to write much code, the CTO of a smaller company (without lots of middle-managers) needs to be close enough to the code to know how to guide and mentor their team, and make smart deployment and technology decisions.

I love a lot about both roles. I love the in-the-weeds problem-solving and feeling of accomplishment that comes with being a developer. I love looking at something I worked on, watching people interact with it and enjoy it, and know “I helped make that! I wrote that code!”.

On the other hand, I really enjoy solving higher level problems as well. Architecture problems, technical strategy challenges, finding the right technology to get the job done. Hell, I even like risk-management. And I enjoy managing people, and finding the right mix of talent to build amazing teams that love working with each other.

But really, let’s put all of that aside for a moment, as there’s something else chewing at the back of my head. If I step down from CTO for a dev gig I really love, does that make me a failure? Will the perception be that I couldn’t hack it? That I wasn’t good at it? Or that I couldn’t handle the stress/responsibility?

I feel this might be complicated by a sense of obligation I feel towards women in my field. Some women look up to me, because not only did I make it in tech, I wrote books on development, I speak at conferences and eventually became a CTO – arguably the brass ring of technology positions. The media wets their pants to interview me because I’m the unicorn they didn’t think existed. (Newsflash: we do. Not that many of us, but we’re definitely out there.)

And I think that’s the problem, this notion that the CTO position is the brass ring we should all be striving as technologists and once we reach it, we’ve “made it”. Maybe it is the brass ring, and maybe it isn’t. But maybe I’ve been blindly climbing towards the top because it’s what I was raised to believe it’s what people are supposed to do.  In fact, when I first made CTO, I was so thrilled, and then realized that I had nothing left to work towards, and it felt weirdly empty. I had been working towards this my whole career, and now that I had it, I wasn’t sure what came next.

I realized this a while ago. It’s why I wanted my Real Women of STEM project to feature women of all roles in STEM. The execs get all the media love, but applications aren’t written by CTOs and servers aren’t managed by CIOs. I would much rather work with a junior developer that loves the shit out of their job than a CTO who wants to be doing something else or had settled so comfortably into the executive role that they are out of touch with their team and the technology.

In discussing this with a few colleagues, many of them have said, “Once you reach the C-suite, you really have to stay there.” I interpreted that to mean that it would be difficult to go from CTO to dev and then back to CTO, as assumptions are made about why you left CTO in the first place. This has proven true for some colleagues, not for all, but in general I agreed with this notion at the time, and decided I would only look for CTO jobs in my job hunt.

And then I realized that was the dumbest decision I’ve made in a long time.  Who cares what my title is? I’m 38 years old, with almost 20 years in this industry. Who am I trying to prove anything to? The only thing that matters is whether or not I love what I’m doing, whether that means going back to a junior developer position, or becoming a CTO again.

The work is what matters. Loving the hell out what you’re going to spend at least 8 hours a day doing matters. The title on the business card just doesn’t matter. I can’t believe how much I used to think it did, but it just doesn’t. If you’re making the money you need to make and you love the work, don’t sweat the title.  Be awesome, help your tech community, and do great work.

If I end up in a dev/devops role, will it make it harder for me to get another CTO gig down the line? I have no idea. And I don’t care. I want a job I love, doing work I love for a company that values me.

For the women I was afraid of disappointing by potentially not being the brass-ring-holding tech executive role model, I will say this: The very best way I can be a role model to you is by pursuing my own happiness and encouraging you to do the same.  You won’t find happiness in a title, and you can end up wasting a lot of your career believing that you can.

There is no shame in being “just” a developer (or sysadmin/ops, etc) – in fact, there is no “just” a developer at all. That mindset is toxic and you should put as much distance between it and you as you can.

I loved being a CTO. And I loved being a dev. I don’t think I could choose which I love more, as there are parts of each that are important to me and that I don’t get with the other.  But I’m finally in a place in my head where I wouldn’t feel like a disappointment if I stepped out of the C-suite for a position I really loved.  I beat myself up over enough things. This isn’t going to be one of them anymore.

I don’t know where I’ll end up. I don’t know if I’ll return to my dev roots, or wind up the CTO of a different company, but I’m finally in the right headspace where it’s the job, not the title, that really matters to me.

PS – Speaking of speaking, I’ll be speaking at Macworld/MacIT in March this year, and keynoting Lonestar PHP in April. Come by and say hello!

About the author


I’m a tech geek/dev/infosec-nerd/scuba diver/blacksmith/sword-fighter/crime fighter/ENTP/warcrafter/activist. I run Grokability, Inc, and run several open source projects, including Snipe-IT Asset Management. Tweet at me @snipeyhead or read more...

  • lomifeh

    It’s not at all strange or a form of failure. You really should be doing something that makes you happy. I can understand the feeling. Sometimes we realize what we’d rather do is something than what we think we should be doing. Or sometimes we see an opportunity that on paper seems like a demotion but isn’t.

    Some people care about titles, some don’t. Hell I have at least three titles at work today and they are pretty much meaningless considering what I do. I’ve found that it’s more important to do what you do well and that inevitably gets recognized. But, expect to be asked why you made your choices.

    • Of course – my point is that I have always felt an obligation, as a reluctant role model for women. I keep getting written up on the “Women CTO” lists, and lots of women reach out to me to say I inspire them. When I’m not on those lists anymore, will my ability to inspire be more limited? (That’s a rhetorical question.)

      It’s not about the title, it’s what the title is meant to symbolize.

    • Also, responsibilities != title. At my last job, I did the job of 7 different people, but I had one title. The title is the thing I’m referring to, and while it’s easy to say “don’t pay attention to the title”, when you’ve been raised to go as high up as you can, that can be harder to do than you think. It’s easier for me to ignore other people’s titles as indicators of their worth than it is for me to ignore my own.

  • veggiespam

    Congratulations, I did not realize you left. Sometimes, leaving a high visibility job is the best thing for you. Best of luck in whatever you do next.

  • Illustrious niteshad

    Just a though, but what about starting your own consulting business? You’d effectively promote yourself from CTO to CEO (and President and Owner/Operator) and it would allow you to find clients who value your expertise. With multiple projects going, you could keep your hands dirty in developing some code, and also provide your CTO experience to clients who need that.

    • I did the consulting thing for a long time, and I’m kinda over it (for now, anyway). Also, I worked for an agency, with tons of clients and different projects. I’m definitely looking for a company that has one main product.

      Agency/consulting can be great – lots of variety ad challenges, but it can be hard to ever get too invested in any one project, since you’re split across so many.

      If I’d do anything, I might start my own startup, where my product is the one I’m working on. 🙂

  • I think you (and indeed, anyone) is on a loser if you think about “they”.

    – “They” will say you were elevated to CTO for publicity/diversity.
    – “They” will say you couldn’t hack it.
    – “They” will say you’re letting them down.

    And so on. But you aren’t the monarchy, trapped in a role you are obliged to do for the masses even if you don’t enjoy it. Abdicate, marry a commoner Dev job that you love, have fun. Life’s too short to not have fun at work.

    As to making it, people were speaking to me when I was being offered a CTO role that it’s making it through the first year that matters. As a TTL at Inviqa I don’t get to cut much code these days, although I do get to do devops and strategise. But I fight to make sure I get a day a week coding.

  • Peter Hancock

    I think rather than focusing on “failure”, I’d be looking at the definition of success. A role that defines success based primarily on compensation is often going to be different to the role that defines it on creativity, responsibility, flexibility, travel or…. nevermind – you get the idea.

    If you’ve just got the role that meets your criteria for success – then that to me is a huge opportunity to be a role model in a non ladder climbing way. You *can* pursue your dream, and it’s OK to not keep up with the Jones’s in the career ladder.

    Importantly, success criteria can change – and somebody that can recognise that change and pursue it is the role model that I’d like my son and daughter to look up to. I’ve got too many friends stuck in the rut of life pursuing something they feel they should be, rather than pursuing something they want to be, purely because some nebulous societal pressure says they should.

  • Pelle

    Only have two thumbs that I can give you thumbs up for this article, but I certainly give you all thumbs I can. In my opinion – especially in small to medium sized companies, one of the biggest mistakes is to lift skilled people to a leading role. The problem with this is that skill in work is completely different from skill in leading and being good at one doesn’t mean to automatically be good at the other. So, judging good skills at a hands-dirty-role should ultimately lead to a more-hands-dirty role and on the other hand if someone shows skills in leadership either by interest or by accident, that my be promoted in the other way.

    Following along this discussion, I do think that leading roles don’t necessarily need to be paid more but rather equally or based on the judgement of the relevant skill.

    Hope I’ve mad my point 🙂

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About Me

I’m a tech geek/dev/infosec-nerd/scuba diver/blacksmith/sword-fighter/crime fighter/ENTP/warcrafter/activist. I run Grokability, Inc, and run several open source projects, including Snipe-IT Asset Management. Tweet at me @snipeyhead or read more...

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