I suppose having my midlife crisis in startup software companies was better than buying a sports car or dating younger women

I’d been a first-level manager in the software industry for 15 years, leading testers and technical writers, when I was passed over for a promotion to Director. It pissed me off. I was a good manager who had accomplished a lot for that company, and I was ready to stretch into the next level. I thought I deserved the chance. I don’t think it’s just my ego talking when I say I would have done a better job than the man they brought in and for whom I had to work.

Then I got a call from a startup software company: was I interested in being a Director for them?

Why yes. Yes I was!

I don’t know where my ambition came from, as I’d had little of it before then. Since I was a teen I had wanted only to work in the software industry. For a long time I was perfectly happy writing technical documentation and testing software to make sure it worked as intended. I didn’t seek to move up the ladder; my first management job fell into my lap.

I’ve had a lot of desks in my career, but only twice a private office.

Yet through my early 40s I felt pangs of discontent. I could see ways to do things better, but as a manager I lacked the authority to do much about it. I itched to have more clout and make a bigger impact. Also, as my kids were headed toward their college years, the extra money of the Director level appealed to me.

I got the job and dived belly first into boiling water. What a mess things were there. Not only did I build their test team from scratch, but I also turned around their broken software delivery system. I wasn’t able to fix the company’s fatal flaw, however: the product was a hard sell, and we kept widely missing our sales goals. We rolled and pitched as upper leadership had us build this and then that into the software hoping something would catch on in the marketplace. Nothing ever did, not enough to make a dent in the market, not enough to satisfy investors. Sales became frightfully poor for six months and it became clear they’d have to cut staff. They showed me the door.

I moved on surprisingly quickly to another young company, beyond its startup stage but not yet mature. I built a couple functions from the ground up as a Director there — another testing team, and a program management team. It was great fun and I liked it there a lot.

Yet I’d started dreaming of being a Director of Engineering. Testing had become old hat for me, and because of changes in the industry opportunities were drying up. But also, I knew that quality starts at the top — you have to build it in. To deliver software as well as I knew it could be done, I’d have to do it by leading the software developers.

My chance came two years ago. An executive I knew and admired wanted me to lead engineering at his startup. I jumped at the chance.

The view from the Director of Engineering’s desk.

I proved there what I wanted to prove all along: that building a product well from the start is better and faster all around. Our product had few bugs, it held up under load, and it scaled with the business.

But after we built the core product, there were internal disagreements about what to build next. It undermined everything. The executive who hired me had ideas, but he didn’t win over the rest of the execs and in the end he resigned. The person they brought in to replace him treated me badly, and as you know if you’ve been reading this blog for the last six months she fired me with neither explanation nor warning.

I had proved to myself that I could do all the things I wanted to do — but so what? It didn’t save these companies, it didn’t give me the feelings of accomplishment I wanted, and it sure as hell didn’t bring me the respect and admiration I was secretly looking for. Instead, I wound up on the street.

The job I was able to get before my family’s finances got rough is as a first-level manager. It stings a lot to have been essentially demoted.

At least I’m still in engineering. Also, I’m a deeply experienced first-level manager; this is a job I can do well. Even better, I’m in an organization that, while not perfect, functions reasonably well. As in all companies there are business challenges, but there are agreed-upon plans to work through them. If you’ve ever worked for me, you’ve heard me say it: even a mediocre plan will work if everybody follows it. Also, because the company is mature it pays market rate, something startups don’t do. I make the same money I did before as Director of Engineering.

I’m dancing on a fine line. To accept where I am feels like giving up on my dream. Even though I found out my dream isn’t all it’s cracked up to be, a part of me wants to double down on it to prove it was good all along. Maybe I should get a new dream. Or maybe I should stop dreaming and be content with what I have, because it is objectively good.


17 responses to “I suppose having my midlife crisis in startup software companies was better than buying a sports car or dating younger women”

  1. J P Avatar

    A tough question. As one outside of your industry it seems to me that you are in a pretty good place. As you become better known and prove your value the kinds of opportunities you want may come, and worst case you are making good money doing something you enjoy/are good at in a stable company.

    1. Jim Grey Avatar

      Here are all the qualifications for “good place”: (1) employed, (2) at a company where it doesn’t hurt to work, (3) making a comfortable paycheck. That’s what I keep telling myself anyway, because I did dream of bigger things and I’m not sure frankly whether I’ll get another chance to achieve them. I’m starting to age out of the startup biz.

  2. Dan James Avatar

    I think appreciating what we have is always a good thing, I’m sure you do that anyway. So yes maybe you need a new dream, but in another direction entirely, and something you can do alongside your job, in your own time? Dreams don’t have to pay the bills, if you have something else stable and relatively low stress that does.

    (I read a random Seth Godin post just yesterday that essentially said if you make art but there’s no market for it, it doesn’t make it any less valuable as art to you, you just need to make your income in a different way – via a different art, or something else entirely. But either way, keep making the art you love.)

    1. Jim Grey Avatar

      I could be better at appreciating what I have.

      This blog and my photography are the other dream I pursue, already. I’m fortunate to have built a popular blog!

  3. DougD Avatar

    Well, for my midlife crisis I’m already dating a younger woman (my wife of 22 years) and I’m working a plan for a Mustang convertible, we’ll see how that goes.

    Unlike you, I was perhaps fortunate to have my dream die early. I’d wanted to be an engineer in the auto industry, and I got to live my dream twice! Both times it was awful; long hours, stress, and lots of yelling. I fell into mining and minerals processing equipment, and as I’ve told people for years, our customers are sane, they pay their bills and our deadlines are reasonable.

    So that dream died, and I’ve found enjoyment in my co-workers, in my modest successes, and the fact that my job isn’t my life but it does finance my life. That probably has more to do with my personality rather than any effort or insight, my wife is currently frustrated in her job (Oncology Nurse Practicioner) and sometime says “Errgh! why can’t I give up and be satisfied like you??”

    I don’t know why :)

    1. Jim Grey Avatar

      I didn’t start out with a dream beyond “work in the software industry,” which I achieved about five weeks after graduating engineering school. I was happy to write technical manuals and test. I got married and had kids along the way. I wanted my family to be my focus. But that marriage ended badly and I only saw my kids a couple times a week and I needed to do something with all the energy I wasn’t able to put into my family anymore. Perhaps that’s where my ambition came from.

  4. Heide Avatar

    Your headline made me laugh out loud, Jim — but your post asks some serious questions. I went through a mid-career crisis myself a couple of years ago and discovered that accepting where I am doesn’t mean I’m “settling.” I could bust my hump to climb the ladder and maybe — MAYBE — end up running a small agency somewhere. But would that really make me happier? Nope. Looking at my job as just one piece of the life pie helped me see that it’s providing me sufficient income and free time to pursue the other things I value (such as traveling with my husband). We each have to find our own path, and unfortunately there are seldom clear or even “right” answers. But no matter which path you ultimately choose, I do hope it will bring fulfillment and happiness.

    1. Jim Grey Avatar

      I think that during my single years my career took on an extra importance. I had all this life energy and a desire to put it into something.

      I really attached to my career dreams. I’m starting to see that it will be difficult at best to maintain them and have the kind of life I want with Margaret. The tricky thing is that we really will be able to retire at some point if we both maintain our current salary levels. The work I do does take a lot out of me. I wish I had more energy for my wife and family now!

      1. Heide Avatar

        You’ve hit the nail on the head, Jim: There’s only so much time and energy, so we must choose how we spend it. No matter what you decide, though, it will at least be a conscious choice for you. So many people invest everything in their careers, only to come out the other end and realize life somehow passed them by. I don’t think that will happen to you.

  5. Andy Umbo Avatar
    Andy Umbo

    Ach Jim! Whata Mess!

    I feel your pain, I was a successful advertising photographer with my own studio, until the bottom dropped out of the market in the city I was in! I moved on to managing a department for a retailer in Chicago, then eventually becoming a Director level person for another company, with a staff of 18. We accomplished a lot, and did some very high quality work. I eventually had to move on because the company kept getting bought, and buying others; an impossibility to keep your plans in effect! I moved on to Washington DC were I had a relatively successful career doing ancillary jobs where my experience was of high value.

    Eventually due to aging parent needs, I came back to the mid-west. which is where it went off the rails. I’ve said for years, everything you read about these wonderful work environments in tech and media, is NOT what is going on in the mid-west. Coastal only, friends, if it DOES happen.

    After my parents both passed, I found myself taking a job in Indianapolis “way” under what my skill level was defined as. Not only had most of this companies departments been poorly set up, and they had zero process management associated with creative media fields; the management people over my head were “super” inexperienced, and probably couldn’t manage a department to figure out how to make lunch! I mean, I never worked anyplace in my entire career that functioned like this, and the people in control weren’t even asking themselves the correct questions about function! It was brutal. They didn’t even know how to call stake-holders from other departments into the process, so things you’d be depending on for your department, would suddenly disappear, and you found out they changed function upstream from you, without telling you! Business 101

    Most places I worked on the coasts and in Chicago, people understood my abilities and just let me run the places and start improving the process, with systematic “check-ins” so they knew what I was doing. This place, whew, I couldn’t figure out if my boss was scared I knew far more them him, or if he didn’t know anything at all and just wanted someone to keep the lid on the department! Needless to say, after about 3 years, I and some others older than 55 were targeted for release, and about a year after that, their parent company sold them off as a problem they weren’t interested in solving! No matter how “right” I was, I was still working for mutton-heads that didn’t get it, and it still resulted in me ending up early retiring (NOT in Indiana, BTW), and not working until I wanted to retire.

    Just have to say, this type of thing seems to be endemic in both the mid-west, and with experienced people over their mid-40’s! Many of my friends in the mid-west, are going through all these problems themselves, as we speak! I learned a long time ago, to save-save-save, as you’d never know when some weird changes would leave you high and dry, and you’d end up having to move to stay employed!.The only people I know that have had complete 40+ year career arcs, are the people I knew that left the mid-west for the west coast shortly after college graduation.

    1. Jim Grey Avatar

      Your story and mine prove that there are no guarantees, that you can be really good at what you do and still not have a career that lines up fully with your abilities and aspirations.

      Here’s hoping I can hang on until I’m truly ready to retire.

  6. M.B. Henry Avatar

    The title of this article is amazing lol. Although I’m sorry to hear of all the frustrations, I know it’s been an up and down journey from some of your past posts. Wishing you an opportunity or a path that brings balance and fulfillment after all the hard work and some heartache.

    1. Jim Grey Avatar

      Thanks so much! It’s just life I suppose: you win some, you lose some.

  7. Sam Avatar

    Thanks for sharing a personal side of your life Jim! Great post.

    1. Jim Grey Avatar

      Thanks Sam!

  8. Steve Mitchell Avatar

    Honest writing! Sometimes when we get to the top of the ladder we discover it has been leaned against the wrong wall. That can be painful, but it can also be a blessing as we discover who we really are…

    1. Jim Grey Avatar

      Steve, I’ve been chewing on your great, pithy saying about the ladder. Life is a journey to discovering ourselves, to be sure.

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