Five jobs in six years

33 comments on Five jobs in six years
4 minutes

I started a new job today. Again.

I’ve changed jobs a lot in my career: 13 times in almost 32 years — including five times in the last six years. It’s true that the software industry, in which I work, is volatile. Everybody in this industry knows we’ll work for several companies before we retire. But I think my career is a little extreme.

All swagged out at one of the five companies of my last six years

I’ve been laid off a couple times when a company’s fortunes fell. I was also fired twice. The first time I was also un-fired, which is quite a story. The second time was just a couple years ago and was the most painful experience of my career. But most of the time I’ve left of my own volition. A couple times I quit a bad situation and the rest of the times I was recruited away for a better opportunity.

My career has been anything but a straight line. I went to school to be a software engineer, but I graduated during a recession and jobs were scarce. The best job I could land was one writing software user manuals. I liked it a lot and did it for eight years, at which point I saw I’d gone as far as I could go in technical writing. My programming skills had gone stale so I took a job in Quality Assurance as a tester. There I was shortly promoted to manager, and over the next 17 years I built and led testing, test automation, and performance testing teams at various companies.

In 2015 I had been Director of QA at a startup (Company Zero) for 2½ years. After some terrible financial results they laid off a lot of people, including me. I did some consulting that summer before being picked up as Director of QA at another company (Company One). While there, I came to realize I’d gone as far as I could go in QA. I set my sights on moving into Engineering, but didn’t know how to get there. Then the company needed someone to lead its Product Management group, so I took that on too.

After I’d been there about 18 months, a startup founder with whom I was acquainted asked if I’d join his company as Director of Engineering. That was a huge stroke of luck! So I joined his company (Company Two). After about nine months that founder was forced out in a management shakeup. The the person who replaced him ran off or forced out the entire management team she inherited. She finally fired me late in 2018.

The best job I could get before money ran out was a step back, as Engineering Manager at a large, established company (Company Three). It was an okay place to work, but I had concerns about the company’s future. I’d been there only a few months when another large, established company (Company Four) recruited me to be a Senior Engineering Manager, leading four teams and their managers. It was easy to say yes. That company had a wonderful culture, an excellent software delivery process, and an outstanding product architecture. It was a genuine pleasure to work there. I felt like I’d hit the workplace jackpot, and decided to settle in for a long stay. I still wanted to be Director of Engineering again, but this company was such a good fit for me that I decided to enjoy the ride. But then last autumn the company made some changes that affected me and my teams in some ways I didn’t enjoy. A couple key reasons I had been happy evaporated, and I couldn’t see my own future there anymore. I was underutilized and bored. I remain shocked by how quickly things changed for me.

Today I start as Director of Engineering at a young company (Company Five) that I would say is coming out of its startup stage. Going on two years ago a colleague introduced me to their Chief Technology Officer and their (now previous) Director of Engineering. They were looking for some perspective on building out their testing team. I was happy to share my experience with them, and they were able to adapt it well to their situation. When their Director of Engineering decided to start his own venture late last year, they called me about taking on the role. This company makes a useful product, has solid financials and a great growth strategy, and has a reputation as being a wonderful place to work. It was easy to say yes.

And so today I begin. Again. I’m eager to stop this merry-go-round of job changes and do good work here for a long time. Everything I’ve been able to learn and discern about this company gives me great hope that I can.

Because I’ve changed jobs so often, I’ve learned how to recognize when it’s time to go. I wrote a couple posts about it on my software blog: here and here.

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33 responses to “Five jobs in six years”

  1. Barry Avatar

    All power to you Jim. I’m routing for you. Good luck, take care and stay safe.

    1. Jim Grey Avatar

      Thank you!

  2. J P Avatar

    I hope it is everything you are looking for. Your experience is so foreign to me, as I have gone 10-20 years between changing organizations. Part of it is my field and part of it is just me.

    1. Jim Grey Avatar

      My industry is very dynamic/volatile and job changes are common. Nobody blinked at my new company at my recent record, it never came up in the interviews. But I’m tired of changing jobs, and hope to stay here at least 5 years.

  3. Andy Umbo Avatar
    Andy Umbo

    Good luck, and I fear changing jobs like this is the new norm for many!

    I was barely able to keep jobs for 3-4 years, and that’s since the 70’s, so it’s not modern “gig” economy stuff. I’ve only been “fired” once, and not for “cause”, but a person that hired me decided he hated me; so sorry for me, especially since he lasted about a month more before they fired him! The rest were based on working for small organizations that didn’t plan correctly, or that didn’t work out to be what they promised, so other opportunities came up that allowed me to change. Of course, in advertising related work, this all starts slowing down the older you get!

    I never attained a semblance of job stability until I started doing my job for internal corporate departments. In fact, in my current state of “forced retirement”, I have my head above water only because of the tiny pension I received after working for a company for ten years. My 401 (k) has been decimated twice in the last 20 years, the idea that this is a valid retirement choice over the defined pension benefit that companies used to have is a laugh!

    A person loses so much money and forward progression in between jobs. Every change, especially when you’ve been laid off and you’re searching for work, is costly! Most “old business” companies have long terms before you’re qualified for their retirement systems, or full medical benefits. When I was running into a lot of problems, I started my own business back in the 80’s, which was moderately successful, but made me realize the market couldn’t support me or pay me enough to buy the benefits that were included in corporate jobs.

    In my industry, I tell every young person with talent that I mentor, to get the hell out of the Midwest! It’s not that there are few “lifetime” jobs here (that’s a given), it’s that you will not be able to put together enough jobs to add up to a 40 year job arc before you start running into external market forces like ageism! As a person who’s lived in 4 different cities, and worked extended months in a few others, I can say doing this to stay employed is not productive to buying a house or establishing a community. For most in the Midwest, house buying (especially as a single person) is predicated on the idea that you have long term, stable employment. Being in the Midwest, they never pay you so much that you can just throw money at problems, and most likely you will also lose money if you have to sell a house in 5 years or less to change cities!

    Every time I listen to my “code writing” pals in my apartment building, I cannot figure out how they’re going to survive working 3-4 years at a “gig”, and then having a 6-8 month ‘down’ to the next job. They tell me the only savings they have is to be used until they get the next “gig”.

    1. Jim Grey Avatar

      There’s no real security anywhere. My dad worked in a factory for 18 years when it was bought, the pension plan fleeced, and then the plant shut down. Dad got nothing for his time.

      Most tech workers I know do not have this gig-down-gig cycle. We all move from gig to gig. I’ve had a couple down times when I was laid off or fired, but they lasted only a few months each. They were tense times, but there’s so much opportunity in tech that I have always been able to be employed again shortly.

      1. Andy Umbo Avatar
        Andy Umbo

        Many of my pals had the same thing happen to their Dads, their companies decimated the pension before going bankrupt! Sometime in the past, the govt. passed a law making the pension and retirement system of a corporation sacrosanct!

        I was happy to see that even as the company I had worked for started their downward slide to bankruptcy in the 20-teens (long after I was gone), their retirement system which was, by law, separate from the company finances, had to funded at a “near 100%” level. When my old company finally went under, the pension was rolled into the govt. pension management system. I called them and asked if I should expect a lower disbursement, and they said no, the average worker gets what they have been planning for, even if they have to pay the senior executives far less than they’ve been getting! I thought that was a nice touch!

        BTW, I received my latest New Yorker, and there is a fabulous article on Americans and work. They track the fall of real income, and the rise of over-compensation of senior management to the rise of platitudes about “loving work” and “finding the work you love” movement. We are now working longer hours than the Japanese when they were committing suicide at their desks!

        1. Jim Grey Avatar

          It’s good that pension funds have been protected that way. My dad never was able to save well for retirement after his pension was decimated.

          I don’t know what’s ahead for American workers. I’m not encouraged by what I see today.

  4. Phil C Avatar
    Phil C

    I hope your new job goes well for you Jim. You made your own good fortune by giving advice previously and that must be one of the reasons you start your new position today.

    I negotiated terms for a new job a couple of days ago and will be starting an employed position later this year. It will bring to a close twelve great years of gig work which will start to dry up post pandemic if there is such a thing. I live in England and expect a lot of other people here will face big changes with their work this year.

    I came to your blog a few years ago for the camera reviews and stayed because of your outlook on life. Thank you Jim.

    1. Jim Grey Avatar

      A principle I try to live by professionally is give away what I know and trust that sometimes it will lead to good things down the road.

      Congratulations on your new job! I’m pleased you enjoy my personal writing!

  5. DougD Avatar

    Well, best of luck Jim. Change gets harder as we age but you seem to be taking it in stride.
    As you know I’m a long hauler in my job, but over the years the company has reorganized or been bought so many times it feels like 7 different companies. Same building and some of the people, but 7 different cultures.

    1. Jim Grey Avatar

      Change has been a constant in my adult life. I do sometimes wish things would settle down. But I also hate, hate being bored.

      Wow, 7 regenerations at your company. You are a true survivor.

  6. Max Avatar

    Similar for me in working 40 years in telecom. Started in the mid 1970s, retired in 2016. Thought that I would work for “the Phone Company” (ATT) for my entire career, but deregulation and digital technology changed everything! 7 companies in total….

    I tell people now to just get used to it, work out your best deal, and when it’s time to make a change, don’t let the door hit you in the butt! There is no single dominant company in place for long, investors are fickle and/ or stupid, so keep your skills and personal performance at their peak as much as possible.

    Good luck. Love the blog!

    1. Jim Grey Avatar

      I started my career in a company that served the telecom industry. It was the late 80s/early 90s and things were changing fast. This was when the #5ESS was taking over

      Yes — sometimes you just have to go. I just wish I haven’t had to go so often in the last few years!

  7. Shaundra Webb Avatar
    Shaundra Webb

    I enjoy your blog! Thanks for being so transparent congratulations on your new journey. Looking forward to hearing how it goes. I’m glad I’m not the only one who isn’t afraid to leave when it doesn’t serve me anymore.

    1. Jim Grey Avatar

      Thank you Shaundra — I’m pleased you enjoy what I’m doing here! Yes, why stay somewhere that isn’t working for you?

  8. Diana Moore Avatar
    Diana Moore

    Jim, your career history is SO familiar to me, as my Hubbs was a tech geek, too. We’ve seen the US because of his opportunities. He had to retire because of disability, and still misses the camaraderie, the traveling and the technology his jobs provided for him. Enjoy!!

    1. Jim Grey Avatar

      So far I haven’t had to do too much traveling — not my bag — but the camaraderie is real!

  9. Victor Villaseñor Avatar
    Victor Villaseñor

    While I haven’t had to shift companies that much, I’ve had to shift around in roles, and navigate changes in management and leadership. Its interesting to read how you have faced the changes, thanks for sharing!

    Seems you have a useful profile, perspective and experience, hopefully all other things not in your control, will align this time.

    Its gonna be a tricky one to translate:

    “A parrot is green anywhere”

    Good luck on the new endeavor Jim!

    1. Jim Grey Avatar

      Victor, thank you very much! I had to look up the parrot line, and I like it! Too bad it’s not an idiom in English, it’s a good one.

  10. Nancy Stewart Avatar
    Nancy Stewart

    Good Luck in your new job Jim. I guess we’re very lucky … My husband worked 42 years for the same company and then another 10 years at a “retirement” job. I worked for 30 years at the same place. Both with nice pensions at retirement. But I know those kind of jobs are not the norm anymore.

    1. Jim Grey Avatar

      Thank you Nancy! I love a new adventure, so in one way I don’t mind changing jobs. But it’s also a lot of work to rebuild relationships and credibility in a new place.

      My dad worked for Oliver’s and a new owner came in, raided the pension fund, and then folded the plant. Dad worked 18 years there for nothing. My lesson from that was: you’d better take care of yourself because your employer might not.

  11. brandib1977 Avatar

    Phew! What adventures you’ve had in your career! They are lucky to have you!! Good luck, my friend!

    1. Jim Grey Avatar

      I love a new adventure, but I will admit — I’d like to stay on this one for some years.

      1. brandib1977 Avatar

        Here’s hoping. I’ll send you some good vibes!

  12. Steve Mitchell Avatar

    The only constant seems to be change. I hope this goes well for you!

    1. Jim Grey Avatar

      If only the changes didn’t come so frequently!

  13. tbm3fan Avatar

    Things can and do change in an instance in tech. I happen to be in Contra Costa County. Starting at Pleasanton in Alameda it is but a short drive down to San Jose and Santa Clara or Silicon Valley as it is known. My practice naturally has lots of workers from there from low level to high level. The stories I could tell you about the original titans and current titans of Silicon Valley would fill a short book. Suffice it to say many are super jerks.

    A long time patient of mine worked for one of the Top four software companies as a lawyer but not as a traditional lawyer but on special software projects for 18 years. Her boss left for another one of the Top four and brought her along for the last six years. He recently left as he was tired of trying to smooth over the nastiness of the founder. She has since given notice also to get out of Dodge having first hand seeing how this well known guy treats people. What I have learned has changed my opinion, and how I see him from now on in the press, greatly for the worse. You would know the companies involved as well as the people if I told you but won’t here.

    So you could love your job and then a new boss comes along or your department gets rearranged suddenly making your dream job less of a dream and maybe a nightmare. Common in tech.

    1. Jim Grey Avatar

      I’ve experienced some jerk founders, and have experienced things changing on a dime so a dream job goes to nightmare. It is how it goes. I don’t know if it absolutely has to be this way, but I can’t change it. I try to ride it as best I can.

    2. tbm3fan Avatar

      Me, same job for forty years and counting on another 10.

  14. Sam Avatar

    Good luck on the job congrats!

    1. Jim Grey Avatar

      Thank you Sam!

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