Sometimes you have the tiger by the tail, and sometimes the tiger has you in its mouth

Today is my 30th anniversary in the software industry. I reflect on what I’ve learned — and how I need to keep learning.

By Jim Grey (about)

Lots of people in our industry have accomplished much, made a lot of money, and even achieved status or fame. It seems like lots, anyway. It’s probably a small but highly visible percentage. Whichever it is, it’s easy to wonder in this industry of plenty why that can’t be us.

When I remove the incredibly successful from the picture, it’s easy to see that I’ve done well for myself. I’m a middle manager of software engineers making a product you’ve probably heard of, in an engaged and positive workplace. We all make an upper-middle-class living.

Yet I sometimes wonder why I’ve made it only this far, why I’ve not gone farther. And I wonder whether I’ll be able to sustain my career as it enters its waning years.

You see, today marks 30 years that I’ve worked in the software industry. It boggles my mind that I’m only two-thirds of the way through my career — I still have 15 years to go before I’m of normal retirement age.

Fortunately this is all I’ve ever wanted to do, ever since I taught myself to write code in the early 1980s. I went to engineering school to get the credential I needed, but graduated during a recession when jobs were scarce. In a nationwide search I couldn’t find coding job. I managed to land job in the software industry writing manuals and online help, and I was grateful to get it.

I liked the work and became quite good at it, so I kept at it for eight years. Then I transitioned to QA, where I led functional testing, test-automation, and performance-testing teams. I did that for 17 years. And now I’ve transitioned back to my roots in a way by leading engineering teams.

I’ve lived through crazy growth and sudden downturns in the industry. Several times I’ve needed to find a job when one ended unexpectedly; several times I’ve been poached away to a better opportunity. I’ve worked with good people who have taken good care of me, and with charlatans and egomaniacs who stabbed me in the back.

Sometimes I’ve had the tiger by its tail, and sometimes the tiger’s had me in its mouth.

Thinking about what you'd taste like

Dozens of people have reported to me since I shifted into management. It’s a small tech community where I live; I bump into many of them a lot. Some of them are still individual contributors, some of them have become managers and leaders, and a few of them have gone on to even greater careers than I’ve had, reaching VP levels or reaping tidy sums when their startups exited.

But I’ll bet every last one of them has had good luck and setbacks all along the way, just as I have. We all sometimes have to figure out how to move forward from here in our careers. We all have to figure out how to stay relevant and vital, especially as we age.

I’ve been in management for 20 years, during which time I focused on being the best leader I could be. It has served me well.

I couldn’t both become a strong leader and keep my technical skills current. I struggle a little bit to swim as fast as my peer engineering leaders, most of whom have written code recently. I can see it’s time to rebuild my technical skills. I don’t expect, and I won’t try, to become the equivalent of a senior engineer. But to have a solid understanding of the technologies involved in my company’s product, to better evaluate the code of someone on my team and maybe even to be able to fix a bug, to be able to write a SQL query more complicated than SELECT * FROM table_name; — it’s time. I’m a little daunted, but in I go nevertheless.

I’ve learned a lot in 30 years. In many ways, I’ve become wise. But I’m still trying to figure things out as my life and career unfold. I can see that this never ends.

By Jim Grey

Writer. Photographer. Leader of geeks.

5 replies on “Sometimes you have the tiger by the tail, and sometimes the tiger has you in its mouth”

I’ve only been a manager for 11 months, but even then I noticed how easy it is to loose touch with the actual programming world. On the other hand, nothing has really changed since the 70s in terms of foundations so I’m pretty sure you won’t have any problem to get back into it. That is, if you can find the time for it. 😉


Imagine having been in management most of the last 20 years.

I can still sort of read code. I’ve done it now in Ruby, JavaScript, Java, and now Scala. I struggle sometimes to understand a change in its context. But I generally see what the change is doing.

I’ll push my way through it this year and see how far I get!


Sigh. I hit enter too soon. Let me start over. Feel free to delete the former comment.

I’ve been a technical manager; the title was “senior advisor”. But I’ve never been in management. I don’t think I ever want to. Managing a technology functional area or running a cyber-security lab or being part of an internal “think tank” is enough for me.


I love being in management, taking care of people, moving the business ball downfield. It’s exactly the job for me. I am open to moving back to the Director level one day. I don’t think I ever want to move up to VP.


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