Product Managers Over 50 Are In Trouble! But...

Issue #50 of The Two But Rule

Image by Midjourney: Old Dogs, New Tricks, and AI

Last week, I was thinking about what story to feature in the 50th issue of The Two But Rule — Yes! We made it to 50! — when I got a call from an old friend…and then another call from a different friend…then another.

They were calling to see what I knew about job prospects for senior product executives. These were folks over 50 with decades of experience who suddenly needed to find a new job. These calls have been coming in all year.

I can’t think of a more fitting subject for this issue.

The Winter of Senior Product Managers?

While some fields are bleeding jobs more rapidly than others, the dilemma facing experienced workers seems to be happening across sectors, at least in high-tech. And senior technical product managers, in particular, are having a tough time finding and keeping suitable jobs these days.

A rough survey of literature from 2023 paints a confusing picture. In general, employment in countries like the US remain at historic highs, and while some suggest that the over-50 segment is more likely to lose their job and take longer to find another, others suggest that Gen X leaders are doing just fine filling the roles left by Boomer retirees. There’s also some rosy news coming out of the AI sector. We’ll get to that in a minute.

High Stakes, Fewer Options

Regardless of what the statistics say, the product managers I’ve been talking with are feeling the pinch. They’re worried about losing their job. Or they’re spending months finding a new one. Or they’re taking positions that pay less, offer less advancement, and are less interesting than the roles they filled in their 30s and 40s. None of them seem to be getting calls from the recruiters that used to hover like seagulls at a picnic. And filling out online applications is, by all accounts, a waste of time.

Add to this the fact that many Gen X-ers started families later in life. That means they’re still covering the cost of education and groceries for ravenous teenagers.

This is happening just as many are starting to support aging parents that are living longer, running out of savings, and racking up epic medical bills.

Out To Pasture? Really?

I was talking about this with my buddy, ChatGPT, who had this to add:

“These are individuals on the cusp of what should be their golden years. They're looking ahead to retirement, dreaming of finally slowing down, embracing leisure, and enjoying the fruits of their lifelong labor. Yet, the reality is often starkly different. Instead of planning retirement parties, they're strategizing on how to stay relevant in their careers, grappling with the fear of becoming obsolete in a field that's rapidly evolving.”

Full disclaimer — ChatGPT’s stereotyping is definitely ‘not okay.’ Do better, GPT.

That said, GPT’s facile generalization of the 50+ cohort as a bunch of tired, golf-obsessed has-beens is the clue, literally, to a silver lining. And the juxtaposition is all the more sweet given that the point was delivered by AI. I’m going to argue that our saggy old buts have just received a fresh new BUT.

We’re Just Getting Started

Ok, so let’s get one thing straight. While there is nothing wrong with looking forward to retirement, I know very few 50+ product people who are winding down and preparing for a life of leisure. The folks that I know are more curious and engaged than ever. In a sane world, it’s our age group that would be going back to school to get our PhDs while our children support us with the revenue from their TikTok-influencer endorsements.

We’re also benefitting from significant advances in medical science, nutrition and wellness. Most of us in my circle are in pretty good shape. In fact, I dare say that we’re in better shape than previous generations were in their late 30s.

So we’re feeling good, we’re sharp, we have the experience to know a good plan from a bad one, and on a lucid day, we can even embrace a brand new hair-brained idea without shooting it down prematurely. In fact, on a very good day, we can turn a crazy idea into an even crazier idea — but one with a chance of actually working. (If you need to work on the latter, be sure to reserve your copy of The Two But Rule today. That’s what it’s all about.)

But, for all this, times are changing. Ladder climbing and ladder-hopping (where you secure a hefty raise by doing your old job for a new company) are not the sure fire strategies they used to be. It’s time to consider new ways to leverage our experience to build wealth.

Old Dogs Just Got A New Trick

Something happened in 2023 that changed everything. Yes, of course, it’s AI. (I told you we’d get back to that.) And you might be rolling your eyes right now as you anticipate yet another gushy story about how AI is a panacea for everything from climate change to curing gout. And you know what? That’s exactly what you’re in for. Seriously. Lots of gush and rainbow unicorns ahead. You’ve been warned.

Lightning Strikes While Waiting For A Meeting

Recently, I joined a Zoom meeting, and the other attendee was late. Twenty minutes late. After three or four minutes, I got bored.

Earlier that day I learned that I finally got off the wait list for GitHub’s AI coding assistant, Copilot, and its integration with Microsoft VS Code, a popular software development environment.

Now, I should say that as a technical product exec, I haven’t been paid to write any kind of code in decades, and frankly I was never very good at it. But, for some reason I never lost interest in what you could do with code. And I believe that:

1. Every line of code has an impact on the business, and;

2. Every business decision in software that doesn’t understand the code risks being a bad one.

So, after a few minutes of waiting in the meeting, I started having a conversation with Copilot. But before I get into what happened, here’s the backstory.

But For Money And Time

In 2000, I had a pretty good idea for a new venture I wanted to build. In those days, the cost of building and bringing this new Web service to market was $10-15 million. I didn’t have that kind of money, and I relied on my steady paycheck to pay the bills. So I told the story to some other people who offered to pay me if I left my job to start this thing. They took a big chunk of equity, and we went to raise money from other people, who would have taken another big chunk of equity. And then, just as we were getting close to a termsheet, the ‘dot-bomb’ of 2000 began. No termsheet. No money.

Years later, I had another pretty good idea, and we raised about $1 million to start that. Once again I gave away a ton of equity, and it took us a year to develop the product. In that time, another company that had a lot more money blew right past us.

Then, several years after that, I had another pretty good idea, and at that point I just wrote an article hoping somebody with up-to-date development skills and a lot of free time would build it. Four years passed. Nothing.

This has been the pattern for my whole career. And it turns out that I’m not alone. Nearly every good technical product person I know has at least one worthy idea in their back pocket. The problem is that until now, doing something serious about that idea has been a game for one of three types of people:

1. The young and hungry with little to lose, a friend with a couch to surf, and willingness to dine mainly on ramen while starting a business;

2. Older people who were lucky enough to have had a nice exit in the past, giving them the reputation and personal wealth to trade sweat equity for time and a big stake in the business;

3. Addicts who will re-mortgage the house and raid the kids’ college funds to take another run at entrepreneurship.

I don’t fall into any of these categories, and most of the creative product people I know don’t either.

Mind…Blown!

Ok, so back to my conversation with Copilot.

As my mind wandered waiting for the Zoom meeting to start, I found myself telling Copilot about the article I wrote. The conversation evolved into one that could have been easily mistaken for me talking with a friend…one with software architecture and development chops.

At some point, I asked, “Do you think we could build this together?” And in 20 minutes, the core codebase was done. We had accomplished in 20 minutes what I had been waiting four years for someone to build.

You might have heard similar stories recently, but here’s the thing: It wasn’t just that Copilot wrote some code I told it to write. No…it had opinions about what components to use, questions about my priorities, and ideas for how to best architect the application for scalability, maintainability, security and performance. Um…wow!

Oh! And at the end I asked it to write in-line comments describing what every line of code was doing and why it was there. Voila — best…documented…code…ever!

Then suddenly my tardy colleague joined the Zoom call, and we were off.

Later That Night

I returned to the code after the kids went to bed, and before midnight Copilot and I deployed the code to the cloud, integrated it with three different services, and debugged a dozen deployment issues.

This is where things got really crazy. I had never tried to create this kind of application, and the APIs and integration issues involved with the platforms we chose were previously unknown to me. Copilot held my hand through every step. More to the point: it told me what steps I needed to be aware of, walked me through each one, and solved every problem that popped up. (Whether a software project is written with AI or humans, there are always unexpected issues when you try to get it to run reliably.)

In one case, we were running into an issue that was preventing information from being written to the database. I pointed out the problem, and this is where I knew that everything about my life as a product person had changed.

It said, “Show me the logs.” So I pasted the error logs from the cloud provider into Copilot and it replied, “Oh, I see that some APIs have changed. We need to handle events differently. Here’s what we can do.” It then refactored the entire codebase. After that, everything worked perfectly.

Along the way, Copilot also deftly handled incompatibilities with different versions of various libraries we were using, helped me locate settings I needed to tweak in the service providers’ control panels, and fixed several issues encountered during compile.

I was just along for the ride, though I’ll tell you that in the process I learned more about modern software frameworks — including what can go wrong and how to approach using them — than I could have picked up from taking a dozen courses.

The Value Of Knowing What You Don’t Know

It’s true that there are “no-code” platforms out there that make it easy to deploy a website or even a simple mobile app without having to get into writing code and setting up development environments. But for truly creative apps and Web services that aim to be the basis of a real business, I think you often need to ‘bake from scratch.’

The key, at least for me, was knowing roughly what questions to ask. I had basic awareness, through years of experience, of what needed to be done, even if I didn’t know how to do it myself. That’s a big advantage. It would have taken me weeks or months to learn or brush-up on database options, front and back-end frameworks, and the endless tools and libraries in a modern developer’s toolkit. But what I had was the knowledge about what I could expect an expert technical team to be able to figure out, if I gave them the requirements. That’s what informed my conversation with Copilot.

The Opportunity for Tech Execs

Here’s what I think. The future isn’t coming…it’s here. If you are a seasoned technical product manager with ideas about how to serve the needs of real people, and you happen to be laid off, you can probably build the software product you’ve been imagining and get it into the hands of real users in a matter of days or weeks. You might even be able to take a few swings at making something that people might pay for before even a meagre severance package runs out.

And if you don’t strike gold, at least the thing you build will demonstrate creativity, problem solving, and initiative that should blow your next prospective employer away.

Phantom Friction

For those of us in our 50s, we’ve been through this kind of shift in basic capability a few times. The personal computer. The Web. Search. Mobile. Streaming.

Each time, we had to learn to throw out our old mental models. Some of us still have to work hard to remember deep-down that we don’t need to go to the library or find an encyclopedia to get the information we need. I still sometimes have to overcome the phantom friction that makes me forget that YouTube has a video on just about anything I need to figure out, and all I need to do is pull my phone out of my pocket to find it.

Right now, that phantom friction is in thinking that loading up VS Code and setting up a development environment is a big scary time-suck. I know. I felt it…then I pushed through.

That phantom friction is, at least in software, the only remaining barrier between you and building something that a few years ago would have required finding a technical co-founder, raising millions, and devoting a lot of time just to learn whether your idea was truly worth pursuing.

What Did I Build, You Ask?

The 20-minute project that Copilot and I built is a Slack plugin that helps teams build up pro-rata equity in shared projects organically over time. No, I had never built or deployed a Slack plugin before and didn’t know the first thing about how to do it…but now I do!

Now, Copilot and I are building an application that I’m hoping to deploy with the launch of The Two But Rule on January 24, 2024.

If you’re a paid subscriber to 2Buts.com, I’m happy to:

1. Do a live session with you and show how I approached these projects;

2. Share the open source code with you;

3. Help you think through your idea.

So reach out on LinkedIn, add a comment here, or go to jwolpert.com and we’ll get some time together. If enough of you are interested, maybe we can do a group session.

Ok, that’s a wrap on the 50th issue. I hope you liked it. Please tell your friends and community about it, and encourage them to join our community of but-heads. With the book launch almost here, things are really going to heat up. Stay tuned!

Until next time, remember that even an old but can be full of gas.