Do you stay in the trenches, or get out? Why? And what does this mean for teams?

You’re 40+ and involved in product management.

Maybe you took some detours in your twenties and thirties: played in a band (that’s me!), started a business (yup, did that), freelanced to be at home with your kids while they were young, or tried something completely different.

You love product development. You want to stay on the front lines and in the trenches. You want to remain a doer. You enjoy coaching, mentoring, and showing people how to fish, but you aren’t a good fit for traditional management roles. You speak product, UX, business, and engineer. The extra money would be nice, but so is your sanity and sense of accomplishment.

Your pattern matching and BS detector is on point. You see organizational dysfunction through the sharp eyes of someone who has played the game for a while. Maybe that’s not your sweetspot.

If you’re engineer, there is a path. Be a 10x behind-the-scenes person. Most orgs welcome that. Craft it up, coach folks, and crank it out. You’re making $200k and still get to keep your hands dirty.

But us older product owners and product managers … we have a different predicament. We’re being told to “advance”, “move up”, “shift companies”, “move out of product management” (for PMs), or “start consulting” (for more UX focused PM/POs). Recently, I was told bluntly that “if this hasn’t happened by the time you’re 40, well that is a warning sign!”

But I like being on the front-lines!

The trouble is that the further you “move up”, the further you get away from where the work is happening, and the closer you get to executive level dysfunction. For some that means a desirable corner office. For others that makes it un-fun. Explains a fellow PM:

I keep struggling with this dilemma. If I care for my career and earning potential I will need to stop doing this! But I work best and provide the most value when I’m with my teams. It seems like my best option is to company hop for a while to keep things interestingAgile prescribes a PM/PO for every one or two teams. As teams scale this necessitates an ungainly product org. The economics kick in and you fill your org with junior and/or associate PMs to fill the warm seat prescribed by Agile. Which in turn pisses off your experienced engineers. You’re being told to leave the area where your impact is needed most.

And then people wonder where the good PM/POs have gone! If you’re a more technically focused PM/PO you might have some options, but for many this is the end of the line.

I don’t have an answer here. But this is a problem if we are to advance the “craft” of product management and product ownership and deliver great value to teams. How do you engage your older team members and keep your best? Or is this the inevitable conveyor belt of talent and career development?