The Life of an Awful Product Manager

Imposter Syndrome is well known, especially in the Product Management world. However, calling myself an “Imposter” does not do justice to the pangs of regret, uncertainty and angst felt often/sometimes/always. “The Awful Product Manager” might be more apropos.

Am I truly awful?

I do not think so. But it must be so, right? 25+ years in the career and I am not relaxing on a beach sipping the proverbial Mai Tai. I have not created a product with millions of users. I have not been a PM of a rocket ship product that yielded riches for VCs. I have not created a framework, waxed poetically about how real Product Management is done. I am not one of the newly minted $1MM/year AI PMs.

What have I done?

I have toiled at those moments when enterprise-esque processes seek to drown ambition. I have fumbled plenty of opportunities. I have talked down customers threatening to leave. I have made the roadmap pitches, led the strategic thinking, filed the JIRA tickets, angered and consoled engineers, studied data to no end and witnessed, whether as a leader or a doer, so many releases that I have lost count.

I have built teams from scratch and rebuilt ones too. I have developed strategies at the same time building POCs to test. Operated at the highest levels but still capable, and experienced enough, to get into the weeds of the product development process. I have been lucky to be part of exits and I have had some financial reward from the such (but still working hard because I have to).

I imagine that I am very like many Product Managers out there in the tech industry today. Successful, it could be argued. But not as successful as the Internet thinks we should be.

Too many frameworks, pundits and easy paths.

Frameworks help. But they should be tools that guide one’s thinking. The PM Pundit, I suppose that I wish I could be one. The actual work of a PM is hard. As I operate now more at the executive level, I find myself offering up platitudes that certainly could reasonable. Still being in the “sausage making factory” though, I generally catch myself; and seek to offer guidance and direction useful.

So why this site?

Seeing struggles, failures, mistakes, learnings are as important as seeing the victories. Our modern world promotes the latter. The former gets stuck behind a veil of privacy, heard mostly through whispers. I believe that it is important to be honest and open both ways. Hence, this conduit for sharing some of what I have experienced and felt and learned, simply so that some Product Manager somewhere might walk away with the notion that while one might feel awful, they are probably actually pretty good, if not great.