How do you know you’re on your way to earning your PM/PO wings? What signals progress? Your first release? Getting “certified” ? Putting together a pretty roadmap?

No …

1. You’ll feel like you are annoying the crap out of your team
2. You’ll find yourself sheepishly asking for an estimate
3. You’ll realize that estimates are worthless, but still be pressured for a “rough sense of timeframe”
4. You’ll struggle to explain why your intuition is valid (and be right)
5. You’ll struggle to explain why your intuition is valid (and be wrong)
6. You’ll be pressured to ship something before it’s ready
7. You’ll try to make something perfect when you should have shipped it months ago
8. You’ll face the harsh reality of a usability test
9. You’ll put together the best roadmap in the world, and get everyone to buy-in, and then everything will change in an instant
10. You’ll forget a seemingly trivial detail that will cause a massive delay
11. You’ll rabbit hole on a seemingly important detail that will cause a massive delay for no apparent customer value
12. You’ll be blamed for being too solution focused
13. You’ll be blamed for being too high level
14. You’ll find out that a new competitor is killing it
15. You’ll have to break crappy news to your team (often admitting that you’re to blame)
16. You’ll be jealous about ___________ and how they do product (and be reminded of that fact because they incessently blog about it)
17. You’ll fancy yourself as technical but be humbled daily
18. You’ll fancy yourself as UX-savvy but be humbled daily
19. You’ll fancy yourself as business-savvy but be humbled daily
20. You’ll say “my team”, but feel oddly distant from your team
21. You’ll be worried about “distracting” your team, and find yourself not being transparent. And this will come back to haunt you
22. You’ll find yourself parroting something engineers told you, and realize just how little you understand
23. You’ll be asked to make your backlog / roadmap more visible, but then be derided when you shift things around
24. You’ll have a day filled with meetings, and realize you added absolutely no value
25. You’ll run a great meeting, and no one will notice
26. You’ll work up a full-fledged wireframe, and then try to tell your UX team member that you don’t have a design in mind
27. You’ll ship a dud feature that no one uses
28. You’ll ship an awesome feature that no one even notices
29. You’ll have to implement an exec’s idea, and know it sucks. And then have to live through the success theater that accompanies the release of said idea
30. You’ll try to follow up on the impact of shipped features, but get overwhelmed by the next batch
31. You’ll want to pull your hair out listening to your team debate the technical merits of two, almost identical approaches
32. You’ll advocate for your pet solution against an almost identical team proposed approach
33. You’ll tell a customer “it’s on the roadmap” and hear them laugh out loud
34. You’ll say “No” to something just to prove to yourself that you have some influence and a point of view, and then realize that doing that is stupid
35. You’ll say “Yes” to a customer in a moment of pure delusion, and then find yourself stubbornly trying to defend a feature that only they will use
36. You’ll hear that you are not technical enough for the role
37. You’ll hear that you are too technical for the role, and lack the soft skills
38. You’ll go to a conference and learn about Lean Startup, and then come back to work and realize that the word hypothesis scares the shit out of people
39. You’ll be the single wringable neck
40. You’ll find yourself running cover for your team
41. You’ll find yourself cursing your team under your breath
42. You’ll be “empowered” on paper, but find yourself taking orders
43. You’ll catch yourself giving orders, and learn to empower your team instead
44. You’ll think you’ve learned from your mistakes, and you’ll magically make them again (just to make sure the learning is ingrained) …. Because being a PO/PM is hard! It’s humbling, demanding, weird, nebulous, and ever-changing. You’re going to screw up! Accepting that is one of the significant hurdles of becoming a better PM. You’ll figure out how little you know and how little power you have, only to be reminded that it is often the little things that count.

The key is never to stop being humble, empathetic, and curious. Don’t be afraid to discuss your needs and challenges with your team. Be human! And resist the slippery slope to burnout, egotism / mini-CEOism / backlog-ownerism, political gamesmanship, and perpetual mistrust.

Start with your own Why. What do you care about? How do you want to work with the people around you? Answer those questions and the rest will fall into place.

— — — — — — — -

As an aside, I have been doing a 100 day doodle challenge. Some of the doodles are funny because they speak to my impending fears for the day as a product manager: