What Happens Next?
Strategy, Career Planning, Dumb Luck, and Old Friends...
After I got married, my wife and I flew to London for what we’d thought would be a 3-week honeymoon. We ended up staying for nearly a year. We hadn’t planned to live there. Our planning had been based on our limited budget. But then, unexpectedly, our budget grew, and we decided to stay.
I suppose that most people know that when you get married, people give you money. We had no idea that would happen. So the day after our wedding, we opened envelope after envelope, and counted check after check. Our family and friends had been so generous!
I imagine the idea is that you give newlyweds money so they can start building a home, or start creating a nest-egg. So what did we do? We decided to spend the whole thing to extend our stay in the UK–turning our few weeks of honeymoon into a 9-month stay. My wife had a good excuse: she spent the time researching for her PhD. Me? I didn’t do much of anything, except spend time with friends and work on fiction projects that are now best forgotten.
At the time, I wondered if we’d just blown that money. Looking back now, I can see that it ended up being an investment in a future I never could have imagined.
Fast Forward: The Future
At least, that’s how it felt last week as, back in London for business, I reconnected with our friends from that period. What a blessing to have old friends–people you’ve grown up with, who you knew back when, and who knew you.
In a perhaps not-so-surprising development, three of my friends have just retired. One, an artist who spent her career as a schoolteacher, told us with great excitement about the plans she’d made to work on her art. She makes exquisite prints from wood engravings and, with her husband, creates hand-made books on a small printing press in their flat. They have a five-year backlog of projects that they will be working through, they told me with sparkling eyes.
The next day, I had lunch with another just-retired friend, a woman who’d spent her professional life as an adventure travel guide. We reflected together on how we ended up doing the work we did, how we chose it, and which of those many choices had been intentional, lucky, or a bit of both. Of course, circumstance and privilege factored into all of this too.
Youth: Stupid and Lucky
After my honeymoon, when I’d gotten home to San Francisco, I found myself out of work. I’d told my boss that I’d be gone for a month. I suppose he didn’t appreciate the way I’d vanished for nearly a year. I should have expected he wouldn’t like it, but somehow, it didn’t occur to me.
I ended up getting a job at a tech company, which was one of those lucky breaks I talked about. This was in the pre-internet days. The years that followed were boom years, and that created a lot of opportunity for me. I tried a lot of roles, some that fit well, some that didn’t. I didn’t have much of a plan, I have to admit. I’d do something for a while, then move on to something else, each time following my interests and abilities. Succeeding sometimes and failing other times, and moving on as well as I could.
Over the decades, I started to recognize some patterns and to learn a bit about myself: I’m pretty good at making complex ideas simple and understandable, I discovered. That served me in my roles as a designer, a writer, and a teacher. I’m pretty bad at politics, it turns out. That made for some mixed experiences as a department head, for example. I’m a lot more successful as an outside instigator I’ve found, and pretty bad as an inside operator.
I didn’t know any of that at the start of my career, in my 20’s. I was stubborn though: you couldn’t really tell me anything back then. I had to figure it out myself.
Maybe that’s a feature of being that age.
Being That Age
Earlier in the week, I had drinks with colleagues who have teenage and college-aged kids. We talked about the difficulty of guiding people that age. One of my colleagues lamented his graduating daughter’s somewhat relaxed approach to landing her first job. (This, by the way, is the same person who has often regaled me with tales of his first job after college: he’d run away to join the circus.)
It’s hard to make plans. To see into the future and to imagine who you’ll be or what you’ll want. To predict how your personal circumstances will intersect with economic and political circumstances beyond your control. My retiring friends worry about where they’ll live on their pensions, how they’ll access healthcare. The ones without children wonder who will take care of them.
My own retirement is starting to appear in the distance—if I squint, I can sort of see it from here. I’m hoping to turn to my creative projects, like my artist friend. I’ve been building a photography practice over the last few years, and hope to continue that. I have a novel in me, maybe. (I’ll write more about retirement in a coming letter, I think.)
What Does This Have To Do With Product Management Josh? *
Readers of this newsletter will perhaps wonder what this all has to do with my usual subjects: design, product management, strategy, etc. I think there’s a connection to be made here to strategy. I know that the story that I just told seems like there was no strategy behind it, but I do think there was a strategy at play here, even if I couldn’t always articulate it.
When I think about strategy, I think about it as a coherent set of policies and actions, designed to overcome an important obstacle. Now, I’ll admit that there wasn’t a lot of design in the way I operated, but I do think there was a mostly-coherent set of policies, ones that I came to see more clearly as I got older. They included things like:
Raise your hand and say yes to new opportunities.
Pay attention to what’s interesting. Avoid boring.
Optimize for learning. Work for and with people that you can learn from.
Don’t work alone: partner with people who have complementary skills.
There’s probably more, but that’s a pretty good start.
How have you made plans in your career? Have you been strategic? Opportunistic? Have you been passive? Active? Lucky? Unlucky?
* Also, everything doesn’t have to be about Product Management.
I enjoyed that Josh. I feel there could be interesting lessons there in terms of emergence, following the feels rather than forcing things, and a different form of sense and respond than what you might normally advocate for. Enjoy London as it goes through some weatherly weirdness.
I identify with this: My own retirement is starting to appear in the distance—if I squint, I can sort of see it from here" .... though you can substitute other things for retirement ...