Sometimes there's advice that you wish was there when you needed it. Pam Hobart's guest post on Paul Millerd's Boundless newsletter is full of such advice. Here's a passage that resonated with me:
I didn’t know at the time, but I was doing the discovery thing all along – saying that I had a plan while actually spending my time and energy trying things and then seeing what happened. But it’s not cost-free to say you have a plan while actually messing around. Deviating from “the plan” while you theoretically still hold one invites you to feel like a failure and to erode trust in yourself when things go off-script.
You’ll be ahead of me if you realize what you’re actually doing – the bottom-up thing, in large part. Celebrating, or even merely admitting, the lack of a specific plan focuses you on your real objective: learning what you can from each work experience, doubling down when it’s right, moving on in a timely manner when it’s not, and limiting the costliness of each iteration. After you’ve had a job or two, you may have some idea of what industry is (or is NOT) for you, or some idea of what kind of management style you need. These high-level considerations are helpful constraints.
I deviated from my top-down plan of going into classical guitar by goofing off while in grad school. There were so many other things that I focused on other than my studies — organizing music events at an art gallery, volunteering for an education technology startup, playing in experimental bands, being a barista, running a music podcast with a friend. Basically anything to avoid the responsibilities of getting a degree to get an associate professorship at a college.
Those tangential activities planted the seeds for where I am now. If I didn't organize those music events, I wouldn't of been friends with the gallery owner's husband who mentored me in Python and my early tech career. If I didn't volunteer for the education technology startup, I wouldn't of met my wife who influenced me to go down the tech career path in the first place. It turns out that these things are anything but tangential.
It reminds me of what David Epstein describes in Range:
The trouble with using no more than a single analogy, particularly one from a vert similar situation, is that it does not help battle the natural impulse to employ the “inside view,” a term coined by psychologists Daniel Kahneman and Amos Tversky. We take the inside view when we make judgements based narrowly on the details of a particular project that are right in front of us.
But there was still the guilt of turning away from the “inside view,” of going off-script that Pam describes. David Epstein mentions as much when describing Northwestern's Integrated Science Program that advocate for broader studies than a top-down focus:
The trouble with courses of study like Northwestern's Integrated Science Program, which impart a broad mixture of strategies, is that they may require abandoning a head start toward a major or career. That is a tough sell, even if it better serves learners in the long run.
Going off-script is a tough sell because it feels like shit. When I dropped out of my phD program, I felt like I let myself down, my family down, my friends down, my fellow graduate colleagues down, my teacher down. It wasn't after a couple years after that I owned up to it. I needed to go off-script in order to serve myself better in the log run.
Now that I'm in a different place with a new career trajectory, it's tempting to go for the top-down path all over again. Still, I want to hold on to the bottom up planning that Pam illustrates; to realize that going the bottom up route is how I got to where I am in the first place. Who knows where else one can go from the bottom up?