When the insight arrived, I didn’t notice the connection to the trail I’d laid on the preceding pages. My experience was of making no progress, and then, finally, making some. In hindsight, I can see that I had been making plenty of progress over those weeks; I just couldn’t tell at the time. I suspect this is pretty common in my work. So, “I feel like I’m not making progress” is probably not a good local heuristic for guiding my work. Alternately, the lesson might be that I need to become more sensitive to the many subtler flavors of progress in this kind of work

ut I’ve also noticed that when I focus my work on particular people in particular contexts, that more immediate emotional connection sometimes overpowers the day-to-day frustration that comes with being lost in the woods. For several long stretches this year, I found the work really gratifying, both in the moment, and retrospectively over the long term.

By contrast, when I’m doing work that I find gratifying and meaningful over the long term, the day-to-day experience is usually frustrating and unpleasant. The work is gratifying because it’s deep and personal and unique. Unfortunately, in my projects, those same attributes also mean that progress tends to be inconsistent and hard to discern; it’s rarely clear what to do next; there’s rarely anyone I can ask for help; I usually feel incapable.

Throughout my career, I’ve struggled with a paradox in the feeling of my work. When I’ve found my work quite gratifying in the moment, day-to-day, I’ve found it hollow and unsatisfying retrospectively, over the long term. For example, when I was working at Apple, there was so much energy; I was surrounded by brilliant people; I felt very competent, it was clear what to do next; it was easy to see my progress each day. That all felt great. But then, looking back on my work at the end of each year, I felt deeply dissatisfied: I wasn’t making a personal creative contribution. If someone else had done the projects I’d done, the results would have been different, but not in a way that mattered. The work wasn’t reflective of ideas or values that mattered to me. I felt numbed, creatively and intellectually.