Chronicle Startups

Day 75 and Expertise

I’ve been slowly ramping up advising, investing and consulting work into startups. Initially I was quite hesitant to do any type of consulting as I was fearful that I would not be able to produce enough work in a quick enough time. I thought advising and investing was a safer and higher leverage activity than consulting. I might have been wrong.

My expectations for work are high not because I’m a perfectionist but because I’m addicted to the feeling of reaching beyond my limits. As a workaholic I struggle to let go of work that is “good enough” as work functions as my dopamine hit. I can always do more, produce more, refine more…more more more. This means I often will find myself in situations where the expectations of the person I am working for do not align with my own. I regularly over produce. I’ve got a classic, and telling, story from my first year in prep school that says it all.

I attended Waldorf Schools as a child. One of the core pedagogical tenants is to teach to the child not to the classroom. This manifests in unique ways, including making your own textbooks. Teachers will put a lesson on the blackboard and students are expected to fill this into their own “main lesson” books which function as your textbook for reference later. A child is welcome to add as much depth to their book as they desire. Main lesson books are often elaborate illustrated affairs with extensive reference materials all completely done by hand. This is great for pushing beyond personal limits and the stagnating effect of teaching to the mean. It also happens to suck if you have a tendency to overwork yourself.

I didn’t realize this was an unusual method for years. So when our town didn’t have room for me in the single Waldorf high school, my mother enrolled me in the town’s private prep school for 8th grade. My history course was American History. On the first day the teacher passed out a map of the United States and told the class our homework was to “full it in” for tomorrow.

I went home and spent 3 hours illustrating geography relief maps, sketching in local points of interest, labeling each state and capital in cursive with my best penmanship. I started crying around 10pm as I had other homework for other classes and I wailed to my mother that clearly I wasn’t academically prepared for prep school. I imagined my other classmates with better illustrated maps with more creative ways of showing base relief mapping.

I got to class the next day and my teacher looked completely baffled by what I turned in. I panicked. What had I done wrong? I started laying out all the detail work complete with my methodology for measuring altitude. The teacher seeing me spiral out said “Julie, when I said fill it in I meant label all 50 states with their name.” I was dumbfounded.

That the assignment was so simple never occurred to me. What the fuck was even the point of assigning something that was so rote? To 8th grades no less! What kind of bullshit low grade busy work was this! I was furious. What a waste of time if this was the standard of work.

How little did I know at the time. While I was spending 3 hours on work to the best of my ability straining to extend my understanding, most kids were smart enough to realize their homework should be working to the “mean” of the classroom not to their own standards. I really was not prepared for prep school. Just not in the way I imagined.

This is all a very long winded way of saying that I still tend to do this. Someone may ask my opinion on how to run an advertising campaign and I will launch into extensive detail on demographics versus psychographics and the importance of building out multiple permutations of creative in your funnel to determine the most effective content for the best return on investment. I will give you as textured and nuanced an wander as possible. You won’t just get “Colorado” on the map I will show you the trail over the pass. This is often great for founders of startups who swear the small stuff as much as I do.

If anything I should agree to more consulting work as you will get so much more out of my three hours than someone who can sense the parameters of the work you’ve assigned them. They mat give you exactly the map you asked for even if you need more and didn’t know to ask. I will draw you a geographic relief map so you can navigate the treacherous mountains of paid advertising. Or any area where you happen to be interested in my expertise. I know an astonishing amount about narrative, branding, public relations, user acquisition and revenue growth. And I should stop convincing myself that I cannot produce work that is of value in a consulting framework. What I wonder work product may be more involved than someone else but that’s not my call. Anyone who hires me can decide if it’s worth a consulting fee or not. And if this story has any lesson it’s that I’ll probably give you well over the median or mean expectation for the job. This is also why I don’t charge by the hour. But that’s another story for another time.