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Career Choices and Making Big Plans

“Make no little plans.”

“I’m sorry, what?”

I admit I heard what he said, but it made no sense. I was in a 1:1 with my new boss, crammed into a phone booth meeting room and we were talking about a project I was about to tackle. I was wavering, being my wishy-washy self. I get like that when I’m dealing with crappy projects — those ill-defined or pointless piles of bland, squishy tasks. Still, I was trying to put my best foot forward and at least pretend like I would be invested in the thing.

He was having none of it.

“‘Make no little plans.’ Don’t waste time on small shit no one gives a damn about.”

I would go on to learn a lot from him, in small bursts over several years and at multiple companies. The beginning of the quote (from Daniel H. Burnham) reads:

“Make no little plans: they have no magic to stir men’s blood,”

(Over the years, I’ve modified it a tiny bit: “Make no small plans — they lack the magic to stir our blood.”)

And I’ve tried to bring that forward as a kind of mantra or a tenet — “Aim high. Swing for the fences.” It’s a great story, a great goal. But really, I struggle with it.

Sometimes I get worried that if I do inspire people with my big plans and magic thinking, there’s a larger chance I could disappoint them — hit speedbumps, unexpected hiccups along the way. Sometimes I feel that maybe under promising and over delivering is a valid approach. I love over delivering.

And sometimes I worry that someone smarter than me will come across my big plans and laugh.

But mostly, I just get lazy and give in to my natural tendency to tackle big projects by not talking about them and instead working them down via a series of smaller tasks.

It’s not that I don’t want to get to the big picture, the grand scheme, the endgame. It’s just that I like feeling like I know my way there. Maybe that’s the introvert in me: unwilling to put myself out there.

If you’re wondering how this kind of nebulous touchy-feely stuff translates to one’s career choices, I have a good example.

While interviewing for a job at a startup, I went through the typical series of face-to-face conversations. One of the first questions each interviewer asked me was (paraphrasing): “Why do we need documentation?”

Well, for me that’s a perfect opening. I talked, passionately, about documentation’s role in the customer learning journey. I talked about converting customers into apostles and boosting NPS and many other Technical Publications-focused topics. I got excited and stood up to draw on the whiteboard. I moved my hands. A lot. I talked for quite a while, and at the end of the day I had sold a Utopian version of a life at that company once they brought me on board as their Technical Publications Manager.

Which they did.

Soon, however, I realized that I had sold them the endgame, but I hadn’t explained the road to get there, how much work it would take. I tried to explain the situation, but now it was too late. They had no patience for my measured pace, for my slow-and-steady-wins-the-race approach. I had made big plans, huge plans filled with blood-stirring magic. But I was a one-person docs department supporting over 40 developers and several products. I set my self up to fail.

Which I did.

Classic over promise and under deliver situation.

Fast forward to the next time I was interviewing for a Technical Publications Manager role. I explained what the vision could be, what I thought it should be, but focused on next steps. I outlined a path to get there and explained the journey. As a result, the experience is night and day different.

Oh, I have those big plans, filled with magic and designed to inspire, but I guard them a bit more closely, share them more carefully.

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