Book review: Deep Work by Cal Newport

When I was in high school, I spent a lot of time with a book called How to Be a High School Superstar by this dude, Cal Newport. The book was great – it inspired me, but that was just about it. I barely scraped my way in to college, and then dropped out of that a semester later.

Turns out, I just sucked at school because I hated it. I turned out okay, and ended up doing okay professionally. I heard rumblings of this book called Deep Work, and vaguely recognized the name of the author. I eventually connected the dots, and procrastinated reading the book for a couple of years.

I recently read it. It’s incredible.

I love Cal’s approach – he takes a sensible line. Not too prescriptive, he outlines a bunch of strategies to help knowledge workers get the most out of their time, without saying that any particular one is the be-all-end-all. Many books focus too much on the why and not enough on the how. Cal has managed to pull both sides off in an effective and balanced way with actionable steps and things to try. His different schedules of deep work offered particularly stand out. Another piece that jumps out is his bit about increasing memory through deck-of-cards memorization, which is something I’ll be trying out.

All-in-all, Deep Work was a great book of an almost exactly appropriate length. It’s well regarded, and for good reason. It’s only been out a couple of years, but I see it being increasingly relevant as time passes and deep work becomes harder to obtain.

On parenting

I will never get bored of the intellectual stimulace of my job, but yes, I did start to yearn for something more physical. Having kids pretty much solved that desire for me. I’m now a full time roboticist and a part time cook, people mover, negotiator, lab manager, construction foreman, fitness coach, gym spotter, goalie, wanderer, professional wrestler, cleaner, etc.

I’m surprised every week by what it’s like to be a parent. I never expected it to round my life out in such a healthy way, both mentally and physically. Not just because I have offspring but because I’m doing a ton of things I haven’t done in years, decades.

Waterluvian on Hacker News

Kids aren’t exactly on my near horizon, although they’re closer than ever with my wedding this year. Compared to a few years ago, the idea has been growing on me and this is such a succinct explanation of why.

This ties in nicely to Digital Minimalism by Cal Newport – he’s a big proponent in the book of getting away from our screens and having high-quality leisure time (i.e. almost every role listed in the quote). I can see being a parent being a good catalyst for exposure to all kinds and levels of growth if you fully embrace the opportunity.

On reading

If “well-read” means “not missing anything,” then nobody has a chance. If “well-read” means “making a genuine effort to explore thoughtfully,” then yes, we can all be well-read. But what we’ve seen is always going to be a very small cup dipped out of a very big ocean, and turning your back on the ocean to stare into the cup can’t change that.

The Sad, Beautiful Fact That We’re All Going To Miss Almost Everything

Upside vs. downside potential in relationship management

I was chatting yesterday with friends Stuart Arsenault and Brian Peters about some partnership things. Stuart mentioned something interesting about “upside vs. downside potential” in relationship management. I thought this was an interesting way to frame things.

In some relationships, you’re trying to limit downside potential. For Shogun, this is our relationship with Shopify. Pretty much nothing we can do with that relationship will result in 1000 leads overnight. On the other hand, they could destroy our business over night if they decided they didn’t like us. Mostly, we’re trying to Not Fuck It Up™.

In other relationships, you’re trying to enhance upside potential. These are your new platforms, your new agency partnerships, your new integrations. Any of these (but definitely not all of them) can result in huge upside for your business, but it’s not the end of the world if any given one of them falls apart.

This feels like a helpful mental model for a bunch of decision making. Defining the type of relationship you’re working in will help you decide how much time and effort goes in to it, what types of activities you’ll do in the context of that relationship, etc.

Things to consider here still: the above examples of each are obvious – but once we get in to greyer territory, how do we identify where on the spectrum a relationship lands? Exactly how does that influence activities? What’s a fair and equitable split of your time among both types of relationships, given that they’re both important for different reasons?