021: Deep Work

Deep Work

Color Commentary

Table of Contents

1. Mostly Invested
2. Focus is a Good Thing
3. Methods of Deep Work
4. Invest in Deep Workspaces
5. Let’s Get Practical

1. Mostly Invested

The universe gives you what you need – especially without you even knowing that you needed it.

A few days ago, I stumbled on a podcast interview with the author Cal Newport, who wrote a book called Deep Work. The content he talked about intrigued me enough to get me to buy his audiobook, and in it, he describes practicing working on deeply intellectually challenging ideas that require deep thought and concentration – “deep work”. His methods track the way I developed Investing Practice.

You guys! I felt so proud of myself while I was listening to this book! I had that romantic comedy smile of vicarious happiness while I was on the tram, and realized I looked like an idiot grinning away to myself, but whatever. Investing Practice came entirely out of my own experience and needs, and voila – here’s this lovely book filled with scientific research that supports my Investing Practice methodology, AND builds on it in some lovely ways.

I had that smile because the timing of reading the science behind Deep Work feels serendipitous. I spent much of the summer writing and filming my course, ‘Mostly Invested,’ about creating and improving investing practice. The content of the Mostly Invested course came from my own experience inventing my investing practice from whole cloth. There isn’t a thing in the course that I don’t do myself and there isn’t anything in there that is not effective in real life. It’s been almost a year of focused creativity and, frankly, hard work, since I first started working on the idea back in January. Now it’s finally coming out – and just as I’ve been working so hard on preparing for the launch with the course website, the supplementary materials, interviewing additional experts for video extras, and writing about it, I got this little boost from the universe saying “yeah, this course is good stuff.”

I’m SO excited to offer this course to you all. Naturally, the course intentionally marries perfectly with being a member of The Invested Practice, with my newsletter focused on week-to-week practice ideas and updates and my course focused on deeply and intentionally creating a conscious, bespoke practice curated specifically for you.

I always want you guys to be the first to know about anything I do, and no one else has this information yet, and of course I’m giving you an exclusive members-only price. (I had to fight my marketing team to get this price for you, but I refused to lump members in with everybody else! You deserve special treatment.) Click here for early release access exclusive to members for a few days after you get this issue, and if you click that link, I’ll send you an email on Sunday 10/26 with all the details.

2. Focus is a Good Thing

Deep Work follows directly on from The One Thing, which I mentioned in the last issue but into which I did not delve particularly deeply. In The One Thing, the gist of the message is that time blocks are the number one tool for attention management and to do deep work that matters. Higher quality work will result from focus. Splitting up the same amount of time and switching around between topics will not produce work that has the same quality of depth and original thought.

In other words, intense focus over an extended period of time leads to extraordinary results.

I can’t really believe that “focus is a good thing” is news. But I guess it is. Remember the Luxury Trap described in Sapiens? It’s the cycle of creating improvements and efficiencies which create more wealth, which lets us being able to buy more stuff, be healthier and live longer, which requires more resources – which requires us to work more to create more wealth, which lets us buy more stuff, be healthier and live longer, which requires more resources – which requires us to work more to create more wealth… And so on. Well, all of that wealth creation has created a world of luxury, and the luxury we’re into creating right now is the luxury of being constantly able to access mind candy and distraction.

Newport argues that all great creators have routines to make sure they get to their deep work – in fact, he sees deep work as a skill, not a habit. A habit is something like walking the dog every day. A skill is something you get better at over time. Which sounds familiar, no? Sounds exactly like how I think of practice, and certainly what I am doing with my investing practice. By consistently are opening my mind to deep work and creating regular space in my schedule to dive in, I improve my focus and depth of concentration – and, presumably, my investing results.

Now, of course, I was already jumping up and down as I read this part because this is how I created my investing practice, with regular practice to delve in and really learn, without having a clue that there’s evidence it produces better results.

3. Methods of Deep Work

Newport defines four methods of scheduling deep work, depending on what works best for your personality and work style:

1. Monastery approach: This one is the most extreme. Think of a monk who detaches himself from the matrix. Not online, full hermit mode. Turn on phone once a week and that’s your life.

2. Bimodal approach: Monk mode plus normal life, like Carl Jung, who had a retreat house for writing and also his regular working life as a therapist in Zurich. A lot of people can’t structure their lives like that, but think about it – does the thought of getting away from it all make you feel a terrible longing for it? If so, that’s good to know about yourself. Full disclosure: I LOVE this one. When we had our house in Jackson Hole, from which you couldn’t see any other houses, we would chill in the living room for days just reading and working and writing. It’s the place I felt like I could really THINK. I miss it often.

3. Rhythmic approach: Like Jerry Seinfeld’s “write a joke every day.” Create a rhythm. X off a day and don’t break the streak.

4. Journalistic approach: Like a journalist who needs to write on deadline. Got to know how to go into deep work on cue.

I’ve been mulling these approaches over for my investing practice. I can’t stop thinking about it. My scheduling methodology thus far has been to do a short Wandering practice on weekdays and then do a longer (often much longer) Focused practice on weekends or days that I have more time. It’s somewhere between Newport’s Rhythmic approach and Journalistic approach. And it works, in real life.

However, I’m always drawn to extremes. What if I ignored real life? What if I skipped out on everything every now and then and went for the Bimodal approach. I already struggle horribly with keeping up with social media (something Newport just completely avoids, and still manages to sell books) and emails because frankly, I find it all incredibly distracting.

Bill Gates famously takes a “think week” to go to a cabin and read a bunch of books and think about the future of Microsoft or his foundation. By the way, if you haven’t watched it, the Netflix documentary “Inside Bill’s Brain” is worth watching.

In investing practice, would it help us to have the space to really delve into specific groups of companies or think deeply about what business will look like twenty years from now? I think it would.

In a way, I recently unintentionally took a break like that. I’ve been out of my investing practice routine. I forced myself to pull away from investing practice to write the Mostly Invested course, then spent weeks filming it and having meetings in the US, then came back to Zurich and had eye surgery, recovered for about a month because somehow that tiny cut into my eye really destroyed my mental power, and am just feeling like my brain is back to normal and getting back into my normal routine. I’m about to have my second eye surgery next week for eye #2 and bam – it will all go to pot a second time. Not excited.

Therefore, I’m focused on defining my routines and WHY I’m doing them so that I can get back into mine more quickly after the surgery this time. I’m trying hard to be awfully grateful for the opportunity to have my eyes repaired by a good surgeon and for the problem of being pulled away from my routine, because the experience has shown me that my routine can be much better. When something is easy, I don’t think about it that much. When something is hard and requires attention and effort to accomplish, I give it the attention and effort it needs.

Because of the surgery, I’m going to pre-write the next issue on the details of Deep Work that I found most thought-provoking. I can’t wait to focus on defining each piece for investing practice because I’m SO obsessed with the ideas. I also recommend reading the book if you’re interested, and then you can agree or disagree with my takeaways next issue.

4. Invest in Deep Workspaces

Newport can’t stand open plan offices because they subvert deep work by enabling distractions. I know I said I’d write about the takeaways next time, but I can’t stop thinking about this one because it directly is showing up in my investing practice itself, with the companies I’m reading about. I’ve been reading about WeWork’s drama in my investing practice this week and thinking about the structure of work in physical spaces: open plan offices, and how harmful they are to completing deep work. Does a given company I’m looking into create a good situation and support for deep work? Which companies have open offices? Which ones have eschewed the impacts of open offices? Which ones allow going away and thinking?

How damaging an open plan office is first entered my consciousness years ago, when I read the extraordinary, life-changing book, Quiet, by Susan Cain. I do not lightly say it is life-changing. When I read that book, for the first time I realized why I had such a hard time being around people all day long. I had been taught as a kid that I was “shy” and that “shy” was bad. It was something I was supposed to work to overcome. So there I was, valiantly trying to overcome how tired I felt after being with people for 10-12 hours. I felt like it was my fault. When I read Quiet, I found out it not only wasn’t my fault that I felt so exhausted, it was normal, and there were a lot of other people who feel like that too. Being introverted does not equal being “shy,” though they often overlap. It’s a simple matter of energy: introverts spend energy to be around people and they gain energy by being alone, extroverts feel the opposite, and lucky omniverts who are somewhere in the middle get to enjoy the best of both worlds. It’s just energy transfer. There are many introverts who are quite social and gregarious, but need time alone to recharge. I also discovered from Quiet that we introverts have skills that extroverts don’t – primary among them, the ability to be alone for long periods of time and think. We are naturally made for deep work.

Open plan offices, Cain writes in her book, are particularly exhausting to introverts because there is nowhere to get energy back. It stands to reason that companies with open offices are not going to be as successful on the whole as companies with physical layouts that support all the energy giving and taking that people need, that support teams who need to huddle together and work, that offer opportunities to talk between teams, and that give individuals the space to close a door and stop being distracted.

Whether a company I’m considering investing in has an open plan office is something I’m going to start taking into consideration. I found this fabulously headlined Fast Company article: “Everyone hates open offices. Here’s why they still exist.”

Fast Company, I love you. Everyone DOES hate open offices – even extroverts. And I don’t really want to invest in companies that have them or anything else that prevents the ability to do deep work.

More takeaways next time. Enjoy your practice!


Deep Work, by Cal Newport (the audiobook, for me, started out a bit hard to listen to, but then I got used to the narrator’s voice and ended up liking him).

Quiet, by Susan Cain. If you got called “shy” a lot as a kid or love having time alone to recover from social time and work people: run, don’t walk, to this book. You will finish it feeling fantastic about yourself and with ideas about how to make space for your completely normal needs in a world that caters to extroverts.

Steve Eisman recently was on CNBC, and as he usually does, named a few really interesting companies.

Inside Bill’s Brain” on Netflix was a nice illustration of just how much deep work can accomplish.

I read a bunch about WeWork this week because I’m kind of obnoxiously intrigued by the gossipy drama. The IPO was canceled. The board voted out the charismatic co-founder with the most obnoxious payout of $185 million “consulting fee” plus $1 billion for his shares. This company doesn’t make money, and they paid him that. Employees are probably going to be laid off, and they paid him that. He walks away from an unprofitable company with a literal fortune. It’s immoral. It’s absolutely immoral and the fact that you don’t hear much outrage about it tells me how commonplace this sort of thing is. I’m totally disgusted by it, and it has made my view of SoftBank’s practices and management take a nosedive as well. Well, their argument will be that they had to buy him out just to get rid of him, but still, not great.

Some fun-to-read articles about WeWork’s drama and its larger implications:

VentureBeat on internal startup controls, or the lack thereof
The Atlantic on why WeWork was destined to fail
What does WeWork’s canceled IPO mean for markets?

TKTKClick here for early release access to Mostly Invested.

Leave a Reply

Your email address will not be published.

Scroll to Top