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How I’ve doubled down on Deep Work

I’ve written about Deep Work many times before, including how I do it in practice and how we do it at Ellipsis. I’ve been a dedicated Deep Worker since I read it in one sitting on a long haul flight 4 years ago, and the longevity of the idea is interesting. There are lots of productivity ideas, but few stick.

Both of my previous posts are now a little dated, so as it has stuck, I thought it’d be interesting to re-review how I’ve doubled down on Deep Work recently.

Remind me what this is?

The idea of “Deep Work” comes from Cal Newport, a Computer Science Professor at Georgetown University, and is something he expands on in his book of the same name. Here’s the idea in Cal’s words:

Deep work is cognitively demanding activities that leverage our training to generate rare and valuable results, and that push our abilities to continually improve… . Deep work results in improvement of the value of your work output… and an increase in the total quantity of valuable output you produce.

Deep work lets you do the above by demanding you focus, distraction-free, for long periods of time. This state of distraction-free concentration gives you the space you need to create valuable breakthroughs in your work.

Here, then, are some of the ways I’ve doubled down on Deep Work.

Time blocking

IF THERE IS ANY ONE “secret” of effectiveness, it is concentration. Effective executives do first things first and they do one thing at a time.

– Peter Drucker, The Effective Executive

My time over the last couple of years has shifted from 100% maker, to maybe 25/75 maker/manager, and now back the other way to maybe 66/33. This creates a dichotomy: two of the highest value things I can do are:

  1. Unblock my team
  2. Do high-value business development work

The trouble is, one requires deep focus and the other requires being available and responsive! What a dilemma!

Time blocking is the way forwards here. Cal discusses this in Deep Work at length, and it often comes up on his Deep Questions podcast. The Market has obviously smelled an opportunity, and you can now even buy a Cal Newport branded Time Block Planner (one does have to be a little amused that Cal says he created his own planner because the ones he was previously using, presumably Moleskine, changed to a lower paper quality, and then his ones have poor reviews from apparently having poor paper quality).

Time blocking is an excellent way of protecting your Deep Work time and effectively splitting maker vs manager time. It’s also, happily, a way of avoiding procrastination as you’re always clear on what your next action should be, and it also makes you commit to realistic timings for your day.

I’m onto my third year of time blocking in a daily planner and it’s an excellent complement to Deep Work. When my planner didn’t arrive in time for my first day of work for 2021, I literally didn’t know what to do with my work day. I’m dependent on it that much.

Embracing asynchronous communication

We don’t have any internal email at Ellipsis, and we don’t use Slack either. We use Basecamp for everything, and it’s excellent. Everything is in one place, and it’s built around asynchronous communication: you let whomever you need a response from know that you need their input, and they’ll get back to you in context with the rest of the task, at a time that makes sense for them.

The result is (for the most part) more thoughtful and less stressful communication. Basecamp does have all-team chat functionality, but it’s not that good. Happily, that stops it from being used too much. It does have a good one-to-one chat function which is good, but that gives a channel for discussing anything private or urgent. Basecamp is, as far as I’m aware, the best project management tool for remote team Deep Work (other options could be Asana, Notion, or something like P2).

We have some fairly extensive rules around how we use Basecamp which, sadly, make it very difficult for our clients to use, so we use Trello for that.

I know if I had Slack I’d check it all the time. Avoiding it has been one of the best things I’ve done for Deep Work.

Exercise / the morning routine

I’ve finally cracked it. No further blog posts are needed. I have the perfect morning routine. Sadly, it’s perfect for me at this moment, but it might give you some ideas.

My perfect morning routine involves exercising, having breakfast whilst reading, and then going to work with a cup of coffee. Sounds pretty idyllic! I do a 5k run on Mondays, Wednesdays, and Fridays, and then a long run on Saturdays. On Tuesdays and Thursdays I do one of a couple of home workouts as cross-triaining.

That’s worked really well for me over the year-and-a-half. The interesting bit for me is that when the lock down started in the UK in March last year (I’ve been working from home since, so I’m yet to go back to my co-working space), I didn’t change this routine. The exercise in the morning is probably the main thing that helps make sure the vast majority of days are Good Days.

Setting expectations

One of the privileges of running my own business is that I get to set the standards and expectations.

With clients, our new client onboarding includes a note on how we are a “Deep Work” business, and the benefits and tradeoffs to them (higher quality work, but they can’t get hold of us instantly).

With my team, they know I’ll either reply to them immediately or in a couple of hours, depending on whether I’m in “maker” or “manager” mode.

Deep Life

Creativity goes hand in hand with the ability to work hard and maintain focus over long stretches of time.

The Deep Work philosophy goes further than just blocking out some of your time. Cal increasingly talks about The Deep Life, a philosophy where doing good, important work is a part, but it’s only one part of many. Doing Deep Work is tiring, so balance is a necessity.

Cal argues that one needs high quality time with friends and family, good exercise, and high quality leisure activities. I’m often tired after work, but I know that forcing myself to go for a walk will lead to me having a much better evening than if I sit on the sofa and watch Netflix until it’s time for bed.

I’m normally very good at separating out work time with non-work time. Over the last 18 months, I’ve slowly been expanding my work hours, though. I used to finish at 5pm pretty regularly, but in the last six months it’s been getting later and later.

This is a fairly regular cycle: I’ll work more, realise it’s resulting in my getting less done overall as I do not do my best work when fatigued, cut back, and then slowly let the hours creep up again. That’s ok: ideally I’d take the message and leave it at that, but I enjoy my work, always want to do more/new things, and thus find myself pushing my end-of-work time back. That’s a reasonable trail of thought! I know this happens, though, so I can keep an eye on it and catch it early.

Phoning distractions

I started drafting this post a couple of weeks ago, and in the interim I’ve struggled with my focus. Realising this, I’ve been trying to work out what’s different. Just two things: I installed YouTube on my phone to watch something, and never uninstalled it. I was spending a lot more time watching YouTube. Easy fix. I also installed the browser back on my phone (this is genuinely inconvenient at times and friends probably fairly mock me for this, but it’s not hard to re-install it). I was spending a lot more time reading social sites using that browser. Another easy fix.,

I normally have my phone set up without these apps, making it a fairly dull affair: if I want to check my phone I can, but there’s nothing of interest on it so I check it less. I may be making connections too wildly here, but I found my general background level of anxiety and impulsiveness to check my phone has gone up. Removing these items off my phone is my usual practice, and an easy one to reinstate.

The routine is constant evolution

This is all extremely personal, and I hope by sharing it I can give you some ideas. The main benefit, though, is making me sit down and think about all these things. This is a constantly evolving process, and that’s something to embrace. For me, that means I’m always looking out for signs that need to be tweaked. My wife would argue I do this too much, but I like it. If I’ve got more/less done, felt better/worse, and done something differently, that’s all information to use.

As all of this is so personal, I find it helpful to try out changes. I want to do more reading and writing this year, so one of the experiments I planned for the start of the year was blocking off the first 90 minutes of my day for Deep Work. I’ve assigned a different activity to each day, reducing friction by allocating the time. It’s also blocked out on my calendar. That all makes sense, but I’ve still found myself struggling to do more than one or two days a week. Now I know that, I can work out why and try and solve the problem. If that doesn’t work, I’ll try again – or scrap the experiment. Either are perfectly fine outcomes.

Deep Work is immensely rewarding

I put all this effort into my Deep Work as whilst it’s a demanding, exhausting, and uncompromising way of working, when executed well it’s also extremely rewarding.

A key test for me is how long I think I can do something. Professionally, there’s two parts to that: how long can I do my job, and how long can I work the way I currently do? For me to be satisfied, the answer to both needs to be “a long time”. That’s why I’ve doubled down on Deep Work: it’s the way of working that lets me do my best work, at a sustainable pace.