Hey all! Dan here—today is a special edition of Superorganizers. We're turning the tables! The amazing Kieran O'Hare who has co-written many editions of this newsletter over the last few months is writing one about me. I think you're going to love it. Enjoy!

I’ve been working with Superorganizers founder Dan Shipper for a while now, so I suggested that he let me profile him for this newsletter. I mean, why not, right?

Well, he agreed—after a little convincing—and we scheduled an interview.

So what would you expect of a guy who started a publication about ‘how smart people organize what they know’? A veritable overlord of organization? A guru of GTD? A nabob of Notion, maybe? A royal duke in the realm of Roam??

Perhaps.

Me? I really wanted Dan Shipper to be a hot friggin’ mess.

Yes, I admit it freely: I wanted Dan Shipper to be a planless putz, a disgrace to productivity, a monument of disorganization—a shambling schlub failing miserably to comprehend let alone impose any order upon the chaos of this unfathomable world. What delicious, soul-filling irony that would have been!

Failing that, of course, it would have pleased me no less if Dan Shipper had been an utter circus freak who listened to two audiobooks and five podcasts simultaneously at 20x normal speed while running his daily marathon, speed-dialing his P.A., and mentally reorganizing his Airtable—with electrodes strapped to his head to track the beautiful upward-sweeping curve of his profoundly expanding neural capacity. All while live-simulstreaming his hopes, dreams, and fears to YouTube, Clubhouse, and Twitch, natch.

The reality? What a letdown.

It turns out that Dan—who spends every day of the week up to his ears in how other people organize what they do, know, and learn—is neither yutz nor savant. 

In fact, he’s a lot like the rest of us: we’ve all had to learn that figuring out how to do our best work is not a destination, but a journey.

Here, Dan gives us the details of his own personal journey: his first forays into productivity as a young founder, the techniques he uses as a perspicacious reader and seeker of knowledge, and his realization that earnest self-examination can be a powerful organizational tool.

From my point of view, Dan embodies what we hope you get out of Superorganizers—that the ways we approach how we work can also help us to lead richer, more meaning-filled lives.

Let’s take a look at what he’s up to.

Dan Shipper introduces himself

I’m the co-founder and CEO of Every, which is a bundle of business-focused newsletters that we started in late 2019. As part of that bundle, I write this newsletter, Superorganizers, where the goal is to interview the smartest people in the world about how they organize themselves to do their best work. 

Before all this though, I was basically out in the wilderness for several years figuring out what I wanted to do with my life. 

I had started a company called Firefly in college and sold it to Pega—a large enterprise software company, but after that I wasn’t ready to fully jump into anything for some time. I did some investing, I worked in a startup incubator, and I even wrote four drafts of a novel—but it wasn’t until fall of 2019 that I landed on this newsletter.

I was thinking about starting another software company, but I wasn't sure exactly what I wanted to build. Maybe some sort of productivity tool? So I decided to start a newsletter in order to learn about the tools people use, and build an audience that I could launch something to. But then the plans changed, and it turned into a media company, and here we are.

It's very exciting and it's exactly what I wanted to do, I just took a very circuitous route to get here. I think that in hindsight, everything looks less accidental than it actually is!

How I got interested in productivity

I was 20 or 21 when I got really obsessed with productivity. As a very young founder, I had to learn a lot very quickly—I felt like I had to be an information processing machine. I was getting bombarded with a tremendous amount of information, whether it was from customer feedback, from mentors, or in the articles and books I was reading.

Some of that info was definitely useful for me at that particular moment in my life, but I felt like most of it was more likely to be useful at some unknown point in my future. I wanted to construct a bunch of systems to keep all that information organized so I could find it whenever I needed it.

I also needed systems just to help me keep my life together—I was running a company at the same time as I was in college. I was taking calls in the middle of the night on our 24/7 customer service hotline, and then waking up the next morning to take a final! Productivity was a way to exert some amount of control and order over what definitely felt like a chaotic and difficult list of things that I was responsible for.

Naturally, my goals with productivity have changed over time. I would say that more of what I do now is about making sure that I'm staying productive and not dropping any balls, and less about trying to learn as much as I can and trying to figure out  how to remember all of it!

On top of that, I have to say that the interviews I do for Superorganizers constantly filter into my life in interesting and valuable ways. As a result, my productivity setup is completely different now than it was before I started talking to people about it.

As Every expands, I’m starting to enter more uncharted territory—I’ve built companies before, but I’ve never built a media company! I'm still learning new stuff all the time, and there are so many aspects of this business that I don't know about.

My ‘typical’ day

I think of my work in general as being divided into what I do on the publication side and what I do as a CEO. In the first case, I'm responsible for Superorganizers—I conduct interviews and do all the editing and some of the writing for that. In addition to that, across the whole bundle of newsletters we publish, I do a lot of editing and help out with planning and scheduling. 

As the CEO of Every, I run things on a day-to-day basis. That involves thinking about everything from last week’s metrics to our goals for the next several months. I spend a lot of time on strategy—where are we going and what are we doing. I handle communication with both our investors and our subscribers. In addition, we built our own platform, so that’s involved an insane amount of work with my business partner Nathan Baschez in trying to figure out how that should work—and what the future should be.

On a typical day, when I get up, I check my calendar to get a handle on what’s ahead. Then on Mondays, Wednesdays, and Fridays I go for a 2-3 mile run and then do a workout at home with a trainer on Zoom. On the other days I meditate for 25 minutes or do some kind of free writing to get myself ready for work. It’s a little inconsistent though—I often just sleep in instead.

Here’s a shot of my calendar (with meeting titles redacted):

I try to leave my mornings open if I can—that's when I do most of the writing or editing I need to take care of. Nathan doesn't wake up until around noon my time because he's on the west coast, so mornings tend to be mostly quiet for me. On the other hand, afternoons are for meetings.

This was a busy day for me—not every day is like that. But days like this are getting more frequent over time as the business expands.

On Tuesdays and Thursdays I have what I call ‘Focus Days’. The goal of those days is fairly straightforward: I need space in my week where I can get creative work done. Ideally, what I want is long blocks of uninterrupted time. It’s really hard to do that if I have meetings—even if there are only a few sprinkled throughout the day. It doesn’t always work out—but I’m trying!

I use Roam as a daily tracker

Once I really get started into my work for the day, I use Roam to keep a record of what I need to do, as well as what I get accomplished. Everything work-related goes into the ‘Every Journal’—that way I can keep everything involving the company in one place.