January 10, 2023

Alexandra Samuel on resetting for remote work, Coda evangelism, tool workflows, and combining technology and mindfulness (Ep46)

“You need to recognize that technology is not going to solve that feeling of overwhelm that I think is honestly intrinsic to being a human being in an era where the world comes at us faster than we are wired for. If you try to solve it all with meditation, you are going to miss your spreadsheet. If you try to solve it all with spreadsheets, you’re probably not going to heal your existential angst.”

– Alexandra Samuel

Tim O'Reilly

About Alexandra Samuel

Alexandra is an authority on remote work and the digital workplace, a speaker and a data journalist. She is the co-author of Remote, Inc: How To Thrive at Work….Wherever You Are and the author of the Work Smarter series of books published by HBR Press.

What you will learn

  • How organisations can set structures for their people to thrive on overload (02:11)
  • How to block time for private focus or sharing information with others for synthesis? (06:55)
  • How to make an overwhelming amount of information effective in any role (10:03)
  • Should organising information be taught as a foundational skill? (13:17) 
  • How to use tools to develop your knowledge with new ideas, information, and concepts (18:27)
  • What are habits or practices for getting information that enhances your work? (24:28)
  • How do we shift our responses to the feeling that we are not keeping up or FOMO? (29:16)
  • Why building a toolkit to seize opportunities is crucial to thriving on overload (33:23)



Ross Dawson: Alexandra, it’s wonderful to have you on the show.

Alexandra Samuel: Thank you so much for inviting me.

Ross: Overload today is a pretty omnipresent issue and the shift to hybrid has played an important role in that. I’d love to get your insights in an organisational context, people working all over the place, how organisations set up the structures or processes, or whatever it is that gives people the space where they can thrive or at least do well in this world of overload.

Alexandra: I hear from so many people who have really struggled with overload since that overnight shift to remote work at the beginning of the pandemic.

It’s been a real flashback for me because I started working remotely before it was even really a known thing. In mid-1998, I moved to Vancouver, and I started working for a company in Toronto, and it was a super weird thing to do. I didn’t go completely crazy but I did drive myself into a pretty intense depression because I was so isolated and I was working all the time to try and notionally keep up with these folks in Toronto who, of course, were waking up three hours earlier than me.

I think some version of that has really been what a lot of people have gone through over the pandemic, the sense that you’re supposed to be at your desk by 9 am but if you don’t get to your desk until 9 am, you’re never going to have a chance to answer your emails, because you’re going to be on calls all day from nine until five, and often booked into multiple calls in the same window. Then people are Slacking you at the same time, and you’re getting emails at the same time, and you’re supposed to do these deliverables for your clients. Then five o’clock comes around, and if you’re lucky, your meetings end at five, and then your workday begins and it sucks, it’s totally exhausting.

Not to mention the fact that it’s incredibly depressing and isolating because if you are living that pace at home, you’re not seeing other humans, and for good or bad, we are wired to be around other human beings and most of us pretty get cranky when we don’t see them.

It really is up to organisations to reset expectations and norms and to, first and foremost, reduce the volume of meetings and the normalisation of nine-to-five video calls, which has had the effect of pushing so much of our work into after-hours.

That comes down to making a mental shift we should have made at the beginning of the pandemic, or arguably 20 years before the pandemic when we discovered the miracle of email, the miracle of texting, and document collaboration, all of these tools have made meanings far less necessary because we do have other ways of working together. But we are so used to working like it’s 1964, the only way to get things done is by putting people in a room together that we never really stopped to look and ask “Does this conversation need to be a meeting or can I just send you a Google Doc and get your comments?”

The pandemic should have been the moment to reflect on that but when everything else turned upside down, keeping our cadence of meetings was one way to preserve normalcy. Then, of course, there were even more meetings, because the stuff that used to get dealt with serendipitously in the hallway, suddenly had to be a zoom call as well.

The bottom line is if people are in meetings more than four hours a day, and I’m pulling that a little randomly, but think about it, if you’re on Zoom calls more than four or five hours a day, there really is no time to get other work done. It’s exhausting. There’s no time for email. You’re probably not making the best use of those four or five hours of Zoom calls either frankly, that’s just a lot more focused, exhausting interaction than most people are capable of in the context of the video.

The one question that needs to be normalised in every organisation is, does this need to be a meeting? And even in a way before that, it’s just get away from the idea that a meeting is a default, and start with the assumption that everything is going to be handled asynchronously. Our normal way of working is to exchange documents, exchange Slack messages, exchange Teams messages, exchange emails, and if we need a meeting, it’s for a very specific reason, and we have a list of reasons in our heads and even better yet in some kind of shared documentation of what actually warrants a meeting.

Ross: Matt Mullenweg of Automattic, of course, has famously talked about the shift to asynchronous. That is the nirvana organisation. But beyond that, I think that’s almost the first step is to say, alright, let’s not just do back-to-back meetings, that’s probably a good start, and give people some space in between the meetings, but what are any specific ways you can give blocks of time for focus or to share information load by allocating that amongst different team members, what are any more specific things beyond asynchronous we can do to make this work for individuals?

Alexandra: The knowledge sharing you allude to is definitely table stakes. If I describe a need for an internal wiki, I guess I’m dating myself, it’s not what we call these things anymore.

Every organisation that has a significant volume of remote employees or where a large number of employees spend a lot of their time communicating online, which is, at this point, most organisations that are in the service, and even a lot of product businesses, any organisation like that needs to start with a question of how do we create information flows that are indexable and searchable?

It shouldn’t have to be that everything you know goes into a wiki and you have to figure out where it belongs and you have to make sure your document is in the right part of the shared drive, all of that is great but most people aren’t librarians and there can be sincere disagreements even between good librarians, so a system of knowledge sharing that depends on everybody putting their stuff in the right place with the right keywords and then also depends on people going and looking for the right stuff with the right keywords is pretty fragile.

It’s a lot more realistic to think about tools like group messaging, like Teams and Slack where just by adding a hashtag or even just by exchanging your message on a public channel as opposed to a direct message, you create indexable information that becomes available to the rest of the team in perpetuity.

I will say one of the things that have been transformational in my own productivity in the past few years, I’ve been very fortunate to have a long-running working relationship with a company called Sprinkler, and to be part of their internal Slack channels. At a certain point, I was several years into my working relationship when somebody on the team I was working with pointed out that the question I just asked her she didn’t know the answer to but I could probably find an answer to in a particular channel that I was then added to. That has become my go-to source for all kinds of questions that come up in the course of my work with them.

I think that’s a pretty typical and realistic scenario for how people can find information. If other people have asked the question in the past, you shouldn’t need to ask it, you should be able to go and find where it’s already been asked. You have to get up pretty early in the morning to ask a question that other people haven’t asked if you’re working in a large organisation.

Ross: I’d like to switch gears a bit, perhaps we can still incorporate the organisational themes, to your practices. Amongst other things, you’re an expert, researcher, and author. You have a lot of information, you’re working with your clients, which gives you even more information. I’d like to get a sense, perhaps dig in saying how do you take that overwhelming amount of information to be able to be effective in your role? What’s the starting point for you?

Alexandra: There are a couple of things. First of all, when I was 11, my mother literally bribed me to take typing in an adult secretarial school. I sat and cried every single day as I sat at my typewriter, but she was right, by the age of 12, I was a fluent typist. I’ve been typing for almost 40 years now. It sounds like a trivial thing but I’m amazed when I am a faster typist than almost anybody I know, and it is actually a transformational practice because if you type as quickly as you think, and to be honest, I think pretty quickly as well, then it becomes possible to capture everything.

The other part of that is I’m like an incorrigible voice reminder dictator, everybody I know makes fun of me because I’ll be walking down the street, and I’ll be like, Oh, remind me to order gum today at 7 pm, or somebody will say something, I’ll say, Oh, just a second, remind me to talk to Ross about why information overload is a problem for so many people.

I run my whole life actually off of reminders now. What’s really effective about that is it feeds thoughts and information back to me at a moment when it’s actionable and if it isn’t, as it turns out, actionable, if, at seven o’clock, I’m actually in the middle of eating dinner, I have the whole cascade of snoozing features and places to send things so that might bounce back to me for a couple of goes before I can put it somewhere to find it again. But eventually, that idea goes into my list of ideas to think about turning into stories or that idea goes into the structured documents/spreadsheet where I keep information related to data journalism.

I have several repositories that I have maintained in different forms for several years. I’ve been an Evernote user for 15 years now I realise and almost all my random stuff goes in Evernote. I’ve been a religious user of a platform called Coda for about three years, I like to describe it as Google docs on steroids, it lets you combine spreadsheet functionality and document functionality, and to essentially build your own apps.

I have built coded documents around every single major aspect of my life, some of them in incredible depth. That means that even though I am in 18 different directions and working in many different organisations and contexts, there is a home base for each aspect of my life.

Ross: I’d like to dig in a moment as to how you use Evernote in particular. But are these skills we should be teaching individuals? Should we be teaching people how to use Coda or giving them some templates or saying, choose Evernote or whatever note-taking systems, and here are some ways to tag or structure that? Are these some foundational skills that people haven’t been taught?

Alexandra: Yes, 100%.

It’s embarrassing what happens in my household, my 19-year-old has not only taken to using Coda but has become a Coda evangelist, and knows that the surest way to curry favour with Mom is to come home from their day at art school and explain how they’ve gotten a whole bunch of art students to start using Coda today to plan their projects.

And my 16-year-old, bless his heart, last year got really tired of the repetitiveness of his math assignments and just built a series of calculators in Coda to do his math homework for him. Every time I see them do something like this, I think like, who the heck knows? Is he ever going to use grade-10 math in real life? Maybe, maybe not. Is he going to use the ability to build his own little DIY work tools in an online platform? Absolutely.

There are a lot of aspects of my parenting I would not necessarily recommend to the general public but my kids are amazingly adept at using these different tools. It’s because they’ve grown up in a household where that’s just how we do. We have 14 different platforms we routinely use as a family. You do not want mom to catch you using a table when you should be using a spreadsheet, that is like bad news. I wish schools spent more time on this.

It’s one of the things that made me super upset about the whole transition in Google Suite is I have a huge problem with the corporatization of education. It is disturbing to see schools relying on a commercial platform, but also, if kids use Google in their school, and they’re using Google Sheets, or using Google Docs, they’re getting used to the platform they’re going to use as adults in the working world. I think that having kids learn how to use digital tools in these playgrounds that are designed for K–12 environments and then have to go and learn a totally unrelated toolset doesn’t make any sense. Let’s get schools and kids running on the kinds of tools that adults use or should use.

Ross: I suppose there aren’t that many adults that are familiar with Coda.

Alexandra: I’m working on it.

Ross: There are a lot of people struggling with saying they’ve got paper, or they’ve got Google Docs, or they’ve got all sorts of things, and no one has ever given them any guidance or said this is how you can organise or structure your life beyond whatever we throw at you.

Alexandra: That’s absolutely true.

Some of that can be addressed by organisations being explicit about tool choice, providing examples, providing resources, providing training, supporting people with templates, and getting started guides, and all of that. All of that would help.

But I also have to remind myself that not everybody’s idea of a fun Friday night is “Let’s try seven different task management apps and make notes on which ones have which feature.” That is my idea of a rip-roaring good time but most people do not enjoy messing around with software as much as I do.

The world is full of people who don’t like spreadsheets, also, I’ve learned that. I can’t even begin to describe how much I love it. I feel my brain is a spreadsheet.

One of the things that have been interesting to me, my younger kid is autistic so I periodically connect with other moms of autistic kids. You would not believe how many moms I’ve met in the autistic community are also big Excel nerds. There is possibly a genetic component here.

I’m not saying everybody needs to fall in love with spreadsheets but I think that if people can find tools that are genuinely a joy for them to use, you don’t have to use 482 different things the way somebody like me does, but if you think about how much time you spend holding your phone or at your computer, if you’re not working in an environment that gives you joy, it’s going to be hard, it’s going to be a slog, so you want to encourage people to take ownership of their tools as part of taking ownership of their work.

Ross: This goes to knowledge frameworks. I describe them as concept frameworks or sometimes visualisations. It sounds like you’re using Evernote and Coda for that. From this frame of developing knowledge, as in finding things and building the connections between those, is that something you do? Or if so, how do you use your tools? Or even just your cognition as ways to develop your knowledge as you encounter new ideas, information, and concepts?

Alexandra: It’s interesting. I don’t think about either Evernote and Coda as knowledge as much as ideas. I keep a lot of web clippings in Evernote. I do often find things in Evernote that I saved seven years ago or whatever that are still useful.

From a knowledge and ideas point of view, what’s probably more relevant, I’m a Zotero user, I used to be EndNote user a hundred thousand years ago, I’m a huge fan of people choosing.

But if you do knowledge work, if you do reading of any sort using a bibliographic software program, Zotero is probably the one to beat now because it’s open source and has a really big user base, it’s pretty powerful. You take all your notes on your reading, you save your reading sources in one place, that’s where you highlight articles as you read them, you can extract those highlights and export them to other programs.

One of the most popular pieces I’ve ever written, at least in terms of the passion of the people who find it and write to me about it, I wrote this piece for JSTOR Daily a few years ago about how I use Zotero and Scrivener together. Scrivener is a writing program for long-form writing. I even use it to write my newsletters and my articles now because it’s just so much easier in a lot of ways than using a word processor. Not easier to learn but more powerful and faster once you learn it. I use them together.

I’ll save an article to Zotero, annotate the PDF in Zotero, use a tool called zotfile which is an add-on to Zotero to extract all the annotations and turn it into ultimately a Word document. Then I import the Word document into Scrivener so that each annotated section appears in Scrivener as a little mini document within Scrivener, and then I just rearrange all those quotes until I figure out the pieces I want to use in my article, and bam, I’m almost done with the first draft, it’s a little more fidgety than that but that’s been really significant for me. I think the knowledge management piece is very therapeutic.

I always feel embarrassed that I’m such a pack rat. I’m a pack rat from a long line of pack rats. When my grandmother died, we had her great grandfather’s clippings books still around. One of the lessons I learned from that is, if you keep it for your lifetime, you’re a pack rat. If the next two generations keep it, then it’s like an heirloom. You just have to keep it long enough. I have every essay I wrote in college in a cupboard upstairs printed out on dot matrix printer paper, in little Duo-Tangs and I still refer to them sometimes.

I can open any file I created within the last 20 years, maybe a little longer, and not just open it, I can find it. I have a heck of a huge, 32-terabyte file server in the house, which is big enough to actually have room left over. Of course, I have most of my stuff stored in the cloud. I’m constantly opening documents from 10 years ago, 12 years ago, and 14 years ago, repurposing a little bit of this or that. Just that ability to not replicate things I’ve already done is so powerful.

Ross: Do you use any tagging system or any structure to Evernotes like an overarching taxonomy or anything?

Alexandra: I have notebooks within Evernote. When I was first an Evernote user, I was extremely religious about tagging and notebooks. It’s been years since I even really bothered to use notebooks, it’s all just a big pile because search is so effective in Evernote, maybe it’s not perfect, and it can be a little messy.

The only thing I do that is really religious is years ago, my husband, this is one of these practices that no longer fully makes sense because computers have evolved but back in the day when things didn’t necessarily have reliable date stamps, he got me into the habit of starting every file with the date in the format, year, month, day, so today would be 2022-12-6.

I actually have a keyboard shortcut in my computer and on my phone that I can quickly add at the beginning of any file, and it’s now automatic that every time I start opening a file or start an Evernote note, I hit that keystroke combo and it starts with the date.

Yes, in theory, the date created, date last modified, whatever, should always be visible within a file but I’m telling you, man, every time I move computers, all the date stamps get screwed up, so that ability, and when you have it in that format, year, month, day, it means you can always sort by file name, and then it ends up in date order. File order is date order. That has saved my bacon many many a time.

Ross: Awesome. Let’s go into inputs. You get lots of new information to come into your consciousness every day. I’d love to just hear about are there any specific regular sources you use. Do you have any feeds? How do you look out and discover the edges of the world? What are your habits or routines or practices in terms of getting the information that feeds your ability to do what you do?

Alexandra: It’s funny, I often joke that my husband is the input device and I’m the output device. We have worked very closely together at various points in our careers. We ran a business together.

I have also had periods of my life where I did have a very structured daily news scan, I had an RSS aggregator, I’ve gone through various things over the years, Feedly, and so on to use RSS aggregation to bring keyword searches to me. I do have a standing Google News search for stuff related to remote work. I use an email program called Superhuman. Within it, I’ve set up a category for regular news and a category for remote news so my newsletters go into the regular news folder, and my Google News search, and a handful of newsletters I subscribe to on remote work, go into the remote news folder, but I really don’t look at either of them very consistently.

I’m trying to deal with this, I would say for me, the biggest problem with information overload is less cognitive and more emotional and psychological. For me, part of that has to do with transitioning the field that I work in. I’ve had a really weird career in a lot of ways. I’ve always been interested in stuff too soon. I was in the Political Science Ph.D. program in the mid-90s, and I decided in 1996 that I wanted to do a dissertation on the political impact of the internet and my department thought I was like bananas. I ended up taking a few years off coming back and doing a dissertation on hacktivism in 2001 and finished in 2004. It was before Anonymous. It was crazy early.

Then I got interested in what we now call social media before it was called social media. My husband and I literally started the first social media agency in the world, because we hung out our shingle in 2005, and said, we’re only going to do Web 2.0 projects.

I’ve had this career where I’ve been unprofitably ahead of the curve, and where usually what I’m working on and writing about, other people are working on or writing about. When I started writing about the personal psychological impact of using the internet, the only other people who were even talking about this at all were in the evangelical community, and I followed a handful of people who were trying to think about how do you speak tweet in the spirit of Jesus, that kind of stuff, long before all the Buddhists, the mindful tech started happening.

Working as I have in the past two or three years, taking my long experience of remote work, my long experience of helping organisations figure out how to build community online, taking my experience of helping people with information overload, with productivity, and turning that into a book about remote work and a pretty active career writing and speaking on remote work has been really disconcerting for me because I’m suddenly in a conversation that hundreds and thousands of people are talking about.

When I was writing about hacktivism, there was no Google News search yet. But when I was writing about social media and digital overload initially, I had searches set up on digital fasts and overload, some of these keywords, there was some stuff, but it wasn’t like a colossal waterfall of other people writing about the same topics.

Now, if I look at my Google News search for stuff on remote work in hybrid, I’m like, way too neurotic. It’s like, oh my God, these are like 45 great articles and I didn’t write any of them and like, I suck, they’re great, I need to go crawl into a hole and die.

Maybe everybody, maybe a lot of people are like that, maybe that’s part of what makes information overload so difficult. I just think as humans, we are the first generation to be continually immersed in what everybody else is doing that we’re not. It’s pretty tough to live in the constant stew of your own opportunity costs.

Ross: Yes, you’re absolutely right. Human cognition is not really geared for this particular environment. But a big part of that is emotional in the sense that we feel that we’re missing out, we want to try to keep up, but it’s impossible to keep up, and this leads to not good emotions.

How do we shift our responses? Some of those are processes or structures and one of those is really adjusting our attitudes. I talked about this idea of we have to be able to let go, and that’s not an easy thing for us to do.

Alexandra: No. My thinking and understanding of these challenges has been so profoundly influenced by my journey with my kid who was diagnosed with autism pretty late.

We spent a lot of time reading a lot of stuff about ADHD and other kinds of sensory disorders, as they’re sometimes called. I’ve read a lot about autism and spend a lot of time paying attention to people in the neurodiversity community who often make very effective case for all the talents and gifts that can come from having a different way of approaching the world. It’s made me very aware of how we fall into a lot of errors of assumption around what we’re supposed to be able to handle cognitively, at a sensory level, and emotional level. Again, the mismatch between what comes at us and what we’re wired to handle.

A lot of the tools that have helped me learn to deal with that in my professional life have really come from my personal life. To just give an example, we went through a very, very difficult time, in the middle of COVID, there was a survey here in British Columbia where I live, of families with autistic kids and literally, every single family in the province that was surveyed said, we are in crisis because of COVID, because there was such a loss of community support and scheduled routine and a lot of things people rely on. That was certainly the case in our household. We went through a really difficult time, and I had a pretty established repertoire of resources to work with, and I needed more.

I started working with a therapist who specialises in hypnosis, and then later with another somatic therapist to develop essentially some very physiological practices for self-regulation, just starting to notice what happens in the body. Because what had happened to me was we had such a series of crises that I was kind of in permanent fight or flight mode. I had to learn how to turn that down.

Having tuned into that at a physiological level and learn to notice like, oh, I’m feeling tightness in my chest, I feel my forehead is tight, I can feel what’s happening in my eyelids as I’m having that response, and then learning very simple techniques like, I’m going to pick an object in the room, and I’m going to really focus on it, and I’m going to look at the color, the texture, I’m really going to turn on my sensory experience to pull my brain out of that panic mode.

That feeling I have when I open my inbox, that same routine now comes into play. It’s not necessarily conscious, I don’t think, oh, no, I’m panicking over my inbox but it’s now become second nature to notice the physiological response so that instead of identifying with panic, I can observe it a little bit and not let it drive me.

Ross: That sounds like a fantastic tool. Our ability to control our attention is fundamental and I think those specific techniques are really powerful. To round out, what are any recommendations you would give from your deep insight and expertise as to how listeners can thrive on overload to function well in this world, which is very overwhelming, to be frank?

Alexandra: It’s funny. I’m just reflecting, is the solution a spreadsheet or a Buddhist retreat? I can’t decide.

I honestly do think that you need to look at both sides of the coin. There’s a lot of advice out there about decide what you want, be really clear on your intentions, you’ll manifest, blah, blah, blah, I actually have moved away and come to find it’s much easier to learn to float on the river and accept that the complexity and pace of our world is almost too much to be able to set really firm intentions.

Instead of thinking this is the thing I’m going to go for and I’m going to have this super linear way of going about it, if instead, you think about building a toolkit that allows you to float on the river and seize the opportunities that come your way, then you realise what you need is really, as I say, both sides of the coin, you need to build the technical tools that let you filter, triage what comes in, rediscover the resources you need to reuse, organise your writing and your work effectively, and you need to recognize that technology is not going to solve that feeling of overwhelm that I think is honestly intrinsic to being a human being in an era where the world comes at us faster than we are wired for. If you try to solve it all with meditation, you are going to miss your spreadsheet. If you try to solve it all with spreadsheets, you’re probably not going to heal your existential angst.

Ross: So a combination of technology and mindfulness?

Alexandra: Something like that.

Ross: That’s a fantastic way to round out. It’s a true and hopefully pragmatic advice there. Thank you so much for your time, Alexandra. That’s been a wonderful, really insightful conversation.

Alexandra: It’s fun talking with you.

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