Digital nomad and CEO: Working efficiently from anywhere with Sam Corcos

In this episode of How I Work, Dr. Amantha Imber invites Levels CEO Sam Corcos to give an inside look at his life working as a digital nomad. Sam shares how an asynchronous remote company lets him maximize the life he wants. He also shares practical tips such as his email processing strategies, how he organizes his calendar, and how he manages to read two books every week.

The value of being a minimalist

Sam’s nomadic lifestyle is made possible by the fact that he has almost no possessions.

I’m at my most aggressively minimalistic stage right now. I’m down to I think one pair of jeans and three T-shirts. Pretty much everything I own fits in a backpack. Being a minimalist definitely helps with the being more of a nomad. I try to optimize for staying with friends. I found that it’s a really great way to build relationships with people that I don’t normally get a lot of time to spend with them…I think in general we underestimate how much cognitive load we put on ourselves when we have stuff. There’s a reason why when people do spring cleaning, it feels really good. You have fewer things, you have fewer attachments, fewer obligations. I found for myself that a lot of these things are just comfort, having a lot of stuff, and that you can become comfortable with discomfort, and you can really use your time focused on the right things.

Moving at a moment’s notice

For the average person, moving is a big deal. For Sam, it’s as easy as breathing.

I think a lot about how I spend my time, and by not having things or obligations it’s very easy for me to make quick decisions and to make changes very quickly. The idea of me moving from one place to another is really – I have a hard time relating to people who for them moving is a really big deal. I think it’s in the top five most stressful activities that most humans experience, up there with the death of a family member. For me, moving and traveling is really, it’s very low stress, maybe zero stress. Part of it’s just because I don’t have stuff to move. I don’t have to worry about the logistics, I don’t have to worry about coordinating things.

Recognize how to mono-task

Sam realized that he can’t multitask and prefers to focus wholly on one thing at a time.

I don’t have multiple screens, which I know a lot of people really like having. I’ve tried it. I just find it incredibly distracting and disruptive. I have the one computer, I have the one screen, and I try to only focus on one task at a time. Sometimes I use things like I have noise-canceling headphones, which blocks out external noise so that I can really stay focused on what I’m doing. I’ve created some other interesting tools, like my… I call them my focus goggles, which are basically safety glasses that you would have in a science lab, and I spray-painted around them so that you can only see a very narrow strip in front of you.

Create structure to stay organized

Undisciplined by nature, Sam has managed to create discipline by using guardrails like morning meetings to keep him accountable.

I’m incredibly lacking in discipline, which is often surprising for people who know me who think that I’m incredibly disciplined. But it’s more like I’ve created artificial structures around my own actions in order to force myself to be disciplined. If I don’t have a meeting – in fact, this morning is a perfect example. In theory, I like to wake up at 7:00 and start working, but my call this morning at 8:00 got canceled, so when my alarm went off, I just went back to sleep. I will often create things, like I will make a meeting at 8:00 AM every day so that I have to wake up, because if I don’t, then if I don’t have that obligation, then I will be incredibly lazy. I have website blockers for things like Twitter, for a lot of other things that I find really distracting. I use a lot of tools to just increase friction, so that I know that future Sam will be more likely to do the right thing.

A news-free life

Reading the news was causing Sam to be anxious and wasting time. He’s cut news out of his life entirely and instead gets high-quality information from books.

As an experiment, I decided that for a month I would stop following the news, which was taking up a lot of my time, and I would try using that time, just a one-for-one tradeoff, to just read books. In that month, I think I read eight books that month, which is probably more books than I’d read in the previous five years. There were so many other impacts that were very interesting. One was that it was amazing how little I actually missed, in terms of things that mattered. It was just recognition that so much of the news is ephemeral and the incentives of the news industry are not in the best interests of the people that are following the news, and that the news is generally very low-quality information, and books have very high-quality information. I would also say that one of the other things that was really surprising was how I physically felt different, which is kind of a hard thing to explain, that my anxiety levels were down pretty dramatically.

Managing email with Superhuman

Sam uses an email program called Superhuman to help him stay on top of hours of email per day.

Probably the biggest one, and this is not within the scope of Superhuman, this is just in terms of time management, really making time for email and making it a first class citizen. This isn’t the case for everybody. This just happens to be the case at my job. I was talking with one of our engineers who he processes something on the order of 10 emails per week. It’s just not his job, he doesn’t do email, he writes code. In my job, pretty much all of what I do is email, so Superhuman is a really great tool because it’s very performance. It allows for scheduling. The nice thing about email relative to other mechanisms, like text messaging, for example, is that email can be triaged, you can decide if something needs to be responded to now or it can be responded to later.

Limit daily distractions

As someone who values distraction-free workdays, Sam set up specific days that can have meetings, and days that cannot.

The first time I really took a leadership role in engineering and was doing a lot less programming, the challenge that I ran into is, and I found it very hard to communicate this to people inside the company who were not software developers or not technical, was how if I have a 30 minute meeting at 11:00 AM and at 3:00 PM, I can’t get any work done the whole day. They’ll say, “Well, it’s only one hour. You still have the whole rest of the day to work.” And it’s just like it really doesn’t work that way when you’re trying to get into a flow state. I can’t work up the emotional energy to even start working on this project if I know that there’s a high likelihood I’ll be interrupted in the middle of it. The different between manager and maker time is manager time, it’s constant context switching and it’s really not a flow state.

Replace your to-do list with your calendar

To ensure things get done and have a place on his schedule, Sam now blocks time for tasks by putting his to-do items directly on his calendar.

I think that one of the biggest unlocks for me was using my calendar as my primary mechanism for time management, and in terms of tasking as well. I used to keep a to-do list, which I think is sort of the default that everyone has, is a to-do list. The challenge that I kept running into is, especially with digital to-do lists, to-do lists can become infinitely long, and they feel infinitely long. I remember a couple years ago, my to-do list was so long it was several lifetimes amount of work that would be required to actually get to the bottom of this list. So I started using my calendar to proactively block off time, so when I would have a task like maybe it’s write the content piece on how I spent the first two years of my time at Levels. I will proactively look at my calendar and I’ll block off… I would expect it’ll probably take me six hours to write it, so I’ll block off six hours to write that piece. Similarly, if there’s something about running errands or writing a strategy document on how we think about podcasts, I’ll block off time on my calendar instead of adding it to my to-do list, and I found that this was a… it was probably the most powerful mechanism for just personal anxiety reduction.

Embrace asynchronous tools

Are your tools truly serving you? Sam and the Levels team do use tools like Slack, but only in very specific ways.

I would say the biggest thing is just to keep things as asynchronous as possible. I would say a lot of my productivity tools would be anti-tools. I would say to the greatest extent that it’s possible, your phone should be on do not disturb mode by default, as mine is, turn off notifications, don’t use Slack, or if you do, use it with a very specific set of SLAs. For example, we use Slack at Levels, but explicitly Slack is not the primary mechanism for communication. Slack is really just for updates, and there’s no expectation that anyone will respond to a message in Slack within 24 hours, and it prevents this fire hose effect of information, because information on Slack – Slack is a synchronous tool that pretends like it’s an asynchronous tool, because you have the same expectation that people will respond immediately, but it’s written, and things just get lost if you’re not paying attention in real-time. So I think that focusing on things that are asynchronous by default is really the most impactful way of being productive, is to really emphasize deep, focused work and to eliminate distractions to the greatest extent as possible.

Go off the grid to reassess

In order to see the big picture on a regular basis, Sam takes one week per quarter to conduct deep thinking.

Every quarter, I take a week, I would say off-grid, but not necessarily without access to internet or whatnot. I actually really like having access to internet. For me, I will often spend a lot of that time reading and reflecting and writing. I do a lot of writing. I’ll often come out of these think weeks with 50 to 100 pages of writing on company strategy or personal reflections or writing of content pieces. I find writing to be a really satisfying activity, and so it is usually during these think weeks that I come up with some of my best ideas, because I don’t taking any meetings, I don’t take any calls. I really just focus as much as I can on the big picture. So a lot of my best ideas have come from taking time away from the day-to-day, when you can think more holistically about your company and what the goals are and what the trajectory is and what the hiring plan is. I find that I’m in the day-to-day, it’s really easy to miss the forest for the trees.

Dr. Amantha Imber:

If you were to take your job on the road and live as a digital nomad, would you be able to keep it up without your life turning into a permanent holiday? Could you do it while also running a global company? Co-founder and CEO at Levels, Sam Corcos, has done just that. He’s been working as a digital nomad for 10 years. So I got connected with Sam via Darren Murph, who is head of remote at GitLab and was one of my favorite guests on the show of 2020. Sam’s company Levels is responsible for creating a fascinating health tech wearable device that tracks your blood glucose levels in real-time so that you can optimize your diet and exercise. Sam is a fellow productivity nerd and things very deeply about his personal productivity and health.

Dr. Amantha Imber:

In today’s show, he shares a ton of really practical tips from his email processing strategies and how he organizes his calendar as a hyper-busy CEO, through to how he manages to read two books every week. Yes, that’s every single week. We also chat about his quarterly think week ritual. I’m Dr. Amantha Imber. I’m an organizational psychologist and the founder of behavioral science consultancy Inventium, and this is How I Work, a show that helps you do your best work. Let’s start by hearing what Sam’s nomadic lifestyle is like as a CEO and how he has managed to make that work.

Sam Corcos:

Yeah, it’s something that I’ve been doing for quite a long time, not necessarily intentionally, just sort of out of necessity. I was a software developer and a contractor for a long time which involved a lot of travel, and a certain point you just kind of get used to it, not having a permanent location.

Dr. Amantha Imber:

So what does that actually look like? How do you move around? What do you own? What do you pack? Where do you go?

Sam Corcos:

Yeah, so I’m at my most aggressively minimalistic stage right now. I’m down to I think one pair of jeans and three T-shirts. Pretty much everything I own fits in a backpack. Being a minimalist definitely helps with the being more of a nomad. I try to optimize for staying with friends. I found that it’s a really great way to build relationships with people that I don’t normally get a lot of time to spend with them. It’s also been fun taking people up on what were likely facetious offers. I have friends who say, “Yeah, anytime you want, come on down.” And I’ll say, “Cool, how’s Tuesday?” Then I’ll just show up at their house. Yeah, it’s been a really great way of building relationships. I try to stay in touch with a lot of people and keep pretty rigorous notes. I think at this point I have I think something, last I checked, maybe 300 people that I have on a list who have offered extra bedrooms or couches that I could stay on if I was visiting, and I cycle through it.

Dr. Amantha Imber:

That is quite insane, and it certainly blows Dunbar’s number out of water, doesn’t it, of 150? So, what prompted you to have a minimalistic approach to your life?

Sam Corcos:

I would say part of it was just reducing cognitive load. I think in general we underestimate how much cognitive load we put on ourselves when we have stuff. There’s a reason why when people do spring cleaning, it feels really good. You have fewer things, you have fewer attachments, fewer obligations. I found for myself that a lot of these things are just comfort, having a lot of stuff, and that you can become comfortable with discomfort, and you can really use your time focused on the right things. Part of it, I think, is the recognition that I’m dying, that we’re all dying, just some of us more acutely than others, and the more time we spend on things that are adding value is really detracting from our long-term goals. I found for me spending a lot of time following the news, thinking about what I dress like and what I’m wearing, accumulating more things, having more responsibilities, that the fewer of those that I had in my life, the more time I could spend towards the things that I really care about.

Dr. Amantha Imber:

That makes a lot of sense. How does applying minimalism to your life help you be more productive?

Sam Corcos:

I think the biggest one is in terms of, I guess, time management broadly. I think a lot about how I spend my time, and by not having things or obligations it’s very easy for me to make quick decisions and to make changes very quickly. The idea of me moving from one place to another is really a… I have a hard time relating to people who for them moving is a really big deal. I think it’s in the top five most stressful activities that most humans experience, up there with the death of a family member. For me, moving and traveling is really, it’s very low stress, maybe zero stress. Part of it’s just because I don’t have stuff to move. I don’t have to worry about the logistics, I don’t have to worry about coordinating things. Another thing is I’ve had a lot of conversations with people relating to environmentalism, and I do think that it is interesting how much we tend to focus on the waste component of consumption and so much less about the input components.

Sam Corcos:

We think a lot about recycling and trash and we don’t think about the inputs. The person who owns several extra homes is contributing a lot more to damaging the climate than somebody who throws away a recyclable jar. So I think a lot about these things, and I think that if most people were to practice some form of minimalism, really just consuming fewer things, I think a lot of societal problems that we’re experiencing would probably get a lot better.

Dr. Amantha Imber:

Given the way you live, what does your work environment look like when you’re, say, staying with a friend’s house, maybe sleeping on a couch, I don’t know, what does your work environment then look like?

Sam Corcos:

I have my laptop. I’m currently sitting cross-legged on a bed. Part of this is related to maybe my own inability to multitask. I don’t have multiple screens, which I know a lot of people really like having. I’ve tried it. I just find it incredibly distracting and disruptive. I have the one computer, I have the one screen, and I try to only focus on one task at a time. Sometimes I use things like I have noise-canceling headphones, which blocks out external noise so that I can really stay focused on what I’m doing. I’ve created some other interesting tools, like my… I call them my focus goggles, which are basically safety glasses that you would have in a science lab, and I spray-painted around them so that you can only see a very narrow strip in front of you.

Dr. Amantha Imber:

Oh, my gosh.

Sam Corcos:

Yep, they’re pretty nerdy, but they’re quite effective at blocking out peripheral vision. It’s interesting because I’m incredibly lacking in discipline, which is often surprising for people who know me who think that I’m incredibly disciplined. But it’s more like I’ve created artificial structures around my own actions in order to force myself to be disciplined. If I don’t have a meeting… in fact, this morning is a perfect example. In theory, I like to wake up at 7:00 and start working, but my call this morning at 8:00 got canceled, so when my alarm went off, I just went back to sleep. I will often create things, like I will make a meeting at 8:00 AM every day so that I have to wake up, because if I don’t, then if I don’t have that obligation, then I will be incredibly lazy. I have website blockers for things like Twitter, for a lot of other things that I find really distracting. I use a lot of tools to just increase friction, so that I know that future Sam will be more likely to do the right thing.

Dr. Amantha Imber:

What are some other tools that you’re using to increase that friction?

Sam Corcos:

Yeah. Website blockers are a big one. I think it depends a lot on what types of addictions one has. For me, for a long time it was social media. A couple things, one, my relationship with Twitter is much healthier now. I discovered muted words, which is a thing where any tweet that has a particular phrase in it won’t show up in your feed. So for me, I know that a lot of the I guess you would call it outrage porn, that makes its way onto Twitter, really distracts me and pulls my focus in the wrong direction. I have easily in the hundreds of muted words, anything from like violence to riots to anything that’s like an angry term, I have it effectively turned off, and I have a lot of blocked accounts as well. As a result, my Twitter experience is quite positive. I also deleted Facebook and got rid of most social media. I’ve been news sober for about eight years.

Dr. Amantha Imber:

What does news sober mean?

Sam Corcos:

That means I have not consumed news in any form, be it written, verbal, television, I haven’t consumed any news since about 2013.

Dr. Amantha Imber:

Wow. What prompted that?

Sam Corcos:

Yeah, I had this recognition. I read a book, Ryan Holiday’s Trust Me, I’m Lying, the subtitle is Confessions of a Media Manipulator, and I think he really did write the book as a confession.

Dr. Amantha Imber:

It’s a great book, isn’t it?

Sam Corcos:

Yeah, yeah. He was talking about how he does all of these tricks to manipulate the media, to cover certain things, and very much saying, “I’m sorry that I’ve been doing this. People need to know about it. It’s bad and it’s getting worse.” This is before the term fake news even existed. He practically coined it in that book. He at the very least defines it very robustly. As an experiment, I decided that for a month I would stop following the news, which was taking up a lot of my time, and I would try using that time, just a one-for-one tradeoff, to just read books. In that month, I think I read eight books that month, which is probably more books than I’d read in the previous five years. There were so many other impacts that were very interesting. One was that it was amazing how little I actually missed, in terms of things that mattered.

Sam Corcos:

It was just recognition that so much of the news is ephemeral and the incentives of the news industry are not in the best interests of the people that are following the news, and that the news is generally very low quality information, and books have very high quality information. I would also say that one of the other things that was really surprising was how I physically felt different, which is kind of a hard thing to explain, that my anxiety levels were down pretty dramatically, in fact almost to the point where it was nonexistent. I used to feel stress and I used to feel anxious all the time about world events, and it was weird in retrospect looking at it and realizing that I was feeling stress about a lot of things that I have no control over, many of which aren’t even real, and it was a weird recognition. So I basically haven’t looked back. I’ve managed to read two books a week since giving up the news, just by doing like a one-to-one trade of time of news to books.

Dr. Amantha Imber:

Wow. Now I love Superhuman and before encountering you, I thought maybe I’m the biggest Superhuman fan in the world, but I believe that you might be that person, so I want to know how are you using Superhuman in ways that make email, and for those that don’t know, Superhuman is an email client more efficient, in terms of processing email.

Sam Corcos:

The biggest one is use of hot keys. I process a lot of email. It’s probably my core competency, on the order… If I don’t process at least three or four hours of email every day, I fall behind. I would say batching is probably the biggest one, and this is not within the scope of Superhuman, this is just in terms of time management, really making time for email and making it a first class citizen. This isn’t the case for everybody. This just happens to be the case at my job. I was talking with one of our engineers who he processes something on the order of 10 emails per week. It’s just not his job, he doesn’t do email, he writes code. In my job, pretty much all of what I do is email, so Superhuman is a really great tool because it’s very performance. It allows for scheduling. The nice thing about email relative to other mechanisms, like text messaging, for example, is that email can be triaged, you can decide if something needs to be responded to now or it can be responded to later.

Sam Corcos:

Some of the other tools that Superhuman allows you to are I think they use the term snooze, but really scheduling is the term, where you can read an email and say, “All right, I need to revisit this in two weeks,” and you can schedule it to resurface in a couple weeks. So getting to inbox zero is really the critical component. Superhuman really enables that and makes it a lot easier.

Dr. Amantha Imber:

I know that you’re a big fan of snippets in Superhuman. Can you talk about what a snippet is and how you use it?

Sam Corcos:

Yeah, anybody’s who’s worked in customer support knows a lot about snippets. A snippet is a common phrase or language that you use in many, many communications. I think right now, within Levels, I think something like 70% of our communications we already have an answer written for it, which is pretty high. I know that for a lot of the emails that I process, I would guess maybe half of the emails are largely written as a snippet, because a lot of the communications that you do area generally consistent. I have a snippet for grabbing a time on my calendar, to use as Caldendly to schedule something, and that works super well. I schedule a lot of things, so it’s useful to have a snippet instead of typing it out every time.

Sam Corcos:

Oftentimes you can compose emails from multiple snippets. I have some snippets that are basically a list of investors asks. I ask a lot of things from our investors. I think that snippet is maybe 20 items long, and I keep it up to date and as I go through the process of asking for things from our investors, I’ll paste the whole snippet and then I’ll cut out all the ones that we don’t need.

Dr. Amantha Imber:

Now, I want to talk about your calendar, and I know you think about delineating between maker versus manager time, to take from Paul Graham’s famous essay on that. But to start with, I guess, can you talk about the different between maker versus manager time, and then how you schedule that into your diary?

Sam Corcos:

Yeah, definitely. It’s something that I guess I would say I’ve learned the hard way. This is actually my first nontechnical role. Historically, I’ve been in software development, usually the person that’s writing code, or in engineering leadership. The first time I really took a leadership role in engineering and was doing a lot less programming, the challenge that I ran into is, and I found it very hard to communicate this to people inside the company who were not software developers or not technical, was how if I have a 30 minute meeting at 11:00 AM and at 3:00 PM, I can’t get any work done the whole day. They’ll say, “Well, it’s only one hour. You still have the whole rest of the day to work.” And it’s just like it really doesn’t work that way when you’re trying to get into a flow state. I can’t work up the emotional energy to even start working on this project if I know that there’s a high likelihood I’ll be interrupted in the middle of it. The different between manager and maker time is manager time, it’s constant context switching and it’s really not a flow state.

Sam Corcos:

It’s jumping in between tasks, and maker time is you’re deeply focused on one thing, and writing code is a perfect example of maker time, any time you’ve been in a flow state where you just lose track of time. There have been times when I’ve been focused on coding and 10, 12 hours go by and I haven’t even looked up at the clock. They’re both useful and important, and the thing that I discovered about myself is that, especially when you’re in engineering leadership where you really have to do both roles, you’re still coding but you also have to manage, I found that intra-day context switching was the problem, not inter-day, and by that I mean jumping from coding to meetings to coding within the same day was what was causing me most of the emotional turmoil. Whereas if I just said, “Meetings are on Mondays and Tuesdays are only programming, I’ll take no meetings, Wednesdays, I’ll do meetings again and no coding,” if I just accepted certain boundaries around it where I would have maker days and manager days, it ended up working pretty well.

Dr. Amantha Imber:

So what do you currently do at the moment? What does a typical week look like for you?

Sam Corcos:

Yeah, it’s funny you say that, because I’m actually in the midst of writing a content piece on how I spent the first two years at Levels, because I pretty religiously keep track of my time. Every 15 minute increment of how I spent my time is in my calendar, so I can retroactively really quantify how I spent my time. What’s funny is that I’d say one of the biggest things is, especially as a CEO, you end up wearing a lot of different hats. There were three very distinct periods in the company’s history where I was basically just a programmer, and I was an individual contributor writing code, because that’s what needed to happen. There were other times, I spent the entire month of May last year on sales and marketing and I just called hundreds of people to try to convert them and to learn from them and do user research, really for the growth team.

Sam Corcos:

Right now, my job is mostly email. I spent a tremendous amount of my time on email, and I think of my role as if the company is a steam engine, my job is really just to be the lubricant. I don’t really have a lot of specific deliverables. My job is to make sure that all of the component parts are functioning effectively and are well-resourced. On a typical week, I would say that certainly for the last month or so, I’m doing a lot of engineering interviews. We’re adding a lot of people to our engineering team this year. I think since February, I’ve averaged between 30 and 40 interviews per week.

Dr. Amantha Imber:

Wow.

Sam Corcos:

Yep. One of the nice things is that, because our team is so capable, I’m able to really singularly focus on one problem and really execute on it effectively. One of the challenges that a lot of startups that I advise run into is the CEOs in particular are pulled in many directions and they have a lot of deliverables they have to do on many different parts of the company. I’m fortunate in that my role is, since probably January, has been largely redundant within the company. I could take a week off and probably nobody would notice, which is very much the goal.

Dr. Amantha Imber:

Now, I want to know what you learnt from tracking your time in 15 minute increments for two years.

Sam Corcos:

Yeah, man, there were a lot of things. I think the biggest one was how wrong I was about how I actually spent my time. I made some predictions in advance of writing this piece on how much of my time went to different types of activities. A couple things that I thought I was spending a lot of time on, one is strategy and thinking about company strategy, and we have a tremendous amount of documentation, I would say way more than the average company of our size. I would have guessed that I probably spent 20% of my time on strategy, and when I analyzed the data, I actually spent about 4% of my time on strategy. Similarly, I thought I probably spent 20% of my time on recruiting, because it felt like I was talking to a lot of people looking for next hires, and I only spent about 2% of my time on recruiting, which was even more surprising. It made me realize that there are certain types of activities that have a disproportionate emotional cost than actual time cost.

Sam Corcos:

The example around strategy is that it can be hard to work up the emotional energy to sit down and write a five page document, but that might actually only take you about an hour, and yet it feels a lot less time to have 10 one hour conversations with different people on your team that doesn’t actually even do a very good job of aligning people, because there’s this game of telephone where you feel like you told them what you thought you told them, but they interpreted it very differently. So it might feel like it’s less work but it might actually be 10 times the amount of hours, with a suboptimal result. That was one of the big lessons was that there are certain activities that I seem to recognize their value but I shy away from in terms of actual time spent.

Dr. Amantha Imber:

That’s so fascinating, just the difference between what you were expecting and what was the output. Having actually been sent a lot of your strategy documents in advance for preparing for this interview, I can certainly attest that it feels like you’re doing a lot of work there.

Dr. Amantha Imber:

Hey, there, it’s nearly time for another ad break, but can I ask a favor of you? If you’re enjoying How I Work, I would love it if you could leave a review or a star rating and a massive shout-out to the hundreds of people that have done this. I’m truly grateful for you taking a little bit of time out of your day to do that. Okay, Sam will be back after this break to talk about his favorite apps for boosting productivity and what exactly this quarter think week looks like.

Dr. Amantha Imber:

Now I want to know about what’s some of your other favorite apps for productivity outside of Superhuman?

Sam Corcos:

Yeah, I mean, Google Calendar. I think that one of the biggest unlocks for me was using my calendar as my primary mechanism for time management, and in terms of tasking as well. I used to keep a to-do list, which I think is sort of the default that everyone has, is a to-do list. The challenge that I kept running into is, especially with digital to-do lists, to-do lists can become infinitely long, and they feel infinitely long. I remember a couple years ago, my to-do list was so long it was several lifetimes amount of work that would be required to actually get to the bottom of this list. So I started using my calendar to proactively block off time, so when I would have a task like maybe it’s write the content piece on how I spent the first two years of my time at Levels. I will proactively look at my calendar and I’ll block off… I would expect it’ll probably take me six hours to write it, so I’ll block off six hours to write that piece.

Sam Corcos:

Similarly, if there’s something about running errands or writing a strategy document on how we think about podcasts, I’ll block off time on my calendar instead of adding it to my to-do list, and I found that this was a… it was probably the most powerful mechanism for just personal anxiety reduction. Because your to-do list can become really optimistic on the things that you can get done, because you can attach an amount of time to each individual item. Like, all right, well, this task takes three hours, this takes four hours, this takes two days, this takes four days. But unless you map it onto the chronology of your actual time, you don’t really know how long it takes and you end up dropping a lot of balls.

Dr. Amantha Imber:

What are some other apps that you’re loving for productivity?

Sam Corcos:

Let’s see, I use TextExpander, which is basically snippets outside of Superhuman. It’s much more extensible. I haven’t used a lot of the extensible functionality. I think in TextExpander, you can tie in and integrate APIs to run different commands and actually interact with a much more robust set of tools. I use it for a lot of common things that I end up typing, either in Terminal or in the console or in text messages. I use TextExpander for a lot of my text message communications. I would say the biggest thing is just to keep things as asynchronous as possible. I would say a lot of my productivity tools would be anti-tools. I would say to the greatest extent that it’s possible, your phone should be on do not disturb mode by default, as mine is, turn off notifications, don’t use Slack, or if you do, use it with a very specific set of SLAs. For example, we use Slack at Levels, but explicitly Slack is not the primary mechanism for communication.

Sam Corcos:

Slack is really just for updates, and there’s no expectation that anyone will respond to a message in Slack within 24 hours, and it prevents this fire hose effect of information, because information on Slack, it’s… Slack is a synchronous tool that pretends like it’s an asynchronous tool, because you have the same expectation that people will respond immediately, but it’s written, and things just get lost if you’re not paying attention in real-time. So I think that focusing on things that are asynchronous by default is really the most impactful way of being productive, is to really emphasize deep, focused work and to eliminate distractions to the greatest extent as possible.

Dr. Amantha Imber:

Now, I know that Calendly is one of your favorite apps. Can you tell me, for listeners that haven’t come across Calendly, what it is and how you use it?

Sam Corcos:

Yeah, I use Calendly pretty religiously. Calendly is useful for me because I keep such a rigorous calendar. Calendly syncs with something like Google Calendar, and it allows people to find open spots on your calendar that you designate, and it allows them to schedule basically self-serve. The typical way that scheduling works is you email somebody, they say, “Cool, I’m available at these times.” You look at your calendar, you check all those times, you say, “Oh, well, I’m not available those times but I am available these times.” They say, “Oh, well, I’m not available those times. How about these times?” It takes multiple days oftentimes to schedule something. Calendly just pulls in the data from my calendar and just lets somebody pick a time that is open. I probably send five plus Calendly links every day for people scheduling things on my calendar. I also let it go three months out, and so yeah, it’s a really great tool to cut through the complexity of scheduling.

Dr. Amantha Imber:

Now, I’ve heard that you have a think week every quarter. What does that look like?

Sam Corcos:

It’s something that I highly recommend to anyone in a strategic role. Every quarter, I take a week, I would say off-grid, but not necessarily without access to internet or whatnot. I actually really like having access to internet. For me, I will often spend a lot of that time reading and reflecting and writing. I do a lot of writing. I’ll often come out of these think weeks with 50 to 100 pages of writing on company strategy or personal reflections or writing of content pieces. I find writing to be a really satisfying activity, and so it is usually during these think weeks that I come up with some of my best ideas, because I don’t taking any meetings, I don’t take any calls. I really just focus as much as I can on the big picture. So a lot of my best ideas have come from taking time away from the day-to-day, when you can think more holistically about your company and what the goals are and what the trajectory is and what the hiring plan is. I find that I’m in the day-to-day, it’s really easy to miss the forest for the trees. So yeah, I usually do it somewhere that’s slightly remote, be it Joshua Tree or Yosemite, but still relatively accessible.

Dr. Amantha Imber:

How do you structure the week? Are there questions or tasks or things that you bring in to guide you?

Sam Corcos:

Yeah, definitely. One of the consequences of keeping such a rigorous calendar is I actually, I have my next think week planned and I already have all of the days blocked off for the things that I’ll be working on those week. As ideas come up, and I realize that I am not going to have time to rethink the primary business model of the company, I’ll jump ahead to my next think week in my calendar and block off a whole day to just think about business model or if it’s for something completely unrelated, something, like a personal thing that I want to reflect on, I can block off a whole day for that. I would say that they’re usually mostly structured in advance of even getting there.

Dr. Amantha Imber:

On the topic of health, what are some of your habits or routines or things that you do that help you stay healthy?

Sam Corcos:

A lot of it has to do with diet, which is not surprising. I try to avoid sugar. That’s really the big one. I try to avoid sugar and refine carbohydrates, but sugar’s really the big one. I go on a lot of walks. Pre-COVID, I think I averaged something like 10 miles per day of walking. I would take a lot of my calls on walks. Most people would do Zooms and I would mostly do walks. I found that that’s just a really good way of getting steps in and staying active. I also really focus a lot on sleep. I try to get a minimum of eight hours of sleep a night, which is surprising to some people but I think sleep is incredibly important, especially when you’re doing strategy work or deep, focused work. Being well-rested, it makes such a huge impact on my ability to perform.

Dr. Amantha Imber:

I’ve heard that you’re having less coffee these days and more tea. Is that correct?

Sam Corcos:

Yeah, I’m trying to cut back. I go through these cycles where I start with one cup of coffee and that becomes three, which becomes five. When you start getting to the point where you’re measuring caffeine consumption in grams and not milligrams, that’s when you know that it’s time to cut back. So yeah, I still have the habitual crutch of a warm liquid, so I’ve been trying to switch to ginger tea and other types of green tea that have less caffeine. But I go through these cycles, and it’s funny, I remember the last time I completely went off of caffeine for probably a month, and then I had my first cup of coffee from a Starbucks, and I remembered that caffeine is definitely a drug. It is a very different feeling when you have caffeine having not had it for a month, and it’s like, whoa, this is a potent substance. But when you’re addicted to it and you just have it every day, it’s a sort of more of a habit.

Dr. Amantha Imber:

That’s so true. Now, I want to talk about Levels. I’m fascinated by the Levels patch, and I will preface this by saying I’m a bit of a nerd when it comes to health, so something I did a few years ago when I discovered a company called DayTwo and I’m sure you’re very familiar with them, but for those that are not, DayTwo is essentially a company that draws on a lot of research that suggests that individuals have very different responses to the same kind of food. So if you take something like white bread versus sourdough bread, most people would assume that your blood glucose levels would spike after the white bread and not after the sourdough bread, but in fact it depends completely upon the individual, and I found that fascinating. So DayTwo then take your blood test data and they get a poo sample, and from there, they’re able to predict using I imagine what are quite sophisticated algorithms, what every individuals person response will be to certain types of food.

Dr. Amantha Imber:

But couldn’t get it in Australia. So, I spent two weeks, I got a little finger pricking diabetes kit from the chemist, and I pricked my fingers, or a finger, although I probably went through all 10 of them, by the end of the two weeks, every half and hour, to measure what my blood glucose response was to different types of food, so that I could eliminate that spike and have better energy. But, what you are working on does that in a much easier way, so can you talk about what this patch is?

Sam Corcos:

Yeah, totally. We use off the shelf continuous glucose monitors. They’re manufactured by Abbott and Dexcom. They’ve been on the market for quite some time for diabetes management, and what they do is they give you a real-time stream of your glucose data. It’s a patch that sits on your arm. So it makes it such that you don’t need to do the finger pricks and you get a much more comprehensive data set. One of the challenges of using a finger prick is that you can often miss the entire peak of the spike, and so you don’t capture all of the data and you might miss the actual response. So we use that to show you how different dietary choices, be it potatoes or asparagus, how these different choices that you’re making are affecting both your long-term health but also really how you feel.

Sam Corcos:

My big learning for my own personal life was how closely tied my energy levels were to my glucose links and how a lot of the things that I was doing that I assumed were really healthy, specifically steel-cut oats and oatmeal. For basically my entire life, I’d been told that oatmeal is the healthiest breakfast and I think it was the first or second day I was wearing a glucose monitor I had this just a 12:00 crash. And I checked my levels and my blood sugar had spiked into ranges that healthy people are not supposed to be able to see, and I had crashed into deep hypoglycemia. Looking up the symptoms of hypoglycemia, I was having shaky hands, feeling tired, unable to focus, and it was just this recognition that all of these things are just hypoglycemia, and it’s what’s called a postprandial crash, when your blood sugar goes up really high and then your body produces a bunch of insulin to counteract that, and it often overcorrects, you end up with low glucose.

Sam Corcos:

That’s when you start feeling really weird. So that’s the core of the product is using really a lot of different data points starting with glucose to try to model the way that your body responds to different choices, so you can live a healthier life.

Dr. Amantha Imber:

Are there any other gadgets or health devices that you use to track data or live a healthier life?

Sam Corcos:

I’ve used the Oura Ring for sleep tracking. I don’t use it currently but I’ve used it before, and that was a really helpful tool. It gives you… I would say the biggest learning that I had from Oura, it’s interesting how you can read something on the internet and it’s very different to experience it data. I’ve read that having alcohol before bed is bad for sleep quality. It’s a very different thing to see it reflected in the data, having like two glasses of wine and then you look at your data and the ring knows, based on your heart rate, based on the number of times you tossed and turned, just how bad it actually is. So I’ve reduced my alcohol consumption, which already wasn’t very high, but pretty close to zero. I’ll probably have a couple units of alcohol at month at this point. It’s just it’s not worth it for me.

Dr. Amantha Imber:

Now I know that Levels is not available in Australia at the moment. What’s the timings on that?

Sam Corcos:

Yeah, hopefully as soon as humanly possible. We’re still in beta. We probably will be until I’m hoping sometime in Q3 of 2021. We actually brought on Josh Mohrer, who was the general manager of Uber New York to help lead international expansion and I think Canada, UK, Australia are the first countries we’re looking at to expand to, so I would say optimistically some time the end of this year, probably sometime next year.

Dr. Amantha Imber:

For guests that are keen to connect with you and Levels in some way, what is the best way for people to do that right now?

Sam Corcos:

Yeah, so I would say the best place to get information on metabolic health is the Levels blog, just levelshealth.com/blog. I’m on Twitter @SamCorcos. You can also follow us on social media @Levels on Instagram and on Twitter.

Dr. Amantha Imber:

Amazing. Sam, it’s been absolutely fascinating chatting with you and just how deeply you think about all things productivity and managing your time. So thank you so much for giving me some of your time in your calendar. I’ve just loved our chat.

Sam Corcos:

Absolutely.

Dr. Amantha Imber:

That is it for today’s show. Next week on How I Work, I’m very excited to have Gary Mehigan, ex-MasterChef judge. We talk about all sorts of things, including his top tips for the kitchen through to bouncing back from challenging times, which Gary has had a bit of experience with. If you’re keen to hear that interview, hit subscribe or follow wherever you’re listening to this show from. How I Work is produced by Inventium, with production support from Deadset Studios. The producer for this episode was Jenna Koda and thank you to Martin Imber who did the audio mix and makes everything sound awesome. See you next time.