Trekking and Ski Gear

When I buy equipment, I research it intensely and I am sharing my picks below in case they are useful for you. I’ve put these gear picks to the test by skiing (12 resorts) and trekking (places like Kilimanjaro, Annapurna Circuit) in harsh conditions over the last 5 years, with some pictures below.

If you buy proper, high quality gear, it is re-useable for both trekking and skiing and will last a really long time. I don’t have any perspective on style (as you can see from my pictures), and this post is primarily about function and some of the products that I like.

Summary

Here are the main takeaways in case you don’t care for the details:

  1. Dress in layers – you’ll typically need a base, mid and outer layer for cold weather.
  2. Your first layer should be merino wool, if possible, as it’s functional in hot and cold weather and you can wear it for a long time without it getting smelly.
  3. Your outer layers should be high quality Gore-Tex shells, particularly for your jacket. Make sure your jacket has a hood.
  4. Get a neck buff. It’s the most versatile thing that I have, and a lifesaver.

Layers

When you buy your gear, it’s best to buy in layers vs integrated (insulated) items. It’s definitely more expensive, but quality gear lasts a long time, is more versatile in seasons, and really makes a difference to your comfort level in harsh (freezing, windy) conditions on the mountains.

  1. Base Layer: Get good quality merino wool base layers for your tops (1 short, 1-2 long sleeve) and bottoms (1-2 underwear, 1-2 tights), and socks (2-3 pairs). This will last a long trekking trip of up to a week, and a week long ski trip, minus the underwear. For value, I like Smartwool, but my preferred merino wool baselayers are from Mons Royale, which are good quality and slightly more thoughtfully designed.
  2. Mid Layer: You really just need one mid layer jacket. I LOVE my Patagonia Nano Air with a hood. I’ve bought one of these for everyone in my family. I also recently read the founder of Patagonia’s book “Let my people go surfing” and it’s hard not to be inspired by his authenticity.
  3. Outer Layer: Get a good Gore-Tex shell jacket (not insulated), and this is more important than trousers. I got mine from Arc’teryx but their stuff is pretty pricey. I got my trousers from Arc’teryx too, as they have some nice synergies (jacket clips to pants) but you can easily get more affordable trousers if you’re budget constrained.

Merino Wool

Merino wool is the best! It’s so much better than synthetics for long trekking trips and ski trips. It keeps you cool when it’s hot and warm when it’s cold, still performs well when it’s wet and you can wear it for 2-3 days without it getting super smelly. It’s more expensive, and a little harder to take care of as you need to wash it in cold water and hang it up to dry. The performance and comfort improvements are well worth the trade off. Here is a good summary of the pros and cons if you want more info.

Outer Layer

I’m not a Gore-Tex expert (good article here) but have owned a few jackets now, and think they are all pretty fantastic. The jacket I have from Arc’teryx is made from the Gore-Tex Pro material which has 3-layers of material to make it even more waterproof and durable. I really like the Patagonia shells too, and they come in at a slightly lower price point than Arc’teryx. Make sure your jacket has a hood (so useful for keeping warm and dry) and make sure that the hood is big enough to fit over your ski helmet.

Neck Buffs

A good neck buff is so useful – it protects your face from wind on the chairlift or if there is ice smacking your face and keeps your neck warm. It’s a must have on trekking and ski trips. Here is the neck buff I have, which is merino wool from Mons Royale (around $30) and it’s great.


A lot of this gear is expensive, and if you buy it all it can add up. You can almost always get everything on sale; I bought almost everything at least 30% off retail. If you look after the equipment, it can last a really long time. My shells are seven years old and still in great working condition. On a cost per wear basis a good quality product always ends up being worth it versus. a lower quality product. Also when you are at the top of a mountain, freezing your tushie off a little less, you’ll thank me.

A Virtual Funeral

My great uncle, Taher, passed away this weekend at the age of 98 years old in my childhood home in Mombasa. He was more like a grandfather to me, as I grew up in the same house as him and saw him every day and my paternal grandfather died many years before I was born. He lived a long and loving life, I will miss him and always think of him when I have soft serve ice cream (his favorite).

Current conditions made it impossible to travel to Mombasa but we were able to have a virtual service for him (over Zoom) a few days after he died. Around 100 people attended from many countries around the world to celebrate his life and one of our family members even organized a priest to come and officiate.

In many ways the service was more inclusive and better than an in person ceremony. We were able to welcome people who would not have been able to attend – because of the distance, cost, time, or their ability to travel (age, health or dependents). Both of his surviving sisters in their 90s were able to brave the technological challenges to say a few words in his honor and we were able to share some photos and memories by sharing our screens and taking turns to speak.

I missed some of the tactile elements of being together (like giving folks a hug), and the longer in person time after the service. However, the positives outweighed the negatives given how quickly it all happened, and how difficult this kind of situation is for people to plan for.

Zoom Service

In a time where most of the focus of the web is how we can adapt to working in a distributed way, it’s also wonderful to see us use these tools for bringing our communities together for a shared purpose as well.

Seeking Leverage

Leverage allows us to amplify the impact of our creations and decisions. If we apply leverage to these things we can create more value for the amount of time invested. Leverage is not easy to attain, and the different forms of leverage either don’t scale easily or require specialist skills and the ability to distribute creations effectively. I’ll summarize the inspiration behind this post, and then go into the different types of leverage below.

Inspiration

I listened to Naval’s Podcast Series a few months ago – I don’t love the title of the series, but I agree with many of his principles. Here is a link to a set of Tweets from him which are a little faster to digest, which catalyzed the podcast.

Here are a few of my favorites from the Tweets:

  1. Seek wealth, not money or status. Wealth is having assets that earn while you sleep. Money is how we transfer time and wealth. Status is your place in the social hierarchy.
  2. Pick business partners with high intelligence, energy, and, above all, integrity. Don’t partner with cynics and pessimists. Their beliefs are self-fulfilling.
  3. Learn to sell. Learn to build. If you can do both, you will be unstoppable. (Aadil Note: The two things we were never taught at business school).
  4. Leverage is a force multiplier for your judgement. Fortunes require leverage. Business leverage comes from capital, people, and products with no marginal cost of replication (code and media).

Gated Leverage

Gated leverage requires an outside party to agree to give you leverage and does not scale without additional marginal cost – for example, raising money from an investor or recruiting a new person to your team still takes incremental time and effort.

People

If you have people working for you who are able to execute your ideas you can (in theory) make more decisions for greater output versus doing it all yourself. This is not costless leverage as recruiting is expensive, developing trust and high performing relationships is difficult, and alignment between people as you scale is challenging. People can be amazing to bring in new skills, different ideas and make a product or organization better but they are not my favorite source of pure leverage.

Capital

Let’s assume you spend 100 hours developing a well reasoned theory to pick an investment (e.g. buying Amazon stock in 2011). If you have $100 of your own capital to invest and it returns 10x, you make $1,000. If you have $1,000,000 to invest because you raised money from others (let’s assume you get 20% of the upside), you would make $2,000,000 in the same scenario. The amount of time you spent crafting the thesis remains constant but the returns are much larger if you have more capital. This is not costless, because you have to convince other people to part with their capital and trust you with it unless you are already wealthy.

Scaleable Leverage

Scaleable leverage has zero marginal cost of replication, and does not require someone else to agree to it. This is the best kind of leverage as it can create value even without ‘active’ involvement from you. Code and Media are both great forms of leverage but distribution and discovery of your code and media is still a requirement for success.

Software

A line of code can be deployed and distributed at scale with very little marginal additional cost. Servers are constantly available, and users can interact with your technology whether or not you’re actively working on it. Imagine, if like a doctors office, Google Search was only available from 9am-5pm, Monday to Friday.

Media

Books, Blog Posts, Podcasts, Youtube videos are all good ways of getting your ideas across at scale. The cost of creating the content is fixed but the marginal cost of a user downloading another podcast episode or viewing another blog post is essentially zero.


Scaleable leverage is both responsible for a lot of wealth creation for modern content creators and technology company builders, with very little invested capital for the relative impact. I think that this kind of leverage will grow in popularity and impact, whereas many companies of the past were built with Gated Leverage.

I would like to spend more of my career seeking scaleable leverage. Working in technology and investing in startups (for equity) will hopefully allow more passive wealth creation than purely ‘renting’ out my time.

Raspberry Pi Setup

A Raspberry Pi is a super cheap ($35-60) computer. I spent a few hours setting up a Raspberry Pi, connecting it to my home wifi, enabling remote access and setting up WordPress.

My goal was to get a home network set up and give myself a platform to try things like hosting a WordPress locally, play with mini home automation projects (e.g. change the light outside my door when I’m in a meeting), or a long horizon timelapse of each day outside our window with a cheap camera.

What do you need?

I spent around $100 to get all these components (with Amazon links):

  1. Raspberry Pi 4 (4GB Ram)
  2. Micro SD Card (32GB)
  3. USB C SD Card Reader (for Macbook Pro)
  4. USB C Charger (for Raspberry Pi)

What can you do with a Raspberry Pi?

I read a bunch of articles, but here are my a few that I recommend:

  1. A couple on Hacker News with my favorite being the good samaritan who shared the live bus schedule with travelers
  2. Hardware add ons and corresponding use cases
  3. A good write up of all the home automation software options
  4. Home automation ideas here and here
  5. Set up a WordPress site

How do you set it up?

I pretty much followed this guide, which was pretty good, and it’s designed for folks who want to use their Raspberry Pi without a screen, as a stand alone device.

The main steps are:

  1. Install the Raspbian operating system on your SD Card (don’t bother with the Etcher step, you don’t need that)
  2. Set up your Raspberry Pi to connect automatically to your home WiFi (SD card slot is on the other side)
  3. SSH into your Raspberry Pi and change your login credentials
  4. Download Real VNC and set up and update the operating system
  5. Install and set up Docker to allow containerization of applications
  6. Install a web app (I installed WordPress afterwards)

A couple of other useful videos are:

  1. Raspberry Pi getting started beginners guide from Crosstalk solutions, but it assumes you have a screen plugged in.
  2. Useful video guide for explaining Docker and containers but it’s a little more technical and in depth.

How To SET up WordPRess?

I followed this guide which let me set up via command line (not using Docker). This was pretty straightforward except when installing MariaDB which needed s different command to install (updated below):

sudo apt install default-mysql-server php-mysql -y
Success!

I’m looking forward to playing around with this some more, and potentially investing in some light home automation in the future.

Product Roadmaps

Over the last few months, I’ve been thinking about how to design a lightweight framework for product development that fits in with different ‘product cultures’ and scales from a few teams of a few people to up to 50 people.

My current ‘best guess’ of this is a modified version of the Now/Next/Later framework that Noah Weiss nicely laid out here. For each product line I’d recommend a separate roadmap of this otherwise it gets pretty unwieldy. You can always roll up specific projects into a higher level company level view, if needed.


Principles

Here are some principles that I suggest for your roadmap:

  1. The product roadmap needs to be publicly visible and easily accessible to folks in the whole organization.
  2. It needs to be easy for folks outside the immediate executing team to add ideas or requests to the ‘New’ section for triaging.
  3. Ideas should be tracked from ideation to completion without duplication of work to update projects by lots of unconnected tools.
  4. The tool you choose is not important, as long as everyone uses it. I’ve enjoyed using Asana in the past (although they don’t integrate super well with other services).

NEW/NOW/NEXT/LATER

New (Inbox) : This is where all new items start to be prioritized. Items could be anything from large feature ideas, bugs or feature modifications. There should be a clear owner for prioritizing these items, usually the product lead, or on call engineer depending on the type of issue. Large projects should be broken up into milestones and prioritized. Try and keep this section at ‘Inbox Zero’.

Now (In Development) : This is what the team is actively working on right now, in order of priority. These tasks should be assigned to individuals on the team and usually correspond the the current sprint. Tasks in ‘Now’ are granular and well defined and have a clearly scoped deliverable and timeline. If you want more granular ordering or filtering in this list, I suggest tagging tasks by priority (e.g. P1, P2, P3).

Next (On Deck): These are the tasks/features that the team will work on in the next 1-2 development sprints. Tasks in this section should be in rough order of priority and have some definition around them, but may be broken up into more specific tasks when they move into the ‘Now’ bucket.

Later (Icebox): These are items that are unprioritized, but you know you want to get to them at some point. They could be bugs, loosely defined features, or feature modifications which should be tagged for clarity. The order or specificity around these is less important (especially for features) as you will prioritize and add more definition when the time comes.

Not Doing (Pit of Despair) : This bucket of tasks is usually hidden but is a list of ideas that you have explicitly decided that you are not doing. I suggest adding in a comment into the task to articulate the reason why you are not doing it, before moving it to this ‘Not Doing’ bucket.

In addition to the execution priority, it’s also useful to include some way to show the relative importance of tasks, so you can clearly see what tasks in the sprint can not drop. I suggest a Priority and Project Size tag like I’ve shown below.

This is an example of what a product roadmap could look in Asana:


In an ideal world, the tool is easily used and accessible by everyone in the organization and tightly integrates with other product development tools you use – e.g. Figma, Github, Google docs. Asana does not do a great job here and it’s hard to get information out of Asana if they whole company does not use it (which probably improves their retention, but makes it a worse tool overall).


Central Teams

These principles don’t just apply to user facing product development teams but would be also useful for ‘central teams’ like data/analytics or platform teams who are working cross functionally with folks across the organization. These teams often have ‘requestors’ of their time and expertise. It allows for better visibility into work and timelines, and also provides a structured system to ask for help or request reprioritization of work which hopefully leads to better visibility and trust between ‘central’ teams and ‘product’ teams.


Every company is different and each team may have different norms, but having a set of common principles, common tools and a shared language can improve visibility and reduce the switching costs for managers who oversee lots of projects and individual contributors moving between teams.

Investing in Africa

I’m frequently asked ‘why’ I invest in startups focused on Africa, and this post attempts to clearly articulate the reasons this is important to me.

I was born and raised in Mombasa, Kenya and my family has been in here for 5 generations (since the 1850s). I grew up in relative privilege compare to most Kenyans. I remember being about 6 years old sitting in our car when a homeless boy about my age knocked on our window. My father opened the window and handed him some candy, and turned to me and said ‘You are sitting here and that little boy is out there. I hope you appreciate that was luck of the draw and will do something good in your life’. I remember that moment quite clearly even now, over 30 years later.

There are many reasons for my interest in investing in Africa, and I don’t pretend that I invest out of altruism, but I think this is what led to my interest in supporting early stage entrepreneurs on the continent.

I always liked maths and science and studied engineering at university. This experience taught me to approach problems from first principles and think through effective systems. I don’t really have skills that I can directly help people (e.g. a doctor), so I needed to approach the problem space differently. In my early 20s, I realized that entrepreneurship and technology could drive economic development, in a relatively capital efficiency manner. I started building my career in technology, starting at Google in London. After spending time at Index Ventures and learning about venture capital, I realized that, with even small amounts of capital, you could have outsized returns both in terms of value creation and impact.

Technology entrepreneurs create products that improve the effectiveness for people and businesses, and create new jobs with new skills. Given all these benefits I decided to start investing in technology companies in Africa a little over 5 years ago, after ‘learning to invest’ in silicon valley as an angel through my own fund, Musha Ventures starting in 2011. As an inexperienced investor, I tried to maximize learning per dollar invested, as I did not have a lot of capital. I tried to be disciplined by writing investment memos (that no one read), conducting reference checks and completing annual reviews for every company. 

In 2014, there was little capital available for early stage entrepreneurs in Africa and even today in 2020, there is still a deficit of capital available for those who don’t have the right networks. With small investments I am hopeful that I’m able to have an outsized impact on this ecosystem. Even when I don’t invest, I try and give entrepreneurs feedback, be clear on my reasons for passing, or share articles or advice that I think might be valuable to them. 

There have are some early positive signals; my Africa portfolio has rougly doubled in value (on paper), and the companies have created thousands of jobs, enabled new startups to exist, and improved efficiency in archaic supply chains / markets. Despite these early signals, it’s still very early in the life of the venture capital ecosystem in Africa and it’s still unclear if these companies will endure and to have a lasting positive impact on the economic development and people’s lives in the markets. Only time will tell.

My plan, which has remained consistent over the last 5 years, is to continue to think very long term and invest consistently and conservatively in early stage (mostly B2B) technology businesses in Africa and support entrepreneurs doing the hard work along the way. 

Physically Distant, Socially Close

I don’t love the term ‘Social Distancing‘ that’s being thrown around by the media as it implies that isolating ourselves will leave us devoid of meaningful social interaction.

I’ve been physically distant from my family for over a decade – I live in NYC, my parents are in Mombasa (Kenya), and my sister lives in London. We are physically distant but still have a lot of social interaction primarily over WhatsApp and FaceTime.

I FaceTime my mum (and dad) for about 2-5 minutes every day during my office commute and we chat on our ‘Family WhatsApp’ on a daily basis. This allows us to maintain close social bonds despite being physically distant.

I don’t think this is a substitute (or better) than in person interaction. Being in person socially gives you more data points (3D vision, touch, smell) and is more engaging. It’s also easier and more engaging to have a group conversation in person vs. over video calls.

I’m quarantined in my apartment in NYC away from my wife (who’s with her parents), as I recently traveled internationally (from Kenya) and am probably at risk.

We now have lots of amazing communication tools (e.g. Zoom, Slack, WhatsApp) and good internet which allows for better, more engaging social interaction when physically apart. I’d be excited to try and use these tools (and others) to connect with friends, family and colleagues and be intentionally even more empathetic and compassionate with each other during this time of required physical isolation.

I’m personally going to try to make time for meaningful social interaction – e.g. having ‘dinner’ with my wife over FaceTime, or a glass of wine with my cousins over Zoom, scheduling a Peloton class with a friend and playing games over Zoom with a large group of friends for their virtual birthday party.

Mental Models for Giving

I’ve been developing my own mental models for giving time and money away. This is a deeply personal subject and each person will think about it differently. I’m sharing these mental models to learn from others and record my thoughts at this point in time.

I gravitated towards Peter Singer’s work on Effective Altruism (if interested his Ted Talk, and Vox Podcast are a good start). Peter talks about how we are all probably consuming too much and not giving enough away. He makes the point that it may be more effective to apply yourself toward higher income activities (that hopefully you enjoy) and then giving these earnings away to the poorest people. This could potentially be a more efficient and impactful way to give (on a unit time basis) versus spending your time running a charity.

My parents have also been involved in our community in Kenya for many years – my father runs our small family foundation which supports healthcare and education, and my mother started the Elimu Foundation which supports primary education in Mombasa.

There are a few mental models that I’m currently exploring below.

Time vs. Money

It may make sense to give your time away or your money away or give a little a bit of both depending on your circumstance.

  • Money may be more effective than time: If you make a very high income, it may make more sense to spend more hours making money, and then give away that money – 1 hour of your time volunteering may be way less impactful that 1 hour of the value of your earning power.
  • All time given away is not equal: If you have a lot of expertise in a specific field (e.g. a surgery) it might be much more effective to perform operations vs. go to a village and use your body/time to dig a well.
  • Non-outcome orientated factors matter: What is most effective may also not be the most fulfilling or enjoying to you personally. This is something to take into account when you decide if and how you’d like to give.

Efficiency vs. Community

A fundamental principle of this section (re: efficiency) is that ‘every human life is equal’ and that an additional dollar given to someone in extreme poverty (<$1.25 a day) would have a larger impact than an additional dollar given to someone who is not living in extreme poverty.

  • Heart vs. Head: There is an interesting tension between giving away in the most effective and efficient way (more data driven) and giving away your community (less data driven).
  • Community giving: Giving to your local community can have additional benefits beyond the impact you’re having to the end cause. It can improve social bonds (supporting a colleagues charity run), give you a regular emotional boost (giving money to the homeless person you pass every day), improve the quality of service (tipping your building doorman a little extra) or improve your standing in your community (being thought of as generous or kind).
  • Efficient giving: There are good resources online like GiveWell that take into account levels of funding, the efficiency of the organization (what % of capital reaches the end person) and the impact of each dollar donated. This is a more rational way of investing but you don’t get the benefits of giving to your community beyond the knowledge that you are probably having more impact per $ given away.

My Current View

I personally like a barbell approach. For example, one could volunteer in a local shelter (100% time + 100% community) for a few hours a week and also donate 10% of their income to Give Directly (100% money + 100% efficiency). This helps to satisfy both heart and head.

I support Give Directly, as I worked with the folks behind it very closely and can vouch for both their character and their data driven (impact and efficiency) approach to giving. It’s an added bonus that much of the money goes to E.Africa, which is where I’m from and I’ve personally visited the communities and homes of the beneficiaries.

I also try to give, to a lesser extent, time to my community (e.g. mentoring entrepreneurs), and money (school fees for a tennis coach, or paying for a porter’s guide training course).

When and how much to give?

I don’t have refined mental models for how much (money) to give and when to give and I’m sure this will vary greatly depending on my stage of life. I have been thinking through the following open questions:

  • The biggest question I have is “give now vs give later“? Warren Buffett famously argued that it was more impactful for him to compound his money at 20%+ and donate it at the end of his life. Earlier in life, some personal wealth can also enable you to take entrepreneurial risk, or invest in your or your children’s education. On the other hand, giving now could mean that problems of today don’t spiral (i.e., social time value of money). There may also be tax benefits in the US (e.g. donor advised funds) to giving earlier in life.
  • How much of your excess capital goes into saving vs. unnecessary additional consumption as your income grows? I’m certainly guilty of this, and need better methods to quantify.
  • When you are later in life or die, how much will each additional dollar left to your family/children benefit them after a certain amount vs. the impact of an additional dollar given away? I think it’s human nature to bias towards self preservation vs. giving, for most people.
  • How much does this calculus depending on your stage of life (younger vs. older) and your total income and capital base? If you have $1,000 vs $100m in your bank account the percentage of your net worth that it’s rational to give away will change (see below for a suggestion).
Peter Singer’s Giving Scale” in the appendix of “The Life You Can Save

My thinking is still evolving and think it will continue to do so – my main motivation was to clearly articulate my thinking and learn from others in the community.

Thanks to my friend Kai Wu for reading a draft and making this post better.

Setting up for Distributed Work

I work at Automattic where I lead a distributed development team. I shared a few thoughts from my first few months working at a distributed company.

Working remotely is a topical issue (March 7, 2020) given the spread of the Coronavirus, and many companies asking employees to work from home.

I will share some additional thoughts on:

1) Why distributed work is going to become even more important and mainstream.
2) Tips for setting up and running your distributed team.

Why Distributed?

The availability of high quality collaboration software combined with the availability of fast, reliable internet all over the world is making distributed work easier and more common by the day, especially for technology companies.

Many amazing technology companies in the world have set themselves up as ‘distributed first’ including Invision, Gitlab, Zapier, Basecamp, Upwork, Stripe (later) and Automattic to name a few and have grown to significant scale (1000+ employees). As companies reach significant scale and become even more global (e.g. Google and Facebook), they run more and more distributed teams collaborating towards the same goal.

Distributed work has a lot of advantages for your business; you’re able to recruit globally, your teammates have more flexible hours, working environments and mobility which ultimately expands the available talent pool and improves employee retention.

You’re also able to set up systems and institutionalized knowledge for your company that do not rely on synchronous, in person interaction which are more durable over the life of your company.

Here are a few good resources about distributed work:

Running distributed teams

If you’re thinking about setting up your company to be a distributed company, then the most important thing to do is set up your company as ‘distributed first’ from first principles. Even if you do have one or many offices you need to set up your culture and systems to make all employees feel like first class citizens no matter their location. At Automattic, we have a written creed and one of the ones I really like is ‘Communication is Oxygen‘.

Practical advice

Set of common tools and norms: Decide on your norms are for the business – this does not have to be perfect in the beginning, but write something down then iterate. For example, we don’t email each other at Automattic – Slack is for synchronous discussion, P2 (our internal blogging tool) is for long form writing and roadmapping, and Zoom is for video communication (we never have audio calls). Here is a minimum set of tools you’ll need all functions:

  • G Suite: This is a no-brainer as you get email, calendar, storage, document and spreadsheet capabilities all easily shared in your organization.
  • Long form communication/collaboration: Basecamp, Notion, and Confluence are all good workplace solutions and the first two are more opinionated wheras Confluence is a bit more flexible and connects better with external tools but needs more set up and customization. Google Docs is also an alternative.
  • Chat: Slack is the most common, and works generally well. It’s not great when you have poor internet and I’ve seen folks use WhatsApp as an alternative given the speed and reliability.
  • Meetings: If you’re going to have meetings, choose a tool like Zoom that everyone uses. For recurring meetings or 1x1s, like to add a Zoom link to the calendar invite and a synced Google Doc for that meeting to it so that notes can be taken and shared more broadly if necessary.
  • Project management: There are lots of good project management tools but I like Asana the best. Trello is great for simple boards and many engineers like GitHub Issues as it’s close to the code but works less well for non-development folks. Jira is the most customizable and robust product for complex and established workflows but requires a fair bit of set up to be useful.
  • Standup: Many teams like to do asynchronous standups. I like the following questions and a tool like Geekbot is easy to use to administer in Slack:
    • How are you feeling? Colors (R/Y/G) or Thumbs (Up, Down) to give this structure.
    • What did you do yesterday?
    • What are you doing today?
    • Where are you blocked?

Async and written: Set up your systems to be “async and written first” and have clear escalation paths to notify your colleagues if something is urgent or you are blocked. Long form, written content forces you to think and communicate clearly and exposes the gaps in your own thinking. It takes more time to write, but ultimately the trade off is worth it especially at scale.

Public by default: Many companies communicate privately or in small groups by default. In reality, most communication which is not about sensitive topics (usually people/hr) should be public, especially if it about product or priorities. Defaulting to public first allows more people across the organization to learn from each other and to dive in and get more context rapidly if they require it. There is some risk of information overload or separating out what is important from what is not, but this is something that you get better at with practice.

Quality video and audio matters: I still think synchronous communication can be important, in particular 1x1s with your direct reports, managers and close peers. When you do have synchronous meetings having quality video and audio matters. Good lighting and a decent mic does matter when having video calls. I recommend a boom headset/mic combo like this Seinheiser USB Mic, over bluetooth alternatives.

Time zones are hard: Even if you set up good systems for distributed, asynchronous work, a very large spread in time zones can be hard for building a team’s culture, feelings of isolation and unblocking colleagues. If you can set up teams with reasonable time zone overlap, it’s easier.

Onboarding guide for new employees: Invest in a written onboarding guide for new employees with a checklist they can complete themselves. Ask each new employee to improve this onboarding guide for the next person.

When being in person is better

There are times where being together is superior to working distributed and asynchronously. It’s also worth trying out virtual meetups – synchronous and distributed versions as well (time zone permitting) which can be less expensive and time consuming for everyone.

New teams / new projects: For new teams working on new projects together, it can be helpful to have some time together to kick off the project, especially if it’s a substantial investment from the company. Group conversation can spark creativity and being in person helps accelerate the process of team bonding, creating alignment and hashing out the inevitable differences between vision, personality types or different working styles. It is be great to summarize this in a co-written document of priorities and team norms and roles.

Change Management: If the company or team needs a change it can be harder / slower a distributed environment. It’s more challenging to rapidly understand and improve the energy and output of teams rapidly as some of the feedback loops from in person real time communication do not exist in the same way. It requires adapting or replacing your mental models as a manger to a distributed working style (an area I where I personally need to develop).

Building human connections: When working with people, it’s simply easier to build trust and better human connections in person. Sharing a meal or a drink and laughing with them in 3D is much more engaging than a 2D Zoom call or Slack exchange.

Personal: Working from home can lead to feelings of isolation or lack of separation of work/life. I’ve personally enjoyed spending more time with existing friends and family (and being fully present) and shutting off your work notifications (closing Slack, Email etc) in pre-set windows.

Helpful resources

There are a lot of good articles and guides out there for remote work and here are a few of my favourites:

Manage Energy, not Time

I read the HBR article in 2009 called ‘Manage Your Energy, Not Your Time‘ and it really resonated with me. I’d felt similarly for a long time but did not have a framework to describe it. I’ve since shared this article and this method of thinking with dozens of colleagues and friends and many have found it valuable.

I find that creative individual work or complex problem solving goes poorly when forced into a pre determined time slot. This kind of work is what highly compensated knowledge workers get paid for and we are often forced to do this during 9-5 and in our office environment.

There are three main takeaways for me and how I’ve applied it to my own life:

  • Understand my own energy level before starting a task, and if I’m not in the right mindset switch the task to something that requires lower energy (e.g. submitting my expenses, or other administrative tasks) or take a break to restore energy.
  • Understand what drains energy and what generates energy – a nap, some exercise or a walk with a podcast are all restorative for me personally and so if I’m unable to get something done, instead of staring at my screen I’ll often do one of these and come back more refreshed and ready to complete the task at hand.
  • Work on creative or complex tasks during high energy times – I usually feel most creative and productive in the mornings and try and do most of my IC work during the mornings. In my current job it’s challenging as I work with many folks in Europe so I block out a few mornings a week without meetings.

When you’re a people manager or have meetings that you have to attend for the benefit of others and (not yourself) you often have to compromise on these principles because you’re optimizing for a larger group which is rational but not always pleasant if you’re low energy.

It is much easier to apply these principles a distributed environment (e.g. at Automattic where I work) as we can work from wherever (and mostly whenever) we feel most productive and, in my opinion, is one of the best advantages of distributed work over a traditional office.