19th September, 2021

Week 38/52

Photo by Taton Moïse on Unsplash

🤪 Repeat

We all know…

Insanity is doing the same thing over and over and expecting different results.


Sorry, no. It isn’t.

Insanity is referencing the definition of insanity over and over without ever bothering to consider if it’s actually the definition of insanity.1

As has been pointed out by others, doing the same thing over and over and expecting different results is perseveration (i.e. compulsively and persistently repeating a sentence or action). Not to be confused with perseverance (i.e. continuing to pursue goals in spite of road blocks or others assuming it’s impossible etc).

I was asked this question again this week by a founder who is facing a bunch of obstacles that feel in the moment to be insurmountable:

How can we tell when we should just quit and try something else?

It’s something that we can probably only decide for ourselves. So, it’s difficult to give advice. On one hand, we only get to be each age once, so trying to do the same impossible thing over and over feels like madness. On the other hand, every day people do things that were once considered impossible. And often, when those people look back and reflect on what made the difference, they point to their perseverance: the hard grind they did every day that compounded into a remarkable result.

In my experience, these are the two important things:

  1. Agree in advance how we will tell that it’s working (a milestone); and

  2. Agree in advance when we will switch to an alternative path (a timeframe).

If we can decide on those in happy times (i.e. at the beginning, when everybody is feeling optimistic) and we can stick to those decisions when needed (i.e. resolve to continue as long as there is sufficient measurable progress, and stop when we said we would if there isn’t), then we can hopefully avoid feeling like we’re losing our minds.

🔀 Asynchronise

From Broadcast To Binge

Once upon a time television was broadcast. If we wanted to watch a show we had to know when it was scheduled and be available to watch it then or we'd miss it. What’s more, there were only a small number of channels, so the selection we had to choose between on any given day was quite limited and mainstream.

Thankfully those days are past, and are now just stories to amuse our kids

(Fun parenting experiences include: explaining that we couldn’t just pause a show when we wanted to go to the toilet; that a “season” would stretch over several months, one hour at a time, at most; and at night the broadcast would shut down for a few hours so we could get some sleep, with a memorable animation to indicate it was time for bed, starring a kiwi and its pet … <checks notes> … cat. 🤷).

Now, services like Netflix give us much more flexibility and control - content is available to watch where and when we choose on lots of different devices; we can watch one episode at a time or binge a whole series in a single sitting if we're so inclined; there are various different business models, including some services that we can pay for on subscription rather than having shows interrupted by advertisements; and the competition for attention means that the quality of the content has significantly increased.

Television used to be synchronous. Now it’s asynchronous.

And it’s much better.2

Working From Home (a.k.a. Living At Work)

Teams that work together in an office are synchronised in two ways: place and time.

For example: "The Team Meeting is in Room #3 at 11am". We know where we need to be and when we need to be there.

Teams that work remotely remove the requirement that everybody is in the same place. This allows those of us who can work comfortably from somewhere else to avoid a commute and ideally choose the location that best suits the work we have to complete.3

(Remember, you are not stuck in traffic, you are traffic)

The next level up is also removing the requirement that everybody is available at the same time. This is potentially much more impactful - it allows us to take control of our schedule, affords fewer interruptions and creates larger blocks of dedicated focus.

Maybe we work best in the early mornings or late evenings. Maybe we have family commitments that means it’s better to start a bit later or finish a bit earlier. Maybe we want to take a couple of hours in the warm middle part of the day to get outside and be active, and make that time up in the evening. Maybe we are not even in the same timezone as our colleagues.4

No Shared Lunch == No Free Lunch

Of course, all of these benefits don't come without some costs and challenges, especially when it comes to communications and coordination.

Teams no longer working in the same place typically end up spending a lot of time on video calls. In the last 18 months "zoom" has taken on a whole new meaning for many of us, as we've had to quickly learn a whole new etiquette.

(Something interesting I’ve noticed recently: Those people who are most effective on video calls are not always the same people who are most effective in-person. And, those who are most critical of meeting via video, and correspondingly more anxious to get back to in-person meetings as soon as possible are nearly always those who are most effective in-person).

However, video calls are still a synchronous way of meeting - we still need everybody to be available at the same time. In making this change, many teams missed the most important question: is an in-person meeting actually the most effective way of having this conversation?5

Teams no longer working at the same time need to use many different ways to communicate asynchronously, picking the best format for each situation, rather than spending all day in (or on!) meetings. Luckily there are many great tools that can help with this.

For example, tools like Slack allow teams to share ideas in a way that the conversation is captured and available for those who can’t be part of that in real-time, and is searchable later. Online software, such as Google Workspace means that documents are no longer written by one person and then shared as email attachments, but rather can be created collaboratively, with comments and suggested edits captured directly in place. New tools such as Notion or Trello or Miro allow information to move off the office walls or whiteboards into shared documents that can be updated and viewed whenever and wherever it’s needed.

Finally, but perhaps most importantly, working asynchronously means understanding that most meetings are presentations rather than conversations. Expecting everybody in the team to stand together in the same room at the same time to get updates is possibly the most synchronous thing traditional teams do.

Instead these meetings can be pre-recorded so the content is planned and the message being communicated is clear; everyone who should can present including those people you may not normally hear from that often; everybody can watch where and when it suits them; and the team gets the chance to react, to ask questions in advance, to discuss the presentations as they watch, etc. The best tools (<shameless plug! />) provide analytics that create feedback loops for those presenting, so they get better over time by learning what is actually engaging and informing the team.

Taken as read

This is not even a new idea.

Prior to a board meeting the CEO and executive team typically share a pack of “board papers” that provide an update on important issues. The directors are expected to read these beforehand, and often they are “taken as read” so that the meeting time can focus on the questions directors have and the decisions that need to be made.

In the same way, remote teams need to strip out the bits that are actually just everybody in the meeting listening to one person giving an update.

If we get this right it creates much more effective conversation when we do get precious time together (either on zoom or in-person) and leaves more time for being human.

✋ Suffice

I’ve had the privilege of working with some interesting people over the years. But one of the most interesting was a colleague from way back in the day, when I was working as an IT consultant in London, in the early 2000s.

He was also a kiwi, but had been in the UK for so many years the distinction was starting to get blurry. He had a long history of short software development contracts, which gave him the benefit of never really needing to get personally invested in the things he was working on, and provided the perfect outlet for his delightful cynicism.

The new new thing for our team back then was Microsoft's .NET framework and associated development tools. Having recently come out of the first phase of Trade Me, where we were constantly wrestling with the limitations of VBScript, it was an absolute breath of fresh air to me. But every time I would get excited about a new aspect of the language I’d understood, or the potential to do something significantly better within the applications we were working on, he would quietly chuckle and explain to me that it actually wasn’t new at all but just a reinvention of an old idea that he’d seen before, back when computer screens were 40x25 ASCII characters and the font could be any colour you liked as long as you only liked green on a black background.

I’m making him sound like hard work, but actually I really enjoyed his company and the work we did together. He always took the time to explain, to put things in context and to make me think harder.

As it is with software development, so it is with self-help, it seems. So humour me while I channel my former workmate...

Suddenly everybody is excited again with the idea of less.6

The most celebrated business owners are the ones who implement four day working weeks. Every item in our house is required to spark joy, or be sent to the charity shop. The ideal diet is strictly plant-based (and it’s not enough to eat that diet ourselves, it’s also very important that we try to convince everybody else we know to do the same, or at least acknowledge their inferiority to do if they choose not to). The perfect inbox is empty. The best meeting is one we don’t have.

After all, life is apparently short,7 so we shouldn’t waste it on people or things that distract us from enjoying it.

Ironically all of this is a lot to take in and constantly worry about. And for most, I assume, exhausting!

Here is a much better question to ask, I reckon: what is enough?

If more people asked that question on the way up, then perhaps there would be far less demand for minimalisation and de-cluttering?

The problem with less is you can usually never get there, and it’s often fleeting on the rare occasions you do. The cake, as they say, is a lie. But the beauty of enough is that it is, at the same time, seemingly un-aspirational, and yet still elusive.

I mean, if you have enough then you can justify backing off, taking your foot off the pedal and enjoying the view. But so few people do that - especially it seems those who we consider most successful.8

For many “enough” is a dream. But for those who actually don’t have much, life is a struggle. To even consider the idea of less to be aspirational is a massive privilege.

Perhaps, like my old colleague, rather than getting excited about these things and immediately assuming they are solutions, just because they are new and fashionable, we should think a bit harder about what problem we actually need to solve, and how these patterns have provided a solution to them in the past.

Top Three is a weekly collection of things I notice in 2021. I’m writing it for myself, and will include a lot of half-formed work-in-progress, but please feel free to follow along and share it if it’s interesting to you.


Except for when somebody on social media spoils the show you haven’t finished watching yet. ¯\_(ツ)_/¯


This is why the experience we've all had working from home during a pandemic is such a poor approximation of remote work - being locked down at home with multiple family members, sometimes including kids who need help with school etc, and taking an hour out of the middle of every day to panic again about the latest reported number of cases is not optimal by any definition!

Also, let’s stop pretending there aren’t some significant downsides that employers need to consider.


This is especially relevant if one of our responsibilities is hiring smart people to join the team, because this opens up the pool of eligible candidates massively! And, remember, that is the constraint.


Consider the different ways that you can consume a press conference, for example:

If required (and if we're invited), we can attend in person. We get to find out what is happening immediately, as it is announced, can observe the interactions of everybody else in the room and maybe even ask questions in response to the news.

Or we can watch a live stream. We get the information in real time, but only the selected perspective of the person controlling the camera.

Or we can watch a delayed recording. We still get all of the information, albeit a little later, but it gives us some more flexibility too - for example, we can watch at 1.5x speed so it doesn’t take so long, or we can skip ahead if there are sections we're not interested in.

Or we can read a transcript. That gives us the full context, if required, or allows us to narrow in on a specific point or question, if that was all we are actually interested in.

Or, far more likely, we can watch or read a brief summary prepared by somebody else who has done one or more of the above. This is more-or-less the model that media companies use - journalists attend press conferences in person or watch recordings, then write or record stories that summarise the details and perhaps wrap around other relevant information to keep us all informed of what was announced, without the full cost of everybody being there in person.

The key is choosing the appropriate level of asynchronicity.


As topical as this list feels to type in 2021, it’s actually mostly copied from a short blog post I wrote in 2007.

See also: Replete from 2009.


I’ve made the case elsewhere that life is not as short as we think, and we’d be better off to not constantly behave as though it is.


How much savings do you think you need to retire? I remember having this specific conversation with various colleagues over the years, and even agreeing actual numbers with some. What I have now is so far beyond any numbers I dreamed to estimate then, and yet I’m still filling my days with work. I’m basically a huge disappointment to my former self.