Weeknotes #262

What I did this week:

Bootstrap problems

My focus this week has been around shaping up plans for the rest of the year to ensure we’re able to develop and deliver the changes to the products that we want. There are all the practicalities budgets, availability, timelines, etc., to consider and coordinate with the ideas that are shaping up for what the products should achieve. How these two intertwine and affect each other as they move towards having the people and time to deliver the scope of work is an interesting [bootstrap problem](https://jonathanweisberg.org/publication/2012 The Bootstrapping Problem/#:~:text=Bootstrapping is a suspicious form,problem and surveys potential solutions.) where all assumptions are based on assumptions. The idea of fixed product teams removes the need for figuring out the complexities of logistics and gives a more solid grounding to base assumptions about the work that can be done. But where product teams are project based, none of that grounding exists. This problem is as old as software, and yet is still very much a real problem for the majority of charities that rely on funding for specific projects.

Change of theory

I took part in a user research workshop on a tool for working with Theory of Change. I found it a really interesting idea and have been thinking about it ever since. Being able to validate some of the assumptions in a Theory of Change to figure out what impact the activities and mechanisms are having and then make decision about whether to change the activities to achieve the intended impact or accept the activities and change the impact to be achieved would be really useful. It could introduce a level of rigor as the data that informs the model builds up over time rather than remaining a hypothesis. The challenge for many social good organisations will be whether they really want to get to that depth of understanding.

Innovation in charities

I’ve pretty much finished the research phase of my dissertation so am moving onto analysis. I’ve already got lots of interesting insights about innovation in charities and I’m intrigued to see what theory I can build as the case studies develop.


I’ve been experimenting with using my website as a notebook to add some of my thoughts more regularly and try to see if it helps me build and develop ideas. I’ve occasionally used Twitter, Notion and paper for this but never with any real usefulness.

What I read this week:

Digital maturity in the not for profit sector

This report is full of insight about “the organisational journey towards improvement and increased capability in using data” and includes findings like “The cost of data is huge, hidden, and often wasted. Most leaders don’t see the value of data. There’s lots of counting but not enough meaningful analysis.”. I wonder how the not for profit sector compares to other sectors.

Talent is evenly distributed, opportunity isn’t

Rand Fishkin, talking on the One Knight In Product podcast about alternative ways to build software startups, says “talent is evenly distributed, opportunity isn’t”. How companies recruit, organise work, incentivise, etc., makes a big difference in how opportunity becomes more evenly distributed.

What I thought about this week:

The future of digital nomadism and off-grid developers

At the extreme of remote working are people who earn their living on the internet and live their lives away from the conventions of mainstream society. Kevin Kelly talks about the right to mobility and how that affects our notion of what a digital nomad is (not just twenty-somethings living in Thailand and setting up drop-shipping websites and affiliate marketing). Alex Standiford is a good example. He’s an off-grid developer, living in a RV in New Mexico. In my thinking about the 21st century Outsider, for the book I’ll never write, the off-grid developer looks like one of the archetypes of a digital nomad, where it isn’t so much about ‘nomad’ meaning ‘always moving’ but more about not being tied to a particular location and being able to make the choice about where to live and work because the internet has decoupled those two.

Contracts and covenants

I had an interesting chat with Ross that started out about type 1 and 2 decisions but moved onto the more interesting topic of contracts and covenants. In trying to understand the difference between the two, I think we’d say that the logic of a contract is , ‘you agree to do what I want and I agree to do what you want, and we both have recourse if either of us doesn’t’, whereas a covenant is more, ‘this is what I’ll do for you regardless of what you do for me’. So many of our interactions with people and organisations are based on contracts, either implicit or explicit, but this seems based on zero sum thinking where one person is only willing to give if they get something in return. The relationship between natural and legal rights and responsibilities that are expressed in contracts are, obviously, very complex, but maybe the idea of covenants, which consider giving as non-zero sum game, where you don’t always need to get something in return, adds another perspective.

Perhaps we are all myth-makers

Ashley tweeted, “perhaps we are all myth-makers rather than truth-seekers, and our real quest is not to figure out what is Real but to steer ourselves towards Good“. Perhaps in a post-truth world we can be more open to Heraclitus’ ontological position that reality is ever-changing rather than Parmenides notion that all being is fixed and static. Arguably, without the notion of the world around us having some underlying static structure to it humans would never have made the scientific breakthroughs that we have, it’s really hard to study something unless you believe it to be the same as when you observed it yesterday, but without adopting that stance we could never have reached our definition of truth, and therefore become truth-seekers.

Of course, it isn’t one or the other, both notions about the nature of reality have existed together for a very long time, and allow us to see the world in complex ways, but we do have a tendency to think that there is an objective ‘truth’ about things for which there really isn’t. The example of this that’s on my mind this week is conversations with colleagues that were full of discussions about misunderstandings around language and how we and others were interpreting what had been said. I wonder if the misunderstanding of misunderstanding is that there is a single truth to be understood. When people discuss things they are making meaning as they go, not explaining a scientific fact, and yet we attempt to understand what they said as if it was.

The Futures Cone helps think about possible, probable, plausible futures. Perhaps we need a Meanings Cone that helps us think of our interpretations as possible, likely, unlikely, impossible to help us understand each other better because we consciously don’t base our understanding on the assumption that there is a single truth in what someone says.

What I’m grateful for this week

Feedback begets feedback

The more feedback I give the more I seem to get. Or may I just notice it more. Either way I’m grateful for being able to give feedback and for receiving it.