I was 22 years old.

When I built the original prototype for megabus.com, I built it using PHP + PostgreSQL. I put together a document detailing my reasoning for these choices. I quoted 33 days for it, built it over six weeks and charged £13,200.

The support contract was £350/month - for one day a month. On the first day, megabus.com sold 200 orders.

When megabus had its first expansion, I was up overnight bringing new servers online and scaling it live. I loved it - my code was finally being tested.

Over a week, I’d probably burned through many days of effort. I remember the project manager specifically asking me to invoice for the extra work I put into it. I even said that I would - except I didn’t.

I’ve had a long time to think about this - why did I not send that invoice? I even had approval.

The answer, as with most things of this nature is complicated. I loved the work and I didn’t want it to end. I didn’t want a potential conflict trying to figure out what a reasonable amount was to charge. I felt that I should have done a better job in the first place - I felt responsible that I had not told them that scaling of this nature would not have worked without prep work.

I had not scaled anything before.

I was 22 years old.

I was super grateful that someone believed in me. I naively assumed that they saw all the extra effort I was putting in and that they would reward me for it - that they would have my back.

I remember adding a bunch of different bits of functionality because I wanted it there. I didn’t want to go through the process of quoting for it, and it getting potentially rejected, not to mention the waiting for decisions. One key bit of functionality I remember is adding in a percentage load column for the loading sheets. I built it, showed it - they loved it! It went live. I did not charge for it.

At this point, the vast majority of my time was spent on megabus - very little of it actually paid for.

At a glance, based on the emails sent, I probably spent a minimum of 10 days each month supporting megabus when I was charging for one day.

In Jan 2004 - I proposed doubling the contract to two days for £4,800/year. It probably kicked in in Feb 2004. By March 2004, the site exceeded that revenue each day.

In the following months, I probably spent, on average a minimum of at least double the time I was paid for. I should have charged for it.

I grew the team, and the support contract based on the minimum I needed to maintain the product - not based on the amount of time I was spending.

For my 28th birthday, my girlfriend at the time organised a cake which was a image representing kraya - which was basically megabus. I felt bad that she thought that kraya was the most important thing in my life - she was right - but it still felt bad. kraya had other clients at the time, but my time wasn’t monopolised by other clients, or indeed by kraya - my heart still belonged to megabus.

And it would all have been fine too, except for a grave miscalculation I made.

In 2010, after trying to rebuild the ticketing system for £500k, and making some mistakes with people I trusted, kraya ended up in £150k in the hole. We needed some money urgently.

I was desperate and naively, I reached out to stagecoach for help. I thought they were my friend - that they would have my back.

They understandably lost a great deal of trust in my ability to manage and lead my company. I trusted the wrong person - but that was still my mistake. They were right.

I thought that I’d built up enough goodwill that they would help me through this. I’d felt I would have way more than that “in the bank” in terms of goodwill. I learned that professional relationships do not work that way that dark afternoon, standing outside my office on the phone, in the rain.

They didn’t make my life easier. Instead, I’d ended up rattling the cage - they were now panicked - realising their over-reliance on an organisation that could disappear at any point.

Instead of support, I had further actions, renegotiating the contract and what felt like punitive, and definitely invasive reporting obligations.

I was hurt and angry. I had poured my heart, my soul - hey, my very life into this product that I loved.

Suffice it to say - I got no help - no loan, no offer of investment - though they did suggest buying us outright - which I rejected.

I signed a contract under circumstances I would not wish on anyone.

The best I got from them was a challenge - if we were really spending more time than we were charging for - prove it. I did! We documented every minute we were spending - I wasted my time on spreadsheets, pointless meetings and work to try and rebuild the broken trust.

We went from £300k in the hole to £200k profit within a year. We charged for a whole year in support around 20% of what the system made in a day.

I was 28 years old.

Around the same time, I was also dealing with the operational aftermath of trying to build a java EE ticketing system over six months for £500k. I thought it would take a year and cost £1m. In hindsight, it needed two years and probably three million pounds.

Over 18 months, I personally answered over 150 out of hours emergency calls. We had a rota and others on call too - but I took the vast majority of these calls. I felt bad putting others through what I knew was gruelling.

All of this led me down a narrower and narrower path to a serious breakdown - though I didn’t know enough to name it until many years later. All I knew - all I felt was that something broke in me.

We managed to resolve all of the issues, but the deployment of that version kept getting pushed.

Stagecoach cancelled the contract in 2012. They had started building a ticketing system in-house two years prior - the cost of my grave mistake. I wasn’t able to make the meeting - I was in India, and at the same time as the meeting, I was meeting for the first time the one who is now my wife.

I was 28 years old. I spent the next 15 years putting myself back together.

How much did it cost them to build it inhouse? If I had charged for my time from the start, would we all have been better off?

I still feel something deep inside me every time I see a megabus - a sense of pride mixed in with a deep sense of sadness - not for what I lost - but for what could have been.

I am 44 years old, and I am starting again.

We had one ADSL connection coming into the office and three of us. I wanted to share the internet. Windows NT didn’t support it cleanly — it had a way, but it was clunky enough that no internet was arguably better. We’d paid hundreds of pounds for it.

I’d heard about Linux. Downloaded Red Hat, installed it, configured it for NAT. It worked — it was like magic. I’m pretty sure I had to recompile the kernel to get some bits working, but there were instructions and they were honest. It did what it said.

Here was software that was completely free — free enough that I could read the source code, make changes, run it however I wanted. It did more than the hundreds of pounds worth of garbage sitting on the desk. And once I set it up, I never had to restart it. Never. Compared to once a week on the NT box.

The difference, in my mind, was simple. Linux was built responsibly. NT was built as a money-making enterprise.

That held for a long time. I moved to Debian, then celebrated when Ubuntu arrived and made things more accessible. I’ve recently been able to abandon Windows altogether — gaming on Linux is finally viable. I came back full time and felt mostly at home.

But there were minor niggles. Things that felt slightly off but that I couldn’t quite name.

Then I started digging into systemd.

I remembered feeling odd about having to run specific commands to read logs. Odd about one tool doing many different things — which ran contrary to the Unix philosophy that had made Linux what it was. When I looked into the history of the opposition to systemd, it was revelatory.

systemd becoming process 1 is, in a word, irresponsible. It makes everything easier and more accessible, which is why it won. But unlike the Linux of old, the tradeoff isn’t visible upfront, and there’s no real choice. The responsible option isn’t the default anymore — it’s the thing you have to go looking for.

I thought I had already done the work. I thought I had found the alternative.

While I was celebrating Linux becoming mainstream, I hadn’t considered what it would cost.

The Linux ecosystem had started optimising for mainstream at the expense of responsibility. It works now, for far more people. But it’s a different thing than it was. When linux was really taking off, there was a joke going around (before memes were called memes) about Microsoft Linux. Turns out the joke was on us!

It is always a tradeoff between security and convenience — something convenient is rarely secure, and vice versa. I think something similar applies to responsibility. The more accessible you make something, the harder it becomes to hold the line on what it was built to do.

There was a time when software going wrong meant losing your work. Now it means losing your money, your reputation, or — in a car, in a hospital — your life.

The context has changed. The attitudes haven’t. And the places that once had better attitudes — the ones built on responsibility, on craft, on caring about the thing itself — are being pulled in the same direction. It gets everywhere.

Do you want your car running Windows? What about systemd?

This isn’t about any of that.

It’s about the fact that none of those decisions show up in the metrics that matter to the people making hiring and delivery calls. The cost is immediate and visible. The return is delayed, quiet, and arrives in the form of things that didn’t happen — the investigation that took two hours instead of two days, the API change that didn’t bleed into the domain model, the bug that the structure caught before it shipped.

Sprint velocity captures the extra day. It doesn’t capture what that day bought.

This is not a new problem. Most engineers who’ve been around long enough have felt it from both sides - made the careful call and got measured on the slowness, or inherited the codebase built entirely for speed and paid the tax. The measurement system was already broken. It has been rewarding the appearance of velocity over the thing velocity is supposed to serve.

This was true long before anyone was generating code with AI. The PR process in a lot of teams was already largely theatrical — review comments on naming conventions while the architectural decisions slipped through unquestioned, approvals given because the diff was too large to meaningfully read. The gate was already not doing much. We brushed it under the carpet and moved on.

AI tooling is changing the volume of code moving through that process by an order of magnitude. The pressure to remove the gate entirely — to trust the output, to ship faster - is only growing. The faster-is-better incentive that was already making review ineffective is about to be handed a much larger surface to work on.

Many years ago, I pitched full redevlopment of a ticketing system from a PHP based system to a Java EE system because it was struggling to scale.

It probably needed a couple of years to build. They wanted it in six months. I accepted the challenge.

We built and deployed the system in eight months. We spent the next year fixing it.

The client then rebuilt it in-house.

When AI runs this experiment at scale, who takes it back?

Dave uses the example of Agile, which is a sore topic for many. He talks about how selling shrinkwrapped agile is not going to work, because it is different for each company, and each team. It has to be custom fit.

It’s hard to disagree. I do think though that a lot of the practices that are talked about as being the “best,” are good practices. However, a challenge is that a lot of these practices depend upon or are meant to encourage “good mindsets.” The mindsets are far more valuable than the practice itself.

The question then becomes about how prepared an organisation or team is to shift their mindset. As you probably know, it sometimes feels like it would be easier to move the earth than some mindsets.

I encourage people to consider practices (good, bad and ugly) with a critical perspective to understand the mindset behind it. Only then is the question of relevancy capable of being answered. If the mindset that is encouraged can be achieved in another way, that could be your version of that practice.

The problem, of course, is that communication is difficult, and our ability to perceive possibilities is limited by our own perspectives. Sometimes, it takes a period of trying out a practice before we can begin to understand its potential value.

What do you think about best practices? Are there universal ones?

Agile really shines here. In fact, it was agile that pointed out that the original estimates (which we thought was pessimistic) was actually still optimistic. The two weeks of user story mapping saved us a great deal of pain.

As Robert C. Martin puts it:

Planning can destroy hope… and show us just how screwed we are.

By constantly reassessing plans, Agile gives us an early warning system when things are slipping.

I used to think that the point of Agile was to be faster. The book Clean Agile argues that the point is to fail sooner.

In our case, Agile gave us an early warning system. It killed hope before hope killed the product.

Instead of going into overdrive and being a workaholic (again), we simplified scope, adjusted the deadline and found a better balance.

We like to think of this as the way of the tortoise.

How has Agile helped/impeded you and your team?

Things are a little better in the non-profit sector. Sure, the currency may be different, with a focus on “doing good” but in my experience, compassion is not a high priority. Justice is often a key element, as is fairness, but compassion is often forgotten.

We human animals have been in survival mode for so long, for so many generations, that we are all carrying around bags and bags of trauma. Few of us do not have real childhood traumas, even if most are unaware of them. According to the UK Trauma Council, “One in three children and young people are exposed to at least one potentially traumatic event by the time they are 18.” Add to this the influence of your parents and family, how much *They F*** You Up*, and we are all in a pretty dire state right out of the gate.

After an incredibly bad burnout and several years of being unable to work, I started my therapeutic journey in mid-2016. It was only through this intense and challenging but healing and learning journey over several years that I was finally able to go back to work (in January 2019).

This journey helped me understand just how much trauma was in my life and how trauma begets trauma.

Will Bowen said, “Hurt people hurt people.” We are all hurt, so we hurt others, sometimes intentionally, often unintentionally. I think there is a corollary to this — hurt people get hurt. The hurts we carry around leave us sensitive to specific triggers. This can put us into a defensive mode that causes a repeat of the pattern, leading to more hurt. You may be able to think of some examples of this happening to you.

Why does it matter? We are all professionals. Shouldn’t we “man up” and leave all this stuff at home? Toxic masculinity aside - this is not possible. We are human, and no matter how much we try, it is impossible to separate our traumas or hurts from our day-to-day existence.

Most of us spend most of our time at work (and recovering from it). We do this believing that it will all eventually be worth it - perhaps when we retire or finally make enough money to take a step back. Are we trapped in the promise of the future? I was! Do we have the mental space to realise when we get to that destination? Are we trapped in Stockholm, at the mercy of the prison we have built for ourselves?

Mindfulness aside, how can we make our day-to-day life more enjoyable? How can we make the journey more valuable than the destination? Ultimately, the destination is the same for all of us. Should we be rushing to get there? (If the idea sounded even remotely appealing, I would encourage you to consider finding a good therapist - they do wonders!)

I think it all begins with compassion, starting with compassion for oneself. What if we could create an environment where failure is not an option — not because we must succeed at any cost, but because nothing that happens is considered a failure? What if mistakes are not chastised but used as opportunities to learn from?

I have not failed. I’ve just found 10,000 ways that won’t work.
— Thomas A. Edison

How do we build an environment where innovation, imagination, and creativity thrive? I believe the key here is a sea change to the fundamental attitude and purpose of the organisation. We can create this environment by making the organisation’s primary focus collaboration (with everyone who wants to collaborate) and making compassion the most vital tool of that collaboration.

I don’t know about you, but I don’t have deep pockets, so I still need to worry about paying the bills. We also do not (yet) live in a “Star Trek”-like universe where money is no longer critical to society. How will we pay the bills if we focus on something other than commercial viability?

If you want to build a ship, don’t drum up people to collect wood and don’t assign them tasks and work, but rather teach them to long for the endless immensity of the sea.
— Antoine de Saint-Exupery

In my mind, a good agile team works in this fashion. The team has a shared vision, a goal and everyone is empowered to make choices they feel contributes to progress to the shared goal.

With my recent post on collaboration, I have been thinking about how a concept like this applies within a truly collaborative environment. In the quote, there is clearly a group of people and one of them wants to build a ship. We do not know what the rest of the group desires. In the context of traditional leadership, what the rest of the group wants is importance mainly in the context of understanding how their wants and needs align with those of the ones in leadership.

Within this context, collaboration is often seen as something the team does for the purpose of achieving the goals or the vision set forth by leadership.

Having been through the gauntlet of various levels of company ownership and levels of leadership, the only thing I feel I have ascertained is that I don’t really like any of it. In positions of leadership, the amount of responsibility and pressure is immense and the higher up the ladder you go, the lonelier the job is.

Being a team member with no leadership responsibilities is liberating. There is a great deal of joy in being able to physically and metaphorically shut the computer down at the end of the day and be done with the job. The rest of your life is yours. The downside, on the other hand, is that I disagreed with (at least) half the decisions made. With little power to improve the quality of life of myself or my fellow team members — mainly because ultimately what was important was the bottom line, not quality of life.

Which brings me to the question: how do you build a collaborative environment where the traditional boundaries of leaders and members are dissolved?

I find the first challenge here is finding like minded people. Having the motivation to build a highly collaborative team is only half the challenge if the people in it are trapped in traditional team roles of member or leader — or even worse, manager!

How easy is it to find someone able to see the possibility of a different way of working when we have all been stuck in the rut of us vs them, infinite growth and shareholder value? How easy is it to then learn to put aside our differences, our childhood traumas and our baggage to be able to express our authentic thoughts and desires without triggering our defence mechanisms or letting our emotional baggage leak out? How much does it matter?

Hurt people hurt people, and humanity struggles to cooperate and collaborate mainly because of our hurts — the ones we are unable to heal and recover from. Because our hurts, particularly from childhood, are so strongly seared in us, we see danger when anything close to our hurts presents itself. Like a soldier who ducks and covers when they hear a car backfire — we all go into defensive mode when something familiarly scary comes into our vicinity. Unfortunately for a lot of us, we live in a world full of little triggers — some of which may be so small that they are undetectable — but it impacts our mood and our ability to reason.

We live in the belief that what is good for “the machine,” is good for the individual - be it capitalism, the government, or society. What if we worked on the basis of the opposite.

Not all those who wander are lost.
— J. R. R. Tolkien