At one point I had four different pitch decks for the same piece of work. Same work, same cost, same engineers, four completely different stories, each one tailored to whoever I needed a yes from in that particular room. And the engineering argument wasn't the lead in any of them, because that was the pitch that hardly ever worked.
Everybody agrees it's there
The odd thing about tech debt, in my career at least, is that I can't remember meeting anyone who denied it existed. Product knew, finance knew, the board knew, and they'd all nod along when I talked about it. Everyone acknowledged it, and very few of them ever wanted to do anything about it.
The term comes from Ward Cunningham, back in the early nineties (worth a search if you've only ever heard it used as a swear word), and the loan is the whole metaphor. You ship something quicker than you should, and you've borrowed against the future. Fine, everybody borrows. What gets you is the interest. Each change made on top of the shortcut costs a little more than it would have done otherwise, and that keeps on stacking.
And somehow, everywhere I worked, the business managed to stay just ahead of the bill coming due. Never quite paying it off, never quite defaulting, just making the minimum payment and taking out a bit more each quarter... while the interest kept going up.
Four decks for one loan
So when I needed money to pay some of it down, the engineering argument was the obvious place to start, and nine times out of ten it was the wrong one. The people holding the budget mostly weren't engineers. Something like "the coupling in the order service is making every change slower" means everything to the team and very little to someone who has to weigh it against a marketing campaign with a forecast attached.
So I'd dress it up, in dozens of different ways. For one audience it was risk, for another it was cost, for a third it was how fast we could ship the thing they actually wanted. Hence the four decks. And on the rare occasion the person across the table was technical, they'd nearly always have their own chain of non-technical people behind them who needed satisfying before anything got signed off... so it was back to the decks anyway.
None of that is lying, exactly. Every one of those stories was true. But it's a fair bit of smoke and mirrors, and I got rather good at it (which isn't necessarily something to be proud of).
A small loan, already approved
Not every repayment was a battle, though. Twice in my career I was brought in specifically to deal with a company's debt, and the two jobs could hardly have been more different. One was a few years' worth, the other was decades, which is roughly the difference between Ben Nevis and Everest.
The smaller one was a startup, a few years into its debt, and I went in as a contractor rather than staff. The job was one explicit thing: automate the deployment pipelines they'd built in CloudFormation, and close the gaps that still needed a human to step in. A deployment took about eight person-hours when I arrived, and I got it down to about twenty-five minutes.
The ask was very specific, so the promises I made there were very reasonable. And, crucially, it had already been sold before I walked through the door. Someone had made the case, got the money and hired me to spend it. I didn't need a single deck. (I liked it so much I stopped being a contractor and went permanent, which tells you exactly how good I am at contracting.)
Decades of interest
The big one was a retailer, with decades of debt piled into a monolith, and the brief I was handed came down to about twelve words: make it better, cheaper to run, cheaper to build... oh, and use microservices!
That is an epic of a brief, and about as vague as they come. I couldn't see a single promise you could make against it and keep, so the promise I made was me. I sold the plan as effectively as I knew how, and it leaned on my reputation enormously. I wouldn't go as far as saying I sold my soul, but it made me kinda wary, even while I was hugely enthusiastic and had big plans to make it all wonderful.
Then came the compound interest. On a debt that size, the bit you can see is hardly ever what you start paying off.
The first thing that had to move was people's thinking, before anybody touched the code. There was a team who'd nursed and maintained that platform since the very beginning, and they knew it inside out, and they were very, very attached to the way it had always been thought about. Getting a group like that to shift how they think about their own system is slow, careful, human work, and very little of it shows up on any report.
Then the house had to be put in order. Shoring up the existing infrastructure, the database and the monolith itself, just so that any forward movement towards microservices was even possible. All of that had to be settled before we could get anywhere near the exciting, visible work that actually dealt with the debt everyone had signed off on.
And to anyone watching, all of that looks like nothing happening. Months of paying interest and not a penny off the principal, from someone who'd stood up and promised the principal.
Guarantor on someone else's loan
Debt work only ever got funded, in my experience, because someone over-promised. The plain pitch hardly ever won. So I've come to see the smoke and mirrors as the price of admission rather than a failing on my part, and the person paying it was whoever did the pitching.
The debt belongs to the company. It was taken out over years, by lots of people, most of whom have long since moved on. But the moment you stand up and promise to pay it down, your name is on it. When the repayment wasn't the kind of success the stakeholders had been expecting (and with compound interest hiding underneath, it often isn't), the reputational damage landed on me, not the company! I was stood in the room explaining that what looked like surface-level debt had a whole lot more owing underneath it, and that all of it had to be settled before the bit they'd paid for could even start.
It's a strange position to be in. You're the guarantor on a loan you never took out, for a lender who'll only lend if you promise more than you know you can deliver.
I've seen it from the other end, too. Long before either of those, I sat in the room while forty grand got cut out of an estimate that was already lean, and watched a brand new loan get written into a contract before a single line of code existed. That one had my name on it as well.
I'd still sign, given the chance, because somebody has to or the interest just keeps going up... I just read the small print rather more carefully these days.
Originally published at phpboyscout.uk on 25 October 2026.
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