The three legged table
Bootstrapping is full of three legged tables. Skip the fourth leg because it's not needed yet, and eventually something expensive lands on the wrong corner. People call it technical debt like it's managed. It's not. Build all four legs.
When bootstrapping, there's a lot of stuff that needs to be done. Sometimes it's overwhelming. That can often lead to the temptation to make shortcuts which can come back and bite you.
Consider the table. It needs four legs. Sure, you could build it with three legs and make sure you have things balanced in the right corner. Just remember that the fourth leg is missing. Until you don't. One day someone forgets. Something expensive lands on the wrong corner. The table tips over and then it's either a mess or expensive to fix.
Bootstrapping is full of three legged tables. There are a million examples in the technical realm. I don't need to go on about them. But there are also examples in the business realm, like doing your taxes and expenses. Are you making sure you record them correctly so that they are auditable later on, or just boxing them through to get to the P&L?
In the software world this is often referred to as technical debt. However, this implies it's managed. Yet these things are never managed. It's just things that get juggled around in one's headspace. And keeping that clear is important for moving forward.
As I near 20 years of bootstrapping software, this is a pattern I've experienced time and time again and I keep saying to myself, well, it ain't gonna build itself. And so just get to it. I don't want to come back to something in the future that I should have dealt with now. It's always going to be harder down the track because of the effort to remember the whole problem from once upon a time.
Build it right the first time. Make sure your tables have four legs.
And now it's harder to justify building a three legged table, unless it's by design ;)