I’ve realized some real differences in how I approach technical debt
with my uISV compared to my “previous live” running a team of 60+
developers. One one hand, I feel more willing to take on debt at times,
because I have the full view of the software infrastructure, at both
the high and low level. With a big team, that knowledge is distributed
across many people and it’s harder for any one person to make educated
decisions on what types of debt are worth taking on and what will end
up costing many times more down the road, and senior
developers/architects are often more removed from the small decisions
that often compound over time to result in the “surprise debt” that
tends to be insidious on big projects.

On the flip side, because I get to dictate the pace and schedule of
development, I have the ability to make the decision to take the time
to wipe out debt before it starts to compound – I can take half a day
to revamp particularly ugly pieces of code or to refactor one section
of the infrastructure to better support future work without having to
worry about arbitrary deadlines that I have no visibility into.

I’d be curious to hear if others have similar experiences, and how
they change (or don’t) as you start to bring in more developers to
assist with the work.