Paying down debt (financial, technical, and otherwise)

Debt is a complicated subject.  On the one hand, it is empowering -- it lets you get a quick start on something, and lets you do things that would not be possible otherwise.  There are times when it is useful, necessary, and unavoidable.

I think about "debt" in the broadest possible terms: times when you are left "owing somebody" (including yourself) for something.  My inbox is in a state of debt right now.  The pile of unsubmitted medical bills on my desk is debt.  Duct tape & bubble gum holding up v0.1 of an app is debt.  Friends or family you haven't called in a while is debt.  Not to mention financial debt, which comes in many flavors.

I am actually a fan of incurring "technical debt", especially in the early days of a project, when you are iterating quickly and you are not yet sure what the long-term architecture of your product should be. I think a "get something up and running quickly" attitude is often best.  So taking on this kind of debt early is a strategic choice that if, done well, can actually save you time and/or money in the long run. 

The challenge with debt, of course, is paying it down.  

It seems as though one of the characteristics of debt is that you overestimate the short-term benefit and underestimate the long-term cost.  The result being that it's easy for things to get out of control, slowly and then quickly.   This article on the nature of a "debt spiral" covers it well.

I always think about paying down debt at the end of the year, as it feels like a time to try and get the house in order and work on a fresh start on the new year.  I don't like "rolling over" debts (at least the kind I can really control in the short-term) into the new year.  So I am doing my best to grind through and catch up on things now.

But better than getting in debt, and then getting out of it, is figuring out how to stay ahead of it.  And again, I don't just mean financial but in every way.  Replying to an email before someone pings you with a reminder.  Checking in on a friend or family member without them asking.  Dealing with bills and expenses as they come in.  Or even better, building capital: write a blog post, build v2 of that app, publish that presentation, make the budget, contribute to your savings or 401k.  Proactively paying ahead.  

Easier said than done, like most things.

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