Paying down debt (financial, technical, and otherwise)

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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.

Google Pixel Slate: First Impressions

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For the past week or so, I have been experimenting with the Pixel Slate, Google’s new hybrid tablet/laptop. Here is me typing this blog post right now, on the train to NYC.  For a longer,  more technical analysis, this review from The Verge is good. The Pixel Slate is an odd machine, and I am still… Read more »

A Visual Guide to the Howey Test

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Disclaimer: I am  not a lawyer, and I am not your lawyer.  I have been in an uncountable number of conversations over the past few years discussing the question of what defines a “security” in the context of cryptocurrencies, cryptonetworks, and token offerings.  Here is my current understanding, including a number of key questions I… Read more »

Crypto Fundamentals

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Our good friend Chris Burniske was on Squawk Box this morning. I got up and watched it.  You can see the video here. Of course there is interest in the crypto market right now, as it is falling hard. I suspect there are many out there who are enjoying the drop, waiting for the bubble… Read more »

Getting Hands-On

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One of my favorite things to do is get my hands into something and figure out how it works, whether that’s an app, or a gadget, or a house. For example, over the past few months I have been renovating our basement, turning an unfinished, dank storage area into a playroom for the kids.  Here… Read more »

The Dangers of Unstoppable Code

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With real-time, interconnected, self-executing systems, sometimes when things wrong, they go really wrong.  I wrote about this general idea previously here. Yesterday, while I was writing my post on Trusted Brands, I was doing a little searching through my blog archives, so as to link back to all the posts categorized under “Trust”.  In the… Read more »

Trusted Brands

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Today is election day.  I’m on a plane today, so I voted early, a few days ago.  I cast my vote and it felt good. I marked my paper ballot with a marker (for optical scanning) glued it shut into a sealed envelope, and handed it to a volunteer who placed it in a secure… Read more »

Suffering, Self, and Service

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The massacre in Pittsburgh is heartbreaking and awful, and another example of the extent to which society seems to be fraying. The Pittsburgh attacker spent a lot of time on social media sites that stoked his fear, isolation and anger.  I think about the internet a lot, and while the internet has the ability to… Read more »

Building a meditation routine

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I wrote recently about the challenge of turning plans into routines.  One of the activities that is the most impactful for me is meditation.  I cannot say that I have a perfect meditation routine, but I can absolutely say that when I do do it, it makes me feel great, immediately. There are a bunch… Read more »

Trauma

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Just about two years ago, my wife’s parents were hit by a truck while crossing the street. The past two years have been both difficult and wonderful.  Wonderful in that two people who were on the brink of death following the accident are still with us (her mother in particular has had a miraculous if… Read more »

Plans vs. Routines

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Sunday night over dinner, my son, parents and I were discussing the saving / investing system we set up for our kids in the spring. The idea was/is: set a monthly budget for purchases (in their case, mostly online movies, tv shows and games), and include a really healthy interest rate (20% monthly) to encourage… Read more »

The Adjacent Possible

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Dani and I have been spending a bunch of time recently thinking about the relationship between applications and infrastructure.  It’s a little bit of a chicken and egg situation.  You need infrastructure to build apps, but often times you don’t really know what kind of infrastructure is needed until you build some apps. For example, we… Read more »

Getting the Chills

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One of the greatest things Frannie and I have in common is that we get the chills from music — typically at the exact same time, triggered by the same musical… something. For me it starts  at the back of my neck, and if it’s really good, it spreads all over my back, head, and… Read more »

The Utility Infielder

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My favorite baseball player is Brock Holt, and has been since his first season with the Red Sox back in 2013.  Here is me last month wearing my Holt jersey that I wear to every game (note the #26 that he started out with, before it was retired for Wade Boggs a few years ago… Read more »

Fear

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I have been helping my son, who is in 4th grade, with his math — specifically, multiplication.  He feels like he is a little bit behind, so we are working on it so he can get more comfortable.  It is going well now — we have gotten into a routine of spending 15 minutes per… Read more »

Form factor

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Over the past few weeks, I have varied up my computing habits a bit.  For a laptop, I have been using a Pixelbook, and I have also been spending more timing using an iPad Pro for work (vs my default of using a Mac laptop for everything). What I have discovered is that the form… Read more »

A little, and then a little more

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Back in May, I had what ended up being a major hand surgery — repairing a torn tendon and in the process reconstructing the end of my pinkie by grafting tendons borrowed from my ring finger.  As a result, I am now recovering from two injuries — the pinkie itself and the ring finger that… Read more »

Layers

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A central concept on the internet is Layering.  Each of the protocols in the internet stack talks to the layer directly above and below it — new protocols can be added as long as they speak the language of their layer.  Protocols at one layer can be upgraded so long as they don’t break compatibility… Read more »

Minimum Viable Economy

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One of my favorite things about the cryptocurrency / blockchain space is that our conception of “what it all means” is still very much in flux. Nic Carter just published a nice analysis of how the functional narrative around bitcoin has changed over time – (roughly) from e-cash, to e-gold, to private currency, to a… Read more »

The path to decentralization: self-destructing companies

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In June, the SEC gave some of its most concrete guidance to date that cryptoassets can start out as centralized projects, possibly initially sold under securities laws, and eventually become “decentralized” and thus no longer sponsor-controlled, and no longer sold or transferred under securities laws. It makes sense that a decentralized protocol does not fit… Read more »