Category Archives: Systems Thinking

Debt Snowball for writing goals

Working on a long-term plan to balance my writing projects. I’ve got 8 writing projects on my mind, of which 4 hold burning urgency.

I’m terrible at this, incidentally.

I’m trying like crazy to cultivate a delivery-focused mindset these days—work on one thing at a time and finish, then move on. I’m really bad at it. I can’t stand the idea of letting go of the other things to focus on one.

But I’m (intellectually) convinced it’s the better path. Say you’ve got five 10-hour jobs, and 20 hours this week. My usual approach would be to split up my 20 hours, get 4 hours into each job, figure I made some good progress, and repeat.

But say I manage to ruthlessly focus on one job at a time. 20 hours in I’m done with two jobs (and can hand them in or hand them off or stop thinking about them), and next week I can do the next two.

Part of my brain still screams, “But you didn’t even start the others!” And that’s true. But IRL, nobody cares how much you’ve started. And it’s actually freeing to get some of the jobs totally off your plate.

In trying to get myself to actually let go of some of my writing projects long enough to actually finish any of them, I realized thinking about it like a “debt snowball” is a great idea. (That’s a personal finance thing where you maintain minimum payments on all your debts but one, and hit that one really hard, then when it’s done up your payments on the next, etc. Good way to gain momentum on early payoff if you can swing it.)

Talked with my genius wife K about this—I had an intuition that the “highest interest first” or “highest balance first” had a parallel here, but needed her help pinning it down. We agreed “balance” means remaining total workload (word count or hours). That approach would mean start by focusing on the one I can finish quickest, then move on to the next quickest, and so on.

But “interest” is where it got interesting. I figured it’s something like impact or earnings potential. But K blew my mind with the idea that interest equals the emotional toll not finishing has on me.

In other words, start with the book that hurts most to have not written.

I did a quick ranking (again, brutally difficult, because I want to do all of them all the time), and also a quick estimate of how many hours each one is likely to take. I don’t fully trust the latter, but it was eye-opening.

My big amazing favorite (but long, complicated) novel Frobisher clocked in just under 100 hours estimated for this (hopefully final) major editing pass. A lot of the others came in around 40-80 hours. A quick, stylish non-fiction book in the form of brief aphorisms, principles, and anecdotes was 110. Frobisher is definitely up there, but I would have expected it to be 5-10x the smaller quicker books. Double feels surprisingly do-able.

Frobisher and one other quick, exciting project topped my “high-interest” list, and it’s surprisingly motivating to realize within an estimated 120 hours of focused work I could have two of the projects I care most about ready for next steps if I just focus on those.

Not that 120 hours is trivial amid life, day job, client work, and four kids. But that’s a goal I can get my hands around, and it gives me lots of reasons to sneak in extra hours writing instead of goofing off.

Certainly more motivational than knowing that with 120 hours of work I could be partway through eight or even a dozen projects.

Big Unified Index Card Productivity System #1: Nouns vs. Verbs

So I’m working on my latest Big Unified System and I ran into a theoretical question. In trying to ask some friends the question, I ended up talking myself through it instead and, in the process, finding the next interesting question.

Broadly, I’m working on organizing my life on index cards with each card representing a (big or small) goal state, broken down into a list of (big or small) steps to get there. As appropriate, each step can then get its own card and get broken down further, until the steps it’s broken down into are concrete things I can just go do.

I was initially going to put values as the top level cards, broken down into more specific target states/quality of life statements (CONNECTION > Healthy marriage / I play with my kids regularly / etc.)

But a target state like that can definitely help fulfill multiple values. (And, similarly, a single project could move me toward multiple target states.)

I was hoping to design a system where all the cards have the same fundamental design, essentially working recursively all the way up or down, but now I’m wondering if I need to distinguish between two kinds of cards, roughly target states and projects/tasks (or, you could say, nouns and verbs). 

Except I typically state my projects as a verifiable end state as well (monthly reporting completed, kitchen clean, firstborn displays willingness to come to me with problems, etc.). So I’m realizing nouns and verbs are not different kinds of cards. It’s more that the title of each card is a noun and then the items listed below that are either the verbs that would move me toward it or additional (intermediate) nouns that should then (recursively) get their own cards. 

Which means the real problem is not fundamentally different types of cards, but the many-to-many relationships that can exist between cards (and which screw up my default hierarchical/tree way of organizing this).

That’s mainly a problem because I was hoping to only ever have one pointer back up to a parent project at a time, but the more I think about it the more I’m not sure that’s accomplishing what I intended (which gets into the fiddly technicalities of implementing the system).

Anyway, turns out the real question is how to cleanly represent (and track progress in) many-to-many relationships. 

Which should be an interesting one, because a big paradigm shift earlier was when I realized that instead of picking my “top priority“ value or quality of life statement and then picking the “top priority“ project within that, it’s wiser to look at all of my goal states (at a similar level) together and creatively brainstorm to find a project that can move me closer to the collective goal state. So there’s probably some more juicy insight to be discovered in that vein.