Category Archives: Productivity + Organization

Feeling the hard feelings

I’ve been taking another whack at breaking down my phone/media addiction lately. I’m rarely without a book or a podcast or a show on in the background or a video game to play or several all at once.

I think I’ve managed to cut it down to one at a time, at least, and I’m rebuilding my old ability to endure silence and practice stillness. I’ve gone on long walks in silence—no headphones, no reading while I walk—and from time to time managed patches of time without a phone or screen in reach, just reading or journaling or sitting and thinking.

And I’m starting to see why I avoid it. There’s a looming sadness that I hadn’t let myself notice. I think I’m happy on the surface and happy at my core, but there are thick strata of loneliness and failure and existential dread in the middle, and I’m glad I’ve stopped ignoring them.

It’s not easy, but it feels healthy to sit quietly and just think and feel whatever I think and feel. I have an intuition that all the bad feelings will be in there until I feel them, and it may take a while to get through it all, but at least now I’m making progress instead of continuing to hide it.

Part of it is the huge changes in the world and closer to home over the last few years—politics and pandemic and the resulting loss of close community and regular feasts with friends. I’m coming to recognize that I miss life as it was, and while my life is good and will likely get better, it won’t go back to how it was.

Part of it is the inevitable reckoning as I approach 40 and see how far I have yet to go to realize my dreams and mission. I realize for all my thinking and talking about books, it’s been forever since I published one of my own. Years in, my program of writing courses has reached thousands and helped many but not broken even. I fear my publishing company may be holding my authors back as much as it helps them. My kids are growing up, and as much time as I spend with them, I’m not sure it’s enough.

And finally, part of it is a growing awareness that I don’t know how to get where I’m going. Our efforts to buy a homestead for rich hospitality seem stymied by the market. I can’t crack the nut of how to get my businesses properly profitable for me and my authors. I’ve got at least eight books burning and burning inside me, and yet I face powerful avoidance every time I sit down to write.

I’m finding I deeply crave a less individualistic culture, where I’m surrounded by traditions and supports, where there are apprenticeships and communal Sabbaths and norms of hospitality and known prayers to pray. It seems I’m tired of making all this up as I go.

I’m not going to try to wrap this all up with too tidy a bow—it’s real sadness and I’m really feeling it, and I’m still in the middle of it—but three things help.

One is that, while there are difficult realities there, I know my read on them and the resulting emotions fluctuate, and I’m pretty sure I’m just in a downswing right now. I’ve been here before, and it does get better.

Second, I’m finding this is undercutting my confidence in planning and effort. I’ve had it up to about here with planning and effort, and I’m increasingly ready to slow down, listen, find the heart of God, and do the one right next thing that is needed instead of all the scattershot things I can think of in hopes that one of them works. That seems like a healthy direction.

Third, and strongest, is that I don’t ultimately depend on any of this going right. I desperately want it to, but if it all falls apart, I’m still with God, already and forever.

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.

A Notebook to Help Break Phone Addiction

I’m on another kick lately of trying to cut down on my device usage and spend time thinking, reading, walking, and processing without a lot of distraction and evasion.

I’m not great at it yet, but when I manage it it’s refreshing, and I’m starting to reach more clarity and depth on some ideas I’ve been processing for a long time.

One trick this time around is that I’m carrying around a notebook—just an old half-filled composition book, nothing fancy—and writing anything I want in it whenever I want, no plan or template or pre-defined direction.

It’s like nicotine gum. Instead of trying to cold-turkey quit all the brain stimulation of shows and podcasts and scrolling on my phone, I’m replacing it with something. But this something takes me deeper and helps me draw out and process what I’m feeling and thinking, not just avoid it.

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.