This month I’ll be corresponding with @annie

Hi Jason,

First - apologies for the past-due letter. Good intensions and best-laid plans and busy weekends. At any rate, here we are now.

My best friend Jennifer and I used to exchange letters over the times we lived in separate places. She moved to Kentucky, then I moved to Puerto Rico, and now we’re both back in St. Louis. We meet for walks and coffee and in-person conversation now, which is its own delight. But there’s something special about receiving a written letter, whether digital inbox or physical mailbox, and words you can absorb at your own pace.

Moving at my own pace is something I’m learning how to do, and slowly, and it’s clumsy. This stage of learning feels less like learning and more like an exercise in whacking my head against the metaphorical wall. But I’ve been in this particular stage enough times to recognize it now. I call it the slog, which I’m fairly sure is not a real word. The SLOG, that mid-point when the excitement of newness and beginning has worn off and you’re not yet making enough headway to trust your progress. This is often the point when - particularly with creative endeavors - I think it’s a good idea to start over. All over. Something must be wrong with the plan. Otherwise, I’d be making visible progress, moving steadily forward, and feeling confident. Right?

What silly expectations I have for myself. Writing them down or saying them out loud, or pausing in any other way and looking, really looking, at what I am expecting of myself brings me up short. All too often it’s not reasoned or reasonable, not even human. I’m expecting something more (perfection?) and something less (emotional neutrality?) than human. But here I am, as I have always been, quite human. 100%, last check.

And that’s the point I am revisiting, the lesson or skill I am learning, one step through the slot at a time. To let myself be fully human and move at my own wide and varied and slow and stumbling pace, to accept the missteps and flailing as part of the dance. Failing isn’t an aberration; it’s a necessary part of any process that involves growth. Knowing this doesn’t always make me feel better, but why do I need to feel good about things all the time? I don’t, as it turns out. The slog does not require me to go forth with shouts of joy. It only requires that I keep going. Doable. (And, also, it’s okay to stop and rest a bit, too.) There’s trust needed to slow down. To move carefully. To breathe deep, to rest, to get there when I get there. Trust in myself. Trust is at the heart of so much of this, maybe all of it. Do I trust myself to focus on what matters, to choose what’s important, to notice, to not miss things, to be okay? The answer I’m finding isn’t a simple yes. It’s more like: I might not it right. I might very well miss things, even important things. And I will be okay.

I often feel a sense of urgency over nothing and everything. Perhaps that’s just a feature of life in the 21st century. The ‘world is too much with us.’ We know too much and don’t know how to handle it. It’s also a residual feature of some of my own experiences in the last few years. It’s kind of an arrogant feeling, as if the well-being of the world or some portion of it depends on me. I’m all for taking responsibility, but that’s a stretch. What if I let my hands be as small as they are? What if I let my reach be short, extending only as far as my arms can actually reach? What if I expected no more of myself than to wake up each morning and do the small tasks that are mine? The world doesn’t end - or it does! - but either way, it’s always been a bigger ball than I can juggle. There’s peace in accepting my own limitations.

I’ve not asked about you, only talked through my own meandering thoughts, but I’m curious, and grateful to be part of this experiment.

Take care, Annie

Hi Annie,

I am reminded of this Ira Glass quote:

“Nobody tells this to people who are beginners, I wish someone told me. All of us who do creative work, we get into it because we have good taste. But there is this gap. For the first couple years you make stuff, it’s just not that good. It’s trying to be good, it has potential, but it’s not. But your taste, the thing that got you into the game, is still killer. And your taste is why your work disappoints you. A lot of people never get past this phase, they quit. Most people I know who do interesting, creative work went through years of this. We know our work doesn’t have this special thing that we want it to have. We all go through this. And if you are just starting out or you are still in this phase, you gotta know its normal and the most important thing you can do is do a lot of work. Put yourself on a deadline so that every week you will finish one story. It is only by going through a volume of work that you will close that gap, and your work will be as good as your ambitions. And I took longer to figure out how to do this than anyone I’ve ever met. It’s gonna take awhile. It’s normal to take awhile. You’ve just gotta fight your way through.”

This, of course, applies to skills as well, where we often reach a stage where it becomes clear what’s possible, but our bodies or minds cannot achieve it yet. Yet is such a powerful, difficult word. There’s so much between now and yet, and that chasm is often left uncrossed.

I think the thing I’ve held onto with similar journeys lately is that it’s ok for yet to become later or never. Sometimes between the start and the yet I realize something isn’t that important to me or maybe I no longer want it at all. I can be caught up in needing to finish what I started– it was years before I was willing to put down a book I started even if it was terrible– but I’ve started to feel like I don’t have time to waste on things that aren’t moving me. There are times we have no choice but to go slow, to slog, to cross the chasm to that future point where we can do the thing. It’s good to practice taking things to completion so that when you have to dig down into yourself and push through you still believe it’s possible. “I have done this before. This is how it goes. We survive this. We will again.” But it’s also ok to say, “Maybe if it’s this hard, maybe the right answer is not now.”

I have been bobbing up and down through cycles of burnout since I’ve been working at the same start up for 9 years. There are periods filled with not trusting myself, feeling like I need to start over, and then energy, growth, pride, and reward. The exhaustion-elation rollercoaster is to be endured, built into the risk-reward of something this challenging. It helps to have a partner I can trust and who can trust me back. In the best times, we’re at different phases on the cycle and can support one another. In bad times, we’re synchronized, or some challenge erodes and weakens that trust and then things get dark for a bit.

I think about how “the world is too much with us” all the time. My work, building operational and administrative software, is all about making processes more efficient and effective but also fast. So much of what I touch would have taken an eternity, relatively speaking, 30 or 40 years ago. It was slower and harder 20 years ago too. The easier part feels good, the always on always, immediate part of faster I sometimes question. Our expectations for responsiveness and information and change keep getting faster, and while on the micro level I have the same demands, I wonder if on a macro level that just… breaks things.

A lot of what is changing all around us is about removing friction. We’re so used to friction being a bad thing that we’ve forgotten that friction has been a signal, a control, a limiting factor. Friction is a guard against impulsivity. The right guard? The best guard? The intended guard? Perhaps not. But remove it, and our impulses win just a little more often, just as our frustration also abates just a little bit.

I’m going to spend sometime this week, inspired by this letter, to think about what I want to rededicate to, knowing I’m in the slog, and what I want to let go of, listening to the friction and frustration and lack as a signal.