How to Rekindle a Sense of Progress


An obscurely introverted path to clarity

Illustration by  dangerlam

Illustration by dangerlam

Ahoy & what-ho! Thank you for joining me in my stone circle this fine stormy night. I had the grass clipped just for you. But yes: mind the bunny poo. Ah, you brought tea, thank you. How wondrous. No I don’t mind the rain, do you? Not at all. It sure is nice to get out of the tower for a bit. To stretch the legs, inspect the wards, pat the paladins and so on.


Ahem. <serious/conspiratorial face>

I’m mighty glad you’re here. We’re fresh on the other side of a solstice, you see, and the wizard in me looks for any opportunity to hijack any events of seasonal significance (be they Gregorian, lunar, orbital, astrological…*). It’s just clicked over midwinter in this region, and it is the perfect time for reflection, introspection and projection. Perhaps you’d like to join me, too? 

* Or even just: birthdays, holidays,° equinoxes, financial quarters, or days where the calendar does weird things… like 11:11:11am on the 11/11/11. I love that stuff. Essentially: any excuse to do something special. One can make magic & meaning of the mundane and meaningless, if one were inclined.◊
° April Fool’s Day, a favourite.◊ Not to be confused with ‘
Magical Thinking’ btw—a state in which otherwise intelligent minds reintroduce ‘essentialism’ (fixed-eternal meaning) into things. It’s one thing for me to say my phone works like magic (with ‘magic’ being a placeholder for ‘that which is of an order of complexity to which I do not yet understand’). It’s quite another to actually believe it is magic—some sort of essential force. Such thinking is lazy, and is a dead-end to curiosity. Like the word ‘soul’—it can either serve as a placeholder for complex emergent phenomenology currently beyond our reckoning,◊ or as an indicator that we have reached a limit. ‘No curiosity beyond this point. You’re overthinking things, and being pedantic.’ 
◊ It’s also worth bearing in mind that complexity requires bandwidth, and the file sizes are huge. If people don’t have the time to download and process it, then it may simply be easier to wave your hands in acceptance and call it magic. For now.‡
‡ It’s also probably worth mentioning here that what we are enjoying in these musings is a form of ‘magical realism’. But by mentioning this I’ve just diminished some of the magic. I must trust in you, it seems.

Behold, dear aspirant:—

How to Rekindle ‘A Sense of Progress’

Yes you can sit on the stones. Actually no: let’s get back into the tower, this is ridiculous.

<snaps fingers>

Better. Put your cloak there, by the fire. Make yourself at home.

Now, I don’t know about you but I am personally quite terrible at keeping to my Word. The worst!* Life has this funny way of delivering new and unforeseen complexities. If you recall at the start of the year I declared my intent for the year: chiefly, to write more.° And yet. Hoho.

* Well, no. I’m generally good at it. But I exaggerate for affect. (Yes, with an ‘a’). My own affect, so that I might have more room to dance amidst the dissonance and constructive discontent.
° I’ve made a self-indulgent post on this. Mind you, most everything I do is self-indulgent.

And yet.

<stares in space, drums fingers>

And so hence thus: I wonder if you might be in a similar pickle? Did you start the year with a bold intention (a Word,* if you will), along with some fine principles to ascribe to? It may well be that, like me, you have come to find yourself a wee bit distracted, and/or that you have succumbed to the default patterns of thinking and behaviour that keep you mired in sameness.

* My riposte to specific and measurable goals.

That’s okay—such is life. It’s amusing. We’re complex beings in a hypercomplex world with perhaps only the illusion of free will (pleasant and useful that it is). It’s only natural that we wander off track.*

* For there is no track.

But I wonder if you might like to take this opportunity to reflect, introspect and project. To ‘rip’ into it, as it were. For it may just allow you to jilt your trajectory back in line with your original intent. 

To rekindle a sense of progress.*

* Of course you know I am referring to ‘meaningful’ progress here—that which brings you closer to future relevance.

Now I’d love to sit with you and do this right now, but as with all good things: it will take some time. Perhaps the better part of a day or two. And I know you’re only here for a short visit. So how about I simply furnish you with the approach I take, in the hope that you might find some time to do similarly? Your cloak ought be dry by the time we are done.

Righto, marvellous. There are three phases to this. Firstly…

1. Reflection

I don’t know how good the world is at reflecting, these days.* There’s so much noise, and we so very much covet the shiny, immediate and new. Further, we tend to find ourselves beholden to an infinite and hydra-like ‘to-do’ list.° There’s always more to be done, just no time. So ‘busy’, and all that. And there seems to be no escape—we’re always connected. Always reachable, always ’on’. Or at least: that’s the grain I’m leaning against. 

* And by ‘world’ I mean: we. You and I.
° Our attempts to diminish it often only serves to grow it. And so I’ve come to learn to treat tasks as entropic weeds. An inevitability—yet something that can be addressed periodically.

But good reflection is necessary if we are to rekindle a meaningful sense of progress. Vital. And so, here’s how I go about it.

First, I write. And I do so in the same way I might approach my ‘morning pages’—but with just a smidge of focus. This is slightly less about entering a writing flow-state* (where your pen does not stop moving for three pages and you let your mind and hand wander anywherever), and more about spending time with some blank paper for a good few hours° whilst contemplating a few pertinent questions.

* Which, by the way, is not ‘stream of consciousness’—for this implies a linearity to your thinking, which can manifest as a ‘forced narrative’ and not the myriad meandering of morning pages.
° Yes: hours. Brew some coffee.

None of these questions are discrete—but if I present to you a cluster, you’ll get a sense of my opening thrust.

How are you?* What’s on your mind? And what else?° Why’s that? Okay cool… so: what’s your intent for this reflection? Why are you even taking the time to reflect?◊ Okay then: let’s reflect.

* This question seems so benign, but its easy to jump in and answer, as a means to get you started. But then, because you’re writing this down, it’s easy to see incongruence and to catch yourself fibbing or not revealing ‘the whole truth’ (whatever that is) to yourself. ‘How am I? Oh I’m fine. Everything is good. Well, not everything…’
° These next two questions come from Michael Bungay Stanier’s fab book The Coaching Habit.
◊ This kind of question is subtly powerful. It softly (yet firmly) establishes a sense of constructive discontent for us to work within. It invites us to consider the implications of our trajectory—if we were to not take the time to reflect… where would that lead us? It also honours and amplifies the initial inkling or hunch you had to do this. By acknowledging to yourself why you are taking the time to reflect, you are affirming that this is important, and a worthy use of your time. (Not that I always think in this utilitarian manner—but this serves as good defence to a mind that is all too eager to find rational excuses to do more immediately ‘productive’ things).

You’ll notice the first phase of questions is about getting immersed into context. I don’t cut to the chase—I positively beat around the bush. This is a reconnaissance. Scouting the territory, so as to harvest useful insight. This first phase ensures you are in the right state to be reflecting. Good reflection is not possible if you feel busy, tired, distracted or generally not in the mood. It can’t be forced.

So buddy,* what was your Word, and/or your intention for your ‘self’ this year? What Principles did you think to subscribe to? And how has this worked out? What do you think have you learned, thus far? And how’s your unfurling narrative reading—what are you making this all mean?°

* Notice how I ask myself these questions from an almost heightened and slightly patronising yet still benevolent perspective? It’s almost as though a wiser part of myself is prompting me to think in this way (in warm and invested yet wry and detached way). My ‘higher self,’ so to speak. All just illusions, to be sure. From this ‘higher’ perspective I can see that any ‘hopes and dreams’ are inherently silly, but I’ll indulge myself anyways.
° We can’t help but hallucinate/manufacture/manifest meaning into existence. Even the staunchest nihilists do this, which must be depressing to them. But: once we accept that meaning is nebulous and malleable, we can then wield it in a way that may ‘serve’ us better. We can recognise where we have ‘chosen’ to make certain phenomena mean certain things—and to then question if that meaning is indeed apt and useful. More on this soon.

Usually, by this point, I’ll unpack some sort of ridiculous narrative that pitches me as the hapless victim of circumstances. Some sort of powerless agent caught amidst the nexus of the many intersecting demands of life.* Here’s me—the good-hearted and well-intended protagonist—on a small lifeboat caught in an eddy, shaking fist at sky.

* Which could be a nice realisation, if I were zen about it.

And then I realise that I have effectively absconded myself from responsibility. Like a comfort blanket, I have woven a narrative to envelop myself in. To keep me safe and warm and still. 

Okay buddy, so… that sure is an interesting story you’ve got happening here. Let’s see if it correlates to the data.

Here I’ll reflect on whatever data points I have amassed—qualitative or quantitative.* This might include reflecting on my calendar,° the emergent themes of previous journal entries, trough/peak experiences, and anything that may point to some legitimate excuses for the current predicament.

* And, naturally, taken with a pinch of salt—knowing that it will be subject to all sorts of distortions.
° Including a look ahead, so as to see the types of commitments my past-self has made.

And there are of course almost always a swag of minor quibbles. The grass is greener, and all that.* And there can also be some significant unanticipated factors too. We craft neat linear stories of how things might unfold, and then we remember that life is non-linear, and loves to dish out the unanticipated. And yet—in the crevices and cracks amongst all this—self-sabotage may be hiding.

* Though the dangerlam and I have a ‘gratitudes’ calendar to remind ourself of our own green grass, which I reflect on too. This sometimes allows me to see the things I’ve been loving in life.

You’ve probably heard me speak of self-sabotage previously. I’ve certainly written about it. The dangerlam and I made a video about it. We are very good at it.

I’ve come to find myself fairly ambivalent to it nowadays, but the presence of self-sabotaging behaviours (getting in your own way, making it hard for yourself—that sort of thing) does flag the opportunity for deeper analysis.

2. Introspection

And so here we arrive at the crux of the matter. My inquisition shifts gears. Here I shall continue to write as I think (with explainers and links in the ‘marginalia’ for you).

Righto then, you odd character, you: what’s going on here? Have you attempted to reconcile your intended dissonance in a lazy, haphazard or reactive manner?* Have you found yourself adopting an incomplete stance (again), rather than embracing the fluidity and nebulosity of paradox?° Are you caught betwixt conflicting values?◊ What’s the payoff?‡ Is this Word (or ‘Grand Intention’) of yours even still relevant—or have you learned more? Have priorities shifted (really?)—or is it that the lessons you’ve chosen for yourself haven’t been learnt yet? Does it feel right, or has some unanticipated incongruence emerged?§ Or is it merely that you haven’t managed the distractions in your context? Have you given yourself the (head)space for progress, or are you inundated with shallow distractions and a rich delusion of progress?∆

* Constructive discontent (creating a discrepancy between your current state and a desired future state) creates a form of ‘cognitive dissonance’—a phenomenon whereby your thoughts, words and actions are not (yet) aligned.
° Learn more via wonderful online book at (all the best ‘truths’ lie at the heart of paradox).
◊ If so, I refer you to The ‘
Immunity to Change’ book, and suggest you follow what it suggests.
‡ I’ve found that most folks view things from an aetiological perspective—we look at the factors that ‘cause’ us to be in our current situation. Our current situation is therefore merely a reaction to (or result of) past events. This is an incredibly unhelpful perspective to adopt (and it’s something I often slip back into). A far better perspective is a teleological one, wherein we instead focus on our covert intentions. We’re in this situation because a part of us ‘wants’ to be here—there’s a payoff. I’m riffing Adlerian psychology here—to learn more, I highly recommend you read ‘
The Courage To Be Disliked’
§ A phenomena I’ve written about previously:
indicators of incongruence.
∆ If so, I heartily recommend the book ‘Deep Work’ to you. Read it, and rekindle your philosophy for depth.

There’s a lot in that, I know. This is just the tip of the proverbial here.*

* Overthinking this stuff is why I’m an arch wizard, and not merely a hedge wizard.

And so at this point I might take a break, go for a walk and possibly even sleep on the whole matter, letting my reflections and introspections steep.* The next morning, I’d reflect upon my reflections and introspections (meta-meta) and—assuming I haven’t encountered any ontological snags—I would then start to project a refreshed sense of what meaningful progress might look like.

* Yes I realise this is all rather ‘lone wolf’ and introverted. I certainly share my thoughts aloud at times with the dangerlam and friends and strangers (so as to triangulate onto my blind spots). But the real heavy lifting (I’ve found) happens at depth. And depth requires time. So: unless you have cognitively and emotionally mature friends who can afford the time to stay in the tension and paradox and go deep into the abyss with you (an incredibly generous act)—without any of you succumbing to ‘practical advice-giving’—I suggest you’ll find the best recourse is to tackle this solo.


3. Projection

It’s here I put my gloves on and begin to tentatively dabble with what some might call ‘practicality’. Yes, sometimes it’s necessary to put theory to practice. I know! Not a habit I wish to cultivate or become known for, but sometimes (when no one is looking) even I get out of my tower and off my high horse to ‘do’ things.* 

* But I always make sure to have a nice warm bath afterwards. And then to fix myself some tea and bickies, and to walk around telling anyone who will listen about The Thing I Just Did. Or thought about doing.

And so, rolling my sleeves up, I set forth to do the following.

» Re-affirming principles and intent.
I rewrite my intent, almost as a letter to myself. Ideally, I’d share this with a few folks close to me, and have the principles I espouse somewhat visible.* I’d choose archetypal affectations (like ‘wizard’ and all its associated) so as to create something more vivid, lively and memorable.

* The dangerlam and I have some ‘shared tenets’ for navigating business and life together. They’re written out in a tiny bound book that we keep on our countertop.

» Sequencing modest projects
Next, I cast ahead to the remaining months of the year and look for ‘pockets of opportunity’—blocks of consecutive time available for deep work.° With the available time, I then choose 1 or 3° modest projects to commit to◊—projects that seem true to my intent. Projects are the concrete counterpart that balance the otherwise abstract and vague notions of your Word, Principles and intent.

* I’ve personally tried to abscond myself from all but the most necessary future commitments (so as to ‘write more’)—but the gods do like to vex me.
° But not two. This will only serve to pitch one against the other.
◊ My commitments are fairly light. I’ve learnt not to grip too tightly to any goals, so as to allow better things to emerge. It’s kind of like coaxing threads of reality from the aether *flaps hands, delicate milking gestures, like so*, rather than grip tight to a fixed and rigid notion of what ‘success’ looks like.

I currently use teamweek for sequencing things out. I love it—but I also have this persistent optimism in what can be achieved. In the past, any and all attempts to Gantt Chart tasks has turned into a distorted celebration of disappointment and despair. Now, instead of mapping out ‘tasks’ into the Gantt Chart, I simply map ‘contextual focus’. That is: on this week I’ll be focused on blah and that week it’ll be blah. I don’t tend to get more granular than that. It gets fuzzier and more vague the more distal my focus, and the sharper and more specific the more proximal my focus. I’ll know what my next few days look like in quite fine detail. Next month? Only at a moderate level.

» Re-establish rhythms
I’m not big on ‘discipline’*—a notion favoured by simpletons of linear reasoning. I rather approach life as a bit of a stumbling but well-intended meander. But that’s not to say there’s nothing that can’t be gained from playing with the qualities of discipline. I’ve just come to think of it more in terms of ‘rhythm’. 

* See The Myth of Discipline.

I’ve never been a musician per se, but I once played the drums. Sometimes you get into a wondrous groove, but somehow you drop the beat. If your stance on life is more attuned to improvisation and jazz* you just roll with it, play with it, find your rhythm again, and make your way back into the groove. 

* As distinct from a classical piece, which is practiced in order to be perfected and played ‘right’.

I find this stance to be far more forgiving to the complexities of life. And there is quite a noble narrative attached to discipline. And I’m sure you could quote famous people that did a certain whatever every single day. Which is fine if you have cultivated an incredibly stable life. But for the rest of us: discipline can be a smidge too rigid and heavy. Which I guess is the point. But still: rhythm.

And so what makes up this rhythm? You guessed it—my old chestnut: rituals. Those ‘sacred routines’, wherein we deliberately carve out time against the grain of busyness so as to progress the things that matter.* 

Yes: it is possible for rituals to get in the way of meaningful progress. But if you’re paying attention from the meta, you ought catch this before it becomes ridiculous.

Across daily, weekly, monthly, quarterly, yearly (-ish) intervals, rituals allow us to tap into quantitative* and qualitative° feedback loops, combining the best of sense-making and reasoning to make us wiser and smarter. Or at least: to feel as we are so. They provide us the opportunity to periodically step back into the meta, and to see ourselves amidst this wondrously infinite game.

* Examples of quantitative feedback loops in my world: number of ‘writing’ days, number of nights at home, my average ‘day rate’ (for work with clients—‘dollars up, days down’ is the general aim), number of gym sessions, reach/impact (a tricky one—but something that has me try invest time in 1:many activities rather than 1:1 activities like email) and so on.
° Examples of qualitative feedback loops in my world: meeting with a collaborator monthly to discuss our evolving protosynthesis (what feels ‘right’, what doesn’t), journalling, offsites with the dangerlam, and so on.

And besides: rituals allow us the excuse to self-indulge—which probably sounds incredibly selfish, like sleep. But what of it?

I’ve recently slipped in a few of my key rituals—I got out of the rhythm, and thus my sense of progress became temporarily opaque. It’s only natural. And… it doesn’t take much to rekindle a good ritual or three.* And in so doing: rekindle a sense of progress.

* A bit of reflection, introspection and projection—like making fire with a stick.

And there you have it: 
‘how to rekindle a sense of progress’

Or, at least: that’s how I go about it.

What—did you want to rekindle actual progress? Bah! A common misunderstanding. I only promised you a way to rekindle a sense of progress. The rest is up to you! How irritating, I know. Yes, we both need to be practical at times.

And so, here’s your coat—how lovely is that? I know: sandalwood—and here’s to rekindling a sense of progress. I wish you the excuse to acquire yourself a wondrous paper journal, the opportunity to schedule yourself at least two half-days, and the willingness to persist amidst the angst of reflection, introspection and projection. 

Now shoo! Be on your way! Give the abyss my warm regards. You have the key to your own liberation—you always had. Embrace this recent solstice (or whatever serves you). The storm has passed, but it doesn’t mean we can’t make our own, eh? Yes this chat has been good for me too, I appreciate your visit. But now scram, dear friend, for I have a book to write.

<waits at doorway as the black coach takes you home, waves as you round round the bend and pass the gate, jolly good>

Toodle pip!


PS: Subscribe to my museletter? I think you’ll like it. I only send about 9 or 11 a year, and they’re almost always brilliant. Well, I like to think so. And some people tell me so, too. Bold forays, etc.