I would guess the best answer here is to write down everything. Keep a journal. Write down events as soon after they happen as possible, write down your thoughts about the event, write down your emotions and connect them to the events that generate them.

I think a somewhat decent mental model here is to think of our brains as write-only memory. Every time you remember something, your brain rewrites the memory. You, on some level, are experiencing the event/thought/feeling again. When you think about what you felt during a past event, you are mostly feeling your current reaction to the memory, and not as much tapping into past feelings as you might think.

One broad example of this is what people call "type 2 fun." This describes events that may not produce positive emotions in the moment, usually some kind of hard physical tasks/achievements. But, looking back, these events produce positive emotions when remembering the event and the accomplishment.

E.g., During a customer interview where I'm trying to understand what they've done (and predict what they'll do), I have vanishingly low confidence in their self-predicted behavior. So I prefer to try to look at what they've actually done in the past, talk to them to understand why they did it that way instead of some other way, tease out the invisible data (like what they tried or researched but didn't continue with), and then come to my own conclusion about how that's all likely to extrapolate.

But in terms of understanding and ascribing purpose to my experiences? Or understanding and empathizing with a friend or stranger? Or sending a message out into the world in a way that can stick and spread? In that case, it's kind of a subjective thing to start with, and it's all about the stories. (To clarify: not intentionally fanciful or fictional stories. Just "stories" in the sense of how we tie all these things that happen into something coherent and ordered.)

That was kind of a non-answer, and I'm sorry I can't be more helpful. I only understand a very, very small number of things. (Three, I think, although I'm working hard on understanding the fourth.) Apart from those few narrow domains, I'm just fumbling through it like everybody else.

I've been working on some personal issues for a little while now and sometimes it's hard to tell where I've made progress due to this exact retroactive-perspective-shifting, until I go back and read my journal from those earlier times and the contrast becomes clear.

Still, I remember being quite struck by how authentically he was working to get to the heart of it and tease out some value from the mess I was making. It really felt like he was on my side, working with me, despite how difficult I was making it.

I grabbed a copy of his book a couple days back (which is maybe what reminded me of this little anecdote) but haven't gotten into it yet since the pile of interesting reading is just a bit too deep. Very much looking forward to it though, cuz nobody knows it better (except maybe Oprah, I guess?)

As a side note since you're here, I'm super psyched that you've taken the time to share what you've learned in your new book -- it's the next one up on my list for serious study, and I couldn't be more excited about it. Based on the reviews so far, it looks like you've written something really special and that I'm in for a real treat. Can't wait :)

I'm sure with experience they have gotten better. Although to your point maybe Andrew is "bigger" than his guests now, changing the dynamic.

Also, getting serious about reining in the drinking acted as an anchor habit that led to a bunch of other positive lifestyle changes. (I still probably drink far more than almost anyone would consider acceptable, but it's down to a level where my body appears able to keep up. So still a work in progress, I guess, but at least my energy is back up.)

As a weird side-effect of that, I noticed myself starting to hold all of my writing to that same standard, which was stopping me from putting out anything more off-the-cuff.

So part of my motivation with this site (which is only about a week old) was to frame it in a way, at least for myself, where I felt comfortable sharing the stuff-in-progress without worrying too much that it wasn't a finished book.

Which I guess is a long way to say that the rambliness is an intentional decision, since otherwise it wouldn't be doing the job (for me) that it was designed for. I already spend 20+ hours a week doing fairly utilitarian writing for my books, so this little site needs to be something different if I hope to stick with it. And in an ideal world, maybe a few other people will happen to enjoy some bits and pieces along the way :)

A specific example came up while trying to explain my first company's pivots through three products (trying to figure out a social/UGC ad stack before Facebook did). If you looked at the business model, our value prop, customer segment, etc. all of that stayed the same. Which was the unifying thread, and which I can now articulate at least semi-coherently.

But when I was describing it to Andrew, it came out as three completely unrelated products, and that we were just wildly changing plans without any coherent vision or direction. I remember that moment due to his look of profound confusion, where he was really trying to figure out how these three things I had just described were related.

I left it moored up at a port along the canal for winter (when the canal gets too shallow to traverse), the folks who were supposed to be keeping an eye on it didn't, uncharacteristic winter storms were blowing rain and muck all over the place, the cockpit drains got clogged, the cockpit filled with water, and things went downhill from there ;)

It was sitting quite happily on the shallow riverbed when I returned, but the inside was a swamp, and I had to tear out and trash the whole interior. At least it was fresh water, so the engine (mostly) survived.

Was the most popular British-made small boat of all time, and some of them have successfully circumnavigated.

Sturdy thing with only 0.9m draft, able to ride into shallow waters and sit happily on its keels when the tide goes out, and surprisingly spacious for its length. Good boat.

Sailing had always been on my "someday bucket list," but I kept putting it off since I could never make the time to take the week or two off to do the course.

But once I started learning, it was so much more deeply satisfying than anything else in my life, that it immediately became a top focus. Before I'd even finished my captain's license, I had already hit "buy it now" on an ebay listing (admittedly reckless and not recommended, but I couldn't wait).

That being said, boats are floating money pits (the rule of thumb is that you spend half the boat's price again, every year, in maintenance and mooring) and take a ton of upkeep, so I think it's only viable if it's a major piece of your life and you're willing to devote considerable time o it. Otherwise, it just sits there, losing money while accumulating chores.

I sold mine during the first lockdown, but I'll absolutely get another someday, once I'm ready to wrap my life around it again.