What Inspiration Feels Like

Today I had a familiar sensation, one which has historically always been an indication that something special is going on. It starts out with a sort of anxious frenzy, as an uninhibited stream of thoughts pours through your brain due to some stimulus. Over a decade ago, in the summer of 2017, this occurred when I woke up the morning after having a second run-in with law enforcement in as many days. The anxiousness was replaced with resolve, and accompanied by a deep drive to pursue being a police officer as a career.

More recently this happened when I returned from a vacation to Jamaica, during which I had done four dives out to the reefs around the island. I was overtaken with a love of the sea and being underwater, something which is certain to play a big role in my future somehow. There is this moment, kind of a flash, and it excites you like crazy and you suddenly cannot consume enough information about whatever it is, or stop yourself from writing down a million ideas. You no doubt can point to a similar moment in your life. This, I believe, is what inspiration looks and feels like.

The kicker about what happened today is that this time, the essential framework for making things happen has started to take shape in my own life. Finally understanding what pursuit of goals really requires, and why they are so important; “protecting the asset” by getting sleep and eliminating non-essentials and vices; just, I dunno, these basic management things that all proceed in the direction of being maximum at life. Without the foundations, the big ideas resulting from the inspiration I had today will remain only as ideas.

Now let us see if we can turn them into reality.

photo: Bamboo beach club, ocho rios, jamaica


One of my big things for September was the formalization of what I called my “Conquer List”. This is simply a list of things that in my past seemed insurmountable, but could be considered essential for life. The thought was to write down anything that I’ve ever said to myself, “I’ll never be able to do that”, or “I’ll never be any good at that.” Classic examples from the past have been cooking, dancing, money, mornings, and math.

But writing these things down and wanting to conquer them of course isn’t enough. Reading Ray Dalio helped me start to formulate a plan for how to approach conquering these things:

  1. Clearly define what it is.
  2. Identify problems that will prevent you from doing it,
  3. Find the root cause of the problems,
  4. Design plans to get around these problems, and
  5. Push through to results.

This is simplistic of course and doesn’t point out some essential goal-setting elements (like measuring, for example), but it sheds some light on a key fact: if there were no problems preventing you, achieving goals would be a cakewalk.

As I’ve built out the list and done further reading, my thinking on the Conquer List has shifted. The List is great but what’s really behind it? I’ll tell you. What are you really conquering? Put the focus on the problems, or as I like to now call them, the Enemies. When you evaluate something in terms of friend or foe, you will identify the things that are in fact existential threats to becoming who you want to be. Could be simple things like drinking, smoking, and/or being lazy. Could also be difficult things like deeply-broken personal relationships that need to be repaired.

You should definitely try thinking about all the stuff that most people wouldn’t put in a dating profile, and then draw some lines between those things and what your goals are. You have just identified some enemies to conquer, and now that you’ve identified them, you can take them out.

artwork: julius caesar


Morning routines, as it turns out, are amazing. There’s probably nothing closer to actually creating time by magic. All these small, easy-to-do things used to seem impossible, but now boom: it’s 6:30 AM and they’re all done and I’m walking out the door to work.

In turn, the routines program the brain very similar to the boot-up routines on a computer. As a young lad I had great fun fine-tuning the scripts for these boot-up routines, and if something was missing or done in the wrong order the computer wouldn’t do what you wanted it to do. Our routines program our brains the same way, and we can choose what our own programming is and design our own personal machine based on what we need ourselves to do.

The end result is, to use one of my favorite new words of 2018, transformational. All that stuff you’ve heard about people who succeed getting up early and getting after it? Super true.

artwork: The Persistence of Memory, Salvador Dali, 1931
The Museum of Modern Art

Who’d Have Thought

Maybe Your Sleep Problem Isn’t a Problem

I always enjoy coming across articles like the one above (you should read it, too) that tell my old story: the story of a person who for literal decades proudly proclaimed “I’m not a morning person”.

I’ve spent most of my adult life lamenting about how ungodly it was to be up before the ass-crack of dawn, bitterly cursing when I needed to trudge to the shower at 5am to prepare for some early obligation. I remember a business trip a few years back with an early-rising sales rep that had me up at 3:30am three days in a row to make 6am flights between cities, rather than my usual routine of evening flights the night before.

Ok, I think that last scenario even dedicated Larks would agree was a ridiculous idea. But what I’m getting at is that nobody (with the possible exception of my oldest sister) can claim more Not-a-morning-person cred than myself.

And I don’t want to sit here and tell people like the author of the above piece that they can change. “Pray-away-the-lazy”, as it were. We recently had Daniel Pink (author of Drive! and When) give a talk at our office. I definitely buy the science that he aggregates for us in his book When which tells us that certain people are genuinely wired as Owls, and that society wants to kill them. I thought that was me; I even remember being spot-tested for my crono-type by Daniel directly and him informing me that I was “owl-ish”.

And then, as if by magic, I changed into a Lark. Or (plot twist), did I actually just discover that I was a Lark all along?

People who love touting the fact that they’re not “morning people” remind me of a similar group of people who are proud of “not being good at math”. For the vast majority of people, lack of mathematics ability equates directly to the level of effort they’ve put into learning it – functionally zero. Relating this to myself, I can honestly say that my lack of morning-person skills were directly attributed to not developing the right habits to support it.

That changed about six weeks ago. I had read a number of books that talked about the need for getting enough sleep. One author said seven hours. Greg McKeown (Essentialism) made a convincing case for eight.  I then got introduced to the “Morning Sidekick” accountability journal and began using it immediately. Six weeks later, I am up at 5am every weekday (hopefully soon I will extend this to weekends as well) and killing it at work two hours later, usually 45-50 minutes early.

This has taken discipline and compromise, but after cutting out the wrong things and adding in the right things here I am. Mr Hates-the-morning guy is now excited to hit the bricks at 9pm on a Tuesday to roll it over and get started early on making Wednesday even better. Perhaps a true Owl would not be able to fight their DNA and accomplish this, but how many Owls out there are just Larks with bad habits? If you think you might be one, there is only one way to find out.

photo credit: david cooper

It’s the Little Things

I recently joined a local Brazilian Jiu-Jitsu school that happens to be run by one of the sport’s legendary characters. I was lucky to have moved within walking distance three months ago. Having been useless at exercising regularly since… I think 2010, learning BJJ was something I instantly knew I needed in my life and it became a personal goal of mine to someday win a BJJ competition. It’s been tough to get myself to the school on account of the ass-kicking I receive, but I try to remember that it gets a little bit better each time and that’s all you can really ask for.

Anyway so after class today, the big boss Carlson Junior stops a few of us on our way off the mat and I received from him the white band you see on the belt above. In BJJ it’s kinda like getting promoted from Private to Private First Class in the army. It’s such a small, silly thing but honestly felt great. Here’s a tangible, almost visceral metric for success. Here’s progress in the flesh, which required blood and sweat (thankfully no tears yet).

Not going to deny it made me feel like a kid again, but maybe there’s something there. Maybe the desire for that feeling of accomplishment is core to our beings and ought to be felt more often. There’s power in doing things you’re afraid of, then having proof that you’re doing them well. I have a feeling Brazilian Jiu-Jitsu is going to be in my life for a very long time.

photo credit: myself

The Hole

I wanted to share something that helped me visualize my life and the changes I’ve been making in it lately. This is the scene right outside my apartment, looking at a tree across the street. It’s about 7am in late July, and the sun is starting to peek through the leaves.

What I saw in this tree, directly in the center of the photo, is a little hole through the leaves. This little hole gave me the best image of how to answer the dreaded question: “Where do you see yourself in five years?” Now, I tell people I want to be going right through that hole in five years. But what is that hole, and how do you get there?

First off, what defines the hole? Only you can really answer that question. In my example, it might be something like: Divemaster. Fluent Spanish speaker. Brazilian Jiu-Jitsu competitor. Business Partner. Every island in the Caribbean under the belt. Things like that. Pick the things that you want to experience, improve, or become, and roll them up into a ball; or a hole, if you will. More on goal-setting to come later, so let’s move on.

Think of your life as being on a trajectory, slowly but inexorably moving towards that tree. I want it to go right through the dead center of that tiny hole. What this requires is setting the appropriate trajectory now and then protecting it vigorously, because tiny errors along the way will mean missing the mark significantly.

Lately every morning I spend a few minutes staring at that hole before catching my train. I think of all the things I need to do or stop doing in order to make it through that hole by the time I’m 40; this illuminates the adjustments that must be made now now to make that happen. Find your own hole, remove anything that knocks you off the path to it, and double down on things that stabilize & refine the trajectory.

photo: just outside logan square blue line station, chicago
credit: myself

Keep the Flywheel Turning

My old thinking, which I held for decades, was simply wrong. I used to be excited when I found myself at home at “only” 9:00 or 10:00pm. I would regularly abandon any more pressing concerns and get on with fun stuff. Stuff, specifically, that was effective at increasing my pleasure factor RIGHT NOW but had no lasting impact or benefit of improvement.

What I never really considered in those moments was the future; building to something greater in life, and the impact that decisions in those moments would have. Annie Duke calls this “mental time-traveling”, thinking ahead and visualizing what difference a small decision right now will make in five or ten years. This gives us a critical new perspective on bets we’re about to make, takes us out of the emotions & biases of the moment and shows us more potential outcomes that will increase the accuracy of the decisions we make now.

Another concept that I learned recently was Jim Collins’ Flywheel. The Collins Flywheel is explained in the context of building momentum in your business to turn a good company into a great one. But I’ve found that it’s just as applicable to your personal life. Betting on your future instead of just your present makes your personal flywheel go a little faster, and you want to keep that momentum building.

So next time it’s 9pm on a weeknight, choose to go to bed and wake up early tomorrow ready to do the essentials again, except this time a little bit better than before.

PHOTO: The Ashton Frost engine at Mill Meece Pumping Station. The flywheel is 19ft 6in (5.944m) in diameter and weighs 31.5 tons (30,481kg).