How I Win Every Day

By in General

Here’s my morning routine and how it works.

This post will take maybe an hour to properly ingest. It’s a blog post I wrote for a few different kinds of people: people who are like me and are structure & strategy geeks, people who want to get to know me better, or people who are trying to learn how to be their own bosses. If any of those feel relatable this is worth your time in my opinion.

At the end of it, you’ll walk away with some new ideas and powerful tools for maintaining a healthy mindset even in busy and stressful situations, and the ability to take audacious goals and narrow them into daily action.

My favorite part of this post is about halfway through the video walkthrough of my daily routine document where I talk about my priming practice where I visualize results I want to achieve and talk about my prayer practice for everyone in my life. But none of that will make sense unless you take the time to get there. Enjoy!

Also, brief aside, I didn’t intentionally write the title of this post just to make this reference, but now I can’t help myself…

Before we dive in, (and while you listen to DJ Khaled yell his own name…) here’s some context on why I’m posting about my morning routine.


I’d like to illustrate how I get things done. One of the trickiest aspects of my entire life so far has been becoming my own boss and learning how to reliably, consistently get things done when I’m the only one in charge of whether or not I do them. So now that I’ve sorted some of that, I’d like to share what I’ve learned. I think this’ll be fun to look back on in 10 years and chuckle, and I know it’ll be useful for people who are trying to do similar things.

As you may already know, I do a lot of wild things. At the beginning of 2019, I reviewed my goals and noticed I missed some important, simple ones for the year. I’d fallen behind on a lot of stuff that really shouldn’t pile up – it should just be handled. And there were a lot of things (mail, clutter, folders on my computer, inbox, etc.) that many people leave disorganized that were also a mess for me. Until this point, I tended to clean those things in a big spring-cleaning style kind of push at the end of each year. I wondered if there was a way to live that kept all of the disorder and chaos in life continually getting better and less chaotic. Was there a sort of anti-fragile routine I could set up that would let me – even on the very tough days – feel like I had succeeded and simultaneously keep things from piling up? Instead, could I make the list of things that pile up smaller and smaller every year?

The answer is yes. Last year my inbox stayed clean all year. My mail stayed checked. My car stayed spotlessly clean. My house did too. Spotify playlists, Evernote, camera gear, and more. It all stayed organized or got MORE organized. No clutter, no re-organization, no pileups. This year I’m moving on to hard drive space, project file management, and photo archives and applying the same process.

The key to getting ambitious things done regularly comes in three parts:

  1. Have huge goals. Setting huge goals lets you figure out what outcomes matter – what things you need to measure and therefore break down into daily chunks.
  2. Weekly routines – these are the key to keeping stuff from building up.
  3. Daily routines – these are the only steps that make the rest of it work. Otherwise, it’s just a lot of goals and dreams and things you “should” do – not stuff you’re doing today.

So today, on the first weekend of February 2020, the time that most people have said goodbye to their resolutions for the new decade already – I’m going to begin a three-post series on goal-setting, self-care, and achieving huge outcomes with small daily practices. This is what has finally worked for me consistently for a year (after 5 years of iterating on different designs). I hope you glean something useful. Thank you for your time in advance!

Okay, so first off, let’s dive deep into #3: My morning routine.

My Morning Routine At A Glance

What did I want out of a morning routine? I wanted to be able to set myself up for the best day ever, every day.

Design Constraints

Here were my constraints:

I wanted to be reminded to meditate, write, read, and go on walks for at least an hour each day, but only feel good about that goal – never like I failed or didn’t do it. I knew that’d be the key to succeeding.

I also needed to create maintenance routines (in daily form and in weekly getting-things-done traditional (GTD) form) which means nothing ever piles up in my life: emails, trash, rooms to clean and organize, folders or files or organize. Everything stays organized and in a presentable state all the time, even if I miss a day, or I miss a week or a month. Totally Anti-fragile and my life gets more organized over time, not less.

I never wanted to feel like I failed at my morning routine or my day. I never wanted to feel like I’ve wasted time or fucked up. Those aren’t super productive emotions to feel – instead you can build structures to notice when you fall short and do better, and then set expectations such that you don’t feel those reactions anymore. this way, you benefit from the same improvement function as worry with none of the pain.

I wanted to have a structure that made quality time with friends and family as urgent and important as angry emails from work at 2 pm on a Tuesday.

Key Constraint: Anti-fragility. The more I need it, the better and more reliable it gets.

I needed something that would set me up with an incredible mindset every day. No bad days, especially on bad days.

If I went on a surprise vacation, I could keep everything on track and still manage projects and get things done effectively.

If I got broken up with by someone I thought I’d spend my life with I had a good day – meaning I was present, I felt the negative feelings openly, I was calm enough to go on a walk and write and journal and know that I’ll be okay.

I wanted to be able to have good days regardless of things that were out of my control – without bringing negativity to those around me or worrying about the people who care about me. Giving to my therapist what is theirs and keeping to myself what is mine and bringing joy and confidence and peace and fun wherever I go for everyone else.

Doing my best internally to manage myself so that I bring the best version of Steve wherever I go.

So those few examples apply, and everything else I can imagine off the top of my head – some of the most dramatic swings life can throw at you. As examples:
If I fell head over heels in love I had a good day.
If I stood on stage in front of thousands of people who adore me I had a good day.
If I had to go to traffic court for I had a good day.
If I got bad health news about someone I love I had a good day.
If I had a tough work project fall through or an angry email or refund, I had a good day.
If I made $10k in a day I had a good day.
If I had to go $10k into debt I had a good day.
I got in a fight with someone I care about, still a good day.
If my flight got delayed 40 hours I had a good day.
If I walked into a surprise birthday party, I had a good day.
If I totaled a Tesla (thank goodness a loaner) by getting t-boned on the interstate (really) and had to wait on the shoulder of the interstate for a tow truck for four hours instead of going to an Apollo landing 50th-anniversary countdown party with friends who flew from across the country, I still had a good day. (This one really happened, and I wasn’t at fault. Wild story tho, ask me sometime.)

As that last item underscores – life is too short not to enjoy and be fully present in each precious moment, even the really tough ones. We make our own rules and set our own constraints, so I wanted to set myself up to absolutely rock every day no matter what happened.

A good day entails meditating, going for a walk, being thankful for my many many blessings, bringing light and joy and happiness and a smile to someone else, and just being present and thoughtful even when things are difficult. Treating people well even when it’s tricky. I don’t do this perfectly, and I don’t know anyone who does, but boy does my process help me be a more reliable human.

I feel like I have a structure to be thankful and to thrive no matter what is out of my control.

The trick to this flexibility is simple: It needed to be doable in 30 seconds or less on rushed days.

Complexity, Simplicity, and Parsability: AKA Nerd Stuff

On complex days it needed to be able to expand to be the only organizer I needed and still let me support 60 people across four teams and track and manage a dozen different projects WHILE maintaining my own personal life goals of getting great sleep each night, spending most mornings getting breakfast with family, and reading, writing, and going on walks at least an hour a day.

It also needed to be simple enough to do on any phone, anywhere in the world, even without an internet connection. So if I get dropped in a developing country the question is: can I find a free phone, visit free WiFi, download Evernote and use this routine? Good. Then it’s robust enough to use.

Also, ALL of the data I input has to be easily parseable by simple XML parsing later, so when I ask Siri in 2030 to make my goals list for the day based on goals I’ve set and achieved handily in a single day, the system will be able to use machine learning to determine what kind of goals they are and build a to-do list for me.

Also remind me to make a whole blog post about how I’m planning to custom build an import bot to onboard all the screenshots I’ve taken in the last 10 years and everything I’ve written privately or posted publicly or said or done and turn it into an instantly randomly accessible completely computerized version of my whole human experience, as both an assistant for myself and duplicate me for others.

Anyway, I digress…

So no tables or charts, categories, totally mobile thumb-typing friendly and project agnostic. The busier and more stressed I am the more valuable it gets, and the more it supports me to be my best self. Doable in 30 seconds, scalable to multi-year projects with many team members.

Something I can do each morning no matter where I am or who I’m with and feel like I already won the day.

Narrated Video Walkthrough

Here’s what I ended up building, highly recommend watching this at 2x speed if you’re into that.

A few things to notice…

Some things to notice as you watch:
Notice that I am kind to myself. This is most important of all when you’re trying to do things and effectively self-direct. Don’t beat yourself up when you don’t do things. Not productive. Just take note of what to do better next time and move on.
Notice that I don’t care how much of the list I get done, just that I make a list.
Notice that I don’t always do all of it, that I reward myself for doing most of it.
Notice that I only change the structure once every month or two, and update the template from time to time.
How cool is it that I do this every 24 hours and the video is 24:24. Nice.

Notice that when I’m done making it, it’s instantly on every other device I own, and everything I need to reference is right at the top of the note. It’s instantly synced to my iPad, watch, laptop. So I can just put my phone on charge and get to work on my laptop, or I can go on an adventure with friends and check my watch. So simple.

Credit Where It’s Due

I also want to credit Nalini Saxena, a friend in New York who is a very talented executive coach and consultant and who really really inspired me to take my morning routine design as intentionally as possible. During early 2019 she was one of a few people I checked in with for feeback on their morning routines as I thought through mine. Her approach to having 8 things to do and only really holding herself to doing some fraction of them is the key that makes this routine so robust and feel so doable and rewarding. You’ll see in my walkthrough below how I have a long list of possible routine items I could accomplish (like meditate) but I don’t press myself to do them every day. Ironically I think that’s the reason I meditated every day last year – I knew I could substitute in other things when I wasn’t feeling up to it, but meditation always felt the most worthwhile out of everything on the list.

Make your own!

Here are copy and paste versions of it directly from my Evernote account, as links to my Evernote templates.

Here’s the original I started with Jan 2019, just sort of made up:

Here’s after 1 year of using it, with a hodgepodge of cool things I’ve learned/discovered/added/tweaked along the way, including this “priming” practice I learned from a youtube interview.

And next year I’ll update this post with my newest discoveries in year 2 of using this system.

In coming posts, I’ll dive into my weekly routine and how all of my daily and weekly routines are all held together by a series of long-term goals that inform what things I say yes and no to. You’ll find my weekly routine kind of boring and not worthy of much detail, which is because it’s just heavily based on the book/structure called Getting Things Done. Nothing new really, just customized for me. Here’s my GTD template too, for reference, adapted from Evernote’s default GTD template. So stay tuned!

Subscribe if you’re not already for updates and extras! And please let me know if you make use of any of this or found any part of it inspiring. Tell me a bit about what you do every day that helps you thrive!

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