37 Simple Life Lessons I Learned Last Month

On fitness, travel, relationships, money, and the ideal work day

Mar 10, 2024

Greetings from 33,000 feet in the air on my way from Scottsdale, Arizona back to Miami, Florida.

The last 5 weeks have been a bit of a whirlwind:

2 weeks home in Miami for an intense work sprint
1 week in Cartagena, Colombia for my business partner’s wedding
2 weeks in Medellin, Colombia exploring the local lifestyle
2 nights in Scottsdale for a bachelor party with my best friends from college.

Luckily, this 5-hour return flight gave me some much-needed processing time without any distractions.

Powered by a couple of espressos, I knocked out my monthly recap where I look back through my calendar, notes, and daily recaps to distill:

Everything that happened
Everything I learned (about myself and the world)

But, I like to take these reflections a step further.

In the past, I would tuck them away in the back of my notebook, only to never look at them again. Now, I like to share them publicly & write about them so I can stamp them into my brain.

And hopefully by doing so, you too can learn from them (while avoiding the mistakes I made that allowed me to learn them).

With that in mind, here’s my list of lessons & realizations from the month—split up into the 6 different areas of my life:

💪🏼 Health lessons
💰Wealth lessons
🤍 Relationships lessons
🌎 Travel & lifestyle lessons
🧠 Operational lessons
💼 Work lessons

Now let’s dive in:

💪🏼 Health lessons & realizations

After going 500 days without alcohol, I’ve slowly reintroduced it into my life. The 2 occasions that are certainly more enjoyable & memorable: weddings + world-class dinners at Michelin-star restaurants
The ideal alarm clock is being woken up to the birds chirping (about 30 minutes before sunrise). This “full circadian alignment” is when I feel & operate at my best.
Short & efficient full-body stretches & workouts before a flight will mitigate 90% of the damage from flying. It’s worth it to sacrifice 30 minutes of sleep to make sure this gets done beforehand.
The best way to improve your mobility is through 5-10 minute mobility “snacks” throughout the day. This is easier & more sustainable than finding time for long & intense stretch sessions.
Don’t drink the water in South America, no matter what they say about it. Trust me on this one.
Having Greek Yogurt stocked as a healthy snack when traveling is the biggest fitness hack. I ordered this by the tub in Colombia which meant easy-to-eat protein was always within arm’s reach.
When traveling, do everything you can to remove the “friction” of working out. Stay somewhere with the most convenient gym, find templated 40-minute workouts you can do anywhere, and do it first thing in the morning before life and other opportunities inevitably get in the way.
The ideal body composition is being “less than 6 weeks away” from being in peak physical condition. You don’t have to be at your top form year-round, but you should never be more than 6 weeks of intensive effort from it.
The easiest way to process an anxious thought:
- Identify the thought
- Reflect on these 2 questions
  1. What would happen if this were true? Would anything actually change?
  2. What evidence do I have that this thought isn’t true? How would I feel then?
- Recognize that you’ll probably be okay in scenario 1 and that scenario 2 is far more likely

💰Wealth lessons & realizations

Spending time in South America but earning in USD is absolute arbitrage. You can stay in the wealthiest, safest, most expensive areas and they cost ~25% as much as Miami / other tier-1 US cities. This doesn’t mean live there year-round, but it deserves a good 3-6 months per year
I can only go so many more days without owning a significantly large piece of farmland in South America. Will not explain.
During times of big financial market moves, commit to holding for the next 90 days. Then, disconnect your account from tracking and revisit it once your 90-day timer is up. This will prevent you from making overly emotional decisions (which is the quickest path to financial ruin).

🤍 Relationship lessons & realizations

I love getting dinner with other smart people, but I absolutely despise the logistics of planning them. So I’m going to design a system that makes planning them something that happens on autopilot (so I can just show up and enjoy)
One of the strongest correlations to my happiness is how often I watch the sunset without my phone with people I care for deeply. Going to continue to optimize my life around making this number go up.
The best relationships strike the balance of 1) enjoying world-class experiences for the first time together and 2) enjoying the everyday, mundane activities just as much. Both extreme novelty & extreme routine should generate feelings of appreciation & gratitude.
Relationships are transactional. But you can use this idea to strengthen them with the lens of always “operate in a surplus”—meaning seek to give far more than you take. And a good indicator to give even more is the moment you most feel like taking.
A handful of lessons & realizations on how to most enjoy a wedding:
- The only night worth drinking is on the night of the wedding itself.
- You can easily miss drinking at the rehearsal dinner, not that fun and lots of sitting around. Plus, you wake up on wedding day without a hangover.
- Stay sober for the ceremony. It’s often too long between that first drink and your next one, which will leave you with a headache if the ceremony drags on.
- First drink post ceremony = espresso martini to get the night going. Also, try this with tequila instead of vodka. IYKYK
- Give up any aspiration of having a productive day after the wedding. However, don’t double up on the damage by eating poorly / drinking again the next day. Instead, just get back to treating yourself well.
- Bolt on some kind of travel experience before and after the wedding weekend itself. Otherwise, you’ll feel too much whiplash flying in and flying out. It’s a good excuse to explore an area you otherwise would never think to explore.
- The best weddings make it easy for guests to create lifelong memories—whether being a destination, having unique cultural elements, or having a top-tier photo booth to take high-quality pictures.

🌎 Travel & lifestyle lessons

Spend more time crafting environments you “love” to spend time in. Your office setup, your gym, your room & bed—reflect on the question of “how much do I love this space” and then figure out what’s keeping you from improving it.
When traveling, keep the habit but reduce the intensity. Rather than stop doing things entirely because you can’t do them all the way, just reduce the scope and stick with them.
I am slowly recognizing how few things warrant staying up past 10 PM. Even 10 PM feels late at this point.
The best travel “lens” is to use it to advance your hobbies. For me, that’s music, sports, coffee, chocolate, flowers, hiking and learning languages. I can’t wait to explore each of these across different areas of the world.
If there is an option to book a helicopter during a travel experience, book the helicopter. Trust me on this one.
Even when you’re flying first class, airplane food is still airplane food. Better to just cram coffee, write, fast, and enjoy the nicer seat.
For hotels, a decent room with amazing hotel amenities trumps an amazing room with mediocre amenities. Having both is ideal, but if you can only choose one, optimize for the amenities (gym, restaurants, walkability, convenience, and service quality).
Always, always hire a private personal tour guide when traveling somewhere. But more importantly, call and ask to upgrade the car to a larger one, even if it’s a little more expensive. Being in a tiny clown car can still make the best of tours miserable.
My ideal lifestyle involves two different exercise sessions per day. One in the morning (cardio) before I have coffee, and another in the afternoon (strength training) once I’m done with work for the day
For me, I find novelty through variations within a routine, rather than variation of the routine itself. For example, having a daily structure that involves writing, training, eating the same handful of foods, and going to coffee shops gives me a rough “structure” to sequence my day no matter where I am. Then, I find novelty by mixing up what I write about, where I train, which coffee shop I go to, and how I prepare my staple ingredients.
The best cities to live in have a barbell of 1) immersion into the action of city life and 2) immersion into a nature experience that feels like an entirely different planet. Medellin, Colombia (where I spent the last few weeks) firmly ticked this box.

🧠 Operational lessons & realizations

My goal of personal reflection is to constantly update a list of “principles.” These help me make decisions & provide a lens through which I view the world. (And this monthly reflection is how I update that list)
Design your habits & constraints for when your willpower is at its lowest, not its highest. That way, your system doesn’t crumble when you’re tired (which you be more than you’d like).
Do it immediately or be behind instantly—speed is king. This is most true for shipping business improvements & responding to text messages.
Immersion >>>> consistency when doing anything new. Relationships, culture, skills, languages, hobbies—you’ll make leaps and bounds more progress doing something for 6 hours per day for 2 weeks than you will with 1 hour per day for a year
You can only appreciate how good something is when you have relative context for a much worse version. Relationships, food, hotels, flights, TV shows, daily moods, workouts, books—each of these requires a relative comparison to appreciate.
During periods with lots of transition, morning processing time becomes even more important. Find a way to get 10-15 minutes of journaling in no matter what, even if it’s just bullet points on your phone. Otherwise, multiple days will fly by and you’ll completely forget what happened
My ideal working day follows a simple template: 4 focused hours of work before noon, 1 hour of light admin work from my phone, and then a mid-day workout before tapping out completely before 3 PM
Every time you do a personal admin task, ask: “how can I automate this?” This takes a few extra minutes of thought, but compounds throughout the year as you save a few minutes per day.

💼 Work lessons & realizations

The most sustainable content creation formula for me: 1) capture an idea 2) outline it with bullet points 3) film a quick talking-head video to flesh out the idea as an outline 4) use that as a transcript and refine it for posting
Either spend the entire morning in meetings or the entire morning doing focused deep work. One mid-morning meeting is enough to derail an entire day of deep work. And trying to do meetings after an entire morning of deep work never works out well.
All employee 1:1 meetings should be walking meetings. Start with a quick minute on FaceTime to say what’s up, then cruise for the next 30 with just audio.

Aaaaand that’s it.

Lots to chew on from these past few weeks.

Also—it’s wild how fast 2024 is flying by.

16% of the year gone already, poof, just like that.

If you have any questions on one of these lessons please hit reply and let me know. I read and reply to every one of them.

📝Monthly writing recap

These were my popular pieces of writing from the month:

A full breakdown of my day in the life working & living in Medellin, Colombia. A deep dive into my approach to work, exercise, nutrition, sleep, dating, everything.
A simple business lesson from a world-class Michellin-star restaurant in Medellin. I plan on implementing this one into my various businesses immediately.

A full breakdown of the tech stack running Ship 30. This post covers every single piece of software we use to run our business.
An explanation of my “Daily Bullets” journaling practice. I’ve used this to journal every night for 1,000 days over in a row. And it’s the foundation of my reflection process that powers these weekly & monthly recaps.
The simple lens I use for all my relationships. In this one, I explain why every relationship is transactional—and thinking otherwise goes against human nature.
9 reasons I’m writing every day in 2024. Reminding myself of why I write is such a powerful way to boost my motivation.
The metaphor I used to double my business last year. If you run a business, a Giant Money Tree sits in your front yard. Here’s what you should do with it.

I’m also committed to writing for 60 minutes every morning this year. But rather than rely on my own discipline, I’m posting about it every day as a way to unlock social accountability. I’m tracking all the days in this thread so I can reflect on the journey at the end of the year.

🎧 The tunes that powered this writing session

I typically refuse to buy Wi-Fi on planes because it helps me focus.

Usually this is fine, because I have plenty of music downloaded on my phone. But I recently switched to the new iPhone, so I had practically nothing saved—except for the last song I was playing before I got on the plane.

Luckily, that song is an absolute banger so I played it on repeat for the few hours it took me to write this. Get this one in your ears ASAP.

That’s all for this month

See y’all back at the end of March. I’m locking in for the next 10 weeks in Miami before I head to Barcelona at the end of May. Then, I’m spending the rest of the summer in Europe. If you have any recommendations for my time there, hit reply to let me know.

And if you need Medellin recs, I’m your guy.

- Dickie

Dickie’s Digest

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