For the first 350 days of Von Wong Daily, I would write first thing in the morning.

It felt like the most obvious time to write – because calls, meetings, and activities would stream in fast and furious the rest of the day.

I would wake up two hours before my first meeting and painfully squeeze out a paragraph before rushing off to my day.

For the last ten days, I’ve been trying a strategy of ease – writing only when an insight felt ready – or if the end of the day had arrived.

Rather than force out a piece of writing, I let it percolate in my subconscious – distributing what once was 2 hours of intense stress over a 16-hour or so waking period.

I’m not entirely sure if the quality of the writing has improved, but the days have absolutely felt more balanced.

How might you better play with ease in your life?

For the last year, I’ve been struggling to replace the word “Should” with “Could.”

The long list of things I used to tell myself I “should” be doing were filling me with a persistent state of guilt, frustration, and unworthiness.

On the flip side, a long list of things that “could” be possible felt much more invigorating and empowering… that is, until I stumbled on a bunch of “Shoulds” that didn’t feel like they could be replaced by “Coulds”

Our duty to protect other humans and the planet, for example, didn’t feel like an opinion that could be left to choice.

Recently, I learned that there’s another word that I could summon to replace the remaining “Shoulds” in my life; the term “Ought to.”

What we “Ought to do” is used to express obligations, suggestions, or advice that is ethically or morally correct… and those feel important to preserve.

Recently, as I’ve tried to become more intentional about who I should deepen relationships with – I’ve noticed an interesting pattern.

Who I spend my time with is less a function of who they are and more of who I become when I’m around them.

Around different people, I can become more curious, playful, and sometimes even smarter – and it has little to do with their profession, upbringing, or pedigree.

Some relationships bring out the best in us, while others bring out the worst. Both compound to shape who we become tomorrow – and it’s up to us to notice and prioritize accordingly.

Who we are in the present is clearly not who we are all the time.

Our present self is but a small slice of who we are, tinged with who we once were, hinting at who we might become.

Yet when we meet people for the first time, we tend to project who they are right now, far into the past, and deep into the future.

And when that experience is negative, we can sometimes default to harsh and unforgiving judgment.

Holding space for people to evolve past a negative first impression is not only kind; it’s wise.

Ht: Conversations with Marshall Hayes

Our experience of reality is hard to describe:

Words are inaccurate.
Emotions are vague.
Perception is limited.

Every moment we live through, interpret, and remember is but an estimation of what’s actually happened.

Yet these vague estimations are used to build relationships, make decisions and plan the future.

While we may never truly see reality for what it is, the better we estimate reality, the easier life will be.

The best way to do that? Archive your thoughts.

ht: Conversations with Marshall Hayes

This morning, I struggled to think of a meaningful gift for a good friend.

During our time together, it felt like he had everything he needed: great relationships, meaningful work, and enough financial stability to buy everything his heart desired.

In other words, I couldn’t figure out how to buy something for someone who had enough.

Initially frustrated, I soon realized how beautiful it was to find someone who had nurtured a feeling of enoughness.

Enoughness is hard to cultivate and even harder to sustain. Perhaps the best gift is simply an acknowledgment for someone with everything they need.

Almost every single app and service sold today offers to reduce friction.

“Do more with less effort and less time, ” the advertisements scream as if the purpose of life was to lead a frictionless existence.

Yet once in a while, we find ourselves chasing after the very friction we try so hard to optimize out of our lives.

Camping is a perfect example – where we pour time, energy, and effort to get somewhere where life is objectively more inconvenient.

But inconvenient doesn’t need to be uncomfortable. Friction is only problematic when we’re doing something we don’t enjoy.

Imagine walking through a public space littered with trash.

The default reaction for most of us would be to walk straight through, ignoring the mess as if it were simply a feature within the landscape.

Not our problem. Not our mess.

But once in a while, someone decides to step up and do something without waiting for funding, approval, or validation. They stepped up simply because they could.

We don’t need to wait for permission to improve the world. We just need to take the time to start.

I spent my day yesterday training on an FPV flight simulator.

The simulator was designed like a video game – challenging me to maneuver the drone in increasingly more complex maneuvers. Every time I completed a challenge, the next one would unlock.

Unlike a video game though, the goal was not to complete the game- but to acquire enough mastery to successfully fly the drone in real life.

Completing the game, in this case, is merely an indicator of competence rather than a symbol of mastery.

The education system trains us to pursue and value certifications and accolades – but what really matters is the value we can deliver in the real world.

In Western Culture, it’s customary to split the bill at a restaurant.

The idea is that by the end of the meal, nobody owes anyone anything.

However, in Eastern Culture – friends fight over the bill and take turns to pay.

This behavior signals that the only way to rebalance the relationship is to meet again. You only split the bill if you have no intention to meet again.

Relationships thrive on a slight imbalance because they create a continuous flow of reciprocity.

To prompt healthy imbalance in your relationships, find ways to offer small, impromptu, and thoughtful gifts.

If you take a paperclip and bend it out of shape, it’s impossible to re-bend it back into position without heating it back up.

When you first apply pressure to the paperclip, it creates a deformation in its crystalline structure. As pressure increases, so does the complexity of the crystal structure – which hardens and strengthens the steel.

Along with the hardening, though, the metal loses ductility (flexibility) and is more likely to fracture if enough force is applied.

In other words, when we bend a paperclip – it gets both stronger and weaker simultaneously.

The same is true when we try to impact the world around us by bending it into a more desirable shape. Whether we choose to or not, we’re constantly making it both better and worse through our choices, habits, and jobs.

Upgrading our awareness of the complex systems and relationships that govern our world is critical to ensuring that our impact is a net positive.

Most professional road cycling teams are made out of 10-20 riders who work together as a team to win a race.

Each team has a captain, the best rider expected to win, while the rest of the crew – the “Domestiques” – are there to support them.

The Domestiques sacrifice themselves to lead and reduce wind drag, offer up their gear when something breaks down, and deliver food and supplies when needed.

The captain only has a chance of winning because they accept the support, nurture, and care from those around them.

To be a successful leader requires us to be good at accepting help from others so that the entire team can win together.

Financial endowments are designed as perpetual gifts to a non-profit, foundation, or public institution.

Unlike regular donations, 100% of the funds from an endowment are invested – leaving the organization with perpetual access to the interest it generates.

This system enables organizations to run (near) indefinitely because the original capital stays untouched.

We must treat our natural resources the same – running exclusively off the interest it generates without eating into the very capital the interest depends on.

Of course, we also have to make sure that the investments we make with that capital align with everything we stand for…

But that’s a whole other conversation.

I don’t do vacation very well.

It isn’t because I don’t enjoy being in a relaxing environment, sampling the local culture while living in luxurious accommodations.

Quite the opposite. I love that piece of it.

But unless there is a clear mission on why the vacationing is necessary, I don’t know how to lean into it.

Having fun WHILE building deeper relationships with people, acquiring new skills TO level up, or discovering a new culture FOR inspiration.

With purpose, vacations become explorations, and exploration is a lifestyle one can build a career on.

Have you ever noticed that the best work in a creative’s portfolio, more often than not, are their personal projects rather than their commercial ones?

Commercial projects have a specific hierarchy. A client comes up with an idea, imagines the roles required to bring them to life, and searches for the talent capable of executing the job description.

In other words, people are hired to fit a role.

Personal projects don’t work the same way.

Because there are limited financial incentives to back up the request, roles and responsibilities must be built around a person’s interests and skills.

In other words, roles are created to fit people.

A genie’s infinite potential is bound by the creative constraints of the person rubbing the lamp. Only when the genie is free can they exceed everyone’s expectations.

ht: Conversations with Rachel Rosenfelt

Imagine the overly protective mother that fusses over the tiniest detail before letting their teenager out into the world for a day out.

In her mind, she’s trying to be helpful and supportive – pouring over the tiniest little detail in hopes of preparing them for every eventual challenge.

But nobody likes being fussed over, regardless of the intention. It takes away time and energy from all parties and provides little value.

The difference between being fussy and helpful is one of efficiency.

How much value are you providing relative to the time and energy you’re taking away?

When in doubt – keep things brief and straightforward.

Most big institutions have a fear of change and novelty.

Rather than see opportunity, they see risk – fearing the reputational backlash that can come from exploring and experimenting on the edges of the bell curve.

Over the years, as media has become more sensationalizing, polarizing, and triggering, that fear of public backlash has only grown larger.

Sometimes, that can be helpful to stabilize against bandwagon fads and trends – but it can also be dangerous to allow the court of public opinion to determine whether something is right or wrong, true or false, fact or fiction.

Yes, we live in a world that loves hopping to conclusions – but that is simply an opportunity for better storytelling; Not a reason to stop taking risks.

The guy that drives me around town is called Bacteria. He has a two-toned beard, half blond, half black, and wears sunglasses with a loose knitted cap and leather outfit regardless of whether it’s morning or high noon.

As a result, everyone takes note of him as he zips by on his motorcycle with a broken muffler and faux-grass-covered seats.

In a place filled with an infinite supply of potential motorcycle drivers, he manages to stand out because of the way he’s created a brand around himself.

It’s a good thing that he’s responsive, punctual, and a skilled driver – otherwise, that same brand recognition would exponentially backfire on him as people rushed to avoid working with him.

As long as you know what you want, building a personal brand can help develop personal accountability.

While touring a cork factory, I noticed that the highest value products were the ones that tried to look the least perfect, while the lowest value ones were the most consistent and ordinary.

The lowest value products looked like the ubiquitous cork boards we all know and love – seamless yet uninspired.

The highest value ones carefully combine imperfection and holes found within the natural texture of the bark without sacrificing any functionality.

When it comes to our differences and imperfections, we often try to hide them from the public eye. Yet it is precisely those distinctions that make us more interesting than the average.

So long as we ensure that our uniqueness doesn’t come at the expense of showing up for ourselves and others, we should celebrate them, not hide them.

ht: Cork tour with Pedro Geraldes