Dear Early 20’s Me,

Life is very real now.

Not the version of real they warned you about in all those cautionary speeches from people who confused surviving with living or the real that shrinks you into practicality and calls it wisdom.

We’re talking about the kind of real that shows up when the training wheels come off and the road has actual consequences, where the choices stack, where the patterns you ignore become the walls you run into, where who you are in private starts showing up uninvited in public.

You are standing at the edge of the most formative decade of your life and you don’t fully know it yet, if you knew the details it would spoil the fun and discovery.

What I do know, standing on the other side of it, is this: the version of you reading this letter is more equipped than you feel, more seen than you believe, and more capable of the life you’ve been quietly dreaming about than anyone in your immediate environment has given you language for.

They meant well, some of them at least. The Caribbean Elder side-eye when you talked about doing meaningful work wasn’t malice, could’ve had more whimsy but it was the survival instinct of people who had been burned by hope before. Try not to hold it against them but don’t let it become your operating system either.

Here’s what I wish someone had said instead.

Validation is a trap set by people who never had to fight for anything.

If they don’t know what it took for you to get out of bed this morning; what you carried, what you survived, what you quietly rebuilt,  they have no standing to assess your worth. You will waste years performing for rooms that were never designed to receive you, stop auditioning.

The people worth impressing will recognize you without a rehearsal.

Learn to tell the difference between supporters and undercover haters. It will save you years and energy.

Some people will celebrate you publicly, call themselves your friend, and won’t hesitate to undermine you privately or when they get an opportunity.

Some people ask questions to gather intelligence, not because they care about the answer. Discernment is not cynicism, in simple terms it is pattern recognition applied to relationships.

You are already good at patterns, use it here too.

The obstacles of your earlier years are building capacity and are not punishment.

When you sit in rooms where other people are rattled, you will be clear and steady. Not out of fearlessness, but because you have already carried and survived worse. Be patient with the process, the weight has its purpose.

The things that feel impossibly heavy right now are developing in you a depth that most people around you will never have to develop and many would crumble under the weight.

Sometimes diplomacy is the right tool. Sometimes you just have to let people know who they’re dealing with.

You were taught that being palatable was the same as being wise. It most certainly isn’t. There are moments when the most loving thing you can do, for yourself and for the other person, is clarity delivered without apology but with empathy.

You are not required to shrink yourself for the comfort of someone who is comfortable at your expense.

Understand the law of thermodynamics as it applies to your life.

Energy is not created or destroyed. It is transferred. Every room you walk into, you are either gaining energy or spending it. Every relationship, every project, every environment is either building your capacity or drawing it down. This is not a metaphor, fundamentally it’s an unspoken law of life. Start treating your time as the finite, non-renewable resources it is.

Go hard with your creativity. Go even harder after your dreams.

You started designing and programming as a teenager to deal with depression and turned pain into craft. That move right there, converting inner life into external work, is one of the most important things you will ever can continuously do. Don’t stop doing it. The world does not need another person who had a gift and was too afraid to use it.

You are Jamaican. You come from people who have built extraordinary things with nothing. Act like it.

Understand your free will, especially as it relates to what you can actually accomplish.

Nobody is coming to give you permission. Not your parents, bosses, institutions, gatekeepers, or the people who gave you the side-eye for dreaming too big.

You will spend your early career waiting for authorization that was never anyone else’s to give. The anointing came before the crowning. You were already in possession of the thing you kept asking for. Stop asking. Keep doing the things.

The generational patterns you were handed are not your permanent operating system.

You will have to consciously choose which things you carry forward and which things you put down. Some of what was passed to you was simply survival code, needing to be refactored, once necessary in the context that produced it, limiting in the context you’re building toward. You are not betraying your heritage by evolving it.

Articulation is not completion.

You will have this problem your whole life if you don’t name it early: you are extraordinarily good at developing ideas and extraordinarily reluctant to circulate them.

The framework in your head is not in the market. The blog post in your drafts folder does not exist to anyone but you. The talk you gave to three people and never wrote down is gone.

Publish the things, ship the imperfect version and evolve, the market cannot assess what it cannot see.

The people you build with matter more than the things you build.

You are going to meet someone who becomes your partner in every sense of the word. What you build together, the company, the family, the life, will be evidence that you chose right. Fight hard to protect that. Not everything or everyone will deserve your time, not every opportunity is worth what it costs.

Some of the best decisions you’ll ever make will look like walking away. Fomo isn’t real unless you make it.

Burnout is not a badge.

You will push yourself into exhaustion so many times that hospitals will become familiar. You will call it dedication but if anything it is a failure to believe that you are worth protecting. The work will still be there when you rest, the version of you that doesn’t rest will eventually not be, learn this earlier than I did.

Grief is not a detour from your life.

You will lose people and animals and versions of yourself that you weren’t ready to release. The weight of it will feel incompatible with being a functional human being.

Grief and productivity can coexist, grief and joy can coexist. What grief cannot coexist with is pretending it isn’t there. Let it move through you at its own pace. It is making you more capable of the depth the work ahead will require.

Success will feel different than you imagined. Don’t let that confuse you.

The room you dreamed about getting into will feel ordinary once you’re in it. The project you fought for will feel like Tuesday by the time it ships. The goal was never the feeling. The goal was always the building. Stay focused on what you’re constructing, not on how the milestones feel when you arrive at them.

Always Upward is not just a motto.

Not a destination. Not a performance. A direction.

When life knocks you down, and rather creatively it will, repeatedly, in ways that will feel unfair and sometimes are, the question is not whether you fell. The question is which way you’re facing when you get up.

But here’s what I really need you to hear.

You can put it down now.

The weight you’ve been carrying, the need to prove yourself to people who were never paying attention, the guilt of dreams that outgrew the rooms you were handed, the exhaustion of translating yourself for spaces that weren’t built for you, the quiet grief of becoming someone your younger self would be proud of without anyone around to witness the becoming; you don’t have to carry all of that into what’s next.

You earned the next chapter. Not because you suffered enough. Not because you finally got it right. But because you stayed and showed up when showing up was the hardest thing to do. You kept creating and going when you couldn’t see the point and things felt pointless. You loved when love required more than you thought you had left.

That’s enough. It has always been enough.

Put it down.

Walk forward.

Always Upward,
David

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The Whisper in the Chariot

Sometime ago I came across a phrase that stopped me in my tracks. Memento mori loosely translated from Latin to mean, “remember you must die.”

Allegedly, the origins of this phrase are credited to the Roman period of time, whenever a victorious general returned home in triumph, parading through the streets while crowds celebrated his glory, a servant would stand behind him in the chariot. The servant’s apparent only job? To whisper in the general’s ear: “Respice post te. Hominem te esse memento. Memento mori!” (Look behind you. Remember you are only a human. Remember you must die!).

At the height of glory, someone was there to remind him he was still mortal.

The Stoics like who embraced this practice weren’t being morbid. They understood something most of us spend a lifetime avoiding, that remembering the end is what clarifies the now.

Marcus Aurelius and Seneca used death as a daily grounding tool. As Aurelius has been noted to say, “You could leave life right now. Let that determine what you do and say and think.”

Even art and religion have their own respective examples, that this concept draws from.

When Everything Changed

As a young lad, death wasn’t a stranger to me, although sometimes I wish it was. I can’t pinpoint the first moment mortality felt real, it just feels like it’s always been the default.

In-between people I had grown to love and respect, from pastors, to people who felt like family but weren’t, to friends that were silently battling demons, and even those who left too soon without warning; grief had been a recurring visitor long before I had the language for it.

But knowing grief and being broken by it are two different things.

Within the span of less than a full year, I lost my cat of 16 years, an amazing woman that took me in like one of her own grandchildren during my formative years, and a good friend who was struggling with more than they let on. Three different kinds of love, gone. I felt angry and sad at the same time. Some would even consider it to be rage. Personally, I think it was love with nowhere to go.

Grief tends to look different on each individual forced to carry it. One thing is certain, it’s a ridiculously heavy load to carry daily and still have to be a functional member of industrial society.

It’s in the little things you start to notice it with at first, laughter feels different, silence hangs a little heavier, and joy carries a hint of ache. You realize immensely that you’re just living on borrowed time, while the clock ticks faster.

The Switch

Something shifted after those experiences. I’m not sure when because it wasn’t a quick experience but it sure was quiet and powerful.

The stupid fears I’d been carrying for years suddenly had light shining on them. The fear of trying. The fear of failing. The fear of being too much or not enough.

So I stopped waiting and started daring myself to start living instead of observing.

My approach to life changed, I found myself slowly having more patience with myself, more love expressed out loud instead of assumed, sharing vulnerability I’d been too guarded to show, embracing goals I’d convinced myself were out of reach.

Little by little the love suddenly had a place to go again and began to realize what nobody tells you about grief, sometimes it cracks you open in ways that let the light in.

What We Should Actually Fear

Memento mori didn’t teach me to fear death.

It taught me to fear an unlived life, that we should fear not living life lovably and abundantly, that we should fear reaching the end having played it safe, having held our love hostage, having let our fears write the story instead of courage and love.

The obstacles will come, pain will always find us at the most unexpected moments but life is ultimately what we make it, and we’re making it every single day, in the risks we take, the love we give or don’t give, the moments we choose to be fully present for or reach for a distraction.

We’re all on borrowed time. The question is what we’re doing with what we’ve been given.

Originally drafted in 2019. Published May 2026.

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Believe in what you do and the energy to endure will be present.

Approach life half-heartedly and it’ll be difficult to see the next step.

So what level do you want to be on?

Depending on the answer you may want to roll up those sleeves and prepare to dig deep in the mud.

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When will you realize that this thing called life can’t be played as an observer? No matter how hard you may try.

When will you learn that all the ways you try to numb the pain won’t truly make it go away?

When will you stop checking your phone and start checking in on your goals?

When will you stop using the past as an excuse and start leveraging it as fuel?

When will you stop letting the “failures” define you?

Seriously, when will you?

The version of yourself, that better version that you see every time you close your eyes is waiting to meet you.

When will you accept the invite?

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“You’re doing great, I know it”, was the sentence my tiny human shared with me as I began pulling the bag out of its container.

A simple sentence that made a mundane task a little more pleasant to endure. I mean, who really likes taking out the trash?

Yet, it’s a task that must be done in order to prevent a much more unpleasant experience from happening.

Much like life, there’s a good and bad side to most anything but especially when it comes to how well you can execute.

Throughout history there have been millions if not more that had a great idea but failed to execute.

The sure thing that the comfort zone provided turned out to be an illusion. Leaving them only with regret in the form of the question, “What if I had tried?”

Unfortunately, millions more will make this same mistake.

Hopefully none of those people will be you.

Life may not seem like a great thing right now but just keep pushing forward.

One step at a time. One moment at a time.

You’re doing great, I know it.

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It’s easier to reach for comfort than it is for growth.

Easier to play it safe than to take a risk.

But what happens when you reach the end of your life, and all you’ve been left holding is a bag of regrets?

What if you were to just get lost in the moment and rise above the noise?

What would happen if you allowed your focus to be on the goal as you go through the messy, mundane, and madness that often is life?

Would your fears still seem bigger than your dreams?

I’m guessing the answer would be no.

There are going to be days when all that you can do is facepalm at the state of things around you.

This mindset of everything has to be perfect before it launches is the killer of more dreams and organizations than anything else.

The whole point of life is to grow by learning…while being a decent human in the process.

So what if you fall down a few times on the way to your goals, keep rising.

Small steps made daily yield more progress than large steps made infrequently.

Train your mind to look above the noise and your steps will follow.

What will you choose today?

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Life literally feels strange.

Yet despite how things may be, I’m ever so grateful.

For the first time in a long time, I feel like I’m back in my zone.

The secret? Focus.

Anything that doesn’t positively add to my life doesn’t get much time.

It’s not worth keeping things around you that reopen the wounds you’ve trying to heal either.

The path upward will reveal all the good stuff as long as you stay focused.

Focused on the things that uplift, encourage, strengthen, and empower you to be the best version of you, that you can possibly be.

It’s because things don’t go as we plan that allows us to find what should really be the plan.

There are two sides to every experience. The lessons we draw from each side impact the steps we take next.

Hence the importance and perspective to choose wisely.

This is what I’ve come to realize.

After all the things life has thrown at me, there must be a reason why I’m still here.

This curiosity lead me to start figuring out what I’ve dubbed as a minimum loveable brand.

But nearly four years after the first talk I gave on the topic, the meaning of what a minimum loveable brand is only recently became clear.

In short, a minimum loveable brand is one where inclusion and diversity is at the core. A personal brand that is heavily influenced by empathy, self awareness, and a passion of improving with rapid iterations.

Where the focus isn’t on anything else but discovering your creative power and how it can be used to create massive good.

The reality is this.

Life isn’t about being happy.

It’s about being whole.

The quicker you and I realize that, the quicker we’ll achieve the growth our souls seek.

See the lane. Walk in it and trust the process.

Stop comparing yourself to others.

Success isn’t a straight line, and definitely not something that happens without great sacrifice.

Embrace all the lights that appear on the dark roads that often exist in life.

Be the person that makes someone aim always upward.

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What you think of yourself and your abilities showcases itself in how you act and approach your purpose.

Devotion breeds excellence.

What kind of excellence that ends up being is on you and no one else.

The reality is that the more you aim to uplift is the more you’ll be uplifted.

But it starts in your mind.

What you feed it with will either strengthen you or leave you feeble.

Creativity can’t exist in a bubble.

It needs diversity, respect, and a devotion to something more than just ourselves.

The reality that exists is simply based on you create.

So why not create more good?

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Sounds like a recipe for the ultimate level of burnout.

If you aren’t taking care of yourself then you’ll be in no position to take care of others. Regardless of how big your dreams to may be.

Thing is this, when we’re not focused on what we’re doing, we become seriously unproductive.

It isn’t selfish to take time to heal your mind, body, and soul.

If anything, it’s the best thing you can do for yourself and those you love.

Because what’s the sense of achieving massive success but unable to enjoy it?

You can still help others while you heal but if you’re not intentional about how you treat yourself, someone is willing to do that for you.

Life isn’t a game with extra lives or do overs.

Drop the expectation of what the world thinks you should be and embrace the creative good inside.

You do deserve to be happy, just be careful that it isn’t at the expense of your ability to create more good.

So drop the world and pick up yourself.

You’ve made it this far, aren’t you curious to see what could happen next?

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How often do you wish for an experience that you’re going through to be easier?

They key to accepting growth is to keep pushing.

Especially in the moments you feel like you can’t.

The thing is growth isn’t complicated.

We make it complicated like most things that we do.

The sooner you accept the growth moments within your life, is the sooner you’ll reach the heights you aim to attain.

So what will it be?

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