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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If you tell yourself that you can, you’re more likely to try.

When you’re more likely to try, you’re more likely to win.

Achieving the unimaginable doesn’t require any special skills, it does require a willingness to show up.

More importantly, how you show up.

If you’re going to a party, chances are you bring something along.

Why not take the same approach with life?

So here we are at this pivotal point in history, hopefully asking ourselves, what unimaginable things can I accomplish in my life?

That’s the question I asked myself as the dread of becoming a year older crept up.

It was time to set the theme for the next year of my life.

Besides, what’s the sense of creating an entire brand development framework and program if I don’t take my own medicine?

The rules are simple, look at three areas that I want to focus on or improve in. 

From there the overarching theme often arises. 

So after reflecting on the past year of returning to the stage after burnout, reigniting my loveable core, and finding the passion to create again, the answer became quite clear.

In order to reach the next level as a creative and entrepreneur, I would need to be relentless in my pursuit of my ambitions, while removing the fear of setting healthy boundaries.

Most importantly, in order to heal, I’d need to create deeply.

Let’s break it down.

Chase Your Ambition

Often we’re told to chase our dreams but what about chasing ambition instead?

Dreams come and go. 

Ambition however requires a much different approach.

The long game, where the endurance levels intensify and only those who see it through will make it to the promised land.

In this lane, it comes down to how bad you truly want to reach a better level that goes beyond financial gain and fame.

We’re talking about the kind of ambition that wields true influence where it naturally sets the standard everywhere it goes.

This only happens when you set your focus on something bigger than what the status quo offers.

It’s an opportunity to stretch farther than your current comfort zone suggests but only if you dare to answer the call.

With that in mind, I assembled a traction list aka a list of things that I want to accomplish before 2020. 

The plan with this strategy is to leverage the trade winds of turning a year older to finish the year strong and build up the needed momentum to crush the upcoming calendar year. 

In short, it’s an ambitious effort to supercharge my loveable core to an intensity that it hasn’t really seen before.

Surprisingly I’ve accomplished a little over 30% of the things on the list with a few months left in 2019 to spare at the time of writing.

That’s the thing about being intentional when you’re chasing your ambitions. It allows you to reach into a source of energy far greater than what the gurus and self help experts can ever offer.

Ambition however, is limited by the boundaries you perceive and the boundaries you set with those around you.

Set Your Own Boundaries

Protecting your energy as a creative and leader is key to being successful.

Let the wrong energy into your life and you’ll spend more time trying to balance things out than anything else.

This is one area where prevention is definitely much better than the cure.

However, if you limit yourself to only achieving what you think is possible, you’ll never go farther than I what you can see.

Setting your own boundaries requires a different type of faith, one that is only acquired by passing through the valleys.

Experience is the only teacher that can deliver this perspective effectively.

As you set boundaries the key here is to balance making the map and filling in the details.

Lean too much in either direction or on anyone’s shoulder too much and there could be a problem.

There has to be a point in time when you’re simply comfortable in your own skin and content with who you are as an individual.

No one else can determine what’s ok for you. 

Only you can decide if you approve or deny of an experience.

Above all, only you can limit yourself. 

It’s about time you started to view your life with a little more appreciation and with the perspective that you can accomplish the things others say you can’t.

There’s a certain level as an individual that you realize that you need to find the limit and push it.

When you think you can’t.

Keep going but be respectful.

Like seriously, if you need to reach that next level.

Like you’ve been dreaming about it until you want it so bad until you want it badly at every step of being awake…

Max it to the limit.

Dig deep into your creative self and unleash ALL the dreams.

Too many people out here in this world living with regret.

Too many people wishing they could just be unchained from the expectations and created the good they wished to see.

Goodness. At what point does that change?

Let’s get real, if you don’t value yourself then chances are others won’t value you either.

The boundaries you set will either give you room to heal or they’ll constrain you to continue suffering in pain.

Create To Heal

Creativity is all about solving problems, so why not utilize a little creativity when it comes to healing?

Whether it’s establishing boundaries, setting goals or in this case with healing, creativity can go a long way.

If there’s a most important thing or “growth hack” it would be this; your creativity shouldn’t be overlooked in the healing process.

Often the emotions and thoughts that don’t fit within the normal boxes of expression find their way out through ones creativity.

When they do the first response is to fight the thought away.

The problem is that the thought builds up to a feeling where at some point the dam bursts.

In some cases that burst is expressed in a constructive manner and in other ways through unhealthy behavior.

One of these allows you to heal and face the fears you’ve been avoiding while the other ends up creating a much bigger mess to clean up later.

Immerse yourself in the creativity of life. 

Take the scars of life and turn them into stories that leave an impact.

Push back on the negative thoughts and reinforce your spirit with love and hope.

Establish the boundaries necessary to protect your soul, extend the vision of your ambition, create that which allows you to heal.

Keep the receipts of thy accomplishments and frequently give gratitude for the experiences that lead to each one.

Find your others, the ones that push you to be better in all the things.

Quality is the result of intentional and intelligent action.

Remember why you started but focus on why you kept going.

It’s not about being liked. 

It’s about being respected and learning to respect yourself. 

Do you respect yourself enough to attempt to achieve the unimaginable?

If you do, go out and live like it.

Live like you’re actually aiming upward and not just wishing it.

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You can have all of the knowledge in this world, even the ability to predict the future but if you do nothing with it, what’s that knowledge really worth?

We’re in an age where everyone wants to be a star and a few are about the execution.

The greats we from history that we often put on a pedestal, as flawed as they may be were individuals that focused on action.

Time to throw away the excuses and embrace the obstacles.

Because if it’s greatness that you seek, take some of that intellect and turn it into action.

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You see, it’ll be 2020 next year.

Up until this point, we’ve really only scratched the surface of the 21st century.

It’s been a wild ride since Y2K, the year 2000 and all of the joys that came after that.

However, there’s one thing missing.

We really haven’t looked at just how important it is.

Within this new age of work, the new age of education, the new age of family, friends and relationships.

We haven’t taken the moment to see just how important our lovable core is.

Up until now, we’ve really only approached work, life, dreams and goals, with a very general and often naive point of view.

We try to put each of these segments into their own container and we become a different person to meet the needs of each and every one.

Ultimately, we become the type of person that grows to become unfamiliar with oneself.

This unfamiliar feeling and perspective then grows into almost a mold of parasitic proportions.

One that goes on to destroy our family, our goals and mentally who we are.

Understanding your lovable core simply means this.

It means that you understand where your values, your priorities, your skills, and above all, who you are as an individual, and not who you are, as a job title.

The most powerful and courageous way to live in this world isn’t to sit on the sidelines and observe or to wish and hope that something grand and magical will happen.

No, instead it’s to go and live boldly.

To embrace each and every perspective, each and every new level that facilitates growth, that produces empathy and that showcases that you are more than just a cog in the machine.

That is the true power of being aligned with an activated lovable core.

So as you embark into the future regardless of what point in the year or a day or time in the life that you are, remember this; It only matters where you are going and how you’re getting there.

Because where you are right now is only one small piece of the grand story that is your life.

The choices, the people we surround ourselves with and our energy that is brought into each and every day is all that truly matters.

Someone will always be smarter, stronger, faster, richer.

There will always be problems that you cannot control or solve or prevent.

But that doesn’t mean that who you are, is diluted in the process.

So, I hope that you take each and every moment especially the moments when anxiety pops up and tries to paralyze you from moving forward.

I hope that you take these moments to lean in and say “I am going to continue aiming always upward.”

You never know who you’re inspiring just by showing up and you’ll never know the difference you’ll make if you never try.

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To go after your dreams is a risk.

To NOT go after your goals is a risk.

But sometimes you have to risk it all for the invisible that you only can see.

Because the biggest risk of all is to live a life that causes you to look back with regret.

Without the leap of faith, you’ll never know what you truly could be.

So do yourself, the world, and your future a favor.

Take the leap of faith and embrace the risk.

What would your tomorrow look like if you started believing in your dreams and goals today?

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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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In a matter of moments it can imagine absolutely anything.

When harnessed for a bigger purpose your mind is capable of contributing to massive positive change.

But on the micro level, your dreams and goals are your responsibility to see through.

Failing is a part of the process.

So are the obstacles.

Because at the end of the day, if you really want to make a difference, you’ll find a way.

You weren’t made to have a common existence.

Know the difference between giving up and knowing when you’ve had enough.

It’s time to stop hiding in the shadows of the comfort zone, and step into the light of your creative good.

Your dream. Your responsibility. Your choice.

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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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