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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If you’re constructing a house, you don’t start by putting in windows and doors before the foundation and frame of the building.

It’s easy to lose focus on the important things.

It’s even easier to get caught up in trying to please others.

However, both of these things will often take you farther from where you need to be.

The smart thing to do is to respect the process.

When you do, you’ll be able to be proactive and make progress.

When you don’t, things can get messy, quickly.

When you show up for yourself, it shouldn’t be in a haphazard way.

You are worth more than you’ve probably told yourself.

But that doesn’t mean you get to have an ego.

The process isn’t an obstacle, if anything it’s your friend.

So go ahead, disrespect the process and see what happens.

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There’s always something to be done.

Work never truly stops piling up.

Especially on the personal development layer.

There’s a ton we interact with.

And there’s even more you’ll barely get the time to even do.

Before you dig into the fun stuff we have to organize and prioritize.

Otherwise you’ll end up spinning your wheels thinking you’re accomplishing a lot, when the reality is that you’re just all over the place.

So what are you procrastinating on? What would your life be like if you cleared the queue of stress, worry, and fear?

Chances are it would probably be amazing and full of the right energy you need around you.

So why not dig in and clear the queue?

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Moving pieces are everywhere.

Some organized. Some not.

Growth isn’t easy.

But nothing worthwhile ever is.

Because if it were easy, would you still enjoy the end result?

But what about the moments you stumble and get a few cuts. Those are the moments we’re never quite prepared for.

This is where having a strong support system will help you to keep things in the proper perspective.

Remember, it’s never really about quantity.

Yet it’s always about quality.

Followed by consistency.

Not just in showing up but also in how you show up when you do.

It’s about remembering where you’re coming from but not staying stuck in the thought of the past.

It’s about trusting the process and failing often.

Most importantly it’s about showing up and helping out. Genuinely.

Those on the outside will only see the tip of the iceberg.

That’s where they make their chess move calculations.

Remember, what you’re doing is inner work.

The deep, below the surface work.

Above all, it’s important to keep in mind that no one can really and truly replicate who you are.

On the flip side, aim to be more of an original than a reenactment.

Whatever you choose to do, focus on what you can do.

Growth was never meant to be easy but that doesn’t mean it should be chaotic either.

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The unknown is scary.

Until you realize that it’s just a remix of the past.

Yet very few take the chance.

Hopefully that isn’t you.

There’s a certain comfort in the unknown.

It beckons with a sweet mystery that can only be solved when pursued.

When paired with a focused curiosity, things become even more interesting and intense.

There are a few things that you must know before stepping into the unknown.

Some are more obvious than others.

But when applied, they tend to yield often unexpected blessings.

The first, stay true to you and you’ll be able to stay true with others.

It’s when you try to be a reenactment of others instead an original you, problems tend to arise.

This is where prevention beats cure each and every time.

The second is, don’t be afraid to ask the tough questions and follow the path empathy provides.

It’s easy to skate around the issues at hand and act as if everything is peachy.

However, it takes courage to be vulnerable.

Keep in mind vulnerability isn’t about sharing every little detail.

It’s about sharing what’s relevant and that which gives value in the process.

And last but least, show up… consistently..oh and help out.

Most importantly, while being authentic and genuine.

Things that should come naturally after following steps one and two.

The more you show up, the more others can establish a relationship with you.

Show up too often however and it may start to work against you.

Simple as they appear, there’s an art in pulling it all together.

But with a good foundation in place, you’ll find that the unknown becomes a little less scary.

You’ll find that the right people will surround you and the right things will fall into place.

That is if you’re aware that great things can’t be done alone.

In the end it really is up to you.

So what will you do?

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Forced connections are awkward.

Especially when there isn’t any prior relationship to back things up.

It’s easy to fall into the trap of wanting to connect and network.

It’s even easier for you to take a moment and say hello.

Yet even with the best intentions things can still get a little messy.

The breakdown happens when we neglect one of the most important factors when attempting to build trust.

When we fail to let that connection occur naturally and organically.

Boundaries help us to move in harmony with the world around us.

Without harmony chaos will exist.

Just because you might not find a problem with being invasive into another person’s space doesn’t mean they’ll be on the same page.

First impressions are crucial.

Don’t mess things up by failing to take the time to properly connect.

Doing things just for the sake of numbers is pointless.

It ruins the ecosystem and takes away from the good within humanity.

Its like receiving unsolicited mail.

No one asked for it yet here we are.

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Times ticking.

Yet you’re probably still sitting and thinking.

To the point you’re procrastinating on doing the right thing.

So you watch another video, purchase another course, like another status.

All to feel busy but in reality aren’t getting you anywhere except on the expressway to regret.

It really doesn’t take much to make a difference.

Just show up and help out.

And be consistent while you do.

It’s helpful to know why you do what you do as well.

Take advice (this post included) with a grain of salt.

Research. Research. Research.

Google is your best friend.

Take the time to dig into your craft, story, and experience.

Leverage that to make a difference.

With growing influence, one must keep in mind the equally growing responsibility.

The responsibility to help those just like we’ve been helped.

How? By doing the right thing.

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There’s a mystery to what is often described as a flow state.

We can spend hours unpacking theories and online searches.

Yet there’s something even more special about creative flow.

It’s said to be insanely creative, one needs to find their flow.

But how?

How does one come so immersed into a state of optimal productivity with all the noise floating around.

The easy way is through collaboration.

In the simple act of connecting with others we find a new level of clarity around our goals.

The hard part is you have to cross the bridges of fear and building trust.

But once those bridges are complete and you begin to connect with like minded people, a certain level of creative energy is unleashed.

It’s almost as if you’re pulled into an alternate universe simply by being around each other.

The best part is when each perspective at the table is respective and loving with the next.

Essentially, it’s one part empathy, a few parts passion, and a hefty helping of alignment around a selfless sense of service.

It’s within that vortex brought about by the gathered creative minds that pathways to new ideas and relationships are formed.

But it doesn’t happen overnight.

It’s what happens when you show up and help out.

It’s also what happens when you learn to appreciate the journey.

The moment you step outside of your creative bubble is the moment you change the course of what’s now possible.

Within you bubble it’s hard to see the path or progress.

But when additional perspectives are applied you’re now able to transition through the lanes of life without as many blindspots.

Besides, if you want to go far, nurture and serve your tribe.

…..

P.s If you’re looking for a tribe to call your own. One that will support you as you find your creative voice. Then join our humble little collective via the image below:

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It’s tempting to think that there’s such a thing as the perfect moment.

Or being completely ready before we can do our thing.

It’s also deceptive to think that time will wait on you to find the right amount of inspiration.

Sure, some days are way more difficult than others.

You may not have all the energy needed to fight the depression, the hurt, or the pain.

But you do it anyway.

Somewhere in the mix of it all you realize that the objective isn’t for things to get easier.

It’s for you to get stronger, wiser, and more agile.

It’s about building up the necessary momentum needed in order to reach the tipping point.

The one that’ll take you where you need to truly be.

It’s also about not giving up.

Why?

Because you have so much good to give in this world.

It would be a shame to make that all go to waste.

To live in regret and ask constantly, “What If..?”, is to put oneself through personal hell.

Your personal brand is YOU.

You aren’t a product.

You are a person.

One with goals and dreams.

A person that has so much good to give this world.

So the sooner you realize that there is no such thing as THE perfect moment.

The sooner you’ll be on your way to achieving the greatness you asked for.

So what are you waiting for?

P.s Looking to connect and grow with like-minded individuals? Then join me on Facebook in the The Always Upward™ Collective!

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To create the good the world needs to feel, you must realize that there is a purpose to why you’re here.

It’s not to compete but to collaborate.

It’s not to hate but instead to love.

It’s not to live in fear but to boldly live fully.

It’s way too early in the journey to be giving up.

Equally, you’re too far in to think about quitting.

So why not see things through?

Stop thinking that change is some huge fundamental shift.

Sure, it’ll happen from time to time.

Usually, it’s the exception.

It’s the subtle shift in direction that when followed with consistency in action, yields results.

The little things compound over time.

Don’t be in the majority that’s seeking to blend in and be comfortable.

We’re all running towards our goals at a different pace.

No need to be in a rush just because it seems someone else is moving faster.

Experience sometimes imparts upon us scars based on the bridges we choose to build, burn, or maintain.

The key is to know which ones should be burned.

Which ones should be built.

And which ones should be maintained.

The majority will choose comfort over character.

Which is why the majority often lives a very basic and unfulfilled life.

Aka personal hell.

It’s time to stop holding back.

Acknowledge it’s your life.

Your vibes.

Your choices that in the end will define.

Show up.

Lean in.

Help out with what you can, wherever you are.

Create that good.

Share your story, your art, and your love with the world.

Aim always upward.

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