Dear Early 20’s Me

A version of this letter was started in 2015. It took eleven years, a child, a company, and a few hard lessons despite having had the right instinct and not enough mileage to finish it.

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