A LETTER TO MY YOUNGER SELF
Closing Remarks for the AmChamTT & IDB Women in Leadership Mentorship Programme 2025-2026
Dear 21-year-old Simone
I want you to picture something. Picture the version of you sitting at that desk at Brieves Road where you felt like the smallest person in the room. Shoulders a little tight. Smile a little too eager. Rehearsing sentences before you say them, in case one of them makes you sound like you don't belong.
I've been carrying her with me for years. And tonight, I want to write to her, because everything I'm about to say to you, I'm really saying to her.
So here it is. The letter I wish someone had put into my hands when I was starting out.
The first thing I want you to know is that you are already enough. Not the polished version. Not the future version. Not the one who finally has the title, or the credentials, or the perfect answer. This one. The one still figuring it out. She's the one who's going to do the work.
You are going to spend a long time trying to become someone you think the room wants. You'll soften your voice. You'll edit your laugh. You'll wear the clothes that feel like a costume and speak in a manner that isn't quite yours. And every single time you do it, a small part of you will go quiet. Please, bring her back. The world does not need a more agreeable version of you. It needs the actual one. Your authenticity is not a liability to manage; it is the single most valuable thing you'll ever bring to a table.
You are going to fail. I want to say that plainly, because no one said it plainly to me. You will pitch things that don't land. You will lead projects that don't work. You will be passed over for that Marketing Manager role, the Commercial Director promotion you were sure had your name on it. And each of those moments is going to feel, in the exact instant it happens, like proof of something terrible about you.
It isn't. It's the tuition, the price every leader you admire has paid it. The difference between the ones who make it and the ones who don't is not talent, it's whether they let the failure define them or refine them. Let it refine you. Then keep going.
Criticism is going to be harder than failure. Failure is private in a way that criticism isn't. Criticism is someone looking straight at you and telling you where you fell short — and your instinct will be to defend, to explain, to make the discomfort go away.
Don't. Sit in it. Let it be uncomfortable. The most important growth of your career will happen in the ninety seconds after someone tells you something you didn't want to hear, when you resist the urge to justify and instead just… listen. Not all feedback is right. But you cannot sort the useful from the noise until you stop flinching long enough to actually hear it.
And while we're on this,… please, please stop pretending you have all the answers. I know why you do it. You think that admitting uncertainty in a room full of confident people will cost you your seat at the table. It won't. The people who earn deep, durable trust are not the ones who perform certainty. They are the ones who can say, in a boardroom full of executives, “I don't know yet — but here is how I'm going to find out.” That sentence is not weakness. That sentence is leadership. Learn to say it before you feel ready to.
There is going to be a few years where it feels like every door closes at once. The job you wanted, the recognition you expected, the path you assumed was yours. I need you to hear me on this: rejection is redirection. I know how hollow that sounds when you're inside it. But every no you receive in the next twenty years is going to steer you, sometimes gently, sometimes brutally, toward the thing you were actually built for. The version of your career you can see from where you're standing is smaller than the one waiting for you. Trust the redirection, even when it looks and feels like loss.
You are going to be told, in ways subtle and unsubtle, that you are too emotional. Especially as a woman in these rooms. And you are going to start treating your feelings as something to hide, like a stain you keep covering with your hand.
Do not do that. Your feelings are not a bug in your operating system. They are the operating system. When something makes you angry, ask what value of yours it just violated. When something makes you uneasy, ask what your instincts are trying to tell you before your logic catches up. When something makes you cry, ask what it means that this,… this specific thing, got past all your defenses. Emotion is a barometer. It is telling you what you care about and what you are worth. Read it. Don't silence it.
Stop waiting to be ready. You are going to talk yourself out of so many rooms because you're waiting until you feel qualified, until the plan is airtight, until you have the perfect answer for every possible question. Perfection is a very expensive type of procrastination. Take the risk before you feel ready. The confidence doesn't come first and then the leap… it's the leap, and then the confidence, and honestly sometimes not even then.
Find your tribe. Not a network. Not a list of contacts. A tribe. A handful of people; mentors, peers, one or two very honest friends, who will tell you the truth when your reflection is lying to you. Who will celebrate a win with you without measuring it against their own. Who will pick up the phone at 10pm when that Ops review has flattened you, and remind you who you are. Build that circle carefully. Tend to it. It is, without exaggeration, the most important infrastructure of your career.
Say the unpopular thing. When you are the only person in the room seeing what you're seeing, the risk no one else is naming, the assumption no one else is questioning, the person no one else is defending ….say it. Yes, it will cost you sometimes. It will make some meetings harder and some rooms colder. But a leader who only says what is easy is not a leader. She is a mirror. Be the voice, not the reflection.
Give yourself grace. You are going to be so much harder on yourself than you'd ever be on the women you mentor. You'll extend patience, kindness, and a hundred second chances to the people around you, and none of it to the woman in your own mirror. Please turn some of that back on her. She's doing better than you're letting her know.
And finally, the most important thing I can tell you, and the thing it will take me the longest to learn.
The point was never the title. It was never the corner office, or the promotion, or the applause. The point was building a life you actually want to live inside. So do the thing that makes you happy. Take the trip. Take that Friday afternoon off. Take that hour with your kids. Find the joy in the small, ordinary, unphotographed moments because those are the ones that will still be with you when the accolades have gone quiet.
You are going to be extraordinary. Not because you become someone else. Because you finally, fully become yourself.
I love you.
I've got you.
Keep going.
With enormous pride, occasional exasperation, and all my love,
Future you
(and yes, you did it).