Dear Me: Reflections, Regrets, and the Strength I Found
Dear Me,
I’ve been thinking about you – the younger version, the braver version, the version who didn’t yet know how easily fear disguises itself as practicality.
I want to start with this: you were not lazy, unmotivated, or lacking ambition. You were cautious. And when you are young, caution can quietly reroute an entire life.
You Should Have Gone to Medical School
Not because it would have been easy, but because you wanted it. You talked yourself out of it by telling yourself the schooling would take too long. Ten years felt like forever back then. When you’re young, everything feels permanent – four years, eight years, a decade. You couldn’t yet see how quickly time collapses once you’re standing on the other side of it, wondering where it went.
You Should Have Told Him You Loved Him
Or at least that you valued him. That he mattered. That you wanted to be with him. You assumed he already knew, or that saying it would make you vulnerable in a way you weren’t ready to be. Silence felt safer than rejection. But silence has consequences too, and they echo much longer than honest words ever would.
You Should Have Told the Other One to Get Lost from the Very Beginning
The moment you saw who he really was, you knew. You felt it in your gut long before you had language for it. You stayed anyway – longer than you should have – hoping clarity would come, hoping he would change, hoping effort could turn into commitment. But he was incapable of real love, at least in the way you needed it, and no amount of patience could teach him what he didn’t have. You weren’t wrong for wanting more. You were wrong only in ignoring yourself.
You Confused Passion with Destiny
You loved writing, so you thought that meant you should pursue it as a career. No one told you that loving something doesn’t obligate you to monetize it. No one warned you that corporate America and public relations would strip the joy from writing until it became transactional, strategic, and hollow. Eventually, you couldn’t write at all – not for pleasure, not for yourself. Something sacred was exhausted by obligation.
You Followed Another Dream Instead
You became a funeral director because you believed in meaning, service, and showing up for people at their most vulnerable time. That part was real. But you apprenticed under a corporate funeral home instead of a small, family-run one, and the experience broke something in you.
You weren’t respected. You were treated as disposable. You were hurt – physically and emotionally – on the job. A calling turned into a lesson about power, profit, and how institutions can crush the very compassion they claim to uphold.
And You Should Have Appreciated Your Mother More
Not in the abstract way we all do when we’re busy surviving our own lives, but actively. Deliberately. She was an amazing woman, and you didn’t always slow down enough to see her fully while she was here. You assumed time would always allow for later.
But Here Is What Surprised You
You are incredibly strong. Not the kind of strength that hardens or intimidates, but the kind that sustains. The kind that keeps going. The kind that learns, bends, and stays open even after disappointment.
You have a deep intolerance for injustice. It still makes you crazy when people do real harm and walk away untouched, when double standards thrive, when the playing field is anything but even. You believe – deeply – that as humans, we should all be held to the same measure of accountability and dignity.
And Yet, You Are No Longer as Judgmental as You Once Were
You’ve lived enough. You’ve seen enough. You’ve made your own mistakes. Who are you to judge, really? Experience softened you in a way youth never could.
You’ve also come to understand that some people simply cannot do what you can do. Not because they are deficient or weak, but because they are wired differently. Some people can only carry so much.
You remember a story from your youth – a cousin’s wife who left him and their children. It was taboo then. Maybe it still is. Your mother once asked, “How can a mother do that?” And now you understand something you couldn’t then: some people don’t leave because they don’t care; they leave because they are at capacity. It’s like asking someone with a broken leg to run. They can’t – not because they don’t want to, but because they simply cannot.
You Also See Relationships Differently Now
You know that no marriage or partnership is perfect, no matter how curated the Facebook posts look. So many people struggle quietly. Many stay not because they are happy, but because they feel they have no recourse, no support, no permission to choose differently.
And You Finally Understand Your Father
You recognize now that those moments – him sitting quietly in his easy chair, lights off, withdrawn – were not indifference or distance. They were depression. You know this because you faced depression and anxiety yourself – and unlike his generation, you sought the help you needed.
You learned that strength isn’t endurance at all costs; it’s knowing when to reach out. His generation didn’t talk about these things. They didn’t ask for help. They endured in silence, mistaking survival for resilience.
You Also Learned How to Draw Boundaries
You cut ties with family members who were toxic long before it became acceptable – or fashionable – to do so. You didn’t do it to be cruel. You did it because they took more than they gave. You learned to draw a line in the sand, and you still do today when people go too far. The younger you would have offered endless chances, explaining away behavior that drained you. This version of you knows that compassion does not require self-betrayal.
Here Is What You Also Know Now
You stepped away from the corporate nightmare, and in doing so, you became an amazing writer. Writing returned when it was no longer demanded – when it was allowed to be truthful instead of profitable.
You are still in the funeral industry – not as a licensed funeral director, but as someone who helps those who need it most. Titles mattered less than presence. You still serve. You still show up.
You have extraordinary friends, and you finally understand that friends are the family we choose.
You became a life coach. Maybe you should have been a therapist – but you help people. And they help you, too. Through them, you’ve learned that you are not alone in your struggles. None of us are. Everyone is carrying something.
And You Learned to Love the Small Things
A roof over your head.
Meals with friends and family.
The moon.
Cotton-candy clouds.
Birds and animals – especially the uncomplicated joy they bring to their days, doing exactly what they were meant to do.
If you’re reading this as part of the Sixty and Me community, I want to invite you to write your own letter.
Write to the version of yourself who didn’t yet know what you know now. Begin however you like – Dear me is enough. There are no rules and no audience unless you choose one.
Write about the dream you talked yourself out of.
The moment you wish you had spoken up.
Something you misunderstood about yourself or someone else.
What surprised you about who you became.
What you know now that you didn’t then.
You don’t have to fix anything. You don’t have to forgive everything.
Just tell the truth – gently.
You don’t have to share it. Let it be just for you.
Because sometimes the most healing thing we can do – especially at this stage of life – is tell ourselves the truth fully, without interruption, and finally bear witness to our own story.
And sometimes, that is enough.
Let’s Have a Conversation:
Have you written a letter to your younger self? What wisdom have you gained that you could never understand back then?
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