High School Me Would Be Proud. So Why Am I Not?

I know who I was back then. In high school, I was just trying to survive, navigating through insecurities, fears, and that constant feeling of not being enough. I had dreams, but they felt distant.

Who I was then

In high school, I was just trying to survive, navigating through insecurities, fears, and that constant feeling of not being enough. I turned that against people and projected a lot… I may have seemed bitter or self righteous, but I was scared, and I tried to cover that fear by bringing others down in the process, even if it was unintentional (the story of my pride getting the best of me is a very long story for another day that spans over years.)

That being said dreams always felt distant, like something for other people and not me. If that version of me could see who I am now, everything I’ve accomplished, everything I’ve been through, everything I’ve set aside, I know they’d be shocked.

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But here I am, looking at my own life, and all I feel is this strange emptiness. It doesn’t make sense. I’ve done things I never thought I could. I’ve faced challenges that would have crushed that high school kid, and yet, I don’t feel the pride I thought would come with it. Why?

Maybe it’s because the bar keeps moving. Every time I reach a goal, it feels like it wasn’t enough. There’s always the next thing, the next milestone, the next ‘should have done better.’ It’s like I’m chasing a version of success that I can never fully reach. And somewhere in that chase, I lost sight of how far I’ve come.

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The bridge between past and present

I think about that kid in high school who was just trying to get through the day, who felt small and insignificant, even though they had to be the loudest in the room. They wouldn’t care about half the things that weigh me down now. They’d look at me and see someone who made it out, someone who grew up and kept fighting, someone who’s still standing despite everything. And I think they’d be proud.

So why can’t I see myself through their eyes? Why can’t I feel that pride? Maybe it’s because I’m too close to it all, too wrapped up in my own expectations and self-criticisms. Maybe I’m scared that if I stop to feel proud, I’ll get stuck or lazy or lose that drive to keep going again.

Or maybe I’ve just never learned how to celebrate myself. Maybe I’ve always been waiting for some external validation that was never going to come, and now I don’t know how to give that to myself.

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Finding pride through their eyes

But if that high school kid could see me now, they’d tell me to stop for a second, to take a breath, to see myself the way they would. They’d tell me that surviving was enough, that growing was enough, that just being here was enough. I may have said a lot of stuff I didn’t follow at the time, but it doesn’t mean I didn’t believe it.

That’s the connection I’m trying to understand: the bridge between who I was and who I am. It’s about more than nostalgia; it’s about acknowledging the growth, the pain, the triumphs, and the scars. It’s about realizing that the journey itself is the victory, not just the milestones. By reconnecting with that past self, by remembering who I was and what I went through, I can finally start appreciating who I am now.

It’s also about entertaining that past self, showing them the world they never thought they’d see. It’s about letting them know that all the struggle was worth it, that there was light at the end of the tunnel. I owe it to them to feel that pride, to carry that sense of wonder, and to keep moving forward. Not just for me, but for who I used to be.

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If you liked this, leave a comment and let me know: What’s one thing your past self would be proud of today?