Judging Our Past Selves

2026 · originally posted on LinkedIn

We spend so much time judging our past selves. Have you ever stopped to wonder how your past self would judge you though?

An old colleague sent me this photo yesterday: Aaron from 2017. On the surface, I recognize him. But 2017 me had so much more going on beneath the surface. The picture initially brought me to tears, reflecting on just how much struggle and adversity was waiting for him right around the corner.

As I sat with it, a compelling thought emerged: why don't we more often reflect on how our past selves would evaluate us today? How would 2017 you feel about who you are and what you've become in 2026? What would leave them awestruck? What would surprise them? What would fill them with pride? What would you grieve together?

I'll always want younger me to be proud of who I've become and what I've accomplished. Better still, I want him to find compassion when it doesn't/didn't work out. There were so many times when my/our failure was catastrophic and the lessons really, really took their toll.

I don't have the slightest idea how 2035 Aaron is going to feel about my choices, decisions, and values nine years from now. Be that as it may, I'll continue to work as hard as I can to ensure he is someone for whom I have all the love and acceptance I can muster.

As I seek deeper understanding of my future self, I really hope it goes both ways, chock full of love and compassion. After all, who and what you are today is already well on their way to becoming the person you used to be.