Which relationship has taught you the most about yourself?
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That’s a loaded question. If you look at it strictly through the lens of traditional relationship advice, we’re conditioned to think that we only learn from epic failures or dramatic heartbreaks. And to be fair, there is truth to that.
Professionally, the worst administrative tenure I ever witnessed taught me volumes about leadership—not by showing me how to lead, but by showing me how not to be as an administrator. In my romantic past, the whole situation with Veronica taught me what it feels like to be breadcrumbed. For a long time, I tried to push for those “where do we stand?” talks, only for them to fall on deaf ears. Walking away from that silence—simply stopping the cycle and walking out when I realized I was getting nothing back—was out of character for me, but it taught me that I finally had boundaries. It was the precursor to the 100% Policy: choosing yourself instead of settling for scraps.
As Yoda says in The Last Jedi, “The greatest teacher, failure is.” We learn through the crashes.
But relationships teach us who we are in the positive spaces, too.
If I want to look at someone who constantly showed up day in and day out without any drama, I have to look at my old man. Between the car accidents, the daily grind, and the moments when life makes you want to crawl into a hole and quit, I don’t know how to give up. I only know how to dust myself off and keep going. I credit that entirely to him.
And then there’s Sierra.
Before her, keeping the “teacher armor” up was just a default setting. It’s easy to do when you’re living at home on a teacher’s salary, working in a challenging school, and carrying the complex baggage of being a divorced dad with kids from previous relationships. But with Sierra, I didn’t hold anything back. From our very first face-to-face meetings, it was complete and total transparency. She already knew the boys from years of online conversations, but she’s the one person who got me to drop the armor completely and just be open.
She isn’t a lesson in failure; she’s the proof of what happens when you stop accepting breadcrumbs and find somebody who checks every single box.
You learn through the failures, yes. But the right people teach you how to finally let the guard down.
Rebuilding a life takes grit, consistency, and a lot of ‘Option C’ thinking. Having crossed the 1,000-day milestone, I’m now charting the territory beyond. The mission remains the same: No glitz. Just the work. New to the blog? Start your journey here to see the blueprint and the ‘Tricorder’ perspective behind the rebuild.
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The article “The Teachers We Least Expect: Failure, Resilience, and Real Love”first appeared on Rebuilding Rob
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