I answered a very similar prompt about a year or so ago. At that time, I said I would probably relive 1994, or maybe 1995. My reasoning was that 1995 was the year I turned 21—peak barhopping days, absolute freedom, and fewer responsibilities than at almost any other point in my life.
However, if you asked me that today, I’d have a completely different answer. Events of the past few months—yes, I’m talking about Sierra again—have prompted me to rethink the whole question.
For the sake of where my brain is at right now, and for the sake of having something original to write about, if I could choose one year to live all over again, it would be 2019.
Back in 2018 or 2019, X2 and I had finally split up for good. We tried one last run that fall—a six-month extension that lasted just long enough for us to remember why we broke up in the first place. If you’ve been following the narrative I’ve been weaving lately, you might recall that it was during that exact breakup window that I first crossed paths with Sierra on a dating app. We texted, we realized we had a lot in common, we vaguely talked about getting together, and then… something fizzled. The timing fell apart. I ended up back in that doomed six-month cycle with X2, and eventually, Sierra ended up in a long-term relationship of her own.
Our ships barely passed in the night. And while I know in hindsight that I needed the last seven years to become the person I am today, I still catch myself wondering about the “sliding doors” phenomenon.
Occasionally, I’ll hear Sierra talk about her ex-boyfriend from those years—a guy who struggled with the heavy stuff, avoided serious conversations, and kept everything strictly surface-level. What’s frightening is that as she describes his shortcomings, I recognize too many characteristics of 2019-Rob in him. Back then, I didn’t initiate the deep conversations; I had to be pulled into them.
Knowing that, I have to be honest with myself: if I had pursued her more aggressively back then, we probably would have gone out. We might have even gotten a few years together. But we likely would have crashed and burned just like they did, and I’d be the one sitting on the sidelines today.
Now, if I could drop today’s version of myself back into 2019—complete with the 100% Policy, Option C, self-awareness, and the mental footing I’ve earned—hell yes, I’d have gone after her in a heartbeat. If we had gotten together back then with this mindset, we probably would have been married by now.
So it’s a strange, slightly frightening exercise. I’m intrigued by the idea of doing things differently seven years ago, but the truth is, the old version of me would have ruined it. Frankly, I’m occasionally pissed off that we lost those seven years. But I also know this: as much as I hate that we missed that time, if I have to choose between a doomed version of us from seven years ago and right here, right now, at this exact point in my life… I will choose right here and right now every day of the week and twice on Sunday.
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.
Thanks for stopping by Rebuilding Rob. Be sure to like 👍, comment and subscribe below. It’s greatly appreciated! Also, feel free to follow me on social media and check out my recent posts!
- The 2019 Files: Why I Wouldn’t Change a Thing (Except When I Would)
- Rob Reviews: Star Trek Strange New Worlds 4.7 – Like Chronitons Through the Hourglass
- Camping, Meeting Dad, and the Art of the Buffer Day
- What My Parents Didn’t Teach Me
- Five mobile apps I can’t live without 
AI art created by Google Gemini
The article “The 2019 Files: Why I Wouldn’t Change a Thing (Except When I Would)” first appeared on Rebuilding Rob
Leave a Reply