Supposedly, turning 50 is a major milestone in one’s life. It makes one re-evaluate their decisions, reflect on the paths not taken and, in many cases, go just a tad cray-cray.

While I have just over 200 days before marking the half-century mark, I haven’t found myself doing any of those things, but that may in large part because I simply don’t feel as if I’ll soon be on the wrong side of the supposedly terrifying number. I’ve kinda felt 26 ever since I was 13 and still do… as long as I don’t linger in front of an unfogged mirror too long after my morning shower.

But a recent conversation left me pondering the kind of question that gives philosophers a reason to exist and drunks a reason to wallow: If I could offer my younger self a few pointers, what tidbits might I pass along? What life lessons have I picked up along the way… and would I even want to give myself a roadmap to avoiding pitfalls which may actually have helped mold me into the person I’ve become?

Putting aside the whole Dr. Who-ish dilemma of how advising my younger self might alter the future and perhaps even bring about the apocalypse, I came up with at least a few bits of knowledge that definitely would have benefited me in the past.

• Stop at one donut. The second one never tastes as good and has been scientifically proven in a totally non-scientific study to go directly to your body’s most vulnerable areas.

• Despite what anyone might say, failure actually is an option. What it isn’t is insurmountable.

• One man’s trash is another man’s treasure. Translation: Those people mocking your love of soaps will eventually become one of the 50,000 Twitter followers loving your daily commentary on the daytime dramas.

• Like air and water, friendship is free. If you feel like you have to buy it, it’s not worth having.

• When people tell you who they are through word or deed… believe them. Ironically, I learned that lesson from the very person who taught me that phrase.

But if I could only scribble one message on a piece of paper and send it through a time portal for my younger self to find, it would say this:

“Contrary to the message you will be bombarded with every single day by the media and those whom it has influenced, it’s okay to be single. You can be alone and not be lonely. The most important person in your life may not be the love of your life, and the love of your life — if you find them — may not wind up being the most important person in your life. The sooner you dismiss the starry-eyed notion of being completed by someone else, the sooner you will open yourself up to the possibilities that exist within yourself.”

Maybe I could avoid the whole step-on-a-butterfly-and-set-in-motion-the-end-of-the-world thing that comes with time travel, I could just give young me a copy of Whitney Houston’s tune The Greatest Love and hope he gets the message.

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