An F-Word For My Son On Your First Day of High School

My Dearest Son Who Would Cringe If He Knew I Was Writing This Letter,

Today you are starting high school!! (Like, no duh Mom.) I know, I am a master of the obvious. But seriously, this is a big deal…at least for me as a mom. And I think I could tell by the nervous expression on your face this morning that you know it’s a big deal, too.

But let me be clear about this: starting high school is a big step, but in the end, these four years you spend in high school probably won’t be a big deal in the grand scheme of things. So, please, babe, do like we always ask you to do—your best—and don’t put too much pressure on yourself. I know Dad and I have already given you some advice (hopefully not too much), but I have just a little more to add to that. I have an F-word I want you to consider as you enter high school.

No, not THAT F-word. And it’s not “freshman” or “friendship” either, though those certainly relate.

It does have four letters, though. It’s FAIL.

Babe, because I know you, I know you’re afraid to fail. And because of that, you’re afraid to take risks. I’m not talking about “risky” behavior, I’m talking about taking a new class or joining a new extracurricular activity. I’m talking about…putting yourself out there.

Admittedly I am totally biased, but I think you’re a super smart, nice, friendly, capable kid who can do a LOT of things well.

But to do anything well, you’re gonna have to TRY something. And know that if you try and fail, it’s absolutely ok. I mean, it might suck, but it’s still ok.

Believe it or not, babe, failure has been a huge gift in my life, and I know it will be in yours as well. Now I’m not saying go out and fail your freshman year…ha ha ha, PLEASE don’t take this little love letter and come away with THAT! But please do try some stuff and mess stuff up and LEARN from it. I know we’ve talked before about how one of my huge failures led me to a place in my life where I was ready to have a relationship with your dad. And well, THAT turned out pretty well, since you’re here and all…right?

Son, I am begging you to learn to be ok with failing now. Because now, you’re in high school. If you fail in a relationship fails, it won’t mean a divorce, if a friendship fails, you will learn how to be a better friend next time, if you fail at a test, it won’t be the one that keeps you from getting your dream job. Fail now babe, and you’ll be so much more successful LATER.

So try, my darling. Try and succeed. Try and fail. But whatever you do, learn from it. These years will be FULL of another f-word, “fun,’ and maybe full of fail, too. But no matter what, I’m cheering you on, ALWAYS.

I sure am proud of you.



Jenny Rapson
Jenny Rapson is a follower of Christ, a wife and mom of three from Ohio and a freelance writer and editor. You can find her at her blog, Mommin' It Up, or follow her on Twitter.

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