“Dear Me: A Letter to My 16-Year-Old Self”

I came across this letter at the Adventures on the Road blog while reading a “Freshly Pressed” selection tonight. It inspired me, what can I say, and it feels like that happens less and less often the older I get. So, in honor of that inspiration, here’s a letter to my 16-year-old self:


Dear Lindsay,

As you turned 16, you were caught red-handed, stumble-down drunk by YOUR GRANDMA. Things get better from there, trust me…though the hangovers don’t 😉

As class president, you have a tendency to believe that your crap doesn’t have an odor. It does. Follow your insistence on being involved, on being busy and go-go-going. Know that this will be a hallmark of who you are as a grown-up woman.It will continue to be something that fulfills you.

Practice the golfing more, would you? You’re THISCLOSE to being a phenomenal golfer at the high school level – and you play in college – but in this area you accept a version of mediocrity that with just a TAD more effort you would grow beyond. Either way, relish the time you’re spending with the girls on the golf team. These are your best girlfriends 15 years from now and though you will scatter across the globe, you will come back to these girls – women – time after time. You’ll have Destination Girls’ Weekends, babies and hangovers with these same girls. Commit the time you have with them now to memory so you can hold this information over their head years from now.

I know you feel like the last virgin on earth as you watch girls in high school have sex, babies or abortions. You will make questionable decisions when it comes to boys you like, certainly, but know that – thankfully – none of those quasi-relationships work out.

Enjoy your time on Clear Lake. You are great at leaving and sending notes to your Grandma and Grandpa there…so when you’re wondering if you should, send one more. You’ll find these in the cupboards of their home, tucked here and there, after they die and it will sustain you for years thereafter. Write the notes. Send the cards.

Your parents are pretty sweet people, though you may think that their seemingly over-protective nature is annoying right now. It is. It will continue to be. But, in 15 years, you choose to buy a house just nine doors down from theirs. Be nicer to your Mom and stop ganging up on her with your Dad. Your Dad is – and will be – fine at it on his own and your Mom could use an ally earlier than you end up coming to the table.

Consider your college choices carefully. You choose Alma College at what feels to be the last minute, mainly so you can keep golfing. Consider this, you’re still staring down student loans 10 years after graduation and they aren’t close to being paid off. You could consider a lower-cost option if you wan to alter the course of, well, everything. On second thought, make the expensive choice. Sure, you make some valuable friendships at Alma as a student — but it ends up being the era when you return to work there as an employee that is most memorable. You fall in love — real love, the heart-pounding-in-your-ears, have-to-see-him-now kind of love — that you write about right now. He’s not the first or the last, but he’s the first real one you’ll stumble into. Because of time and circumstance, you will think to squelch the feelings, the emotions and to end the relationship before it gets off the ground. Override your instincts on this one, would you, and just enjoy it for a moment instead of fretting about what people think. It doesn’t last long, so treasure the time with him. It will be a sustaining memory-of-time as you grow older.

Enjoy this time in your body. It will get harder to look like this:


Me and my Dad...can't find the junior year photo album, so sophomore year is going to have to do!


I know how you wonder about your future, how you plan for it, how you want to know NOW what your NOW-15-YEARS-LATER holds. I’ll give you this: You own a home, a car, have a pretty stellar job, and a sweet, sweet baby girl. None of the names you have picked out for your children are what you and her Dad end up naming her. So, spend less time choosing your children’s names and more time on your golf game – or anything else for that matter. Don’t let your parents get you down on your studies – you are always above average in spite of their worries.

More than anything, be nice to more people and less mean to the ‘dorks’ the ‘geeks’…it will bother you in a big way as an adult.

In short, know that you will love and lose BIG. You will make great memories everywhere you go.

Keep doing what you’re doing — you’re going to like where you end up — but if I could make one request: please, take more pictures would you?





2 thoughts on ““Dear Me: A Letter to My 16-Year-Old Self”

  1. Loved this, Lindsay. Since we haven’t seen each other since high school, I still think of you as that 16 year old self. You told your 16 year old self a lot of the same things I’d say to my 16 year old self. Funny how our “troubles” at Clio High seemed so huge. 🙂

  2. Pingback: Dear Me: a life of its own in the blogosphere | Dear Me

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