Day 15 of Countdown to Oliver: Letter to My Son

Halfway mark! It’s hard to believe. 15 days down, 15 to go.

I have to admit that part of me was dreading writing a letter to Oliver. Where do I start? What do I say? I’ll be raising a tiny baby boy into a man, and that’s terrifying and exciting all in one.

I have so much I want to say, and I want to say it perfectly. Plus, it’s emotional, and who wants to deal with all that? Regardless, it felt good to write it, and although I’ll never be able to say everything I want in one letter, I’m still happy with the everything I am able to say. I can’t promise I won’t continue to edit or add to it though.

Letter to my son,


I don’t even know where to begin, nor do I truly believe you’ll appreciate this letter until you’re in your late twenties, at least. I’ve read that’s the age men really grow up and become mature, right? I don’t know, ask your dad.


I might refer to that phrase quite a bit. Being an only child and never even having changed a baby boy’s diaper in my life, I’ve got a lot to learn in this relationship too.


That being said, there are plenty of things I want you to know and a few of them I hope to express in this letter. First and foremost, of course, I love you. You’re in my basketball-sized belly right now kicking up a storm, and I cannot wait to see your tiny, precious face for the first time. Also, if you could sleep through the night from the beginning, unlike your sister, that’d be great, but we can negotiate later.


There are many, many different types of people in this world, different paths you can take, truths you’ll discover and beliefs you’ll come across. Please remain open, accepting and unbiased. Don’t judge something or someone you know nothing about and always make an effort to learn.


Things are never as dramatic and life-altering as they may seem. Don’t get wrapped up in things that are null, try to see the big picture and know there are times when it’s just best to let things be.


Your feelings will get hurt one day (probably several days) in your life, your heart will be broken at one point or another, and you will learn the meaning of lose. Remember, you’ll eventually come out the other end stronger, and as time passes, you’ll be able to see things as they were meant to be seen. And heal. It may not always feel like this is true, but I promise you it is. These are the times that it’s best to remember there are people who love you; lean on them.


Life isn’t always fair, and that’s okay. It’s also okay to be frustrated about it, as long as you pick yourself up and make a change, make a difference or just keep moving forward.


Be nice to people. You never know what battle they’re fighting. And even if it’s been said thousands of times, treat people how you want to be treated and make a conscious effort to think about it in every situation. It will eventually become second nature.


Your life is what you make it. If you want something, work hard for it and don’t give up, because if you do, there will be someone else in line to take it in a second. No matter how impossible something may seem, it is always possible. If you really want to do something, you will find a way.


Remove negativity from your life. If something causes you pain, if someone brings you unnecessary drama, if a situation makes you unhappy, change or remove it. It’s not worth it.


The grass always seems greener on the other side, but truthfully, the grass is greener where you water it.


Our imperfections are what make us perfect. Embrace them, in yourself and others.


Be financially responsible, research, learn to save. Now.


Think for yourself.


“Words are, in my not-so-humble opinion, our most inexhaustible source of magic.”


Health is important–know what you put into your body.


Life seems long while you’re living it, but in retrospect, it’s so short. Take chances but make respectable choices, truly live and gain all the knowledge you possibly can. Knowledge and truth are two of the most ugly, beautiful and liberating things in this world.


You’ll be my son forever. Treat me well, because I love you more than you will ever know. The little things matter, show you care even if it’s slightly embarrassing and say the things you feel. It’s important, even if you’re rolling your eyes right now. It makes you more of a man to show your feelings, not less. Remember this for your wife someday too.


There are many, many girls and women in this world. Know the difference. In a woman, seek depth, a strong mind, adventure and honesty. I don’t care what your friends do but don’t be immature; it’s not attractive and that doesn’t draw-in the kind of person you want to attract anyway. Games are pointless, don’t play them. Communicate. Be spontaneous and be kind. Don’t split the bill, pay for it. If you find you don’t have feelings for someone, tell them; they’ll appreciate it eventually. Don’t string people along and go after what you want, even if it doesn’t work out.


Be honest, be direct and be faithful. Always.


When and if you choose to be a parent, your life will change forever. You’ll care for your beautiful, innocent child so much that it hurts. Life will get messy, chaotic, frustrating and you’ll rarely ever use the bathroom (or do anything else for that matter) in peace again. I can tell you with confidence that even if I could come up with hundreds of difficulties that come along with being a parent, one tiny moment on any given day makes it all worth it. Be silly. Instill values. Maybe even write a letter. Work hard and play hard–don’t sacrifice one for the other. It will be gone before you know it, so make as many memories as possible while you still can.


Finally, marriage, a relationship and love is a beautiful thing with the right person. It’s the reason you’re here and this letter to you exists. However, marriage is not a fairy tale; it is work. Love is not always an overwhelmingly exuberant feeling; it’s something you maintain and continue to create and nurture. When you choose to be with someone, choose to be with them no matter what, because it is a choice–not something you can just expect to work out. Sometimes it’s hard, sometimes it’s easy, bad, good, lows, highs, boring, exciting, ugly and beautiful, but with the right person, it’s totally worth it. Ask your dad.



Letter to Oliver


The Countdown List:

1. Create the segment “Countdown to Oliver” and make list
2. Make a hospital bag
3. Create a baby registry
4. Prepare the baby’s space
5. Set-up pediatrician visit/appointments
6. Install the car seat
7. Have a pampering day
8. Prepare birthing plan
9. Wash shower curtains, rugs and sheets
10. *Reader’s idea* Virtual gift-opening
11. Finish an art project
12. Finish a book
13. Create an exercise regimen for the final 4 weeks
14. Take a sewing class and make something for the newest babe
15. Have a special mom and daughter day with Ella
16. (Re)organize files and paperwork
17. Finalize plans with the OB
18. Prepare for visiting family
19. Cleaning day
20. *Reader’s idea* Clothe diapering
21. Meal prep (frozen meals)
22. Write a letter to the new baby
23. Design birth announcements
24. Date night
25. Invest in post baby clothes
26. Clean pumping and feeding items
27. Take a class
28. Clean the carpets and floors
29. Stock up on toiletries, diapers and groceries
30. *Reader’s idea* Put feet up and rest

10 thoughts on “Day 15 of Countdown to Oliver: Letter to My Son

  1. I think I will read the letter to myself every day until *I* grow up. Thanks for writing it. I have to find room on the fridge. And where’s my box of Kleenex, damnit!

  2. This is such a good idea. I started writing a journal to my daughter before she was born, wrote two entries and never did again. If only I would have known more about blogging then. I really do love the letter to your son! Its wonderful. 🙂

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