5-year-old Jen: In a few months, you are going to start going to school. You will continue to go to school for a very long time. Most of the time, you are going to love it. Sometimes, you will not like it as much, but that's okay - in schooling endurance is everything. It is important to be a life-long learner. It is also important to seek knowledge and truth in everything that you do. What is more important than knowledge and truth, however, is having the skills to find them. School is also where you will learn one of the most important keys to a happy life: how to make and keep good friends. Go learn and occasionally fail and have fun. School will represent some of the happiest times of your life.
10-year-old Jen: Oh, Jen. You are only ten years old, but you already have the weight of the world on your shoulders. You should be giggling and frolicking and living without a care in the world, but for now that is just not you. My challenge to you is this: trust that the world will always be right, just sometimes in a complicated way. Learn to lighten up and find the simple joys in life. In a few months, you are going to have a baby sister and you will have to show her the way. What you don't know yet, though you will soon enough, is that sometimes your baby sister will show you the way. Your world is about to open up in a brilliant and lovely new way. Embrace it.
15-year-old Jen: I'll give you this: Fifteen is hard. Thirteen and fourteen weren't so great either. It's hard to straddle the jagged line between being a kid and an adult. I promise that you are going to come out on the other side of it, and magnificently so. But first, there will be some significant challenges ahead. Those challenges are going to hurt like hell but they are going to soften your sharp edges. They are going to make you compassionate toward other suffering souls. And they are going to later give you clarity about your life's work, which will be work that defines the very essence of who you are. Hang in there. You won't always see it, but you will be better than fine on the other side. You will also be a much kinder soul.
20-year-old Jen: You know this already - college is one of the best times of your life so far. It will continue to be a cherished memory and a highlight for the rest of your days, so make the very best of it. You are learning all the things you need to know to make it in this complicated world on your own - a scary proposition. Most of the things you are learning can't be found in a book. You are learning how to help other people, how to lead, and how to mend a broken heart. You are also learning that you are capable of making big mistakes, but equally capable of recovering from them and not repeating them. Take it easy on the "Shots of Fun" but not too easy - you only get one chance in your life to legitimately act this foolishly. Enjoy it.
25-year-old Jen: You think you have the world by the tail right now, but here's a little something for you to think about: you don't. What might make you a better version of you would be a little more humility. You are capable of great things, but you have a lot to do to prove yourself before that can happen. You have your work cut out for you. If you make the right choices, pick the right mentors, and follow your heart you will get there in due time. Be vigilant in your pursuit of excellence.
30 year old Jen: I am proud of you for finishing your graduate degree. This degree is really just a piece of paper, but it's a piece of paper that will open up all kinds of opportunities for you. Your career is about to really begin now. As usual, you have your ideas of how things will transpire and you think you are in control. I must caution you, that is not the case. You will have a tendency to get really upset when things don't go as you've planned. Let that go - the worry and the angst aren't worth it. The universe will always take care of you and deliver you exactly where you need to be. Trust that, and appreciate the lessons along the way.
35-year-old Jen: So your life just got turned upside down, and you feel like a hot mess. The truth is, you are a hot mess. The other truth is, you created it. Yet another truth is, you needed it. You are going to head into a dark place, and you are going to take a good, long, painstaking look at your ugliest self. When you are done with that, you are going to make a vow of responsibility for your own happiness. You will find joy in places and in ways you didn't know possible. You are going to travel, make new friends, and find true success in your life's work. The passion inside of you is going to open up, and you will find your authentic self. Hang in there....at the end of this bumpy ride you will arrive at a most spectacular place.
40-year-old Jen: I think you are really starting to get it, and that warms my heart. You are learning to let go and to have faith. You are not so afraid of change. You have confidence in yourself as a leader, and you've learned how to lift up those around you. You laugh more, fret less. You care about your impact on the world. You still have worries and doubts, but that only makes you human. You have a new set of career opportunities before you that are going to challenge you in ways you may not be fully prepared for - hold on tight, and sharpen those diplomacy skills. Above all else, keep working on achieving balance. You'll be needing it more than ever before.
What I will tell myself today: Your life is imperfectly perfect. You are doing work every day that inspires you and lights you up. You are surrounded by people who believe in you, and a couple of haters who keep you humble. You are armed with the strength to make it through adversity of any sort. You have a beautiful home and two terrible cats to love. You are not wealthy by any means, but you have everything you could ever want. Above all else, you have the best possible family and friends, and this continues to be a source of joy you are not even entirely sure you deserve. You have it all, my dear Jennifer. Tend to all of it with loving care, because the gratitude you have found will continue to bless you a million times over. Now go get a pedicure and eat some cake - you deserve it.