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  • Writer's pictureSydney Davis

Lessons from the Past: A Letter to My Younger Self


writing a letter

A recent trip to Colorado this summer brought back many memories as we went through Boulder and stayed for a night. When I was 25, I made a bold move and left a comfortable teaching job in Alabama to shed my Southern roots and live out West for a change. I packed up my red Ford Explorer (the first car I bought), found a dear friend willing to drive across the country with me, and left on an adventure that felt incredibly bold and exciting.


So, as we were hiking around the base of the Flatirons (almost the only landmark I recognized after 30 years), I was flooded with memories – not just of the people, places, or work from that time – but more with the feelings of anticipation, excitement, and optimism I held back then for what I knew was my own life as an adult unfolding before me. In my imagination, I started writing this letter that I wish she could have read then:


Dear Sweetheart,


What a daring, courageous move you have made to follow your heart…you are sometimes so fearless it can have the appearance of moving too fast. Why do you want to be in such a

hurry to figure it all out so quickly? I wish you didn’t see it as selfish or wrong to just take a little more time to be with yourself and your dreams – and loosen your grip on the expectations others have for you. You are wildly optimistic about the future ahead and can’t possibly prepare for some of the loss and heartache that awaits. But that is okay because, through the journey, you will learn the most powerful lesson there is to know. You have everything you need…and it is all inside yourself. You will gradually come into this Knowing when life takes unexpected turns. In an unfolding beyond your control, you will be shaped into an amazing mother, dependable friend, and unstoppable entrepreneur. You will find loves and lose them, and open your heart enough to keep trusting the future and yourself. You will learn that your life depends on surrounding yourself with community and friends who feel like family. You will create work for yourself and others that has passion and purpose and land your dream of living where you can see the ocean. So, don’t sweat the small stuff in these youthful years…the tapestry is being woven with a bigger picture in mind, and the small decisions that feel so big will eventually make sense and serve you. Love, YOU in 30 years


As hard as it is to still wrap my head around, my oldest daughter is turning 26 next month. I cannot believe the speed at which 30 of my own years have passed since those youthful days in Boulder. And the next 30 will only go faster. My mother just celebrated her 88th. If I imagined my older, wiser self 33 years from now looking at my 55-year-old self, I imagine her message might be simple and to the point…



Pretty Young Thing,


Feel young because you are. Age is entirely relative, and you need to work harder to cherish the one you have now. These are some of the best years of your life because you have the wisdom and experience to realize what matters and make the right choices. Life is a gift, and you will feel lighter when you practice gratitude for all of it – the highs and the lows. Some people were not meant to stay with you on your journey for the whole ride – that is okay – you can bless them and love what was shared while it lasted. Take care of your heart, and life will take care of you. Make the memories you will look back on and feel glad you created, even if they seem crazy. Oh, and don’t forget to dance your ass off whenever you hear music that makes you want to move. Do the things, see the sights, and hold on tighter to the ones you love. Love, Your Older Wiser Self


Now it is your turn…what could you discover by writing such letters to your younger and present self? You, too, have everything you need – we forget to trust it sometimes, but it is always there willing to talk if you’re willing to listen... Take a few moments this fall to reflect on yourself. See what you have to say.



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