A Letter to my 20-Something Self

Yet another genius blog has been found, thanks to San Francisco’s Daily Candy newsletter I receive. Yes, I receive daily reminders of all the cool things going on in San Francisco that I am not quite able to do / see / visit / eat, in hopes that once my zip code begins with a ‘9,’ I will be in the know.  Predictably, it’s written by a career coach, although to limit her to that title is restrictive.  One of her posts asked her readers to write a letter to their 20-something selves, an interesting concept that she herself read about and was intrigued by.  Always up for a challenge, and yes, home alone on a Saturday night, I’m up for the task.  Tissues are at the ready.


Dear 20-Something Eileen,

I know. This was not what you were expecting upon graduating college.  The idea of saving money goes out the window. Yes, you will learn the NYC subway system, I promise. You will find some of the kindest people you have ever met in a city not known for its compassion. You will get stamps in your passport.  Heck, who would have thought that quiet little you would sign up for a martial arts classes so you can be the next Sydney Bristow?

It won’t be an easy time of it.  You will never pray as hard as you did when the city shut down on that warm September Tuesday morning. You will never forget that smell.

You soon realize that your shyness needs to be turned into charisma very fast in order to be heard and acknowledged.  That you’ll crave the companionship of a dog until your heart bleeds.  That you’ll not only get back into horseback riding, but discover that it has a healing power.  You’ll say goodbye to someone you spent years with, only to quickly fall hard for someone living in another country.  PS – that doesn’t last.  And then, after you ditch the Brit, you’ll experience love far deeper than you thought possible, someone you would set your life down for, only to not have it returned.  You think you might die.  But you don’t.  But it may be wise to buy a wine fridge and start a collection because you’re going to be drinking a lot of it.

Life is not going to go according to plan.  Instead, it’s going to progress much slower, but you’re going to know yourself inside and out because of it. You will learn what you will tolerate and what you won’t.  What you will forgive, but what can’t be forgotten.  And your strength, character and will are all going to be very close companions that you will call on daily.

You have a desire to write a book one day, but can’t imagine what it would contain. You think you have nothing to write about.  You will.

Some friends you think you’ll have forever will be lost for many years, until a very smart young guy invents a website to connect all of them again.  You will have a job, not a career, but here’s to hoping you figure that out.

You’re an insomniac who stays up all night, stressed because you don’t have the answers and the uncertainty of life is sometimes too much to handle.  Get some melatonin because this continues well into your 30s.  You are making decisions that only you understand, but get used to it.  Others are going to judge, no matter what you do. We cannot make other people happy.  Put that on a postcard on your fridge. Refer to it daily.

Stop worrying about everything.  It will cause three deep wrinkles in your forehead, trust me. Things will happen when they happen, and not one moment sooner. Patience will be one of the hardest tests to endure.  Giving up control is practically impossible.  Just do the best you can. I can’t say it all works out because I still don’t know.  Just keep listening to your heart.   And it just has to.

Much love,

30-Something Eileen


3 thoughts on “A Letter to my 20-Something Self

  1. Eileen,

    This is SUCH a beautiful letter. Your last words about patience are what resonated with me the most. Your 20-something self is lucky to have such words of wisdom given with such love.

    Thank you for sharing!


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