A letter to my future self

My last day of work (for the school year) is today. When I started five months ago, I never dreamed I’d love it as much as I do, or be as sad to see it end for summer break as I am. Don’t get me wrong; I’m looking forward to our summer plans, but I will miss the interactions with teachers and students.

Interviewing for the position last winter, I was skeptical about my future if I started working. I felt like I was losing something. I could not imagine that I would find something more valuable than money in it. It started out as something I thought I had to do for financial reasons and has turned in to something I need to do for me.

During the interview, I was asked a question I usually dread: “Where do you see yourself in three to five years?” I’ve always felt like this is a question meant to trick me into saying whether I see myself in this job long-term or not. When I hesitated, the interviewer explained, “I ask this question so I know if you have goals.” I think I may have sighed with relief. I told her what some of my goals were, personally and what we’ve set as a family. We’re not always super intentional about goal-setting, but we definitely have dreams and plans.

A few weeks later, when the calendar year turned over to the year I would celebrate my 40th birthday, I started thinking more about the future. What did I want the next years of my life to look like?

So I made a list. Not a bucket list, exactly, but goals and dreams for the future. I started a notebook, too, where I began collecting quotes that inspire me around the theme I’ve chosen for my 40s, a record of big prayers I’m praying, and a list of gifts for which I’m grateful (not necessarily material things).

In the few months that I’ve been doing this, it’s been an exercise in present- and forward-thinking.

My past has had enough attention.

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This week, the eighth-graders at our school were given letters they wrote to themselves in seventh grade. And they had the opportunity to add to that envelope a letter to their senior selves to open four years from now when they are finishing high school.

I remember this exactly from my middle- and high-school years. We wrote letters in eighth grade to ourselves and opened them our senior years of high school. By the time my high school career was nearing its end, I had forgotten what I had written, and I was shocked at how much of my eighth-grade attention was on other people. My letter was full of jealous, envious words directed at classmates, other girls particularly, because I was not popular and desperately wanted to be.

I wasn’t popular by the time I was a senior, either, but I didn’t care as much. Besides, I was going to a college seven hours from home. I was leaving my hometown behind and couldn’t have been happier. (I feel differently now.) Reading my eighth-grade letter to my future self was eye-opening and a little bit sad.

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Not too long ago, I re-read a blog post I wrote five or so years ago. I didn’t remember writing anything about my future self, but I had and it made me smile that in the time between I had done the work I aimed to do to improve myself.

Why don’t I do this more often?

Letters to our younger selves are common, and I don’t think it’s wrong to look back at the people we were in the past and want to comfort and assure that part of us that everything’s going to be okay, that we can give ourselves more grace than we think we deserve, that life will go on.

But we can’t change the past. 

We can affect the future.

Why don’t we write letters to our future selves?

For me, I think it comes down to fear. If I write a letter to future me full of my hopes and dreams and goals for the next stretch of life, what happens if I don’t accomplish those things? Will I feel worse about myself? I can’t see the future. It’s so unknown. What if something terrible happens between now and then?

Those are extreme fears. If I’m really going to be honest, I’m afraid of the work I’ll have to do to become the person I think I can be years from now. Putting it in writing means I can’t float along and let life happen to me. I can’t stick my head in the sand and pretend everything’s going to be okay without my intervention or attention.

Maybe I’m also afraid nothing will change in that time.

But I’m not sure any of those are good reasons not to write a letter to my future self.

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Here’s a question I haven’t answered yet: When is a good time to do this?

Should I write one now and open it next year on my birthday? Or wait till I’m 45? Should I write it at the beginning of the year and open it at the end of the year?

I don’t know yet.

But I know I want to do something like this and soon.

Have any of you ever written a letter to your future self? Tell me more.