Long-Term Goal Planning: Write a Letter to Your Future Self

I just celebrated my 45th birthday. Not as major a milestone as 40, but I believe that 15 years is a significant interval, and 45 feels important to me. One of the things I most looked forward to this birthday was opening a letter I wrote to myself at 30. I was convinced that I had written it to my 45 year old self, but it seems I was going to open it at 40. It actually worked out better to wait the additional few years since it meant that I had even more to compare to my life at 30. I opened it at the end of the day and laughed, cried, and thought for a long time about all the things I had said to myself. A couple of days later, I wrote my 60 year-old self a letter and am excited to read it in 15 years.

The letter I read this year is actually one of two I have written in my life. The first one I wrote was when I was 19 years old, and I planned to open it at 30. I store all of the letters together in a sealed envelope to be opened on the birthday listed on the envelope. This time, it was so interesting to read not only the perspective I had at 30 (when I had just become a mom with a 3-month old baby) but also at 19 (when I was still in college). I was amazed at how optimistic I was about my future and how kindly I wrote to myself– making sure to say it was okay if I didn’t get to do all the things I thought I might. It was also fascinating to remember what it was like for me at those ages. So, although I now have written three such letters, they definitely won’t be my last.

Why write your future self a letter?

I honestly cannot remember who suggested that I start writing these letters, but if you search the internet, you’ll see I’m not the only one who writes these. I consider mine to be birthday letters, since I read them on my birthday. Other folks write themselves every year on New Year’s Day. Others write in longer increments than just a year or five. Regardless of how often you do this, writing this sort of letter preserves a piece of your personal history and helps tabs on your aspirations. These letters are like written time capsules that both memorialize your goals and values while allowing you to see your change and progress over the months or years. It feels like a way to travel through time to send yourself a message. As a fan of time traveling movies, this totally appeals to me. 😁 More importantly, you don’t have to start when you are a teenager or when your first child is born. It’s your letter, so it’s never too late to start writing to your future self!

How to go about writing a letter to your future self

As with anything, there’s no right or wrong way to do this. You need to just figure out a few things such as:

• How long between letters– this is totally up to your personal preference. For me, there’s an element of surprise when I’ve waited 10-15 years to read a letter from myself. I in no way remember what I wrote and I’ve often changed so much from that younger woman that it makes me realize how much I’ve grown. While you can do 1, 5, 10, 15 or longer intervals, I do not recommend doing less than 1 year in between letters so you will see some progress in yourself.
• The format you will use to write to yourself– this is also up to you. My first letter was handwritten, so it wound up being pretty short. By the time I wrote my second letter, I was using my laptop to do everything, so I typed it. I’ve also typed my second letter. As long as you can read what you’ve written, the format shouldn’t matter.
• Where to store the letters– my friends who have asked about how I do this are always curious to learn where I keep my letters. With the first letter, I asked my mother to hold on to it for me and send it to me when I turned 30, which she did. For the second (and now every additional letter I write), I store it in our fire-safe lock box. It is small and holds important documents such as birth certificates, passports, and whatnot. It’s the perfect place to keep these sorts of letters.

This little Sentry fire-proof lock box is just like the one I bought years ago to store important documents like my birthday letters (#Ad):

What to include in a letter to your future self?

There are so many things that you can write about which will be interesting and fun to read later. You can also use the letter as an opportunity to remind yourself about long-term goals that you fear you might never accomplish unless you are reminded later. The sky’s the limit. But the following includes items that most of these letters should include:

• A kind greeting. If you are doing it on your birthday, like I do, wish yourself a Happy Birthday. If you’ll be writing on a holiday, send yourself a positive holiday wish. You want your future self to smile when she starts reading the letter.
• Hopes for the future. There are so many things you can do with this such as reminding yourself about certain milestones you planned to reach or bucket list items you want to cross off. Write with all the optimism in the world.
• Goals you have set. This is a little more tangible than just your general hopes or someday bucket list items. If you’ve read my previous post about goal-setting planners, you know that I’m a big fan of setting tangible goals for yourself that help you feel like you’re being intentional about your life. I looked at my PowerSheets Goal Setting Planner as I wrote this year’s letter.** Writing a letter to yourself is a great way to memorialize any long-term goals that simply cannot be achieved in your current season of life.
• A time capsule section. I love this section of my letters. They remind the older me about what life was like when the letter was written- where I was living, where I was working, what were my interests, and who were the people I spent most of my time with. It’s interesting to have a “snapshot” of what life was like at a certain time in your life.
• Advice about your relationships. Are there any people in your life that you would like to remain close with as the years go by? Do you worry that as your kids grow up, your relationship with them will change? Acknowledge that in your letter and gently remind your future self about the way you feel about these folks now and encourage yourself to nurture (or reestablish) those relationships if that’s appropriate in the future.
• Values you want to maintain across your life. For me, that is usually about how I’m raising my kids. But, it can be about anything- self-care, fitness, putting family or certain relationships first. It has helped to read about what I thought really mattered when I wrote the letter and have found myself renewing my commitment to getting back on track with things I had let go since the last letter. This can also include warnings to yourself about things you want to be sure to avoid in the future.
• Encouragement. Most importantly, the tone of your letter should be kind and understanding. The letter to my 30 year old self had no idea I would have a second child with medical issues, or that I would find a job that I liked so much I would abandon my hopes of becoming a part-time worker. My letters made room for these changes by reassuring myself that no matter what I did after the letter was written, I would have done my best to do the right thing. Hold back on any judgment and let your love for yourself guide your writing process.

There are so many things that I love about reading and writing these letters, but letter-writing is definitely not the only way to check in on yourself and see what life was like for you in prior years. Some folks keep journals for this purpose, and the most popular seem to be 5-year journals. These notebooks are like a 365-day diary except that each page is divided into 5 equal parts. The goal is to write in the journal every day for 5 years straight. After the first year, you go back to day one and write in the second space provided. Because the first space contains the prior year’s entry, you can read a mini time capsule every day. I’m curious about trying one of these and am looking forward to a season of my life where I have the time to give it a go. That didn’t stop me from researching them, of course. Here are some brands that they carry on Amazon:

The Leuchtturm Some Lines A Day journal is one of the nicest on the market (#Ad)-

A less expensive version is the One Line a Day: Five Year Memory Book (#Ad)-

I love the floral cover of this One Line a Day journal (#Ad)-

There are even guided journal versions of these such as the One Question a Day Five Year Journal (#Ad)-

Writing letters to myself to read at milestone birthdays has been a fun and meaningful way to keep myself grounded in the things that have mattered most to me across the decades. Until time travel becomes an option (hello McFly!), it is likely the only way I will be able to send myself messages that are meant to remind me about my goals, aspirations, and what my life was like in the various seasons these years represent.

Do you write to your future self? Do you have a 5-year journal and can share your experiences with it? Leave a comment below.

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** The One-Year PowerSheets Planners for 2020 are sold out. However, they just released the new 6-month version here.