Writing Letters to Yourself for Self Reflection

I often get asked “How do you take care of your mental health?” “What is your secret?” And although I wouldn’t necessarily call this a secret, I’d like to share one of my favorite activities for self reflection in this post.

Getting Started

I write my letters inside my journal so that I can easily access and keep them in one place. Before I had my journal, I wrote my letters and placed them into envelopes with the date and year on the front. Another option is to type it on a word document or to use https://www.futureme.org/ where you can submit the letter and have it emailed to yourself after x amount of time. I prefer to have a physical letter but whatever you do is up to you!

Before you start writing, it might be helpful to make sure that you’re in an environment that you’re comfortable in. Get a glass of water, turn on some music, sit near a window or outside – whatever works best for you.

Guiding Questions for Your Letter

1. Check-in with yourself

We often ask others “How are you?” or “How are you doing?” but how often do we ask ourselves this question? This is your opportunity to check-in with yourself and ask your future self ‘how are you really doing?’. You might sprinkle questions into your letter to get your future self thinking and reflecting – e.g. ‘Right now I’m feeling really anxious about the future, do you still feel that way?’ or ‘You were worried about starting that new job, how do you feel about it now?’

2. What are your goals?

At this moment in time, you may have some goals – short-term and long-term – that you’d want to check-in with your future self about. ‘How is your journalling goal? Are you writing every day like you planned?’ or ‘Last year around this time you were hoping to apply to law school – how is that going?’ These guiding questions may feel weird to ask yourself, but imagine you’re catching up with an old friend who you haven’t seen in a year. We may think we know what we want and have it as a goal but in a year’s time, it could all change.

3. What are some reminders for your future self?

Upon reflecting on your past, present, and future self, you may come across some things that you want your future self to know. For me, I always like to remind myself that my family has been there for me and that they are people I should treasure. I imagine that, just like my past self, my future self will come across many arguments and disagreements with my family. Nevertheless, I still love and cherish them the same regardless of how I feel about them in that very moment.

I also like to remind myself that I belong. I may feel unqualified and that I don’t belong in the places I’m at, but I do belong there. Hearing this from someone (even if it’s yourself) could make a large difference in your day. Think about what you’d like your future self to hear and write it to them!

4. What do you want your future to look like?

The goals we set for ourselves contribute to how our future will ultimately look. Our future is also shaped by the events that happen to us as each day passes and right now there is no way to predict in which direction our lives will go. Consider visualizing your future and writing that in your letter. This will definitely be interesting for your future self to review and compare the progress!

2011 Queenie wrote: Focus and work hard for your family. I know in the future you’ll make them proud and be the doctor you were destined to be. You’ll be a great OB/GYN and I can’t wait to meet your family and kids soon.

The 2019 Queenie that is reading this letter is no longer pursuing medicine and no longer has the goal of becoming an OB/GYN. Neither does she plan on having kids anytime in the near future. I’m amazed at 2011 Queenie’s perception of time and how fast they thought we would breeze through life events!


I encourage you all to try this activity at least once! It is definitely rewarding to “receive” a letter from yourself in the future and to be able to check in with yourself in a month or a years time. It will definitely feel weird to write to yourself but trust me, it will feel great reading it in the future.

Have you tried this out before? Let me know what you think!

2 thoughts on “Writing Letters to Yourself for Self Reflection

    1. Glad you’re trying it out! Definitely okay if you read it before the date you specified too – I like to check in with myself like “what goal did I set again?” as I tend to forget (a lot) haha!

      Liked by 1 person

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