5 Things to Include in a Letter to Your Future Self

If you’ve sought to make new resolutions and form new habits it can be a challenge to keep at it. It doesn’t matter if you’re sticking to your plans or if things are falling by the wayside. As creatives or freelancers, we don’t really get annual performance evaluations so it’s entirely up to us to check in on ourselves, evaluate, assess and be completely honest about our goals. There are so many ups and downs that come with following a creative path. 

When I first started my journey. And about the time when the appeal and excitement of freelancing started to wane, I found an envelope with my name on it, written in my handwriting. How bizarre. I inhaled as I opened the self-marked letter, unsure of what I was about to find.

“Dear future Adetutu,” the first lines read.

The memories of my first weeks of freelancing came rushing back as I read this letter with curiosity and vigor.

My letter to Myself was a healthy dose of projection, introspection, and gratitude.

Why Should You Write To Yourself?

For me, writing a letter addressed to my future self is a way to clarify and revisit experiences that I’ve been through during the past few months. It’s a bit different from journaling because

1) it’s more of an assessment rather than a just a summary of events and

2) more importantly, you are writing to a new you – a future you.

I think of these letters both as a roadmap to my long-term goals so that I don’t have to anticipate the unexpected and also as checkpoints to a creative life fulfilled. These points are just recommendations and not hard guidelines of what to include so be creative and be flexible; write about what you fear the most or what brings you joy. And as with introspective exercises, you don’t need to share these letters with anyone else.

Unsure of what to include in a letter to yourself? Below are 5 guiding points:

Be Real And Check Yourself

It’s so easy to get caught up in the momentum of life that we sometimes forget to check up on ourselves truly and deeply. Did you take that design course that you’ve been meaning to? Remember to list out your short-term goals i.e what you want to accomplish in the next three months and tie that into how it fits into your long term goals.

Reassure Yourself. It’s So Necessary  

Remember that your journey is your own. And it’s definitely not the same as someone else’s, so try not to compare yourself. Sometimes it might seem like everyone else is winning but you, but it’s essential for you to reassure yourself in your letter that the steps that you take to accomplish your short-term goals, will ultimately lead you to your long term goals.

Remind Yourself of Your Worth

Know your worth! When scoping for new work and signing new contracts – know your negotiables and non-negotiables. This list will definitely increase as you gain more experience but for example, if you already know that you want a job or project with work from home flexibility, don’t take on work that demands that you be in an office from 9 to 5. You’ll be miserable, and it could show through your work. As creatives taking on new projects, it’s especially important to know what type of work you will and won’t do. Write it down, speak it out and be firm.

Give Yourself A Pep Talk

I always seem to find my letters when my momentum and energy has died down when it feels like shit’s hitting the fan and I’m faced with rejection after rejection. I use these letters to take notes of the wins that I’ve accomplished, the people I’ve worked with, the people I’ve met and the new experiences that I’ve created. Remember that start-up you started working with? Remember the connection you made at the wine tasting? Oh Yeah! Revisiting my wins, both big and small, always give me another boost of energy to keep hustling and working towards my goals.  

What Lessons Have You Learned?

This is usually the introspective part of the letter. What did you learn about yourself and the situations you chose to put yourself in? Be present and take note of your current emotional and professional state. Write about what you’ve learned in the past few months. Maybe you’ve come to realize a new core value or had a work experience where you came to realize another one of your non-negotiables. Maybe you were in a situation and realized new things about yourself and your work/life experiences.

What first started out as a one-time assignment when I started freelancing has turned into a quarterly ritual of introspection without the weight of guilt or shame. So far, I’ve written three letters to myself and I try to keep it at equal parts pep talk, gratitude letter, and introspection.

So instead of checking in with yourself on a yearly basis, I’m going to ask you to take it a step further and check in with yourself a few times a year.

What will a letter to your future self look like?


Photo Credits: Unspash

Adetutu Adekoya

Adetutu Adekoya is a writer and photographer with a healthy obsession for all things social media. She uses her experience as a researcher, expat and content creator to curate on-brand storytelling. When not looking for Insta-worthy pictures, she can be found trying out the street food in her favorite cities. Adetutu holds a Masters degree from Columbia University and in her former life was a public health researcher.


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