Five journaling ideas to try on Dear Tomorrow Me

Teniola Yusuf

Teniola Yusuf

June 14, 2026

4 min read

Five journaling ideas to try on Dear Tomorrow Me

Journaling is a habit that can be difficult to maintain, but it can also be a powerful tool for self-reflection and growth. Here are five journaling prompts to help you get started on Dear Tomorrow Me.

Let's help you start journaling again with Dear Tomorrow Me!

The art of journaling is one habit I embraced during Covid. To this day, I still can't figure out what gave birth to that sudden hobby. Six years later... it's no longer a habit I can even call a hobby anymore. It has become something I only do once a year; either at the end of the year or at the beginning of a new one.

Now, most times I find myself staring down at a blank notebook with nothing to write even though my head feels clouded. And knowing my 2020 self, that feels strange for something that was once dear to me. The journal that founded this habit has travelled across countries with me and moved through four different homes. That is how much I cherished that version of myself and that period of my life, a time I unfortunately can't return to.

In my attempt to rediscover that habit again, I decided to help anyone who may be going through the same phase***. So, dear reader, come along on this little journey of rediscovery as we explore ways to make journaling feel easier again through the prompts, you're about to read.***

Five prompts to try on Dear Tomorrow Me

"What are you proud of this month?"

Quite often, we forget our successes when life changes suddenly or becomes overwhelming. Writing them down and having them sent back to you by your past self can be a reminder of how far you've come and an act your future self will appreciate.

Dear Tomorrow Me can be used to document these successes! And remember no success is too small. This can be consistently going to the gym or simply getting through a difficult month.

"If you could make immediate changes in your life, what would they be?"

If you are in difficult season of your life, this prompt can offer a moment of hope for you. It allows you to think about the changes you'd like to make and explore what may be standing in the way.

With Dear Tomorrow Me, you can write about your future goals, aspirations, and hopes for the future. Quite frankly, I consider journalling as a medium of escape, that allows you to imagine what life could look like beyond your current situations. Writing down your thoughts can help you see what matters most and identify steps that can be taken towards it.

"What does a dream career look like to you"

One of the best things about journaling is seeing that the things you once dreamt about is now your reality.

Use Dear Tomorrow Me to create a vision board of what you'd like your career to look like in the future. You can also use it to write about the skills you hope to develop to achieve this dream career- send this to your future self!

Even if your goals have changed by the time you receive it, your message can serve as a reminder of what mattered to you at that moment you wrote it and perhaps offer direction for what comes next.

"What are the relationships in your life like? And are there anything you'd change?"

Taking time to reflect on the people in our lives should definitely be done more often than we do. This helps you to consider the relationships you should be grateful for, and whether there are aspects of these relationships you'd like to strengthen or change.

Journaling about this can help you recognise what you have been taking for granted or even re- evaluate some relationships.

"What type of community would I like to build?"

Moving to a new city or country often means rebuilding your support network and finding a sense of belonging all over again. While that can feel daunting, taking time to define what community means to you can be a helpful first step.

What kind of people would you like to surround yourself with? What values matter most to you? What would make you feel connected and supported?

Journal about it, send it to your future self, and reflect on it when the message arrives. You may be surprised by how much your community has grown and evolved over time when you finally receive it.

Journaling should feel like an act of hope and kindness which you feed to your future self. We hope Dear Tomorrow Me becomes that space for you. Start journaling today.

PS: Since I consider this a journey for you and I, I shall update you about my rediscovery journey with Dear Tomorrow Me in a future blog, so stay tuned!