Letters To My Future Self

Letters To My Future Self

On my debt free journey I’ve learned that motivation is everything. If we want to see progress we have to engineer our environment to bump ourselves along to success. Gamify, Automate & Habitify (GAH!) are my watchwords!

Support is a major component of achievement, so surrounding yourself with people who encourage you is key. It’s why I joined the #debtfreecommunity on Instagram when I first started getting serious about paying down my $130,000 student loan debt. Working toward a common goal along with hundreds of others brings a sense of community and accomplishment unlike anything else.

No one has a bigger stake in our goals than us, so how can we channel that energy to motivate ourselves even more?

To get future me FIREd up, I send her encouraging letters from the past. How? Since I don’t have a time machine (yet!), I use a free website called futureme.org. It’s just like sending a regular email, except that you can change the delivery date so that your email will be sent to the future! Keep in mind that your email must be sent at least 30 days into the future. Also, I know I said it was free but if you feel like donating to keep the site going there is an option to do so. 


I like to send a few encouraging words when I hit certain milestones, like paying down my debt below a certain number or maintaining a positive habit. You can write whatever you like!

The best part is, I quickly forget when I sent them and what I wrote so these emails are usually a surprise! It’s great to get a note in my inbox from my past self, telling me to stay the course and reminding me of the progress I’ve made. Thanks, past self! I try to pay it forward by writing a new email that day for future me. In that way it can be a self-perpetuating cycle since each email reminds me to send a new one and continue the chain.

Check out Future Me to send your future self some love! Or, if you prefer an analog version, you can write some post-dated letters and stash them in a drawer to open later.

What are some fun methods you use to stay motivated?

16 thoughts on “Letters To My Future Self”

  • That’s a pretty cool way to stay motivated. I’ll definitely give it a good look, especially for my goals outside of personal finance.

    How do I stay motivated/keep along the path? For me it’s pretty easy – I decide what savings rate I can handle, then I save that money the moment it hits my bank account. This way there’s no room to deviate from the plan. This keeps me more in check rather than keep me motivated.

    But it works for me!

    Awesome post!

    • Saving up front is a major part of my strategy too. Can’t spend the money if it’s already gone!

  • This is a clever way to stay motivated! One method I use is to tell my friends and family about a goal I have; not in terms of “I want to do X”, but in terms of “I will do X”. Then, I feel pressured to do it because I feel that I will lose credibility if I don’t. Just the way my mind works.

  • That’s really cute! I have never heard of that, and didn’t know the Interwebs was so sophisticated (these smart people think of everything, don’t they!). That’s a great way to stay motivated.

    For me, I just write to-do lists, I have scraps of paper everywhere and I still carry a day planner (I keep track of my spending in it) and have not really adopted using a Google Calendar (or whatever people nowadays use).

    • The net is amazing, isn’t it? To-do lists and planners are awesome! I love watching bullet journaling videos on YouTube, although everyone makes them look so perfect!

    • Thanks! It’s pretty fun to get little reminders of your progress along the way. I keep the emails in a folder so I can remind myself of how far I’ve come.

  • So true about forgetting what you put in the email shortly after you click send! I just tried this out in January of this year, and can’t wait to get an email from Past Me in December! It’s been a crazy year (good AND bad) so I’m anxious to see how well I stack up with my planned progress! 🙂

    • Awesome! Seeing your progress after a whole year would be intense. I remember some of my goals from the beginning of 2017 and it feels like I was a completely different person then!

  • Nice post and good find.

    I wish there was a way for future me to send a note back in time to previous me!!!

    That would be even better.

  • Ooh this sounds like a wonderful idea… especially because I am a words of affirmations love language (if you ever read that book!).

    I’m in a difficult situation now where I own a home that my ex is currently renting from me. Now is not the best time to sell so I’m holding on while he’s living in it… some words of encouragement for future me will keep my spirits up and remind me of the bigger picture instead of the acute pain and discomfort. Thanks for this suggestion!

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