The Email from My Past Self That Made Me Ugly-Cry (and Restored My Faith in Humanity)
Me: Chugging lukewarm coffee.
My inbox: 47 unread messages.
My brain: "Why did I agree to teach recorder to 30 third-graders today?"
Subject Line: 🎉 "Your 2020 Letter Has Arrived!"
"FutrLtr? Is this another phishing scam?" I muttered, nearly hitting delete. But something stopped me…
The Time Capsule I’d Forgotten
Turns out, 2020 Jake—freshly laid off, drowning in student loans, and binge-watching Tiger King—had written Future Me a love letter. Here’s the chaos he unleashed:
"Yo 2025 Jake!
If you’re reading this, CONGRATS! You survived:
I BEG YOU:
P.S. If you quit teaching to sell NFTs… I will HAUNT YOU.
— Past You (currently eating ramen in sweatpants)"
Laughed so hard I scared my cat off the couch.
Cried realizing Maria’s now my fiancée.
Cringed remembering the potato-filtered date.
Fist-pumped because my band renamed itself "Jake & The Responsible Adults" (progress!).
Journaling apps (felt like homework)
Therapy ("How does that make you feel?")
Drunk-texting my ex (0/10 do not recommend)
But THIS? This was my past self high-fiving me across time. Because:
✨ It was SURPRISE THERAPY – No pressure, just pure "oh damn, I remember being that mess"
🥹 He roasted me WITH LOVE – Like a best friend who knows all your flaws but cheers loudest
📈 Proof I’d grown – 2020 Jake was broke and lost. 2025 Jake? Still broke but engaged + slightly less lost!
Shoutout to the FutrLtr Team
Y’all built something special. How you do this 100% free while fighting server costs with tiny non-intrusive ads? Absolute legends.
A time machine in my Gmail
A permission slip to laugh at my chaos
The best pep talk from the one person who gets it: ME
Special thanks for:
✅ The "attach voice memo" feature – Hearing my 2020 voice say "NFTs are a scam!" was prophetic gold.
✅ No paywalls – Unlike that other site charging $36/year to email yourself 😒
📝 Write to your future self NOW – Takes 2 mins at futureletter:https://www.futureletter.org
❌ FORGET you did it – Let Future You discover it like a buried treasure
💌 When it arrives? Come back here and tag me (@ChicagoJake) – I wanna hear your chaos!
P.S. Dear 2020 Jake: Maria said yes. The band still sucks. And I’d still take ramen in sweatpants over 2020. You made it, buddy. 🥂