Man Finds a Letter He Wrote to His 30-Year-Old Self at 15 and Realizes He’s Living a Completely Different Life Than He Planned — Story of the Day

“You really owe me for this,” Ashley teased as she lugged another box through the doorway.

Ian smirked. “Yeah, yeah. Dinner’s on me, remember?”

This wasn’t just another temporary place for Ian; it was his permanent home, the one he had always wanted. His mom had even sent all the stuff they’d stored at her place over the years. As a result, there were a lot of boxes. A whole lot.

When they finally finished unloading the truck, both of them stood in the living room, gazing at the mountain of boxes that seemed to take over the space. Ashley let out a long, exaggerated sigh.

“I never thought I had this much stuff,” Ian said, looking around.

“Do you really need all of this?” Ashley asked, raising an eyebrow.

“Probably not. I bet 70% of it is going to charity,” Ian replied, scratching his head.

“Good. I want to add ‘charity work’ to my résumé,” Ashley said with a grin.

Ian chuckled. “Thanks, Ashley. I really don’t know how I would’ve done this without you.”

Ashley shrugged. “It’s no big deal. Besides, you promised food, remember?”

“True,” Ian said, pulling out his phone. “Pizza or Chinese?”

“Pizza,” they both said at the same time, then laughed.

“Okay, pizza it is,” Ian confirmed, tapping his screen to place the order.

Ashley sat on one of the boxes. “Good choice. Now let’s hope the pizza gets here before we pass out from exhaustion.”

When the pizza finally arrived, they wasted no time digging in. Between bites, they started unpacking boxes, each item sparking a memory. “Do you remember this?” Ian would ask, holding up old trinkets, and Ashley would laugh or shake her head, reminiscing about their shared past.

Ian pulled open a box his mom had sent. His hand brushed against something familiar, and he pulled out a pair of old skinny jeans, complete with a chain dangling from the waistband. Ashley took one look and burst into laughter.

“I can’t believe you actually wore these. Even back then, they looked terrible!” Ashley said, shaking her head.

“Hey, I looked cool in them!” Ian replied, holding up the jeans. “The girls liked it.”

“Yeah, sure, only the blind ones,” Ashley laughed, rolling her eyes.

“You’re just jealous,” Ian teased, laughing too.

Ashley snorted. “Jealous? Of those?”

Ian reached into another box and pulled out a yearbook. “Look what I found.”

“Our yearbook!” Ashley exclaimed.

“I don’t want to look at it,” Ian said, shaking his head.

“Oh, come on!” Ashley grabbed it from his hands, flipping through the pages. She stopped at a picture of Ian, looking like the classic “cool guy.” Her picture followed, with her bangs covering half her face and dressed all in black.

“And what was that you were saying about my jeans?” Ian laughed, pointing at her picture.

“Oh, shut up!” Ashley said, playfully hitting him with the yearbook.

Just then, something fell out of the book and fluttered to the floor.

“What’s that?” Ashley asked.

Ian bent down, picking up an old envelope. “I completely forgot about this.”

“So, what is it?” Ashley asked, leaning in closer.

“It’s an assignment I did when I was 15. We had to write letters to our future selves,” Ian explained.

“Well, you’re already two years behind, so open it!” Ashley urged.

Ian opened the envelope and began reading aloud:

“Dear future me,

First of all, you better have a convertible so all the girls will be yours. That’s priority number one. You’re still able to do 300 push-ups, obviously. And you’ve legally changed your name to Cool Jack. If you haven’t done that yet, what are you even doing? Cool Jack is way better than Ian…”

“Cool Jack? Seriously?” Ashley asked, barely able to keep a straight face.

“I was 15!” Ian replied, rolling his eyes.

“Right, right,” Ashley said, trying to stifle her laughter. “Sorry, continue.”

Ian cleared his throat and continued reading. “...Your wife, let me clarify: blonde, 5’9″, has amazing… um… assets, and comes running at your first call,” Ian read with a cringe.

Ashley raised an eyebrow and smirked. “You just described your mom.”

Ian froze, then looked horrified. “What? No!” After a second, he added, “Wait… Ew, did I want to marry my mom?”

Ashley burst into uncontrollable laughter. “Yup, you totally did!”

They both laughed so hard, Ian had to stop and catch his breath. After the laughter died down, Ian continued, “…You still wear those skinny jeans with the chain, because dude, you look fire in them. And most importantly: you’re saving the world. If you’ve become some lame corporate rat, do me a favor and jump off a cliff, because you’re a loser and I’m Cool Jack.“

Ashley was gasping for air, literally rolling on the floor, while Ian sat with a straight face, reflecting.

“Yeah, hilarious,” Ian said, his voice flat. “I’ve become a lame corporate rat. I work for the worst bank ever. I was supposed to be an environmental lawyer. Now look where I am.”

“Oh, come on, Cool Jack,” Ashley said, shaking her head. “Everyone grows up and gets a real job. It’s called life.”

Ian stood up and started walking toward the door, his face serious.

“Hey, where are you going?” Ashley called out, confused.

“I’ve got work to do,” Ian said without looking back. “I’ll be back later.”

Ashley frowned, watching him leave. “Ian, come on. Don’t take it so hard.” But Ian was already out of sight, leaving Ashley standing alone in the room.

Ian was lying flat on the gym floor when Ashley found him, sweat dripping down his face. She walked over and stood next to him, arms crossed.

“I went to your office because I thought you were going to quit,” Ashley said, staring down at him. “Then I realized I’d probably find you here.”

Ian sighed. “I wanted to prove to myself I could still do something from that stupid letter. But I couldn’t even manage 50 push-ups.”

Ashley smirked. “You can still fit into those old skinny jeans if you try hard enough.” But Ian didn’t even crack a smile.

“I’m nothing like the person I imagined at 15,” Ian said, his voice low.

“And that’s a good thing,” Ashley replied, kneeling beside him. “You were a jerk at 15. You were obsessed with Cool Jack.”

“But I was supposed to save the world,” Ian said, staring at the ceiling. “Now I work for the most evil bank in history.”

“You still will,” Ashley said, shrugging. “I’m sure of it. You’ve already done way more than you set out to. You bought a house, and you’re always volunteering. That’s not nothing, Ian.”

“It’s not the same, though,” Ian muttered.

Ashley sat down next to him on the gym floor. “One thing at a time. When we were 15, we thought 30 was old. Now, it feels like we just stopped being teenagers.”

Ian sighed again, sitting up. “Maybe you’re right.”

“I’m definitely right,” Ashley said, nudging him. “You’re a good person, Ian. People are lucky to have you in their lives. Doesn’t that matter?”

“Maybe, but I was supposed to have a wife by now,” Ian said, rubbing his hands over his face.

“Yeah, one just like your mom,” Ashley teased.

Ian groaned. “I don’t have anyone.”

“Maybe if you paid attention to the people around you, you’d have someone,” Ashley said, her eyes locking with his. Ian’s heart skipped a beat, but he quickly looked away.

Ashley stood up, brushing herself off. “Come on, we still have a million boxes to unpack at your house, Cool Jack.”

“I forbid you to call me that,” Ian said, standing up.

“Why not? That was supposed to be your name by now.”

“Alright, not all the ideas in that letter were great,” Ian admitted.

“Good to hear you admit it,” Ashley said, wrapping her arm around his shoulder as they left.

As they exited the gym, the cold air hit them. Ashley glanced at Ian, who seemed lost in thought again.

“Hey, you know, it’s okay to feel lost sometimes,” she added, breaking the silence. “We don’t have to figure everything out right away. We have time. You don’t need to save the world overnight.”

Ian looked at her, a small smile creeping onto his face. “I guess you’re right. It’s just hard, feeling like I’m not who I wanted to be.”

“That’s life, Ian. Plans change, people change. But that doesn’t mean you’ve failed. You’ve done so much already. And it’s okay if it looks different than what 15-year-old Ian wanted.”

He let out a soft laugh. “Yeah, Cool Jack had some crazy ideas.”

“And thank goodness you didn’t turn into Cool Jack,” Ashley smiled, winking at him. “I think the Ian you are now is way better. No more chains on your jeans, please.”

Ian laughed softly. “Yeah, those chains were pretty bad, weren’t they?”

“Terrible,” Ashley agreed. “But seriously, you’re doing fine. You don’t have to be some superhero to make a difference.”

Ian looked at her, feeling a bit lighter. “Thanks, Ashley. I really needed to hear that.”

As they walked back to Ian’s house, the weight on his shoulders didn’t feel quite as heavy anymore. Maybe he wasn’t saving the world like he thought he would, but maybe that was okay.

As Ashley rummaged through Ian’s stuff, picking up random items and debating what she might want to take, Ian sat down at the table. A blank sheet of paper in front of him, he decided to write another letter, this time to his 60-year-old self.

“Dear future me,

I just want to say, no matter how your life turned out, I hope you don’t regret anything. I’m not going to pressure you with a list of goals like last time. Instead, I just hope you followed your heart…”

Ian paused for a moment, thinking about what to write next. Before he could continue, he noticed Ashley in the corner of his eye. She had found an old pair of his glasses and was trying them on. They were clearly too big for her face.

“They’re bigger than your head,” Ian replied with a grin, shaking his head as he turned back to his letter.

“…But as long as Ashley is still in your life, you’ve done everything right. I hope it didn’t take you another 15 years to realize that. At least, I already have. And one more thing: dude, I mean, sir, never buy those awful grandpa shirts everyone wears.”

He smiled to himself, finishing the letter with quiet satisfaction.

Tell us what you think about this story and share it with your friends. It might inspire them and brighten their day.

If you enjoyed this story, read this one: I was eager to finally meet my fiancé’s sister after hearing so much about her. I imagined we’d have a warm connection and everything would go smoothly. But from the moment we met, things began to fall apart. Her presence felt strange, and soon I realized something unsettling—she wanted me out of his life. Read the full story here.

This piece is inspired by stories from the everyday lives of our readers and written by a professional writer. Any resemblance to actual names or locations is purely coincidental. All images are for illustration purposes only. Share your story with us; maybe it will change someone’s life. If you would like to share your story, please send it to info@amomama.com.