The Jasmine Star Show

The Letter I Wrote to My Younger Self (And Why It Changed Everything)

• Jasmine Star

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What would you say to your younger self?

In this raw and vulnerable episode, I’m sharing the letter I wrote during a leadership mastermind exercise—a truth I never planned to make public.

It’s a reflection on the pain that fuels our purpose, the “chip” we carry, and a powerful reminder of Solomon’s Paradox: we often give better advice to others than to ourselves.

This episode is for anyone who’s ever wondered if the hard parts of their story were worth it. (Spoiler: they were.)

Let’s dive into the truth of the journey—no metrics, no masks.

Click play to hear all of this and:

[00:00] Why Writing a Letter to Your Younger Self Can Be Transformative

[01:45] What’s Your Chip? The Pain That Fuels Purpose

[04:12] Vulnerability in High-Performing Rooms

[05:45] Understanding Solomon’s Paradox in Entrepreneurship

[06:50] Why This Podcast Exists: Documenting the Journey

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📧 Join my Newsletter for a weekly cocktail of insider business strategy, personal reflections, and the journey of being a thought leader: https://jasminestar.com/newsletter 📧

For full show notes, visit jasminestar.com/podcast/episode565

Jasmine Star 00:00:00  If you could go back and tell yourself something, what would you say? And if you could go back and tell yourself something. How old would you be? I want you to hold that edge of yourself. And I want you to start thinking about some of the things that you would go back to tell your former self. So I am a part of an executive group coaching program. In fact, the way that they call it is a private network for high growth founders. And it's called Hampden. I have been a part of a cohort. There's about eight of us for three years, and it's been one of the best things I've done in my business. On a recent call, our facilitator, his name is Casey. He asked us to do something different. He said, in preparation of our next call, I want you to write a letter to your former self. Tell me what you would say now. In all of the three years that we've been meeting together, it's never been this, like, warm and fuzzy or sentimental.

Jasmine Star 00:00:53  What some people might call sentimental. It's all been like, strategy. And what are we doing and how are we innovating? So this is a big change for me to see my fellow cohort members in a totally new light. Now, these are all eight and nine figure entrepreneurs who I look back and I'm just amazed when I look at my cohort. It makes me very happy to say I am the dumbest person in the room, which means I'm in the right room. They are inspiring and they're powerful. And these are the types of people that you read in business magazines doing really incredible things. In my mind, these people are every definition of mind blowing. So it was a very delightful surprise to hear them read letters to their younger selves. They were beautiful. They were sometimes heartbreaking, but they were mostly inspiring. Now, when one of the members read a letter to himself, another member by the name of James had said this.

James 00:01:50  I'll throw something out there. Like one thing I always love talking to other entrepreneurs about is like, what gives you your chip? You know, like, why are you doing this? Like, this is not an easy life.

James 00:02:01  For the most part. And I feel like I heard a deal explaining the moment he got his chip. And I think that, like, it's always such a cool thing to hear someone share that because it's it's probably been a huge part of your life's path for the last however many years. And so I think the other thing I always think about with this stuff is like being thankful for the chip. And so like, like even writing this letter, I was thinking like, you know, what would you say to yourself to, like, I'm happy with my life. Ended up like, you wouldn't want to change this moment where you're at, right? Like, but, you know, can you imagine a life that got you here without that chip being so painful? And, you know, I just thought about that moment of seeing your mom and that moment. I mean, it would feel so helpless and terrible, especially as a teenager. But, you know, I'm always thinking about this like, the chip has to hurt for it to work.

James 00:02:53  And.

Speaker 3 00:02:53  Yep, yep.

James 00:02:55  You know, so, like, in some sense, you're thankful for the pain. So yeah, I don't know. It's It's always just makes me think really deeply about, like, you know, what led you here? What led me here? Why are we all here? So it's, It's a beautiful, It's a pain. You're thankful for it. So it's it's fun to hear about.

Speaker 3 00:03:13  Well, yeah, absolutely.

Speaker 4 00:03:14  That one James. That. That's. Yeah. That's great. Could I ask Jasmine Star? She always has a unique angle. Something that I would not have thought of out of that that's always like, oh that's awesome. So you got one or not to put you on the spot, but.

Jasmine Star 00:03:32  No, for for a deal specifically, it just, it just hit like. I like hearing that our humanity, it just draws us closer together and has a deeper appreciation for the climb. And so I just have a much deeper appreciation, a deeper respect for a deal and what he's what he's built and like in reference to what James says, we all have a chip.

Jasmine Star 00:03:53  And I'm like, I have a basket of chips. Somebody make up some walk away like it all. Heard it all her I will just, I will I'll be out here tossing chips, so like that. And, you know, you said it has to hurt. And I was like, if that ain't the truth. No. Good. Thank you. Thanks, Neal.

Speaker 3 00:04:10  Thanks, guys. Appreciate you.

Jasmine Star 00:04:12  When I wrote my letter, I thought that I was just going to share it with the guys in my cohort. I was literally just writing a letter to myself that I was going to share it with them. But when one of the members by the name of JT had said, Jasmine, this letter made me see you in a different light. I saw a new side of you. He's like, oftentimes when I hear you talk about your journey, it's very put together. It's packaged, it's branded. He's like, but this, this just felt entirely different. And so I asked them if it was cool, if I could share that letter here with you.

Jasmine Star 00:04:48  And with their permission, they said, and I'm not sharing any of their letters. I'm just going to share my own. And I feel open, and it makes me feel very vulnerable to put it out in this capacity. But I've always been committed to documenting the journey. And so you guys are going to be able to hear why I'm creating this podcast. I create this podcast to look back and tell myself the truth of the journey. There's something called Solomon's paradox. I don't know if you've ever experienced that. You have the ability oftentimes to give friends or peers really great advice. But when it comes to giving yourself advice, sometimes you're a little bit stuck. Like sometimes you're just like, I don't even know what I would say. Well, Solomon's paradox is the ability. Now, if you're not familiar, it's a biblical character. King Solomon was known for his wisdom, and people would travel lands in years to get wisdom from King Solomon. But like his life, was completely speckled with a lot of missteps and things that a wise person purportedly wouldn't do.

Jasmine Star 00:05:43  Right. So Solomon's paradox means we can give advice better than we could take it ourselves, but oftentimes we can give ourselves advice to our younger self because we look at that as a different version of ourselves. And so being able to write this letter was just the truth of the journey. And so, because I want to share the truth of the journey, I'm going to be open and vulnerable and share my letter right about now.

Speaker 3 00:06:07  All right.

Speaker 4 00:06:07  Let's keep going. Could we have a reading from the Book of Jasmine? Is that an option or would you?

Jasmine Star 00:06:12  I just I had a feeling you were going to call on. I just I was like, airman, because you guys already know. In the back of my mind, I reverse engineered. I was like, there's no way if each of us have minutes, we were running out of time and I have to actually leave the call like 15 minutes early. So I was like, girl, you're good. And then I knew case wasn't calling me.

Speaker 3 00:06:30  And so I was born.

Speaker 4 00:06:31  At night, but not last night, you know.

Jasmine Star 00:06:33  That. Okay. So. So, you know, studies prove that women will, on average, use about three words to a guy's every one. So I'm probably three ex of a deal. I hate to break it. I'm so sorry, guys. No, sorry.

Speaker 5 00:06:45  I probably did this thing wrong. okay. I wrote a letter.

Jasmine Star 00:06:50  To my 18 year old self, but specifically at the start of my senior year. Okay. Dear Jasmine, you're receiving this letter from your future self Yourself before you freak out and page your boyfriend. That something crazy is happening on his beeper. 911. Astrid 143. Let me get to the main point. The future is amazing. So much better than you can imagine. Right now, it's the start of your senior year, and you believe you'll be attending UCLA law school to major in English. The bad news is, you bomb your S.A.T. and you don't even try applying.

Jasmine Star 00:07:21  You end up getting an academic scholarship to Whittier College and major in business. You're broken hearted, but the highlight is that you're still texting your boyfriend in college because you decided to date long distance. You both talk every night for two years from a payphone outside of your dorms. In a beautiful turn of events, you get a waitressing job at a barbecue restaurant while waiting to get accepted to law school. You take the Lsat, but this time applied only top 15 law schools, hoping your entrance essay and 4.0 GPA will miracle. Berkeley, UVA, USC all say yes, but when UCLA offers a full ride scholarship, it feels like a full circle moment. You're officially Bruin, and your boyfriend moves you into your brand new apartment on Veteran Avenue, just two blocks from the Bel Air sign. At this moment, you'll think you've made it. A few minutes later, you'll get the news that mom had a relapse of brain cancer. You'll lose your appetite, you'll stop sleeping, and you'll find yourself running eight miles every day at 4 a.m..

Jasmine Star 00:08:16  You dread school. You find yourself a loner in the law library, and you struggle to make friends. You'll be diagnosed with depression at 24 years old. After mom's brain surgery on New Year's Eve, you decide to quit law school and move home to be with her. Your high school sweetheart proposes? Yes. You marry him. Everybody is shocked that such a remarkable human is volunteering to spend his life with you and Mom and dad walking down the aisle on a beach in Hawaii, when it's time to return to UCLA to get your scholarship. You ask your husband if it would be crazy to wait a year to see if he could try to become a photographer instead. You don't even own a camera. Two months later, you unwrap a Christmas gift from your husband. That brand new camera. Two years later, you ask him to quit his job and join you. Two years after that, you're named one of the top photographers in the world. You start a blog, your posts go viral. You begin traveling the world to shoot and speak about photography.

Jasmine Star 00:09:02  You're then hired by large photography companies to consult on their branding and marketing. You'll begin to build an online store and sell your digital resources for photographers, and print a magazine of your own. You'll soon expand to create courses not just for photographers, but for business owners to help them build their brands and their business. Around this time, the business gets so big, you realize it's time to hire a CFO to manage the streams of revenue. You'll start a membership in 2017, and you hope that 500 people join in the first five days. 2444 people joined in 2021 after four years of expansion. Knowing you need more tech infrastructure, you hire a CTO and build a SaaS platform to integrate with every social platform so business owners can create and plan their marketing. In 2023, you decide to create a holding company you either outright own or have equity in a series of companies, all under the umbrella company. You don't know what you're doing, but the opportunities that come your way blow your mind. On the days that you're tempted to question or doubt your big crazy vision, you remind yourself that at every step along the way, you didn't know what you were doing, but you figured it out.

Jasmine Star 00:10:02  And it's so much better than you can imagine. Along the way, you fell more in love with your husband. You adopted a beautiful, magical, incredible daughter. And mom survived brain cancer. And the best part is, even though it's been the hardest thing you've ever done, building this has been breathtaking and it's made you happy. To be honest, I want to tell you to apply to UCLA for undergrad, to finish law school, to take more risks, to go on more vacations, to dance until the morning sunrise. I want to tell you to get those investors to double down on tech, to demand to be in those rooms, to take strategic debt, to make bigger bets on yourself. But I won't. I won't do any of that. This future life is so much bigger than you. Allow yourself to dream. And it happened as it should, and it took as long as it needed. And everything is preparing you for the next big move. So right now, as you begin your senior year, don't be so hard on yourself.

Jasmine Star 00:10:50  Live more in the present moment and trust that everything is working out for you. I'm so proud of you.

Speaker 4 00:10:56  Wow. Whoa! Good turn. That was.

Speaker 3 00:11:00  Incredible. That was really incredible.

Speaker 4 00:11:04  She understood the assignment. That's fantastic. Jasmine, why did you choose that point? To write the letter to yourself?

Jasmine Star 00:11:17  I was really, really, really hard on myself in high school, but specifically my senior year. I kind of just felt like I had failed. I'm just. I'm not a standardized test taker. I never have been. And, How sad. Like when you're 18, you just think your life's over. When your plans, you know, don't go as planned. And I think that I kind of carried I think that was probably one of the first trips on my shoulder is just, you know, going to a school I didn't want to, struggling to be there. I tried transferring out and then doors closed, doors closed. And so then you just knew you had to be there for reasons you didn't quite understand.

Jasmine Star 00:11:50  And so I think I needed to tell myself it was going to be okay.

Speaker 4 00:11:54  Yeah, I heard and I heard how you were giving your younger self Herself room to to grow into the life that the advice you wanted to share. You won't, because that's an important factor. And in what it can be and what it what what it will be. So I thought that was insightful. It's pretty cool.

Speaker 3 00:12:15  Jasmine, do you, do you ever think about if you were back into your your 18 year old shoes and you're looking at where you are now and reflect on the things that maybe moved much faster than you would expected, and things moved a lot slower than you would expected. I'm curious. I'm curious to hear, like what some of those things are for you.

Jasmine Star 00:12:39  my my photography career took off like a rocket ship. I didn't even I didn't even know what was happening. And so I thought, well, that's the way most things work. Which boy, was I wrong? And then I think, like, the second rocket ship moment was, social curator.

Jasmine Star 00:12:55  It just it just it just was so much bigger. It was so much bigger than I could have ever imagine. It took off so quickly. And I think part of like the, the quick off take really impacted how much we can grow and how we could sustain. And, you know, not all not all rocket ship growth is good growth extended to me. And that's good to another chip. Like I said, gentlemen, I'm waking. Welcome away. Like I can go on and tell you all the chips. All the chips.

Speaker 3 00:13:23  Well, I went slower than you expected.

Jasmine Star 00:13:26  What was slower? I think the what has been the slowest hands down has been the entire journey of me being in Hampton. It has been the slowest, most arduous three years of my professional career. And I think, you know, I am paid really well to see around corners. People hire me to do strategy. And I think it's been to be completely candid, so hard not to be able to see her on my own corners, in my own strategy.

Jasmine Star 00:13:54  And I think that what's taken me the longest is trying to figure out, like, what a holding company looks like. you know how we're getting there. There is that balance between long term and, current cash flow. What are the bets that we make? How to be strategic. All that stuff. It's been really slow.

Speaker 4 00:14:11  Thank you very much for sharing.

Speaker 3 00:14:13  That was awesome. And then I heard one. No surprise is that you are the best at telling the narrative of your life compared to anybody. I think in Hampton, probably like, it's. That was no shock to me. I was like, yeah, this is killer. Like, you know, your chips, like you said. And then but I also thought, even though I've heard you, whether it's your podcast or your social or here, I also heard vulnerability as like like an undertone, you know, like, sometimes it's like you're so good at it that you're like, boom, that's the like that. These are the words I'm going to use in the sentence because I know it lands.

Speaker 3 00:14:54  But like on this one, I heard like that vulnerability perspective. And I wonder if it's just because you're writing to yourself instead of, you know, an audience or. But I really appreciated that extra level of vulnerability.

Jasmine Star 00:15:08  Thank you. Thank you. And you're right. You're right. Like, I just felt like I'm softer, nicer with myself, by myself. I think I'm much harder with myself publicly.

James 00:15:19  I don't know much of the The Jasmine Star story. I'm pretty new here still. But I heard a lot of reassurance, you know. And I think kind of like giving yourself strength. I'm curious if, looking back, you feel like you needed that, or if that was something that you had developed or, you know, just curious why you wanted to say that to yourself.

Jasmine Star 00:15:38  You're so thoughtful. That that the last comment that you had made towards the deal, I thought it was very thoughtful. And I feel like this is a very thoughtful question and it's crazy. I wrote the letter to my former self, but the person who needs to hear it is my present self.

Jasmine Star 00:15:52  I think that in 13 years, I'm going to write a letter back to myself and give myself the same advice I gave to my 18 year old self. Like, don't be so hard on yourself. I'm gonna cry. Oh, no I'm not. We're good. Don't be so hard on yourself. Live more in the present and trust that everything's working out for you. I'm going to say the same thing. And so I was like, just last night, kiss baby girl's head. And I was like, man, this is it. This is it. This is it. I'm gonna wish for the day to come back to this day. It's almost like live now. Like this is it. This is as good as it gets.

Speaker 6 00:16:30  Good answer.

Speaker 7 00:16:31  Yeah. I think you said, like you would want to write the same letter to yourself 13 years later because, like you said, you were hard on yourself because you did that on the standardized tests in many ways. Actually, it was so good for you.

Speaker 7 00:16:46  You did bad on those tests, right? Had you done well, you've gone to law school. Or maybe you've been, you know, some midmarket lawyers, some somewhere instead of all the stuff you've done.

Jasmine Star 00:16:55  Like, like get an R, I know.

Speaker 7 00:17:00  Whatever. I'm just saying, like, fine. Like, imagine being a partner at a law firm. Like, is that any better? You know? But I think for me, when I say, like, I'm really good at standardized tests. Like, I aced all my tests. And then I go do some meaningless job for for a paycheck. Instead of, like, life forcing you to do something you should be actually doing instead of what kind of society pushes you to do it? Because, you know, that's what standardized tests push you to do.

Speaker 4 00:17:31  I mean, it's not not really a paradox, but it's not the right term. But isn't it interesting how most of our lives we wouldn't change a thing. Look at how much confidence that is and that you are where you're supposed to be.

Speaker 4 00:17:45  Or at least I guess you know or you don't know any better. And so you wouldn't change a thing. But it is an interesting study to say, well, where would I be differently? Would I be a would I be better and worse? And how do I judge what's better or worse? There really is no such thing. It is I am what I am, it is what it is. And so there are in theory, there are no wrong decisions. Some in retrospect that's not practicality. But in theory, from a philosophy perspective, there are no wrong life decisions. You get where you're supposed to go. If you if you want to call that, if you want to call that faith or belief or random theory. Yeah.

Speaker 3 00:18:19  By the way, I'd like to see a stat of all of the founders and entrepreneurs and what their test scores were. I would I would guess, I would guess that actually they lie on the lower end and, and and I, I'm the same way.

Speaker 3 00:18:40  I was never a good test taker. And that forced me to compensate in other ways, which I think improved me and pushed me harder in other ways, made me, you know, be a better communicator, a better designer. I worked harder, all those things. But yeah, it's an interesting data point.

Jasmine Star 00:18:54  Real quick, gentlemen, if it's okay and if not, just, just DM me. One of the things that he had said was that he felt like a different level of vulnerability. And I that rang true with the capital T, do you think that I can clip out my letter and then use it as part of a podcast in the future? But you guys, your voices might be in the back, but just just my part. Nobody else's. Nobody else is okay. But if not, I'm very much open to it. So just DM me on slack or text me. Okay, cool. Thank you guys. Thank you. I feel all warm and fuzzy. You guys are the best.

Speaker 4 00:19:24  Thank you. Jasmine. Thank you. I always I'm always worried. Sometimes if you're going to go allow yourself to be that open to us. And so I'm really was pleased to see that you did. So that's.

Jasmine Star 00:19:36  Great. Well, in a room full of gentlemen I cannot resist. So thank you. Thank you. Before we go on any further, I want to say Casey, James, Adeel, JT, love, Remi, Anar and Blake. Thank you friends. Gracias, amigos. Like truly for creating this space for three years and seeing me on this journey. And now it's time for me to say thank you to you. Thank you for watching and listening. To the Jasmine Star show. Thank you for sharing these episodes. It is a small group of crazy entrepreneurs who somehow find themselves listening to it and watching it. You're that crazy cohort. It's just a small group of us doing some really incredible things, and most days they don't feel incredible. But one day when we're 85.

Jasmine Star 00:20:26  Looking back at this version of us today, we're going to say, wow, job well done. Like you did what you thought was impossible. And so on this day, I hope that you think of yourself at 85 years old and with deep pride and appreciation for the hustle and for the journey and for the joy and for the success and for the failures and for the lessons and for the ups and for the downs. You say, take it easy on yourself. You're doing a great job. Thank you for watching and listening to the Jasmine Star Show.