On Purpose with Jay Shetty - Ask Jay: The Right Opportunity Might Not Be What You Expect

Episode Date: September 2, 2026

Jay answers four listener calls about what to do when the path forward feels uncertain. From career rejection and financial risks to knowing when openness becomes self-abandonment and how to keep going after repeated disappointment, Jay explores how to navigate the moments when what you want isn’t working out the way you hoped. Drawing on Seneca, Pema Chödrön, and Taoist philosophy, he shares how shifting from an outcome mindset to a growth mindset can help you see rejection differently, keep your momentum, and stay open to the right opportunity. With Love and Gratitude, Jay Shetty Mazda crafts cars for people who do more than simply move. Visit Mazdausa.com to learn more. Consumer reports does not endorse products or services. JAY’S DAILY WISDOM DELIVERED STRAIGHT TO YOUR INBOX Join 900,000+ readers discovering how small daily shifts create big life change with my free newsletter. Subscribe here: https://news.jayshetty.me/subscribe Check out our Apple subscription to unlock bonus content of On Purpose! https://lnk.to/JayShettyPodcast What We Discuss: 00:00 Intro 00:30 Navigating Career Rejections 01:31 The Smarter Way To Get Your Foot In The Door 06:32 Jay’s Personal Story With Rejection 08:56 Is The Dream Worth The Financial Risk? 10:24 Before You Take The Leap, Ask Yourself This 14:22 When Does Empathy Become Self-Abandonment? 15:40 Setting Boundaries Without Closing Your Heart 20:44 How To Stop Letting Rejection Kill Your Excitement 21:26 Shift From An Outcome Mindset To A Growth Mindset Learn more about your ad choices. Visit podcastchoices.com/adchoices

Hey, it's Jay. I don't know what your day's been like, but I was just thinking about you for a minute. And I hope you're being a little patient with yourself because you deserve it. And yeah, I'll talk to you soon. Today's theme is opportunity, and I'm grateful for the opportunity to listen to you all. Let's get started. Going back to school for logistics and supply, I graduated early in June, but I still have one semester left this up-and-coming fall. One of the requirements for my degree, I need an internship. I have applied to over 100 places, and I keep getting denial letters.

It's very stressful. Like, I feel like I don't know how many internship applications I need to put in. It seems hopeless. Like, I see so many people on LinkedIn, they have their internships. I don't know. Maybe I wasn't active enough on campus. work full time, mother full time, and then also going to school full time. Now I need to lock in on an internship.

My question is, why is it this hard to get an internship? First off, I want to recognize something before we even get into the job market. You're going to school full time, working full time, and seeking another commitment on top of all of that. That isn't just a busy schedule. that is an extraordinary amount of responsibility, and the fact that you graduated early while holding all of that up tells me everything about your drive. You asked why is it so hard to get an internship right now and how to keep going when it feels hopeless. Let's start with why it's so hard.

When you apply to 100 places online, you enter what recruiters call the cold funnel. In a saturated market, a cold application often has a response rate under 2%. Out of 100 applications, getting 98 rejections or silences isn't a sign that you did something wrong. It is the real math of a clogged system. And when you look at LinkedIn and see other people landing positions, it's easy to assume they worked harder or did more on campus. But campus activities and blind applications require one specific resource, unstructured free time, the very thing you had to give to your work and your other full-time responsibilities. So you aren't failing at the game.

You've been playing a system stacked against anyone who has to balance real life at the same time. There's a stoic philosopher named Seneca who wrote a lot about how we measure our progress. He noticed that we tend to complain about a lack of opportunity when what we're actually suffering from is misplaced effort.

He talked about how easy it is to exhaust ourselves pushing against things that won't move, confusing sheer ever, effort with actual movement. His point was simple. When a door isn't opening, the answer isn't always to throw your shoulder into it harder. It's to pause and see if there's another way in. When Alex Hormosey came on my podcast, we talked about what it takes to break into an industry when you don't have a built-in network or a shiny resume. And he made it a point that applies directly to where

you're sitting. He said that when you have zero leverage, you don't offer your need. You offer you your value. Most people send a cold application that says, I need an internship to graduate, here's my resume. But the person reading it has 500 of those. Alex talked about shifting from broadcast to direct outreach. Instead of applying to another 100 giant portals, you pick 10 mid-sized supply chain companies. You find the logistic manager or the head of operations on LinkedIn. And instead of asking for a role, you send a short message showing that you understand their specific operation or offering to help solve one small tedious problem for free just to prove your output. You don't need 100 companies to say yes to your resume. You need one

manager to realize that someone who can juggle two full-time commitments and a degree is the most reliable person they could ever hire. I know you asked why it's so hard and it is hard, but I want to lay out the math so you stop taking a structural obstacle as a person. personal failure. This market is tough and looking for work is exhausting, but you're not hopeless and you're not behind. Shift your effort from cold volume to direct leverage. Show them the worker you already are and let your effort land where it can actually be seen. There are a few things I want to share with you. One is I deeply believe in the law of odds. The more doors you knock on, the more likely a door will open.

You're already knocking on lots of doors and I wouldn't stop that. The second thing I'm going to say to you is you don't need a hundred yeses. You just need one yes to change your entire life. It may take 500 applications before you get an internship, but that internship could change the entire trajectory

of your career. So the benefit far outweighs the cost of sending more email. emails. It far outweighs the time that you're going to spend putting those applications together. And the third thing is going through your network, going through people you know, building that high leverage approach on LinkedIn and other social media platforms will more likely convert to an interview stage, a internship, actual success because you're making it easier on yourself. You're working smarter, not just harder. You're already a driven, ambitious, hardworking individual. And now you're learning the aspects of strategy,

networking and connection that will only help you be more successful in the long term. I know for a fact that referrals, connections, direct reachouts sound like hard work. And often it can feel quite uncomfortable to put yourself one-on-one with someone. The reason why I appreciate your question so much is I can actually relate to it. When I left the monastery and came back into the world of work, I had a three years gap on my resume. And surprise, surprise, no one wanted to hire me because who wants to hire a former monk? They're wondering, what are your skills? Being silent and sitting still. Like, we don't need that in a company. I applied to 40 companies that rejected me before I even got an interview. And I remember just consistently feeling like I had

no idea where I was going to find work. I was moving in and living with my parents in the bedroom I grew up in and not knowing what I was going to do next. The way I got my role was I reached out to someone who went to my university in my year, but I didn't even know that well on LinkedIn and asked him if he would refer me to the company he worked for. Thankfully, he did. and it was because of his referral at the company he worked for that I got expedited to the interview stage compared to any other company that I'd applied to online. It's kind of easier to apply through a company website or at a general email. Emailing or LinkedIn messaging someone directly can feel quite intimidating. But that's why it works. It works because all you need is for one

person to see the value you can bring and give you a shot. I promise you, do not be scared of even if you have to send a thousand emails or a thousand LinkedIn messages, because what's on the other side is a career that you're going to crush. I'm wishing all the best. This episode of On Purpose is presented to you by Mazda. Peace of mind doesn't happen by chance. It's created through the habits we build before we ever need them. That's the philosophy behind every Mazda, with proactive safety features that help keep you

more aware, more connected and more engaged, Mazda helps you feel ready for whatever the road brings. It's why Mazda has been named Consumer Reports' safest new car brand. And as of July 26, Mazda has won more 2026 IIHS Top Safety Pick Plus awards than any other car brand. Visit www.IHS.org to learn more. A lot can happen when an accident doesn't. Visit MazdaUSA.com to learn more. more. Consumer Reports does not endorse products or services. I live in a condo in Toronto that I

purchased after my divorce. I live with my 20-year-old son who attends university for another three years. He lives in residence and comes home to Toronto for holidays and over the summer months. My son chose to live with me because he loves the area and it's close to his friends and his summer work job. Recently, I was let go for my full-time employment after 26 years, so I'm thinking now a good time for a fresh start somewhere. So I found a place up north that I'm very interested in and would love to make an offer to purchase it. I can only afford it if I sell the condo, which I don't want to do. I was hoping to buy the second property up north, move up there and rent out my condo in Toronto. My fear is that I would be taking on too much financially, especially since I no longer have

full-time employment. I don't want to give up on my dream house, and I don't want to give up my condo in Toronto for a few reasons. Starting over alone in a place I don't know anyone. with no help. My son also won't have anywhere to come home to in the summer months when he wants to come to Toronto for work and to see friends and family. And he also wants me to keep this condo so he can rent it or buy it from me after he finishes school. My question is, should I take the plunge, the risk, buy the second property and move up north, but still keep my conno in Toronto? Or do I wait till I'm in a better financial position when the condos paid off? My son is out of school, but then I risk losing the dream home.

So you have a lot going on right now. You have a kid in college losing your job, finding your dream home. First, I want to acknowledge losing your job. I'm sorry about that. 26 years is a lifetime. You had that job longer than you've had your son. And that's a real loss. And I hope you're taking care of yourself and coping okay.

But I also want to congratulate you because you sound genuinely excited about the future. and that energy is so powerful. Now, you asked whether you should take the plunge on this second property up north while keeping your Toronto condo or wait until your finances settle. I'm not a financial advisor, so I can't tell you to buy or not buy.

But I am a big believer in leading with what you want, and if this is your dream home, you owe it to yourself to figure out what it would take to make that possible. When money expert Nisha Shah came on my podcast, we talked about how to assess risk when you're making a big career or life pivot. And she made a great point that risk isn't just about math.

It's about finding the specific boundary where your financial choices align with your peace of mind. If a dream home causes nightmare anxiety, it loses its magic. The goal is finding the path where you feel financially grounded and excited. So instead of seeing this as an all-or-nothing gamble, map it out practically.

Look at the real numbers. You mentioned renting out your Toronto condo, which could bring in steady rental income. You can also cost your net for work both in Toronto and up north. You might even find seasonal work that lets you spend winters in one place and summers in another. Getting creative with how you structure your income can open up doors you didn't know we're there. I also hear your concern about your son having a place to stay during his university summers. But remember, he's 20 years old and you two can tackle that together. finding summer housing or a sublet in a major city is a normal problem to solve,

not a reason to hold back your life. At the end of the day, if taking on both properties is going to drown you in anxiety, it probably isn't worth it. If you buy your dream home, you should be able to enjoy it. But if you run the numbers, explore rental income, look at work in both areas and find a plan that feels solid. Then it isn't a reckless gamble. It's a meticulously calculated move. I have complete faith in you, to figure out what you most want. Map out the practical steps to get there and enjoy this exciting new chapter.

What you don't want to do is end up with both the condo and your dream home, but the dream home becomes such a source of anxiety and stress that it loses the joy that you had, the excitement that you have right now of having it. And I think a lot of people take on a lot of pressure and stress thinking that having this thing is going to solve all their problems, only to realize it causes a host of more problems. So that's why I'm encouraging this meticulous calculated logical approach

so that you don't end up setting yourself up for failure and so that you don't end up in a situation where you feel more stressed and more anxious than you already are. You're also worried about losing your dream home. One thing I want to point out is every time you feel that, realize there is another dream version of your home. If you waited a couple of years to make sure you felt grounded, to make sure your finances were in order, you might even be able to afford something better than you ever imagined. And I think often we find something really good and we think this is the best I could ever get.

This is the best I could ever have. Not realizing that there's something so much more bigger and better out there if we were patient and waited for the right time. So if you don't get your dream home right now, realize that that's your current dream home. That could change in one, two, three, five years based on your affordability, based on the foundation you've built, and based on who you are at that time. Don't settle for something less that could create more stress and anxiety when you could be patient for the real thing. I stayed in a marriage after repeated betrayals over the course of several years.

Part of me knew I was getting hurt, but another part of me genuinely wanted to understand someone who experienced the world very differently from me. With empathy, to question my own beliefs and to remain open to difference and growth rather than retreating into judgment and anger. I wanted to know I had tried my best. I left my marriage a year ago.

Looking back, staying brought me some of the deepest pain I've ever experienced. It also brought me peace because I left without regret, knowing deep in my heart that I had reached the end. There was still sadness and grief, of course. It made me realize this isn't just about relationships. It's about life. We hear that we should protect our boundaries.

But we also hear that growth comes from challenging them. That's where the most meaningful experiences of our lives come from. Other times, it's where we get hurt the most. So the question is, how do we know when openness is helping us grow and when it's quietly becoming self-abandonment? How do we stay open-hearted without losing ourselves? Thank you for sharing such a vulnerable story. First off, I am so sorry for the betrayals you experienced in your marriage.

Betrayal's heavy, it's a painful weight to carry. But I want to honour how you showed up. Many couples are able to rebuild after betrayal, and giving your marriage a real empathetic chance wasn't a flaw in you. Walking away with no regrets, knowing in your heart that you gave it everything, is something you should be truly proud of. Now, you asked a deep question.

How do we know when staying open is helping us grow and when it quietly turns into abandoning ourselves? You use a lot of thoughtful terms to describe what you went through, but let's slow that down and talk about what's actually happening underneath it. When you talk about staying open, you're talking about curiosity, a genuine desire to understand someone else. Self-abandonment is a big term, but in plain language, it just means ignoring your own truth to keep the peace with someone else. It's when their comfort or their perspective becomes more

important to you than your own emotional safety. It is always worth stepping back to look at our best qualities, like empathy or patience, which you clearly have in spades, and ask, Is this giving me an opportunity to grow, or is it just letting someone take advantage of me? There's a famous Buddhist teacher named Pema Children, who talks about how true compassion requires what she calls a strong back and a soft front. I love that image because the soft front is your capacity to stay open, caring and empathetic. But the strong back is your backbone. It is your boundary.

It's knowing who you are, what you stand. for and what you will not tolerate. When you don't have that backbone, staying open isn't kindness. It's just leaving your front door wide open with no lock on it. You don't lose yourself by staying caring. You lose yourself when you stop enforcing boundaries within that openness. Because to abandon yourself, you first have to know who that self is. Knowing your non-negotiables and your values gives you that backbone. And when you have that, you can stay empathetic

towards someone else without worrying that you're being taken for a ride. When you're open, you ask questions. When you abandon yourself, you believe any answer you get. When you're open,

you're still in control but willing to adapt. When you self-abandon, you give up all control and just follow where they're going. When you're open, you still see yourself as part of the equation. When you abandon yourself, you dissolve and make it all about them.

Often we use openness or compassion and empathy as ways of people pleasing, as ways of gaining validation, as ways of feeling like we matter. That's when it's self-abandonment, because we're willing to let go of our own values, our own beliefs, and our own principles simply to make something work. If you find yourself negotiating, compromising, or abandoning your values, principles, or beliefs, that's self-abandonment.

If you find yourself questioning, dissecting, discussing, debating, then you're being open. We want to stay open because we don't want to miss out on opportunities. But even the word open is being open-eyed. If you're open, it means you can see the red flags. It means you can see the mistakes. It means you can see the parts that you may have to lose and compromise. That is where the real opportunity is right now.

This clean slate gives you a chance to take all that curiosity and empathy you gave away for years and direct it back at yourself. Get curious about what you want, what you deserve and where your line is. When you know who you are, staying open isn't scary anymore because nobody can shake your foundation. This episode is brought to you by Mazda. Some of life's best moments happen because nothing went wrong. The drive home, the conversation that continues, the plans that stay exactly as planned. That's the feeling of safety. Every Mazda is designed with proactive safety features that help keep you more aware,

more connected and more engaged with your drive so you can feel confident on the road. That's why Mazda has been named Consumer Reports' safest new car brand. And as of July 26, Dave won more 2026 IIHS top safety pick plus awards than any other car brand. Visit www.IHS.org to learn more. A lot can happen when an accident doesn't. Visit MazdaUSA.com to learn more. Consumer Reports does not endorse products or services. Hi, Jay.

How can I stop a specific dynamic, which is getting a case. excited about a new position or job opportunity or even to date somebody that I really want. I get excited. Then I get disappointed. It happens in repeat, either rejected or the door closes or disappointed and nothing moves. And it's been like this for the past three years. And I want to get this dynamic out of my life. I would really like to create new story. So I wanted to ask do you have any advice for that? This is such an important question that I believe everyone can relate to. And it honestly, it makes me so empathetic to where you're sitting.

Spending three years in a loop where you get excited, step up to the plate, and then watch the door close is exhausting. I love that you aren't writing and asking how to stop caring or how to numb your excitement. You want to rewrite the story completely. And that decision right there is you actively creating an opportunity. for yourself. When you get excited about a job or a person, that energy is a gift. The problem isn't your excitement. The problem is that right now, every opportunity can feel like an isolated island. You build all your hope around one door, and when it shuts, it feels like your entire momentum resets back to zero. In Taoist philosophy, water is used as the ultimate model for how to handle

obstacles. When water hits a rock, it doesn't stop and it doesn't lose its nature. It just keeps flowing, using the obstacle to alter its course while maintaining its momentum. It moves around what is rigid rather than exhausting itself fighting it. To break a three-year cycle and write a new story, it comes down to shifting your perspective away from an outcome mindset and into a growth mindset. An outcome mindset attaches your entire sense of momentum to getting a yes on a single job interview or date. When you put all your stakes on one specific outcome, it can accidentally create a lot of internal pressure. We might hold our breath or try so hard to win them over that it can sometimes create a sense of pressure in our interactions. A growth mindset on the other hand keeps your

momentum moving across multiple possibilities. It allows you to stay relaxed, curious and grounded because no single answer has the power to stop your progress. And as you open those paths, remember to give yourself full agency in the process. With the growth mindset, you aren't just waiting to be chosen or taking whatever says yes first. You get to step back and ask, is this company actually right for me? Is this person actually in alignment with what I want? You're evaluating them just as much as they're evaluating you. Nothing in the last three years was wasted.

Every interview gave you sharper answers, every date gave you better clarity on what you actually want. You aren't starring over from scratch every time. You're building a foundation of experience. The new story you're writing isn't about hoping the next door stays open. It's about knowing that you have your own momentum and that a closed door is just a quick redirection on your way to the right match. finding the right partner or finding the right job is rare especially when you're an excited enthusiastic person who wants to do something you love and be with someone you love it's funny isn't it we know love is rare we know passion is rare we know doing what you love is rare but we're confused when we get

more rejections than yes is if something's rare by nature it means more things should not work out than the things that do work out. And almost going through this experience only allows you to get closer and closer and closer to the rare opportunity you're truly looking for. See, when you've been through 99 knows but you get one yes, that one yes makes you feel so much more connected, it feels so much more real, it feels so much more valuable, because you realize there's an actual match. If a job turns you down, you may look back on that in years and realize you're grateful. I look back to so many jobs I got rejected from, so many interviews that didn't go anywhere,

so many meetings that didn't result in anything. And now I look back and I feel so grateful because otherwise I would have been stuck in a job that I didn't really want to be in, even though at that time it felt like the dream. Imagine if every person you thought might be right for you said yes. Now you look back and you think, I was crazy to want to be with them.

I can't believe I even liked them for that long. It's fascinating how when you look back and in hindsight of your life, the things that you dreamed of are things that you're so happy you don't have today. And then there are other things that you dreamed of that you're still pursuing today. And then there are other things you dreamed of that you do have today and feel grateful for. And now it's time for Maximize the Day presented to you by Chase Sapphire. When life gets busy, it's easy to keep saying next time to the things that matter, dinner with friends, a spontaneous weekend away, or simply spending time with the people you love. But a meaningful

life is built from saying yes to these moments. Chase Sapphire helps you make more of them count, with rewards and benefits designed to help you maximize every single day. I think so many of us fall into this habit of saying, I'll do it next time. I'll take that trip next time. I'll have dinner with my friends next week. I'll call that person when I'm less busy. I'll make time for myself when things calm down. But the reality is life doesn't always calm down. And when we look back at the moments that really mattered, we rarely remember how many things we checked off our to-do list. We remember the experiences we said yes to and the people we shared them with. I've been thinking a lot about this idea of asking yourself a different question at the beginning of the day.

Instead of asking, how much can I get done today? Ask, what would make today meaningful? Maybe it's having dinner with someone you haven't seen in a while. Maybe it's booking the weekend away you keep talking about, or maybe it's simply putting your phone away and being completely present with someone you love. Because maximizing your day doesn't mean filling every minute of it. It means being intentional about the moments that are actually worth showing up for. And especially as we come out of summer and get back into our routines, I think that's such an important reminder. Your calendar can be full without your life feeling full. Sometimes maximizing your life starts with simply saying yes to the moments that matter.

The Chase Sapphire Reserve card actively rewards you for maximizing your life with four times the points on flights and hotels, three times the points on dining, and reserve tables at coveted restaurants. Learn more at chase.com forward slash Sapphire Reserve. Cards issued by J.P. Morgan Chase Bank, N.A. member FDIC, subject to credit approval, terms apply. What I'm trying to say is that a rejection is not the end. It doesn't mean it's a full stop.

It doesn't mean it's not going anywhere else. It simply means that you learned a little bit, you gained some feedback, you continued with your momentum, and you kept going. And I think it's the people that keep going in life, just like the flow of that water, that ultimately get to their destination. Imagine water just stopped when it hit a rock. We wouldn't even have the beautiful formations that we do because of it. And the water would definitely not reach the ocean, its destination, where it ends up.

And so for you, I want you to keep that excitement. And that's what your question really has to be. How do I keep my excitement despite rejection and failure? And the way you keep it is that you're more focused on the goal than the, obstacles and the obstacles become feedback not failure points when you're focused on the goal because you're in love with where you want to get to you can move through anything you will break through anything because you know the direction in which you're moving and if you don't like the goal anymore that's okay change the goal it's okay to pivot it's okay to shift sometimes the best

things in your life happen because you were able to pivot instead of stay focused on something that you stopped wanting. I really don't want you to lose that energy that you have. A closed door is rarely the end of the road. It's usually just a redirection towards something that actually fits who you are today. Again, I'm wishing you all the best and I can't wait to see what you go on to do. Those are our memos for today. Trust your momentum as you take that next step and keep those voice notes coming.