Ask Jay: The Right Opportunity Might Not Be What You Expect

This episode is brought to you by Mazda. Confidence isn't something Mazda finds, it's something they practice. That's the thinking behind every Mazda, with proactive safety features designed to help keep you more aware, more connected, and more engaged with the road ahead. It's why Mazda has been named Consumer Reports Safest New Car Brand and has won more 2026 IIHS Top Safety Pick Plus Awards than any other car brand, as of July 2026. Visit www.iihs.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. This episode is brought to you by Orange Theory Fitness. One of the best investments you can make is in your own strength. The choices you make today can help shape how you feel for years to come. Orange Theory Fitness provides a one-hour workout to build strength, burn fat, and lose weight. It's a one-hour workout to build strength, burn fat, and lose weight. lot can happen when an accident doesn't. 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 from my full-time employment after 26 years, so I'm thinking now's 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 if I'm not able to afford it. I don't want to be able to afford it. 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 condo in Toronto, or do I wait till I'm in a better financial position when the condo's 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 cast 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 were 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 too 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, and I'm sure you will. 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 you felt 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. This episode is brought to you by Walden University. Balancing work, life, and big goals isn't easy. That's why Walden University helps working professionals get the W with tempo learning, so you can earn your degree at your own pace while gaining practical skills through real-life scenarios. You'll also learn from faculty with support start to finish. Walden University, set a course for change. Ready to start? Visit waldenu.edu today. Certified to operate by Chev, tempo learning available in select programs. This episode is brought to you by Amtrak. You know that feeling when you're already tired and you haven't even gotten there yet? That's where Amtrak comes in. Leave the driving behind and settle into a comfortable seat with plenty of room to stretch out. Catch up on work with Wi-Fi, grab a snack at the cafe car, or just sit back and enjoy your favorite podcast. Choose a cellar or northeast regional and get there without the stress of getting there. Visit amtrak.com to plan your next trip. This episode is brought to you by Indeed. 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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. It was 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? 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 honor 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 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 Chodron, 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 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, you're 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 to you. 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. 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 to 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 2026, they've won more 2026 IIHS Top Safety Pick Plus Awards than any other car brand. 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 you, 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 is gone. And you're like, oh, I'm so excited. I'm so excited. I'm so excited. Reset 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, you need to be able to do it. You need to be able to do 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. But when you put all your stakes on one specific outcome, it can accidentally create a sense of pressure in our interactions. When you put all your stakes on one specific outcome, it can accidentally 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 starting 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 yeses. 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 noes, 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 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 they were. And that's why I think it's so important to 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 Facebook. 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 JPMorgan Chase Bank, NA 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 going to go. 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. On any journey using Uber, it helps to know you're getting into the right car. Pin verification adds an extra step to make sure your ride is your ride. Before the trip begins, your app gives you a unique pin. Just tell it to your driver, and they'll enter it in their app before the ride can start. That way, you know you're in the right car taking the right trip, and your driver knows you're the right passenger. Make sure your ride is your ride. With Pin Verification from Uber, one more way Uber is putting safety at every turn. Learn more on the Uber app. I just want to give you the space to process it, Michael said. Elena paused. I don't think I want to see anybody else. This is the love story of real hinge couple Elena and Michael, written and read by me, Raven Smith. Listen to the free audiobook now. Endless summer escapes start here. Travel the worlds of Netflix IRL. 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