Reddit Stories - ULTIMATUM INHERITANCE At Stake For SPOILED Kids! Will They Step Up Or Lose It All

Episode Date: June 19, 2025

#redditstories #askreddit #aita #spoiledkids #ultimatum #inheritance #stepup #loseitallSummary: ULTIMATUM INHERITANCE At Stake For SPOILED Kids! Will They Step Up Or Lose It All. Find out if the entitled children can rise to the challenge and secure their inheritance, or if their behavior will cost them everything.Tags: redditstories, askreddit, reddit, aita, tifu, ultimatuminheritance, spoiledkids, stepup, loseitall, familydrama, wealth, entitlement, decisionmaking, familyrelationships, drama, money, inheritance, parenting, characterdevelopment, moralvaluesBecome a supporter of this podcast: https://www.spreaker.com/podcast/reddit-stories--6237355/support.

I hope you enjoy this story. I informed my indulged and privileged children that they would forfeit their legacy unless they straighten out their lives. Hello Reddit, I am a 55-year-old father and accomplished entrepreneur. I have been managing my own company for nearly 30 years now, and I've done pretty well for myself. My wife, 53F, and I have been married for 29 years, and we have two adult children, Caleb, 28M, and Maya, 26. My parents left me a substantial inheritance when they passed away, which is part of how I managed to build my business to where it is today. So, let's just say, we're financially comfortable. Now, this inheritance isn't just a chunk of change. We're talking about a life-changing

amount of money that, in the wrong hands, could easily be squandered. My wife and I always believed in the value of hard work. We didn't come from money, and we built our life. from the ground up. We wanted to give our kids opportunities we didn't have, but I'm starting to feel like maybe we overdid it. I guess that's why I'm here. I need some advice. My parents were pretty well off, not extremely rich, but we did okay, and when they passed, they left me a substantial inheritance, mostly real estate because it was pretty cheap back then. However, I didn't touch that money until I had earned my own. I wanted to prove to myself, and maybe to them, even after they were gone, that I could make it on my own. So, I poured my sweat and tears into building my business

from scratch, and now it's doing really well. My wife and I have always lived comfortably, and we've made sure Caleb and Maya have had everything they needed growing up. They went to the best schools, had every opportunity, and never really had to struggle like I did. But here's where they're things got tricky. Once I started making real money, I wanted to give my kids the life I didn't have. They went to the best schools, wore the nicest clothes, and never wanted for anything. We set up trust funds for them when they were born, so by the time they hit 21, they had more money in their accounts than I did at that age. Caleb and Maya grew up in a world completely different from mine. They never had to work summer jobs or worry about paying for college.

And now, they're adults living off those trust funds, with no real jobs or ambition to speak of. They're living in their own little bubble, completely disconnected from the real world. I'd always hoped that when they got older, they'd want to make something of themselves, but that hasn't happened. Caleb spends his days hanging out with friends and blowing money on flashy toys, while Maya's into the whole influencer lifestyle, trying to build a brand around herself without any real substance. They're both entitled, lazy, and honestly, bullies. They've never had to struggle, and it shows.

Now, I love my kids, but seeing them like this is frustrating. It's like they don't understand the value of anything because they've never had to earn it. My wife, bless her heart, is more patient than I am. She keeps telling me that they'll figure it out eventually, but I'm not so sure. And that's why I finally decided to take matters into my own hands. It all came to a head at a family dinner a couple of weeks ago. My wife and I were talking about our retirement plans, nothing too serious, just throwing around ideas about what we might want to do when we step back from the business.

Caleb and Maya, predictably, weren't interested in the conversation until I mentioned that we'd to decide how to handle the inheritance. Suddenly, they were all ears. I brought up the idea of them eventually taking over the business, but they shot it down immediately. Caleb laughed and said he didn't want to waste his life working, and Maya made some snide comment about how she's too busy with her career to think about it. I could feel my blood boiling. I asked them what they planned to do with their lives, and they basically shrugged it off. Caleb said he didn't need to work because the trust fund was enough, and Maya said she was building her brand, whatever that means. That was the moment I realized just how far gone they were. That my biggest

mistake might have been giving them too much too soon. When I was their age, I was already busting my ass to make a living. I was on construction sites at the crack of dawn, learning the trade from the ground up. My kids, on the other hand, seem content to sit back and live off the family's wealth without any ambition to create their own success. I tried to explain that life isn't just about coasting on what you've been given, but they weren't hearing it. They made it clear that they had no intention of ever working a real job or contributing to society in any meaningful way. It was like talking to a brick wall. After dinner, I couldn't stop thinking about it. My kids are grown adults, but they're acting like spoiled teenagers.

I couldn't shake the feeling that I'd failed them somehow. I spent years building something that could set them up for life, but instead of appreciating it, they're just taking it all for granted. Something had to change, and fast. The next morning, I sat my wife down and told her what I was thinking. We needed to put our foot down, or our kids were going to end up as useless adults with no purpose. She wasn't thrilled at first, like I said, she's more patient than I am, but she eventually agreed that something needed to be done.

So, at the next family dinner, I told Caleb and Maya that I was changing the terms of their inheritance. From now on, they wouldn't get a dime unless they held down real jobs for at least two years. And by real jobs, I mean full-time work that isn't connected to our family business, with a paycheck from someone other than us. No begging us for a position, no calling in favors with our friends. They needed to find their own way. The looks on their faces were priceless.

Caleb actually snorted, like he couldn't believe I was serious, and Maya just stared at me like I'd grown a second head. I explained that this was non-negotiable. They could either step up and prove they could make it on their own, or they could kiss their inheritance goodbye. Caleb was the first to react. He slammed his fork down and said it was unfair that I was holding their futures hostage. Maya, never one to be outdone, chimed in, saying that I was trying to ruin their lives because I didn't understand the modern world. My wife tried to mediate, suggesting that maybe we could find a middle ground, but I stood firm. I told them that this was for their own good, even if they couldn't see it right now.

Caleb and Maya didn't stick around long after that. They both stormed out, furious and shouting about how I was ruining everything. My wife just looked at me like she wasn't sure if she should be mad or proud. I told her I wasn't doing this to be cruel, I just wanted them to grow up. But even as I said it, I wondered if I was making a huge mistake. The fallout from that dinner was immediate and intense. Caleb and Maya didn't speak to us for a week. which is pretty unusual given how much they usually rely on us for everything. My wife was torn

between supporting me and wanting to smooth things over with the kids, but in the end, she stuck by my side. She agreed that they needed a wake-up call, even if it was a harsh one. When Caleb finally did call, it wasn't to apologize. Instead, he wanted to argue. He said I was being unreasonable and that expecting him to find a real job was setting him up to fail. He told me I didn't understand how hard it was for his generation, how the job market was different now, and how he shouldn't be forced to do something just to prove a point. I listened, but I didn't back down. I told him that everyone needs to start somewhere and that if he was serious about his future, he'd find a way to make it work. Maya took a different approach. Instead of confronting me directly,

she tried to go through her mother. She told my wife that she was being supportive of her brand and that I was undermining her career by forcing her to take a job she didn't want. My wife, bless her, tried to be diplomatic, but she ultimately told Maya that she needed to stop relying on us and start building something on her own. Neither of them took it well. Caleb accused us of being out of touch while Maya insisted that we were sabotaging her success. They both threatened to to cut us out of their lives, which, frankly, felt like a slap in the face. But we didn't back down. We told them that this was non-negotiable and that they needed to prove they could make it on their own if they wanted to inherit anything from us. Now, we're in a bit of a standoff.

My wife is trying to keep the peace, but the kids aren't budging. They've made it clear that they think we're being unreasonable, and they're not shy about telling us so. Part of me feels guilty, Like maybe I pushed too hard, but another part of me knows that this is the right thing to do. They need to learn how to stand on their own two feet, even if it means they're angry with us for a while. So, Reddit, am I the asshole for giving my kids this ultimatum? I want what's best for them, but I also don't want to push them away. Did I go too far, or is this tough love exactly what they need? Update 1, one month later.

After I posted about the situation with my kids, things got even more complicated. Caleb and Maya, still furious with my ultimatum, decided to involve the extended family. They went straight to my in-laws and even reached out to some of my cousins, complaining about how unfairly they were being treated. It wasn't long before I started getting phone calls and texts from various family members, some of whom I hadn't spoken to in months, all wanting to weigh in on the situation. My parents-in-law were the first to call. They were concerned, of course, and wanted to understand what was going on. My father-in-law, who's always been a bit of a softy, thought I was being too harsh and that maybe I should ease up on the kids.

My mother-in-law, on the other hand, was more supportive of my decision. She's seen firsthand how spoiled Caleb and Maya have become, and she's worried that if we keep enabling them, they'll never learn to fend for themselves. Then, my cousin started chiming in. One of them, who's more like a brother to me, said he understood where I was coming from but warned that I could be pushing Caleb and Maya too far. He reminded me that our generation was raised with different values, and that maybe I needed to be more understanding of the pressures young people face today. Another cousin, who's a successful lawyer, outright accused me of trying to control my

kids' lives and said I should just let them figure things out on their own, even if it means they fail. Despite the differing opinions, I stood firm. I explained to everyone who asked that this wasn't about controlling Caleb and Maya's lives, it was about making sure they had the skills and mindset to succeed on their own. I wasn't asking them to become CEOs overnight, just to show that they could hold down a job and contribute to society. I knew it wasn't going to be easy for them, but I believed it was necessary. Predictably, Caleb and Maya didn't take this lying down. Caleb, always the more rebellious of the two, decided to start a business. He claimed he was going to get into day trading because he'd read online about people making a

fortune with it. He poured whatever little savings he had into it, but within weeks, it was clear that he was in way over his head. He lost almost everything and then had the nerve to call me, asking for more money to invest. I told him no, that this wasn't the kind of work I was talking about. He hung up on me, and we haven't spoken much since. Maya took a different route. She started going to all these networking events, which from what I can tell, are just parties where they sip cocktails and talk about their brands. She claimed she was making important connections that would help her build her career,

but I knew better. It was just another way to avoid real work. When I asked her how these events were translating into actual opportunities, she got defensive and accused me of not believing in her. I told her I believed in hard work, not playing pretend. At this point, it's clear they're both trying to find loopholes in my ultimatum. They want the inheritance without having to put in the effort, and it's frustrating to see them waste time on these half-baked schemes.

But as much as it hurts to watch them struggle, I'm not backing down. As the weeks went on, Caleb and Maya started calling less and less, and when they did, the conversations were usually heated. They both tried to guilt-trip my wife and me, saying that we were abandoning them and that they couldn't believe we were willing to ruin our relationship over money. Caleb even went so far as to say that he was considering cutting us off completely if we didn't back down. My wife was heartbroken, but I could see she was also starting to see things my way.

She's always been the peacemaker, but even she was beginning to get frustrated with their attitudes. We both knew this wasn't just about money, it was about their futures, and we couldn't let them continue down this path. Still, it wasn't easy hearing our kids threatened to cut ties with us, especially when all we wanted was for them to succeed on their own. At one point, Maya tried to turn some of our friends against us. She told them that we were being unreasonable, that we didn't understand the modern job market, and that we were setting her up to fail. Some of our friends, particularly those who had kids around the same age, were sympathetic to her, which only made things more complicated. We started getting unsolicited advice from people

who had no idea what was really going on, and it felt like the whole world was suddenly involved in our family drama. Despite all this, my wife and I stayed the course. We knew that caving now would only reinforce the behavior we were trying to correct. But it was tough, really tough, and I couldn't help but wonder if we were doing the right thing. To make matters even more real for Caleb and Maya, we decided to cut back on their monthly allowances. Up until now, they've been getting a pretty generous amount from us each month, which they used for everything from rent to shopping sprees. But if we were serious about them learning to stand on their own, that had to stop. We also cancelled the credit cards linked

to our accounts. If they wanted to keep living the way, they had been, they'd have to find a way to pay for it themselves. The reaction was immediate. Caleb called, furious, saying that we were trying to bankrupt him. Maya sent a long, emotional email accusing us of being heartless and saying that she didn't know how she was going to survive without our support. My wife and I read it together, and while it was hard to see her so upset, we knew this was the push they needed. We replied, telling her that this was part of growing up, and that we were confident she could figure it out if she really tried. For the first time, they were facing the reality of limited funds.

Caleb couldn't afford his expensive hobbies anymore, and Maya had to cut back on her socializing. They were both angry, hurt, and confused, but we could only hope that this would be the turning point. It was a tough love approach, but we believed it was the only way to get through to them. So, Reddit, what do you think? Are we going too far, or is this exactly what they need?

I'm standing firm on my decision, but it's definitely taking a toll on our family. I'd appreciate any advice or insight you can offer. Update 2, 6 months later. Hey Reddit, thanks for all the support and advice you've given us over the past few months. It's been a rough ride, but I thought it was time to update you on what's been happening since my last post. First off, I want to say that I did take some of your suggestions to heart, especially the ones about balancing tough love with emotional support. So, here's what's been going on. Let's start with Caleb. After our last big blowout, he disappeared for a while. He wasn't returning calls, and when we did manage to talk to him, it was clear he was still furious about the whole situation.

I knew he was going through a rough time, but I also knew that he was. needed to figure things out on his own. So, we gave him space. About two months after the ultimatum, Caleb finally realized that he couldn't keep coasting on the little bit of savings he had left. With no income and no support from us, he was forced to look for a job. At first, he tried applying for high-paying positions in fields he had no experience in, but when those didn't pan out, he had to lower his expectations. Eventually, he landed a job. at a local manufacturing plant. It wasn't glamorous, and it definitely wasn't what he wanted,

but it was a real job, with real hours, and a real paycheck. The first few weeks were rough. Caleb complained constantly about the physical labor, the early mornings, and the monotony of the work. He hated every minute of it and made sure we knew it. But my wife and I stayed supportive, encouraging him to stick with it and reminding him that everyone has to start somewhere.

Slowly, and I do mean slowly, he began to adjust. He started to take some pride in his work, and though he'd never admitted to me, I could tell he was beginning to see the value in what he was doing. He's been at the plant for about four months now, and while it's still not his dream job, he's no longer talking about quitting every day. He's even started saving a little bit of his paycheck, something he never did before. It's a small step, but it's progress, and I'm proud of him for sticking with it. It's clear he's not fully there yet, but I'm seeing glimmers of the person I always knew he could be.

Now, on to Maya. Her journey has been a bit different, but no less challenging. After we cut off her allowance and cancelled her credit cards, she tried to keep up appearances for a while. She'd still post on social media about her fabulous life, but it was obvious that she was obvious that, things were starting to fall apart behind the scenes. Eventually, Maya realized that she couldn't keep pretending everything was fine. The networking events dried up when people realized she wasn't really in a position to offer anything valuable in return, and the party stopped being fun when she couldn't afford to keep up with the crowd. It was a harsh wake-up call for her,

and for a while, she seemed lost. But then something interesting happened. One of the contacts she'd made at a networking event mentioned an entry-level position at a marketing firm. It wasn't anything fun, and it definitely wasn't the influencer lifestyle she'd been chasing, but it was a job. After some convincing, and a lot of encouragement for my wife, she applied and got the position. The first few weeks were rough for her, too. Maya wasn't used to answering to anyone, and she had a hard time adjusting to the structure and deadlines of the job. She called us more than that. than once in tears, frustrated with her boss or overwhelmed by the workload. But, like with Caleb,

we stayed supportive while reminding her that this was part of growing up. Over time, she started to find her footing. She's been at the firm for about three months now, and while she's still not loving it, she's beginning to see the value in what she's doing. She even mentioned taking some courses to improve her skills, which is a huge step for her. With both Caleb and Maya and now working, things have started to shift in our family. Our once tense and awkward family gatherings have slowly become more relaxed. There's still some stress, Caleb and Maya aren't exactly thrilled about their new realities, but there's also a sense of relief. My wife and I have tried to be there for them as much as possible without giving in or bailing them out, and I think

they're starting to appreciate that. Interestingly, Caleb and Maya have started to bond over their shared experiences in the workforce. They've always been close, but this is different. They're commiserating about their jobs, sharing stories about their struggles, and even giving each other advice. It's nice to see them supporting each other instead of just relying on us for everything. Our extended family has also started to come around. The relatives who initially criticized our decision are beginning to see the benefits. They've noticed the changes in Caleb and Maya and have even commented on how much more mature they seem. My wife and I still have our moments of doubt, but overall, we're feeling more confident that

we did the right thing. I'm not going to lie, seeing my kid's struggle has been hard. There have been moments where I've questioned whether I made the right decision, but seeing them slowly start to figure things out has been rewarding in its own way. I know they're not out of the woods yet, but they're making progress, and that's all I can ask for. So, that's where things stand now. I know this journey isn't over yet, and there will be more challenges ahead, but I'm feeling cautiously optimistic. Thanks again for all the advice and support. It's been invaluable as we navigate this tricky situation.

I'll keep you all posted if there are any major updates. In the meantime, any thoughts on how we can continue to support Caleb and Maya without coddling them would be much appreciated. Update 3, 1 Year Mark Hey Reddit, I'm back with another update. It's been about a year since this whole thing started, and I wanted to share where we're at now. First off, I want to thank everyone who's been following our story and offering advice. It's been a challenging year, but also one of growth, for all of us. Recently, we had a big family meeting to discuss how things were going.

Caleb and Maya were both there, along with my wife, and it was the first time we'd all sat down together like this since the whole inheritance ultimatum began. I won't lie, I was nervous. I didn't know how they'd react, or if they'd even be willing to talk about their progress. But to my surprise, the conversation went better than I expected. I started off by telling them how proud I was of the steps they'd taken over the past year. Caleb's been sticking with his job at the manufacturing plant, and while he's not exactly in love with it, he's made some real progress. He's developed a strong work ethic, and his boss even told me, through a mutual acquaintance, that Caleb's been doing a great job.

He's started to save a bit of money, and he's even considering taking some night classes to improve his skills. Maya, on the other hand, has really started to find her footing in the marketing world. She's still at the same firm, but she's taken on more responsibility and even led a couple of small projects. She's started to talk about her job with a sense of pride, something I hadn't heard from her before. She's also enrolled in some online courses to further her knowledge, and she's beginning to see the value in working her way up rather than expecting everything to come easily. We talked about the inheritance conditions again, just to make sure we were all on the same page. I reiterated that the condition still stood, two years of consistent, real work before they could access their inheritance. Both Caleb and Maya accepted this without argument, which was a big relief.

It's clear they're not thrilled about it, but they're also not fighting it like they were before. As we were wrapping up the conversation, something unexpected happened. Caleb mentioned that his boss had been talking to him about a promotion. It's not a huge leap, but it would mean more responsibility and a bump in pay. He seemed surprised that he was even being considered, but I wasn't. I've seen the changes in him over the past year, and I'm not shocked that his hard work is being recognized. He's still figuring things out, but for the first time, he's talking about his job in terms of a long-term career, not just something he's doing to fulfill the inheritance

requirements. Maya also had some news. She's discovered a real passion for the work she's doing in marketing, particularly the creative side of things. She's been talking to her boss about the possibility of moving into a more specialized role, and she's even considering going back to school to get a degree in marketing. This is a huge shift from the Maya of a year ago, who was more focused on her social media following than on any real career path.

It's been amazing to see these changes. in them. They're both starting to find their own way, and while they still have a long road ahead, they're making strides I never thought possible a year ago. One of the most unexpected and rewarding outcomes of all this has been the improvement in our family dynamics. There's a sense of genuine connection now that wasn't there before. Our conversations are deeper, more meaningful, and less about money or material things. Caleb and Maya are starting to see us not just as parents with deep pockets, but as people who care about their futures and their happiness. We've also noticed that Caleb and Maya's relationship with each other has improved. They've always been close, but there was always a competitive edge between them, fueled by who could get more from us or who could live the most lavish lifestyle. Now, they're supporting each other in ways they never did before.

They've even started to talk about working together on some side projects, combining Caleb's practical skills with Maya's creative talents. It's early days, but it's encouraging to see them thinking about how they can support each other instead of just relying on us. This experience has also brought my wife and me closer together. We've had to make some tough decisions as a team, and while we haven't always agreed on everything, we've learned to communicate better and support each other through the challenges. It's been a growing experience for both of us as parents and as partners.

So, Reddit, that's where we're at. I'm optimistic about the future, but I know we're not out of the woods yet. The next year will be crucial, especially as they approach the two-year mark of the inheritance conditions. We'll keep supporting them as best we can, and I'll keep you all updated on how things progress. Any advice or thoughts on how to keep this momentum going would be greatly appreciated. update 4 final update hey reddit it's been two years since i first came to you for advice and i wanted to give you one final update it's been a long journey and i can't express how grateful i am for all the support and wisdom you've shared with us along the way this experience

has been challenging but it's also been incredibly rewarding as we approached the two-year mark there was a sense of anticipation in the family. Caleb and Maya both knew that the inheritance conditions were about to be revisited, and while they didn't say much about it, I could tell it was on their minds. They've both come a long way since that fateful dinner when I first laid down the law, and I was eager to see how they'd handle this final test. A few weeks before the two-year deadline, we had another family meeting. I wanted to sit down with Caleb and Maya, hear about their experiences over the past.

past two years and talk about what comes next. My wife and I were both nervous but also hopeful. We've seen so much growth in them, but we also knew that this was a critical moment. When we sat down for the meeting, I started by acknowledging how far they'd come. Caleb and Maya both looked a little nervous, but I could see a sense of pride in their eyes. They knew they'd worked hard, and I wanted to make sure they knew that we recognized and appreciated that. Caleb was the first to speak. He talked about his job at the manufacturing plant, how he'd started to see it as more than just a means to an end.

He'd been promoted twice since my last update, and while it's still not his dream career, he's starting to see the value in hard work and steady progress. He's also started to take on some side projects, using the skills he's developed at work to build something of his own. It's clear that he's thinking about his future in a way he never did before. Maya then shared her story. She's still at the marketing firm, but she's moved into a more specialized role, focusing on creative campaigns.

She's also taken some college courses in marketing and design, and she's discovered a real passion for her work. Maya's always been creative, but now she's channeling the creativity into something tangible, something that could lead to a real career. She's proud of what she's achieved, and she's excited about the future. After they finished, my wife and I shared our thoughts. We told them how proud we were of their progress, of how they'd faced challenges and grown from them. We talked about the importance of the journey they've been on, and how it's prepared them for whatever comes next. Then, I surprised them. I told them that because of the growth we've seen in them, we were increasing their inheritance.

I explained that this wasn't just a reward for getting through the two years, but a recognition. of the people they'd become. They were shocked, and I think a little overwhelmed, but mostly they were grateful. For the first time, I felt like they truly understood the value of what they were being given, not just the money, but the lessons they'd learned along the way. So, where are we now? Caleb and Maya are both in a much better place than they were two years ago. Caleb is continuing to work at the plant while building his own projects on the side, and he's talking about possibly starting his own business someday. Maya is thriving at her marketing firm and is even considering pursuing a degree full-time.

They've both grown so much, and I couldn't be prouder. So, this is it, my final sign-off. Thanks for following our story, and for all the help along the way. If there's one thing I'd leave you with, it's this. Don't be afraid to challenge your kids, even if it's hard. Sometimes, the toughest decisions lead to the greatest growth. Good luck to all of you, and I hope your own parenting journeys are as rewarding as ours has been. Take care, Reddit.

And who knows, maybe I'll be back someday with another story. Until then, cheers.