They Won’t Get It (And That’s Okay)

There’s a particular kind of loneliness that comes with building something from nothing. You’re working sixteen-hour days, you’ve turned down job offers that would pay you three times what you’re currently making (which is nothing), and you’re explaining to your parents for the fifteenth time that no, you don’t need them to ask their friend about that opening at his company.Here’s the uncomfortable truth: unless your family members built serious wealth before they turned thirty, they probably won’t understand what you’re doing. And I don’t mean that dismissively. I mean it literally. They lack the reference points to even process the journey you’re on.Think about what wealth before thirty actually requires. It demands a tolerance for risk that feels reckless to most people. It requires believing in something that doesn’t exist yet with such conviction that you’ll sacrifice years of your life and financial security for it. It means operating in a world where the rules are different, where a “stable job” is actually the risky choice, where burning through savings isn’t irresponsible but strategic.Your parents likely followed a different playbook entirely. They got an education, found a good job, worked their way up over decades, saved diligently, and retired comfortably. That playbook worked brilliantly for them. It’s a genuinely good path. But it’s also a path that requires fundamentally different instincts than the one you’re on.When you tell them you’re reinvesting every dollar back into the business instead of building an emergency fund, they hear “financially irresponsible.” When you explain you’re not taking a salary yet, they hear “being exploited.” When you say you’re pivoting the entire business model three months in, they hear “can’t commit to anything.” They’re translating your decisions into their framework, and in that framework, you’re failing catastrophically.The friend who made his first million at twenty-seven building a software company? He gets it immediately. He remembers the month he had $847 in his bank account and a team of four people depending on him. He remembers the Thanksgiving where he tried to explain equity and runway to relatives who kept asking when he was going to get a “real job.” He remembers lying awake at 3am doing mental math on whether the business would survive another quarter.Your aunt who worked in corporate HR for thirty years? She has no framework for understanding why you’d turn down a $120K offer to keep working on something that might fail. In her world, you take the good job when it’s offered. You don’t gamble with your twenties. The certainty of a steady paycheck isn’t limiting, it’s adulting.And this is where it gets tricky, because they love you. Their concern is real and it comes from a place of genuine care. When your mom asks if you’ve thought about going back to school for an MBA, she’s not trying to crush your dreams. She’s terrified you’re going to wake up at thirty-five with nothing to show for these years. When your dad forwards you job listings, he’s not undermining you. He’s watching his child struggle and trying to help in the only way he knows how.The hardest part is that they might be right. Most businesses fail. Most startups don’t make it. The statistics are brutal and your family members reciting them aren’t wrong. Their risk assessment, from their perspective, is actually sound. What they can’t account for is that you’ve already decided you’d rather bet on yourself and potentially fail than spend decades wondering “what if.”You can’t really explain this to them because the explanation itself sounds naive. “I believe in this” sounds like something someone says before they learn a hard lesson. “I’m willing to sacrifice now for potential massive upside later” sounds like gambling. “I’d rather try and fail than never try” sounds like something you say before you’ve experienced real failure.The person who got rich young understands that sometimes the naive-sounding thing is actually the sophisticated play. They understand that confidence before you have proof isn’t delusion, it’s a requirement. They’ve lived through the part where everyone thought they were crazy and came out the other side vindicated.Your family’s going to worry. They’re going to ask pointed questions at holidays. They’re going to bring up that cousin who “has a great stable job in accounting.” They’re going to suggest you at least do this “on the side” while having something “secure.” And every bit of that is going to feel like they don’t believe in you.But here’s what I wish someone had told me earlier: their not understanding isn’t the same as them not loving you. Their inability to support this specific dream doesn’t mean they don’t support you as a person. They’re doing the best they can with a situation that’s genuinely outside their experience.You don’t need them to understand. You need them to not actively sabotage you, and you need to not let their confusion become your doubt. The person who gets it, who really gets it, is probably someone you haven’t met yet. They’re another founder grinding away, wondering if they’re crazy, dealing with their own family’s concerned questions.Build anyway. The understanding comes later, usually right around the time you don’t need it anymore. And if it doesn’t work out, at least you’ll have learned something they never will: what it feels like to go all-in on yourself.