I can definitely relate to that cautious mindset, but honestly, I've seen people get burned on both ends. A friend of mine jumped into a startup job he was passionate about with barely any cushion because he figured the opportunity was too good to pass up. It worked out great for him, but I've also known others who took similar leaps and ended up scrambling when things didn't pan out.
You're right though—there's definitely a sweet spot between caution and action. When I bought my first house, I obsessed over every detail (seriously, spreadsheets on spreadsheets...). But looking back, some of those scenarios I worried about never even came close to happening. Maybe if I'd relaxed a bit, I could've jumped in sooner and saved myself some stress (and money).
Still, I think it's less about having the "perfect" financial setup and more about knowing yourself. If you're someone who can pivot quickly when things go sideways, you might not need as big of a safety net. But if uncertainty stresses you out...well, maybe that cushion is worth the wait.
I get what you're saying about knowing yourself—it's huge. When I left my stable banking job to become a mortgage broker, I definitely had some sleepless nights. Thought I'd prepared enough, but the first few months were rougher than expected. Still, once things clicked, it was totally worth it. Bottom line, there's never a perfect time...but having at least some cushion helps you sleep better at night.
I'm right there with you on the cushion thing...when I bought my first house, I thought I'd planned for everything, but unexpected costs kept popping up. Makes me wonder—can you ever really be fully prepared, or is it always a leap of faith?
Honestly, I don't think you can ever be 100% prepared for big life changes—whether it's buying a house or switching careers. I've seen plenty of people crunch numbers and plan meticulously, only to have something unexpected pop up (like your cushion example). But that doesn't mean you should just jump blindly either. Maybe the key is finding a balance between preparation and flexibility?
When clients ask me about making big financial moves, I usually suggest they build in some wiggle room—like an emergency fund or backup plan—because life has a funny way of throwing curveballs. Have you thought about setting aside a specific amount or timeframe to test out your dream job idea without fully committing? That way, you're not completely diving into the unknown...just dipping your toes in first.
I get the idea of dipping your toes in first, but honestly, sometimes that cautious approach can hold people back. When I bought my house, I spent months analyzing every detail—interest rates, neighborhoods, market trends—and still ended up with surprises. At some point, you have to accept that uncertainty is part of the deal. Sure, have a safety net, but don't underestimate the value of fully committing. Sometimes the only way to truly know if something works is to dive in and adapt as you go.
