My parents were Polish immigrants who built millions in real estate. Then they lost it all.
The world doesn't end with a scream or a bang. It ends with a whisper. And I barely noticed because I was too busy being a selfish kid to fight for it, help with it, or even acknowledge it was happening. I was there for the whole thing. I just wasn't really there.
This isn't a story about real estate strategy gone wrong. It's about what happens when capable, hardworking people refuse to let go. When "I'll do it myself" becomes a prison. When holding on costs more than walking away ever could.
If you've ever watched someone you love burn out trying to do everything themselves—or if you're the one burning out right now—this is for you.
The Dream They Chased
My father came to America first. That's how it worked for a lot of immigrant families—one person goes ahead, establishes a foothold, then brings everyone else over.
When I was five, my mother and I joined him in Chicago. We landed in the Polish neighborhoods, surrounded by language and food that felt like home. The American Dream was simple: work hard, build something, leave your children better off than you were.
My parents chose real estate. The classic immigrant playbook.
Buy a property. Fix it up. Rent it out or flip it. Use the equity to buy another. Repeat for decades. Let compound growth do the heavy lifting while you sleep.
It worked. Really well. They moved us from the Polish areas of Chicago to Morton Grove, then Glenview, finally Evanston. Each move was a step up. Each step came from another deal closing, another property appreciating, another rent check depositing.
At their peak, my parents controlled millions in rental property assets. For immigrants who arrived with nothing, this was everything they'd dreamed of.
Then they filed for bankruptcy and lost it all.
How They Built It
Understanding how my parents built their portfolio is essential to understanding why it collapsed. The same qualities that made them successful became the vulnerabilities that destroyed them.
My mother was a real estate agent, so she found the properties, negotiated the deals, handled the books. My father was the muscle—he fixed everything up pretty much himself, handled the worst of the tenants, did all the cleanup and property maintenance week by week across every property they owned. Together, they showed up personally for every crisis.
They didn't hire contractors unless absolutely necessary. Why pay someone $80 an hour when my father could do the work himself?
They didn't bring in a property manager. Why give up 10% of rent when my mother could handle tenant issues?
They didn't outsource anything they could possibly do themselves. Every dollar saved was a dollar reinvested.
This was the immigrant work ethic distilled: if you want something done right, do it yourself. If you want to save money, do it yourself. If you want to make sure it actually happens, do it yourself.
For a long time, this approach worked brilliantly. My parents were smart, capable, and relentless. They could handle anything. They could work longer hours than any contractor they'd hire. They could care more about their properties than any property manager ever would.
But "can do" and "should do" are different questions. And they never learned to ask the second one.
The Part I Don't Like Admitting
Here's where I need to be honest about something uncomfortable: I was not the best kid during this time.
My parents were working constantly. Building a real estate empire while raising a child and navigating life as immigrants—that takes everything you've got. Weekends meant property visits. Evenings meant paperwork. Vacations meant traveling to check on out-of-state investments.
And while they were grinding, I was in my own world.
Gaming was my escape, my identity, my life. I didn't have many friends growing up, so I spent most of my time in front of a screen. World of Warcraft. StarCraft. Final Fantasy Online. Quake. Doom. Hours and hours while my parents dealt with tenants and broken pipes and bank negotiations.
Did I help with the properties? Sometimes, when forced. Did I understand what they were sacrificing? Not really. Did I make their lives easier during the hardest years of building something? Absolutely not.
This wasn't a phase I grew out of. It started when I was a kid and stretched through my teens and into young adulthood. Solitary by nature, lost in digital worlds, disconnected from the struggle happening around me. Years of being somewhere else while they carried everything.
The weight my parents were carrying—financial stress, the pressure of proving themselves in a new country, trying to build generational wealth while their son was checked out—I didn't see it then.
I see it clearly now.
There's no rewriting history. I can't go back and be more present, more helpful, more aware. What I can do is be honest about it. And carry the lessons forward.
When the Cracks Appeared
Real estate wealth is largely a leverage game. You borrow against what you have to buy more. The more properties you control, the more wealth you build. Appreciation, rental income, tax advantages—it all compounds.
Until the music stops.
I was too young and too disengaged to understand the exact mechanics of what went wrong. I don't know the specific trigger—whether it was the market timing, a few bad tenant situations that cascaded, overleveraged positions that couldn't survive a downturn, or some combination of everything.
What I do know is the feeling in the house changed.
Conversations got quieter. My parents looked tired in a different way—not the satisfied exhaustion of a hard day's work, but the hollow fatigue of worry that doesn't stop when you close your eyes.
The phone calls came more frequently. Banks. Lawyers. Names I didn't recognize. My father spent hours in the home office with the door closed. My mother wasn't sleeping.
Properties that were supposed to be building wealth were now bleeding money. Tenants weren't paying. Repairs were piling up faster than income could cover. The debt that had fueled the growth was now crushing them.
And they were still trying to do everything themselves.
There was no property manager to handle the crisis tenants. No team to help with the endless repairs. No advisor they trusted enough to guide them through the options. Just two people, grinding harder and harder on a machine that was breaking down.
When you build something where you're the only mechanics, you have no backup when you need it most.
The Two Lessons That Changed How I Work
Watching my parents build something incredible and lose it all left marks. Some of those marks are scars. Some are wisdom. Most are both.
Two lessons emerged from the wreckage that I carry with me every day:
Lesson 1: You Can't Do It All Yourself
My parents' greatest strength—their willingness to work harder than anyone, to handle every detail personally, to never rely on others—became their greatest vulnerability.
When you do everything yourself:
- You become the bottleneck. Every decision, every task, every crisis flows through you. Your capacity becomes the ceiling of your entire operation.
- You become the single point of failure. If you get sick, everything stops. If you burn out, everything crumbles. If the workload exceeds what you can physically handle, there's no backup.
- You never build institutional knowledge. The systems, relationships, and processes exist only in your head. Nothing survives beyond you.
- You trade short-term savings for long-term fragility. Yes, you save money by not hiring. But you're building on sand.
My parents never built a system. They built a machine that required them to personally crank every gear, every day, with no breaks and no redundancy.
That's not a business. That's a trap you build for yourself.
Lesson 2: Sometimes You Have to Let Go
I think about the years my parents spent holding on. Fighting. Trying to save properties that were underwater. Negotiating with banks. Refinancing. Restructuring. Refusing to admit that the game was over.
I don't know if there was a moment when they could have cut their losses and walked away with something intact. Maybe there was. Maybe if they'd let go of some properties earlier—accepted smaller losses, sold what they could, preserved capital for what mattered—they could have survived.
But letting go felt like failure. And my parents didn't believe in failure. They believed in working harder.
That's the trap.
When your identity is "the person who works harder than everyone else," you can't see when working harder is the wrong answer. You can't see when the smart move is to stop, cut, walk away.
Holding on isn't always brave. Sometimes it's just expensive. The sunk cost fallacy doesn't care how hard you worked to get here. The money and time you've already spent are gone regardless. The only question that matters is: what's the right move from here?
The Psychology of "I'll Do It Myself"
Why do capable people insist on doing everything themselves, even when it's clearly unsustainable?
After years of reflection—and catching myself falling into the same patterns—I've identified several psychological drivers:
The Control Illusion
Doing it yourself creates an illusion of control. If I handle everything personally, nothing can go wrong that isn't my fault. I won't be let down by employees, contractors, or partners.
The problem: this "control" is actually fragility disguised as strength. You're not in control—you're trapped.
The Competence Curse
Highly capable people are often the worst at delegating. They genuinely can do most tasks better than the average hire. So why would they pay someone to do a worse job?
The problem: even if you do each task 20% better, you can only do a fraction of the total tasks. Ten people doing work at 80% of your quality still produces 8x more output than you doing everything at 100%.
The Identity Trap
For immigrants, entrepreneurs, and self-made people, work ethic often becomes identity. "I'm the person who works harder than everyone else" isn't just a description—it's who you are.
The problem: when working harder becomes your identity, you can't see when working harder is the wrong solution. You'll grind yourself into the ground before admitting that more effort isn't the answer.
The False Economy
Saving money by not hiring feels like prudent management. Every dollar not spent on contractors or staff is a dollar you keep.
The problem: you're not accounting for the true cost—your time, your health, your bandwidth for strategic thinking. The "savings" from doing it yourself often cost far more than hiring help.
Framework: When to Delegate vs. Do It Yourself
Learning from my parents' experience, I've developed a simple framework for delegation decisions:
The Delegation Decision Matrix
Ask these four questions about any recurring task:
1. Is this task critical to your core value proposition?
- If YES → Consider keeping it close
- If NO → Strong delegation candidate
2. Does this task require your unique expertise or authority?
- If YES → Keep it, but document everything
- If NO → Delegate
3. Would doing this task yourself prevent you from higher-value activities?
- If YES → Delegate immediately
- If NO → Evaluate based on other factors
4. Is this task time-sensitive in a way that only you can address?
- If YES → Handle it, but build systems to prevent recurrence
- If NO → Delegate
The 70% Rule
If someone else can do the task at 70% of your quality level, delegate it. The 30% quality gap is almost always worth the bandwidth you reclaim.
Exception: tasks where quality is make-or-break (legal documents, critical client relationships, core product decisions). But these should be a small percentage of your total work.
Building Redundancy
For any critical function, ask: "What happens if I'm unavailable for a month?"
If the answer is "everything stops," you have a vulnerability, not a strength. Start building backup systems immediately:
- Document processes others can follow
- Cross-train team members on critical tasks
- Create relationships with contractors who can step in
- Build systems that don't require you to function
Framework: When to Hold On vs. Let Go
The other lesson from my parents' crash was knowing when to cut losses. Here's how I approach this now:
The Hold vs. Fold Checklist
Ask yourself these questions honestly:
1. If you were starting fresh today, would you make this same decision?
If you wouldn't buy this property/start this project/hire this person today with what you know now, why are you holding on? Sunk costs aren't a reason.
2. What's the realistic best-case scenario from here?
Not the hopeful fantasy. The realistic, evidence-based best case. Is it worth the continued investment to achieve it?
3. What are you sacrificing by holding on?
Every resource spent on a losing position is a resource not spent on winning ones. What opportunities are you missing because you're tied up in something that's not working?
4. Are you holding on for strategic reasons or emotional ones?
Pride, fear of admitting failure, unwillingness to accept losses—these are emotional reasons, not strategic ones. They're valid feelings, but they're bad advisors.
5. What would a trusted mentor tell you to do?
Sometimes we need external perspective to see what's obvious. If every advisor would tell you to cut your losses, that's meaningful information.
The Pre-Commitment Strategy
The hardest time to make rational decisions about cutting losses is when you're emotionally invested. That's why pre-commitment matters.
Before starting any significant project or investment, establish:
- Clear success criteria. What does "working" look like?
- Time-bound checkpoints. When will you evaluate progress?
- Kill criteria. What conditions would make you walk away?
Write these down before you're emotionally invested. Then honor them when the time comes.
How This Shows Up in My Business Now
I run a company with my wife. She's the CEO (51% owner), I'm the CTO. We've been building Chykalophia together since 2011.
I'd be lying if I said I don't see the parallels to my parents' situation.
We're a husband-and-wife team. We know every part of the business intimately. The temptation to do everything ourselves is constant. Why would we pay someone else to do something we can handle?
But I remember what happened when two people tried to run an entire real estate empire by themselves. I remember the burnout, the isolation, the fragility. I remember the machine breaking down because there was no redundancy.
So we fight against those patterns:
We hire help even when it's uncomfortable. The short-term cost of paying someone else is almost always worth the long-term benefit of not burning out.
We delegate even when it feels inefficient. Yes, we could do it faster ourselves. But doing it ourselves doesn't scale.
We build systems so the business doesn't depend entirely on us. We document processes. We cross-train. We create redundancy wherever we can.
We use EOS (Entrepreneurial Operating System) to clarify who owns what. Ambiguity about roles caused huge problems early in our business—similar to the role confusion that made my parents' division of labor unsustainable.
And when something isn't working, we try to ask the hard question: Is holding on the right move, or should we let this go?
I don't always get it right. But at least I'm asking.
For Those Who've Experienced Family Financial Trauma
Maybe your parents went through something similar. Maybe you watched a family business implode, a parent lose a job, or decades of savings disappear. Maybe your family never talked about it directly, but you absorbed the anxiety, the fear, the lessons that weren't explicitly taught.
Family financial trauma is strange. It's not your failure, but you carry it anyway. You learned lessons you didn't ask to learn. You developed fears that might not make sense to people who didn't see what you saw.
Here's what I'd say to you, if it helps:
The Lessons Are Real
Being cautious about leverage isn't paranoia—it's wisdom you earned the hard way. Being aware of burnout and single points of failure isn't anxiety—it's pattern recognition.
The experiences that shaped your parents' downfall gave you knowledge that people who never experienced financial trauma don't have. That knowledge is valuable. Use it.
The Fears May Need Calibration
At the same time, trauma can overcorrect. Fear of leverage can prevent you from taking necessary risks. Fear of delegation can trap you in the same patterns that hurt your parents.
The goal isn't to ignore what you learned. It's to calibrate—to distinguish between the genuinely useful warnings and the reflexive fears that might hold you back.
You Were a Kid
If you were young and checked out while your parents were struggling, like I was, that doesn't make you a bad person. It makes you a kid.
Children don't have the context to understand adult financial stress. They don't have the capacity to meaningfully help. Being selfish as a kid while your parents were drowning in work is normal, even if it doesn't feel great in retrospect.
What matters is what you do with that awareness now. How you show up for family now. What lessons you carry forward.
It's Worth Processing
If you've never really processed your family's financial trauma—if you've just carried it silently, letting it shape your behaviors without examining it—consider doing the work.
Therapy, journaling, honest conversations with family members who were there. Understanding where your financial fears and behaviors come from helps you keep what's useful and release what's holding you back.
The Questions I'm Still Figuring Out
I don't have this all figured out. Some questions still haunt me:
Could anything have saved my parents' business? Would hiring a property manager in year five have changed everything? Would selling half the portfolio in 2007 have been brilliant foresight? I'll never know.
How much did my absence matter? Would a more present, more helpful son have made a meaningful difference? Probably not financially. But maybe in other ways I can't measure.
Am I overcorrecting? Are my fears about leverage and doing-it-myself actually useful wisdom, or am I letting old trauma limit what I'm willing to build?
What do I owe them? Not money—they never asked for that. But something. Presence. Attention. Making sure the lessons they taught me (intentionally and otherwise) weren't wasted.
These aren't questions with clean answers. They're the kind you carry, turning them over occasionally, learning something new each time you examine them.
What I'd Tell Someone Building Right Now
If you're in the middle of building something—a business, a career, a portfolio—here's what I'd say based on everything I watched and everything I've learned since:
Build systems, not heroics. My parents were heroes. They worked harder than anyone I've ever known. But heroics don't scale. Systems do. Ask yourself: does what you're building work if you take a month off? If the answer is no, that's a vulnerability you need to address.
Delegate before you have to. Don't wait until you're drowning to hire help. Build the muscle of delegation early, when the stakes are lower and you have time to train people properly.
Set kill criteria in advance. Before you're emotionally invested, decide what conditions would make you walk away. Then honor those commitments when the time comes.
Your work ethic is a tool, not your identity. Being able to work harder than anyone is valuable. But it's a tool in your toolkit, not the definition of who you are. Sometimes the right answer is working smarter, delegating more, or walking away entirely.
Learn from others' crashes. You don't have to experience your own bankruptcy to learn the lessons. That's what stories like this are for.
Conclusion
My parents built something incredible. Immigrants from Poland who arrived with nothing, who turned hard work and smart decisions into millions in assets. For a while, they lived the dream.
Then they lost it all. The very qualities that made them successful—the refusal to delegate, the identity tied to working harder than anyone, the inability to let go—became the vulnerabilities that destroyed them.
I watched the whole thing. And I've spent years trying to learn from it.
You can't do it all yourself. Not sustainably. Not at scale. Not without building fragility into the foundation of everything you create.
And sometimes, the bravest thing isn't holding on. It's letting go.
If this resonated with you, the shorter version is on my Substack, where I write about entrepreneurship, leadership, and figuring it out as you go.
Have you watched someone close to you build something and lose it? Did it change how you approach risk, work, or money? I'd like to hear about it—reply here or reach out directly.