If you achieved your ultimate financial goal tomorrow morning—the number you’ve been chasing—what would you actually DO differently on Tuesday?
It’s a harder question than it sounds.
Most syndicators can give me their financial targets instantly.
-“Ten million net worth.”
-“100 million in assets under management.”
-“5,000 doors.”
But when I ask what they’d actually do differently once they hit that number? The room goes quiet.
That silence reveals something profound: we’re often so focused on chasing the milestone that we never stop to ask why we’re chasing it—or whether it will actually deliver what we want.
The Billionaire’s Bad Advice
A few years ago, I was at a real estate event in Canada where Grant Cardone was speaking. His net worth is said to be over a billion dollars. Private jets, yacht, former model wife—all the symbols of “making it.”
He was asked about work-life balance and having a happy family while still being successful.
Here’s what he told the room full of syndicators: ‘You don’t deserve to be happy until you’ve worked yourself to the bone for years and accumulated massive wealth. Happiness is something you earn through grinding it out.’
I sat there thinking: This guy has everything society says equals success. But listening to him, watching him… I had to ask, is he really happy? Would I trade my life for his?
It seems to me he’s just chasing the next billion because the first one didn’t fill the void.
In Grant’s book called “The Millionaire Booklet” he said: “If you’re going to be unhappy, be as rich as possible.”
That doesn’t sound like someone I want to take life advice from.
What’s the point of having a big pile of money if you’re going to be unhappy? Wouldn’t it make more sense to figure out how to be happy rather than mindlessly accumulating money and hoping you figure out why later?
His advice was essentially: Put your life on hold. Sacrifice everything now for some future payoff. Chase the biggest numbers possible, and happiness will follow.
I fundamentally disagree.
The Perfect Time That Never Comes
Here’s what that billionaire’s philosophy gets wrong: The “perfect time” to start living your ideal life is an illusion that keeps you building someone else’s version of success.
I learned this lesson in the most heartbreaking way through a friend of mine. He spent his entire career accumulating—not just money, but books. Hundreds of them. Maybe thousands. Every interesting title he came across, he’d buy and add to his collection, telling himself, “I’ll read all of these when I retire. That’s when I’ll finally have time.”
He had this beautiful vision of his retirement: sitting in his study, surrounded by his library, finally diving into all that knowledge he’d been saving up.
Then, right around retirement age, he developed macular degeneration.
All those books he’d been saving for the “perfect time”? He can’t read them. The future he’d been deferring his dreams for arrived, but circumstances had changed in ways he never anticipated.
This happens more than we want to admit. Health issues. Family obligations. Market crashes. The “perfect time” we’re waiting for either never comes, or it comes with complications we never saw coming.
The Caribbean Question
When I was around 30, my wife and I made a decision that surprised some people: we packed up and moved to the Caribbean to do volunteer work.
We didn’t have a huge savings account. My business was still young and struggling. By conventional wisdom, it was exactly the wrong time.
But we asked ourselves a different question. Instead of “Can we afford to do this?” we asked, “If we were going to make this happen now, what would have to be true?”
That shift changed everything.
Suddenly, instead of seeing obstacles, we saw engineering problems:
- Who could check our mail and handle important items while we were gone?
- What would we need to rent out our house and cover the mortgage?
- How much money would we actually need to live on each month?
- How could we generate income that wasn’t location-dependent?
None of these were impossible. They were just problems to solve.
We ended up living in the Dominican Republic for six years. It required some creative problem-solving and adjustments, but we figured it out as we went. After returning to the States, we continued applying this same mindset—spending a month exploring Mexico, a month traveling through Europe, two months immersed in Asia.
These experiences weren’t about escaping responsibility. They were about designing a life and business that could accommodate what mattered most to us.
The Golden Handcuffs You’re Building
Here’s what most syndicators don’t realize until it’s too late: every level of “success” you achieve using conventional metrics often means LESS freedom, not more.
That bigger house you’re working toward? It comes with a bigger mortgage, more maintenance, higher property taxes, more rooms to furnish. You become a servant to your square footage.
That growing portfolio of properties? Each one demands attention. More tenants, more maintenance, more problems, more travel to visit them, more complexity in your life.
The luxury car, the country club membership, the lifestyle creep that comes with “success”—they all become obligations. Golden handcuffs that require you to keep grinding just to maintain them.
I’ve watched syndicators hit their number—whatever that magic number was—only to realize they’ve built themselves a beautiful prison. They have everything they thought they wanted, but no time or energy to enjoy it. They can’t stop working because their “success” has created obligations that demand constant feeding.
Meanwhile, I know syndicators with smaller portfolios who designed their business intentionally. They work four days a week. They spend summers at a lake house. They never miss their kids’ games. They have time for creative pursuits.
Who’s really more successful?
In their landmark 2010 study, Daniel Kahneman and Angus Deaton found that emotional well-being (everyday happiness) rises with income up to about $75,000/year, but then levels off—meaning more money beyond that doesn’t buy more joy. I’m sure you’d have to adjust that number for inflation. But the principle remains true.
Study after study confirms it: past a certain point, more money doesn’t make you happier—especially if you’re already unhappy.
If you reach the number goals but fail to reach the bigger-picture goals of doing what you really want with your life, is that really success?
In my opinion, you’ve won the battle but lost the war.
Success isn’t about stacking zeros.
It’s about building a life you don’t feel the need to escape.
The Reframing Question That Changes Everything
Here’s the framework that’s transformed how I think about business and life:
Instead of saying, “I can’t do that until I have X dollars or Y doors,” ask yourself:
“If I were going to do this now, what would have to be true?”
This simple reframe transforms impossibilities into engineering problems.
Want to work a 4-day week? Instead of waiting until you’re “successful enough,” ask: What would have to be true for me to do this now? Maybe you’d need to:
- Build systems that handle routine decisions without you
- Train a team member to handle specific responsibilities
- Set up automated investor communications
- Structure deals that don’t require daily firefighting
Want to spend a month every summer at a lake house with your family? What would have to be true?
- Being able to manage investor relations remotely
- Deals structured with professional property management
- Clear boundaries with partners about availability
- Income streams that don’t require your physical presence
Want to pursue photography, music, writing, or whatever lights you up? What would have to be true?
- Passive income that covers your basic expenses
- Specific time blocks protected for creative work
- A business model that creates space, not just money
- The courage to value fulfillment over vanity metrics
Notice how none of these require you to be a billionaire first?
From Cage-Building to Life Design
The difference between building a business and building a cage comes down to one thing: intentionality.
When you’re clear on what you actually want your Tuesday morning to look like—not someday, but as soon as possible—you can reverse-engineer your business to deliver it.
This isn’t about lowering your ambitions. It’s about raising them to include things that actually matter: time with people you love, pursuits that energize you, the flexibility to say yes to opportunities that don’t show up on a P&L statement.
Some of the most successful syndicators I know—successful by any real measure (meaning ones who are living the life they want)—aren’t the ones with the most doors. They’re the ones who built their business to fund their life, not consume it.
They asked better questions. They solved for freedom, not just finances. They designed intentionally instead of defaulting to conventional metrics or status symbols.
The Strategic Design Approach
This strategic clarity—knowing what you’re building toward and why—changes everything about how you approach your business.
Instead of just asking “How can I raise more capital?” you ask “How can I raise capital in a way that preserves my freedom?”
Instead of “How can I scale to more doors?” you ask “What size portfolio actually serves my life goals?”
Instead of “How can I grow faster?” you ask “What pace of growth maintains the life I want to live?”
These aren’t limitations—they’re design parameters. Just like an architect doesn’t see the building requirements as restrictions but as guidance for creating something purposeful.
This is the kind of strategic thinking that separates syndicators who build fulfilling businesses from those who build impressive-looking prisons. It’s about being intentional with every decision, ensuring your business serves your life rather than consuming it.
Your Move
I’ll leave you with this challenge:
What have you been waiting for the “perfect time” to do?
And more importantly—what would actually have to be true for you to start moving toward it now?
Don’t wait for permission. Don’t wait for the perfect circumstances. Start asking better questions and engineering the solutions.
Because the “perfect time” you’re waiting for? It’s not coming. But the life you want? That’s something you can start building today.