During a recent podcast recording, we interviewed a guest who shared a personal realization that resonated deeply with me.
After several years of climbing the corporate ladder and achieving professional success, she discovered this path wouldn't deliver the financial freedom she truly desired, despite following all the “standard” career growth and financial planning advice.
Her insight reminded me of something a mentor of mine often says:
“One of the worst things that could happen is that you spend most of your life climbing a ladder, only to get to the top of it and realize that it was up against the wrong building the whole time.”
The first time I heard that, it hit me like a ton of bricks.
And as I've gotten older, I've seen this pattern play out more than once: smart, capable professionals dedicate decades to scaling corporate hierarchies, believing financial freedom awaits at the top. But when they finally reach those upper levels, they discover they've been climbing toward the wrong destination all along.
So today I want to ask you a simple but profound question: Is the ladder you're climbing actually leaning against the building you want to reach?
Two Buildings, Two Ladders
To be clear: I'm not suggesting corporate careers are worthless. Far from it.
The “corporate ladder” provides immediate income, builds valuable skills, and creates a level of stability while you build wealth elsewhere.
But here's the uncomfortable truth: even the highest-paying careers rarely create true financial freedom.
Outside the tippy-top of the 1% of the 1%, working a job (even a prestigious, high-paying one) has fundamental limitations:
Income is linear and directly tied to hours worked
Your wealth-building potential is capped by your time
Earnings are taxed at the highest rates with few sheltering options
Your financial security ultimately depends on someone else's decisions
When combined with traditional financial/retirement advice (max out your 401(k), buy index funds, work until 65+, etc.), you often end up with what I call the “vanishing nest egg” problem:
The entire traditional retirement model is built on accumulating assets that you then systematically deplete.
Is it any wonder that nearly half of retirees say their top fear is outliving their money? Anxiety is the natural response to watching your account balance shrink month after month.
Building Your Second Ladder
The solution isn't necessarily jumping off your career ladder. (Although it might be for some, like it was for me.)
Instead, most people are better suited building a second ladder against a different building.
This second ladder has fundamentally different characteristics:
It's built with assets that generate passive cash flow
The income comes with significant tax advantages
It leverages other people's time and expertise
Growth can be exponential rather than linear
And the real beauty of this approach? Your career success accelerates the building of your second ladder. The higher you climb professionally, the more capital you can allocate toward building lasting wealth.
But it works the other way too: as your second ladder grows taller, it creates options in your professional life.
When you have passive income covering part or all of your living expenses, you can take bolder risks in your career, say “no” to toxic environments, and negotiate pay increases or promotions from a position of strength.
The compounding effect between these two ladders is where the magic happens. Success on one ladder fuels progress on the other, creating a virtuous cycle of growing wealth and expanding freedom.
Where Do You Start?
The first step is simple but crucial: assess if the ladder you're climbing leads where you want to go.
If you're following traditional financial advice without questioning it, pause and ask yourself if the outcome this path creates actually matches your vision of financial freedom.
And if it doesn’t, it’s time for a change.
For most high-earners, the answer isn't abandoning your career to start a business or become a full-time real estate investor.
Instead, consider how you can leverage your current career success to build passive investments alongside it. This might mean investing in real estate syndications, where others handle the day-to-day management of a property while you focus on your career.
The goal isn't to choose between career success and financial freedom – it's to use the former as a powerful tool to build the latter.
So I'll leave you with this question: When was the last time you stopped to consider whether your ladder is leaning against the right building?
The sooner you start building that second ladder, the faster you'll create options for yourself.