When you hear the words “retirement plan,” what comes to mind? If you’re like most people, you probably think of a 401(k), IRA, or some other traditional investment account—a system that has been ingrained in us as the “right” way to prepare for the future. But what if there were better ways to ensure financial freedom, without stashing cash away for decades and hoping for the best?
Long before I became an entrepreneur, I rejected the traditional idea of retirement. The thought of working my entire life only to stow away money in an account that penalizes me for using it early just never sat well with me. Why would I work for decades, saving every penny, only to finally enjoy life when I’m too old to fully live it?
I want my cake and to eat it too—because let’s be real, what’s the point of having cake if all you can do is look at it?
For most of history, people didn’t “retire”—they worked, built wealth, and passed it down. The modern concept of retirement as we know it didn’t come into play until the 19th century, and while it may have been well-intentioned, the system was designed around the idea that people would only live for a few years after retiring.
Fast forward to today: we’re living longer, costs are rising, and there are countless ways to generate cash flow that don’t involve locking money away in a retirement account.
And here’s the kicker—retirement accounts don’t even save people in taxes the way they think they do. But that’s a conversation for another day.
Today, I want to challenge you to think differently about how you create financial freedom and introduce three ways business ownership can cash flow your life—both now and in the future.
Let’s be honest—this is the dream, right? Start a business, grow it, and eventually step out of the day-to-day while still getting paid.
It’s not impossible, but it does require intentional design.
If your goal is to build a business that pays you for life without requiring your daily involvement, you need to prioritize systems, leadership, and scalable revenue models from the start. The businesses that fail to do this often become glorified jobs, where the owner is stuck working more hours than they would at a 9-to-5.
If you love what you do and want to be involved forever, that’s fine. But if you want financial freedom, you need to build with the exit in mind. This is why we build sellable businesses here at Progress to Profits, because a sellable business is a scalable business.
Starting a business from scratch isn’t the only way to generate wealth. In fact, one of the fastest ways to shortcut the system is to buy a business that’s already successful.
We’re currently in what’s called the “Silver Tsunami”—a wave of baby boomers who are retiring and looking to sell their businesses. Many of these businesses are profitable, established, and prime for acquisition.
Think of buying a business like buying rental property:
You need to do your due diligence—this means analyzing financials, evaluating the customer base, and looking under the hood to make sure you’re not inheriting hidden problems.
A well-chosen business can immediately provide cash flow, without you having to build from the ground up.
With the right guidance, you can optimize the business and increase its value while still earning from it.
Owning a business isn’t just about making money today—it’s about building a long-term asset that pays you well beyond your working years.
Most people are familiar with the stock market. You’ve probably heard financial advisors talk about investing in the S&P 500, which has historically averaged around 9% annual returns over time.
Sounds decent, right? But there are two things they don’t always tell you:
Management fees and hidden investment costs can often reduce those returns to around 7%.
Private equity (investing in privately held businesses) has significantly outperformed the stock market over time.
Consider this:
Over the 36-year period ending in 2022, private equity had an average annual return of 14.28%—far higher than the stock market.
According to Tony Robbins in The Holy Grail of Investing, if you invested $1 million in the S&P 500 in 1986, it would have grown to $26.3 million by 2022.
But if you had invested that same $1 million in private equity instead? It would have grown to a staggering $139.6 million.
That’s a $113 million difference.
Investing in private businesses—either by acquiring them outright or investing in businesses you believe in—can generate wealth far beyond what traditional retirement accounts offer.
The idea of stashing money away for decades and hoping it’s enough is outdated. Your business (or businesses) can be your greatest financial asset—one that funds your life today and sets you up for the future.
Instead of waiting for retirement to enjoy life, ask yourself:
✅ How can I build a business that generates wealth without needing me daily?
✅ Is there an opportunity to buy a business instead of starting from scratch?
✅ Could I invest in private businesses to grow wealth faster than traditional investing?
The key to financial freedom isn’t working harder or saving more—it’s learning how to make money work for you.
And that starts with rethinking retirement.