What a 10-Year-Old Playing Life Understands About Retirement (That Most Adults Forget)
Key Takeaways
Multiple income streams beat single-source dependence, which you can achieve through self-directed retirement accounts.
Waiting for ideal market conditions can cost you compound returns.
Consistently deploying capital matters more than finding the one "perfect" investment.
Expert guidance prevents catastrophic mistakes, such as prohibited transaction violations that can destroy your entire retirement account.
Someone mentioned the board game Life to me recently, and it got me thinking. I haven't played that game in decades, but I remember the basic mechanics: land on paycheck spaces, adapt when things don't go your way, keep moving toward retirement, and ask for help when you need it.
After three decades of working with high-net-worth investors, I realized something: kids playing Life instinctively understand wealth-building principles that sophisticated adults often forget when planning their actual retirement. They're not being foolish — they've just lost sight of the basics.
4 Intuitive Wealth-Building Principles from The Game of Life
I’ll tell you firsthand, after three decades of working with high-net-worth individuals, the best retirement strategies often mirror what kids understand playing The Game of Life:
Principle #1: Multiple Income Streams Win the Game
In the Game of Life, kids instinctively try to land on as many paycheck spaces as possible. They don’t put all their hopes on a single career card or one big payday: they want every opportunity they can get.
The Adult Mistake: Single-Source Dependence
Adults planning retirement tend to do the opposite: funneling decades of savings into a single traditional 401(k) or IRA investing in market securities they don’t control. This leaves them with one income source, one asset class, and one hope that the market performs.
The Self-Directed Solution
Self-directed retirement accounts change this equation entirely. Instead of depending solely on stock market performance, you can build multiple streams of retirement income through income-producing assets:
Rental properties generating monthly cash flow
Private lending arrangements producing regular interest payments
Real estate syndications distributing quarterly returns
These aren’t “instead of” traditional investing; they're additions that complement and provide the diversification retirees need.
Principle #2: Bad Spin? Pick a New Path Immediately
When a ten-year-old spins a bad number in Life, they don’t quit the game. Sure, they might feel disappointed or frustrated, but their instinct is to immediately evaluate their options and move forward.
The Adult Mistake: Waiting for the “Right Time”
Adults approach retirement investing with a contrary mindset. They wait for interest rates to drop before buying rental properties or keep retirement funds parked in underperforming accounts because they haven't found the "perfect" alternative investment yet.
As years pass, compound returns that could have been building never materialize. Lost time becomes lost income.
The Reality of Cash Flow Investments
Cash flow investments don't require perfect market timing. A well-structured rental property produces monthly income regardless of when you bought it.
Waiting for ideal conditions almost always means missing out on the time a portfolio needs to build meaningful wealth-building momentum.
I've watched clients wait for the "right time" to start self-directing for years. The right time was yesterday. Every month you delay is another month of potential cash flow you can’t get back.
Principle #3: Reach Retirement Wealthy, Not Perfect on Every Move
The end goal in the Game of Life is to retire with the most money. How you get there, as long as you follow the rules, doesn’t really matter. No one expects perfection at every turn.
The Adult Mistake: Analysis Paralysis
Adults have this bad habit of treating every investment decision as if it will make or break their entire retirement. There’s nothing wrong with wanting to be informed and educated before making a decision. Sometimes, though, gathering information and striving for the “right” choice means making no choice at all.
The Long-Term Portfolio Approach
Building a retirement portfolio through income-producing assets is a decades-long process. No single property, no individual investment, no specific deal will determine your success. What matters is consistently deploying capital into cash-flowing assets that produce returns while you're still working, and income when you're not.
The most successful self-directed IRA investors I work with refine their strategy over time based on real experience, not theoretical perfection.
Principle #4: Ask for Help Without Ego
When a child doesn't understand a rule in Life, they ask immediately. "Mom, what happens if I land here?" They’re not embarrassed to ask, and they don’t pretend to know. They just want the information they need to keep playing the game.
The Adult Mistake: DIY Confidence
By contrast, adults often approach self-directed retirement accounts with DIY confidence. They read a few articles online, watch some YouTube videos, and assume they understand the prohibited transaction rules well enough to do it themselves.
Then they inadvertently create a prohibited transaction, like using their SDIRA-owned rental property for a weekend getaway, paying a repair bill from their personal checking account, or structuring a deal that benefits a disqualified person.
The IRS won’t accept "I didn't know" as an excuse, and these mistakes can cost you your entire retirement account.
Why Expert Guidance Matters
Self-directed retirement accounts offer incredible flexibility and control, but that freedom comes with strict regulatory requirements. You absolutely need an expert to help you structure deals properly, maintain arms-length compliance, and avoid the landmines that can destroy decades of tax-advantaged growth.
At Chicago Trust Administration Services, we've guided thousands of investors through these decisions for over 20 years. We don't give investment advice — that's not our role. We help you evaluate opportunities through a compliance lens so you can build wealth without risking your retirement savings.
The Life Lessons Worth Remembering
Sometimes, kids get the things adults easily forget. Those childhood instincts can be enormously helpful throughout your life and as you plan your retirement.
Self-directed retirement accounts give you the freedom to apply these principles to your actual retirement planning:
Build multiple income streams through real estate, private lending, and other alternative investments.
Start now instead of waiting for perfect market conditions.
Focus on steady accumulation of income-producing assets rather than agonizing over every individual decision.
Work with experienced professionals who help you avoid costly compliance mistakes.
To see how we can help, we invite you to schedule a complimentary meeting with us by calling 312-869-9394 or emailing steve@ctasira.com. Let's work together to create a retirement strategy that captures the wisdom your ten-year-old self already understood.
Frequently Asked Questions (FAQs)
Q: How do I know if self-directed investing is right for my retirement strategy?
A: Self-directed investing works best for entrepreneurial individuals who understand alternative assets, have existing business networks that generate deal flow, and want more control over their retirement investments.
Q: What's the biggest mistake new self-directed IRA investors make?
A: The most common mistake is treating SDIRA-owned assets as personally owned investments. Investors pay repair bills from personal checking accounts, use rental properties for family vacations, or hire their children to manage properties — all prohibited transactions.
*The content and opinions in this material are for general information only and are not intended to provide specific advice or recommendations for any individual.
**CTAS professionals are not financial advisors and cannot provide advice or recommendations regarding specific investment decisions.