Sailing Into Retirement, Building Empires, and Finding Financial Peace
When it comes to planning for the future, I’ve always believed in balancing logic with a little inspiration. And this week’s discussions delivered both—from the technical ins and outs of buying a sailboat to the inspiring story of Kathy Ireland’s rise from supermodel to mogul. If you’re thinking about how to make your money work while living a life you love, there’s a lot to take away.
Let’s start with the dreamier side of finance: sailboat ownership. For many people, the idea of retiring on a boat is the ultimate fantasy. But as Ric Edelman and Brandon Corso explained, it’s not just a fantasy—it can be a practical lifestyle if you approach it the right way. We looked at a 70-foot luxury yacht listed for $2.1 million, and while that’s obviously high-end, many families start with entry-level sailboats around $50,000. You don’t need to be a millionaire to get started.
Sailboats, especially compared to motor yachts, have lower operating costs and are often designed for owner-operators—which means you won’t need to hire a crew. Most people start small, build experience, and work their way up to larger boats as their skills and net worth grow. Just remember: boats depreciate like cars, not like homes, so don’t buy thinking of it as an investment. Buy for the lifestyle and freedom it brings.
And speaking of freedom—how about financial freedom? At a recent investment advisor conference, there was unanimous agreement: financial success is still within reach, even in uncertain times. Advisors emphasized patience, realistic expectations, and the importance of staying invested. Markets tend to revert to the mean, and after recent underperformance, the next decade could be strong. A diversified portfolio—with a mix of assets that respond differently to market conditions—is still one of the best tools for long-term growth.
On the topic of financial decisions, a common question came in from Bill in Bowie: Should he switch from a traditional 401(k) to a Roth 401(k)? With a $125,000 family income and $18,000 in annual contributions, our advice was to stick with the traditional 401(k). Bill is in a relatively high tax bracket now, and prepaying taxes in the hope of lower rates later doesn’t make sense in his case. Take the tax break today, and reevaluate if your income drops in the future.
We also had a question from a 62-year-old with a pension, wondering if he should withdraw retirement funds now to invest elsewhere. Ric’s advice? Only if absolutely necessary. Otherwise, keep the funds growing tax-deferred, and make sure the current investment allocation inside the account is appropriate. Too much risk—or too little—can derail the plan.
A quick point that came up: life insurance for children. Unless your child has dependents (which is rare), you likely don’t need it. Focus your resources on saving and investing for their future, not insuring it.
One of the week’s highlights for me was Kathy Ireland’s story. You probably know her as a supermodel from the 1980s and ’90s, but what she’s built since then is incredible. She now runs a $2 billion retail business, and her mission is centered around helping families and busy moms find affordable, high-quality products—from wedding gowns to furniture. What struck me most was her mindset. She never saw modeling as her endgame—it was just a stepping stone. She talked about embracing challenges, listening to customers, and never letting others define your limits. That message applies to all of us.
Ric wrapped the week by reminding us to stay focused on what’s working. Yes, there are challenges in the economy, markets, and life. But there are also amazing breakthroughs in health, technology, and global innovation. Your success, both financially and personally, will come from staying optimistic, working hard, and being strategic.
Whether you’re exploring retirement on a sailboat, investing through uncertain times, or dreaming of your own business empire, the message is clear: Success comes from planning, patience, and positivity.
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