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Post: OK Boomer, It’s Time to Build Your Legacy

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Why focusing solely on your retirement portfolio isn’t enough—Discover how to create a lasting impact that truly defines your legacy.

You’ve spent decades building a career. You’ve climbed the ladder. You’ve earned the title, the corner office, the retirement portfolio. But lately, something feels off.

mature maleIt could be the way colleagues look past you in meetings. Maybe it’s the subtle comments about “fresh perspectives” and “digital natives.” It may be watching your expertise get overlooked while someone half your age gets promoted.

Or maybe you’ve realized that the job you gave everything to could disappear tomorrow—and all you’d have to show for it is a severance check and a LinkedIn profile nobody’s looking at.

Here’s what nobody tells you about working past 50: the system isn’t built for you anymore. But that doesn’t mean your best years are behind you. In fact, they might be just beginning.

The Numbers Don’t Lie—And They’re Not Pretty

Every single day, 11,200 Americans turn 65. That’s according to the Alliance for Lifetime Income, and this pace will continue through 2027. We’re in the middle of the most significant retirement wave in American history.

But here’s the painful truth about staying in the workforce: AARP’s 2024 research found that 64% of workers age 50 and older have seen or experienced age discrimination in their workplace. Nearly a quarter—22%—feel like they’re being pushed out of their job because of their age.

And it gets worse when you try to find something new. According to the same AARP research, 74% of older Americans believe their age could be a barrier to getting hired. That’s not paranoia. That’s reality.

The message from corporate America is clear: “OK, Boomer. Thanks for your service. Now step aside.”

What They’re Not Telling You

over 50 in the officeWhile employers quietly show experienced workers the door, they’re missing something important. According to the U.S. Census Bureau, more than half of all U.S. businesses—52.3%—are owned by people 55 and older.

Read that again. The people being pushed out of jobs are the same people building and running America’s businesses.

The Kauffman Foundation reports that nearly one-fourth of new businesses are now started by founders aged 55-64, showing how experience fuels a growing movement of older entrepreneurs.

And here’s what makes this really interesting: research from Gusto found that Baby Boomer entrepreneurs take home an average of $60,000 in their first year of operation. That’s six times more than Gen Z founders earn in year one—experience matters. Your decades in the workforce aren’t a liability—they’re your greatest asset.

Beyond the Portfolio: What Legacy Really Means

You’ve probably been told to focus on your retirement portfolio. Save enough. Invest wisely. Watch the numbers grow. And that’s important—nobody’s saying it isn’t.

But a portfolio is just money. It doesn’t get up in the morning with a purpose. It doesn’t create jobs for others. It doesn’t build something that outlasts you.

A legacy is about waking up excited to work on something meaningful, using your experience to create value beyond just your bank account—impacting family, community, and employees.

Gallup found that 83% of baby boomer entrepreneurs started their businesses for lifestyle choices or to increase income. But dig deeper, and you see something more profound. These aren’t people chasing money. They’re people reclaiming their independence, pursuing their passions, and building something they can be proud of.

Career Ownership: A Different Path

mature executiveFor over 40 years, we’ve helped professionals at exactly this crossroads. People who’ve given decades to their careers and suddenly wonder: “Is this all there is? Is my future really just waiting to be pushed out or phased out?”

Career Ownership is about reclaiming control-building something where your experience is valued and your age becomes an advantage, empowering you to shape your future.

This isn’t about retiring early or giving up. It’s about channeling everything you’ve learned into something productive. Something that generates income. Something that creates jobs. Something that becomes your legacy.

A Career Ownership Coach® offers guidance and support, helping you navigate this transition with confidence and clarity, so you feel supported every step of the way.

Making this transition alone can feel overwhelming. What business model is right for you? How do you leverage your experience? What opportunities actually exist?

A Career Ownership Coach® doesn’t sell you anything or push you toward any particular path. Instead, through Career Ownership Coaching™, you’ll explore questions that matter: What does your ideal day look like? What income do you really need? What skills have you developed that could translate into something you own? What would make you excited to start each day?

female over 50Many people we work with discover options they never knew existed. Business models that fit their lifestyle. Ways to leverage their expertise without starting from scratch. Paths to building something meaningful without betting everything on an unproven idea.

The clarity that comes from this process is powerful. Instead of feeling stuck between a job that doesn’t want you and a retirement that doesn’t excite you, you see a third path—one where you’re in control.

Your Next Chapter Starts Now

The “OK, Boomer” generation isn’t fading away. They’re pivoting. They’re building. They’re creating legacies that will outlast any corporate job ever could.

You have two choices. You can wait for someone to decide your future—hoping the next round of layoffs doesn’t include your name, hoping age discrimination doesn’t catch up with you, hoping your retirement portfolio is enough to last.

Or you can take control. You can explore what Career Ownership looks like for you. You can turn decades of experience into something productive, profitable, and lasting.

A legacy isn’t just what you leave behind in your bank account. It’s what you build while you’re still here. It’s the business you create. The people you employ. The impact you make.

A Career Ownership Coach® can help you discover what that looks like for you. No pressure. No sales pitch. Just an honest conversation about possibilities.

Because you’re not done yet. Not even close.


Your Career Revolution book coverAbout Your Career Revolution

Our mission is to help individuals explore self-sufficiency as an alternative career.

We help them define their Income, Lifestyle, Wealth, and Equity goals and provide education on the best ways to achieve them. We don’t sell franchises – we help people achieve their dreams of self-sufficiency through business ownership. The approach is different, the experience is different. And it works.

Order on AMAZON

Learn More About Career Ownership Coaching™

If you are considering a career change, invest in yourself to discover your options, possibilities, and dreams. Chat with one of our coaches to begin your career revolution. To learn more about Career Ownership Coaching™, visit www.entrepreneursource.com or check out our guidebook, “Your Career Revolution: Reimagine and Reclaim the Life of Your Dreams.”

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The post OK Boomer, It’s Time to Build Your Legacy first appeared on The Entrepreneur’s Source.

Lora Helmin

Lora Helmin

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