I Rewrote the Boomer Script — Here's How I Learned, Adapted and Grew as a Millennial Entrepreneur

I'll let you in on a secret that will be unpopular with my fellow millennials: I learned a lot from my Baby Boomer dad.

I watched him — like so many people of my generation watching their Baby Boomer parents — work hard. Sixty, seventy, eighty hours a week working on growing his business.

So when I started my first business, I followed the script that many Baby Boomers follow — life as a three-act play. The first act is developing who you are and figuring out what you want to do. The second act: build a successful business. The third act: living a life of significance with aspirations outside of your business.

But I'm still a millennial. So, when I sold my first business at a young age, I was hungry for more. I regretted selling my business almost immediately, and months turned into a year as I searched for my next stage in life. I had broken the script and was in search of personal purpose. My phone had stopped ringing, my name wasn't on the side of a truck anymore and I had no one to work with.

That's when my dad gave me a piece of advice that would get me back in line with my fellow millennials — a generation of entrepreneurs who are more likely to start or buy businesses than exit from them over and over throughout their lives.

"Don't fall in love with your business," he told me. "Fall in love with business."

RELATED: The Millennial Takeover: How the Generation is Shaking up the Workplace

What millennial entrepreneurs value

Millennials have big plans for their lives, but those plans are unlikely to follow a straight trajectory. We value meaningful work, and that meaning will change throughout our lives. Our first act was defined by the dawn of the new millennium and significant technological evolution. We adapt. It's also why we've earned the reputation of having many jobs over our lifetime — in 2024, according to Gallup, 21% of Millennials changed jobs.

We're ambitious. Exit Planning Institute — where I serve as President — conducted a nationwide survey of business owners in 2023, the National State of Owner Readiness Report. No generation among the surveyed owners had a higher percentage of companies with annual revenue over $100 million: 20%.

The survey also showed that Millennial owners were more likely to regularly measure and formally track business value, with 65% of Millennial owners doing so compared to 47% of Generation X owners and 33% of Baby Boomer owners.

Millennials also tend to earn to spend. According to a report from Boston Consulting Group, of consumers with an annual household income of over $250,000, Millennials were the most likely generation to spend on luxury goods. Growing the value of their company is also important to Millennials, not just to harvest the wealth for themselves but to complete what we call a "boomerang exit," purchasing or investing in another company after the sale of their existing business. Eighty-five percent of Millennials plan to buy or invest in another company post-exit, significantly higher than other generations, including their Gen Z counterparts.

So, lots of big dreams, ambition and a preference for personal spending. That's our Millennial generation. Where should we focus our attention when it comes to exit planning?

RELATED: How to Succeed as a Millennial Entrepreneur

Here's the good news: no generation focuses more on exit planning education than Millennials. The 2023 National State of Owner Readiness Report showed our generation is most likely to believe that having a transition strategy is important for the future. Moreover, we are best at giving attention to an exit and are more likely to be familiar with all of our exit options — and, as a result, seeking outside advice at a higher rate. We like feedback, and we're more likely to have a formal transition advisory team and an outside board of advisors.

What we're not often good at — because we struggle to hone in on one thing — is trusting a framework for driving value in our business.

Here's where a Certified Exit Planning Advisor (CEPA) can help. The Value Acceleration Methodology that every CEPA uses calls for a three-year strategy, followed by a one-year plan, which is actioned through 90-day sprints to achieve that plan.

Driving value is a process, and by implementing this three-tiered approach, you can be ready for that boomerang exit — and build a significant company that will be attractive to a potential buyer.

Good exit planning seeks to balance what the Exit Planning Institute calls the "Three Legs of the Stool." Business planning isn't enough: it must be done in harmony with personal planning and personal financial planning. Millennials typically have personal planning down in spades: we know all the ambitious dreams we want to accomplish.

However, since we earn to spend, we need to focus more on personal financial planning, as it aligns with our business and personal goals.

Our 2023 National State of Owner Readiness Report asked business owners to identify their most trusted advisor. Of the three most active business-owning generations — Millennials, Gen X and Baby Boomers — the wealth or financial advisor ranked lowest among Millennials. 40% of Millennials named their personal financial advisor as their most trusted advisor, lagging behind Gen X (50%) and Baby Boomers (52%).

Don't think of your financial advisor as your retirement advisor. Since Millennials are likely to boomerang exit, having a diversified portfolio will help you navigate your business exit and re-entry nimbly, while still meeting your current personal financial goals.

RELATED: 7 Interesting Financial Facts About Millennials

Focal Point 3: Decentralize

As a generation, we're less likely to want the 60-80 hour work week that Baby Boomer entrepreneurs prized. We want more work/life balance because we've seen our parents regret not having it.

Even when our generation is less likely to hold on to a business for a long time — 48% of Millennial owners plan to transition within the next five years, more than Gen X (39%) and less than Baby Boomers (58%) reaching a traditional retirement age — it's important to achieve your personal goals alongside your business goals.

Focusing on driving value in your people, your systems, your customers and your culture can help your business hum along as you spend more time focusing on the things that matter to you outside of your business.

Related: Why Nearly 3 in 4 Young Workers Are Ready to Quit

Lean into what makes you great

Generational differences aren't about deficiencies — they're about what defines us. Knowing your strengths just as much as you know your weaknesses can help you identify your goals as you work to get help on the things that you are not generationally predisposed to care about.

Finding a diverse team of advisors can help you achieve your goals and live the life — both at work and at home — that you want. Ideally, that team should be led by a Certified Exit Planning Advisor, someone who can assess your business, personal and financial goals and lead a team of advisors to set you up for success and significance.