My husband and I have spent decades building. We’ve scaled businesses, invested in others, diversified portfolios, navigated boardrooms, and navigated the high-stakes world of teenage sports schedules and boarding school and college drop-offs. We are experts at the “long game” when it involves a P&L statement or a five-year market projection. But recently I pondered the thought, When was the last time I applied that same rigorous, visionary strategy to the woman staring back at me in the mirror?

I recently hit a milestone birthday, and it forced a bit of an internal audit. It’s funny; we spend the first half of our lives sprinting toward a finish line that someone else drew for us. We want the successful exit, the respected reputation, and the well-adjusted kids. And then, suddenly, you find yourself in a quieter house with one son navigating through the gauntlet of young adulthood and another closing in on his high school years.

You look around and realize: The “someday” I was working for is actually right now.

But if you don’t have a plan for “right now,” you’ll end up default-living. You’ll keep saying “yes” to boards you’re bored with, “yes” to social commitments that drain your battery, and “yes” to a lifestyle that feels more like a polished cage than a playground. It is time to stop being the Chief Operating Officer of everyone else’s needs and become the CEO of your own life.

Deep soul-searching isn’t just for 20-somethings on a gap year in Bali. In fact, it’s arguably more critical for us. We have the resources, the wisdom, and the “been there, done that” scars to actually execute a 20-year vision that matters. This isn’t about what you want to do; it’s about who you want to be when the hustle loses its hum.

If you don’t decide what the next two decades look like, I promise you the world (and more accurately in many cases, social media) will decide for you. Your inbox will fill up with other people’s priorities, and your calendar will become a graveyard for your own interests.

So, let’s get intentional. Just as you wouldn’t acquire a company without due diligence, don’t walk into your next decade without a roadmap. Are you going to be the person who finally masters that second language and spends a year living in Bourgogne as a Francophile? The one who spends three months a year traveling with her husband because the businesses are finally automated? The one whose physical health is a hydrated and toned “well-oiled machine” rather than a series of SOS signals?

Building a life that feels as good as it looks on Instagram requires the one thing most high-achievers hate: slowing down enough to listen to your own gut. It requires looking at the next 5, 10, and 20 years and asking, “If I keep doing exactly what I’m doing today, will I like the person I am at 70?” If the answer is a hesitant “maybe” or a flat-out “no,” it’s time for a pivot.

The “CEO of Your Life” Vision List

To move from the “successful but exhausted” living of today to the “intentional and inspired” living of tomorrow, you need a strategy. Here are 8 things you can do right now to determine what you want your next chapters to look like:

The “Funeral Test” (With a Twist): Don’t just think about what people say at your funeral; think about what you want to be doing on a Tuesday afternoon when you’re 65. Who is there? What does the air smell like? What are you not worried about?

Conduct a “Joy Audit”: Review your calendar from the last three months. Highlight the activities that gave you energy in green and the ones that drained you in red. If your life is a sea of red, your 10-year plan needs to start with a “Stop Doing” list.

Define Your “Non-Negotiable” Wealth: We know how to measure financial wealth. Now, define your time wealth and health wealth. How many hours a week of pure, unadulterated “me time” does your future self require?

The 20-Year Health Projection: Be honest about your physical trajectory. If you want to be hiking mountains at 70, what does your strength training and nutrition need to look like at 50? Treat your body like your most valuable business asset.

Identify Your “Legacy Projects”: Beyond money, what do you want to leave behind? Maybe it’s a foundation, a book, or simply a family culture of presence and adventure.

Schedule a “Solo Retreat”: Get out of your house and away from your family and business for 48 hours. No spreadsheets, no Slack, just a notebook, your thoughts, and maybe a spa.

Draft Your “Life Prospectus”: Write down your goals for the next 5, 10, and 20 years in four categories: Health, Relationships, Personal Growth, and Contribution.

Audit Your Inner Circle: Are the people you spend the most time with living the kind of “intentional” life you crave, or are they still trapped in the “busy is a badge of honor” cycle? Diversify your portfolio of human connection.

A Final Word of Encouragement:

The transition from “building” to “being” is the hardest merger you will ever manage. You might feel guilty for wanting more than “just” success, or you might feel terrified of the quiet. That’s normal. But remember: you’ve built empires before. You’ve raised humans. You’ve taken care of aging parents. You’ve beaten the odds. Designing a life that actually fits you is simply the next great venture.

Start today. Not because you have to, but because you’ve earned the right to be the boss of your own joy and the next 20 years won’t design themselves. 

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