Why Successful Entrepreneurs Need a Love Life Strategy

You’d never build a business empire without an A-team of advisors.

So why are you winging it in your relationship - something that is ultimately far more important to your success in life?

For your business life, you have a financial advisor. A business coach. A board of advisors. Because you know success isn’t about guesswork—it’s about smart decisions, expert insight, and long-term strategy.

So here’s the real question: If your business deserves that level of care, why doesn’t your love life?

When it comes to balancing your career and love life - the status quo tells us that relationships are supposed to ‘just happen’ - left to chance, and your childhood wounds.

But this cultural default has come back to haunt successful entrepreneurs.

Case in point:

“I was prepared for all the business challenges,” says Brian Chesky, CEO of Airbnb in an interview on Diary of a CEO. “People told me what it’s like to scale a team, hire executives…”

“[B]ut we weren’t really well-prepared for the psychological emotional journey that we would go on.”

“And so I remember going from being incredibly happy to feeling incredibly isolated, not having been prepared.”

Chesky talks about how many entrepreneurs hope to become ‘something’ in order to feel good. But instead of feeling accomplished with all their success,

“You have to go bigger to get the feeling you had before.”

It’s a never-ending escalator.

“It turned out,” says Cheksy, “that what I wanted was love.”

Many of my clients have climbed the ladder of success - only to find themselves lonely, their life lacking meaning.

This can happen even within a marriage, as addiction to work and success take their toll over the years - not just to men who are single.

Warren Buffett says that the most important financial decision you will make in your life is who you marry.

It’s the person with the single biggest influence on you, with whom you could share 30,000 meals over four decades.

I’ll go even further and say it’s not only who you choose, but how you strengthen the quality of your relationship over time.

Because if you’re just winging it in relating, your unconscious narratives and projections will make a mess of it.

I’ve seen it over and over in my work - and you don’t want to untangle that mess, believe me.

It’s time for another way.

Instead of autopilot, what would it look like to play your love life on offense?

Want more dating advice for successful entrepreneurs?

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Here’s the thing about finding the balance in your career and love life. You didn’t build an empire on chance and luck, so why are you winging it when it comes to dating?

Dr. Jessica,

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