Dear Leaders, Your Most Important Decision Has Nothing to Do With Business

A guy reached out to me a few months ago. He was smart, hungry and early in his entrepreneurial journey. He had a solid idea, a little bit of traction and a lot of energy. But buried in the middle of his message was one line that stopped me cold:

“My wife thinks I should just get a real job.”

I’ve gotten versions of that message more times than I can count. And every time I know exactly how that story ends.

Here’s what nobody tells you when you’re starting out as an entrepreneur or stepping into a serious leadership role: The most important decision you will make isn’t about your business plan, your funding, your product or your team; it’s who you choose to stand beside you.

Of course, business partners matter enormously, but I’m talking about your life partner—your spouse. I’m talking about the person sleeping next to you while you’re lying awake at 2 a.m., working through a problem that won’t let you go.

That choice will either fuel everything you’re trying to build or quietly dismantle it. There is rarely ever any middle ground. Because here’s a truth that’s hard to say and even harder to hear:

A partner who doesn’t support your journey will end it.

Maybe not today, maybe not this year, but eventually you will be forced to choose: the business or the marriage; the vision or the relationship. I’ve watched it happen over and over—good people and real talent—forced to walk away from something they were built for because the person closest to them wasn’t in it with them.

The entrepreneurial and leadership journey is not a 9-to-5. It doesn’t respect weekends, holidays or anniversaries. It demands more than most people are prepared to give. And it will ask that of the people closest to you, too, whether they signed up for it or not.

So, if you’re not married yet, listen carefully. Choose someone who sees what you see—someone who actually gets it. Choose someone who can sit across from you on the hard nights and say “keep going” when every rational voice in the room is saying “Stop.” That person exists. Don’t settle for less.

And if you’re already married, this message is just as important. Have an honest conversation—not the watered-down version, but the real one. Your spouse needs to understand what this journey actually looks like—the missed dinners and late nights, the financial pressure. They need to understand the mental weight you carry when you’re responsible for a vision, a team or a company. They need to be genuinely on board with your vision, not just tolerating it “for now.”

I know what it looks like when someone is truly in it with you. My wife, Alisha, has been by my side for more than 30 years. She watched me chase ideas that didn’t make sense yet, take risks that scared both of us, and pour everything I had into a dream most people couldn’t see. She never asked me to shrink it. Not once. She just stood there, rock steady, and let me be exactly who I needed to be.

I don’t take that lightly. I never have.

The same principle applies to the partners you choose in business. The wrong one will drain your energy, dilute your vision, and slow you down at the exact moment you need to move fast. Alignment isn’t just nice to have; it’s oxygen.

So, before you say “I do” in a chapel or a boardroom, be sure to ask the hard questions, and don’t try to sugarcoat the real answers. Does this person actually believe in where we’re going? Not just today when it’s exciting, but when the money is tight, the doubt is loud and quitting feels like the smart move?

Because that day is coming. It always does.

The entrepreneurs and leaders who make it aren’t always the smartest or the most talented. They’re the ones who had the right people beside them when things got hard. That’s not luck. That’s a choice they made deliberately—early—and it paid off for the rest of their lives.

To the guy who reached out: I hope you have that conversation with your wife. A real one. Because if she’s not in it with you, you’ve got a much harder road ahead than you think.

Choose carefully. Talk honestly. Build with people who are actually in it with you.

Everything else is details.