Married to an Entrepreneur

Charles says he married an entrepreneur, and he and his wife have different personality styles. How can he best communicate to her and not hold her back from her ambitions? Dave thinks Charles's wife needs him in her life in order to bring stability to her life.

QUESTION: Charles from Cleveland says he married an entrepreneur, and he and his wife have different personality styles. How can he best communicate to her and not hold her back from her ambitions? Dave thinks Charles’s wife needs him in her life in order to bring stability to her life.

ANSWER: You’ve identified your opposite personality styles. You’ve identified that she’s a hard-driving, hard-charging entrepreneur. God sent you to her to slow her down enough that she can keep it between the ditches. In a sense, that’s what my wife is for me. It’s not that you’re holding her back. It’s not that Sharon holds me back. I’m just wide open, man. I’ll just run into a brick wall until the stupid thing cracks or my head cracks first. She’s finally like, “Uh, you’re bleeding.”

This idea that you can slow down enough to be wise rather than rash is the benefit that you bring to this relationship. And the more she respects that, the more that you guys are going to win because you’re going to make steady progress that’s predictable, reasonable risk-taking versus just these launches off into the stratosphere that result in continuous crashes. That’s one side of the equation.

The other side of the equation is that you can’t be such an anchor that the boat never leaves the harbor. The anchor has to be there to steady things, but anchor up and let’s go and let’s charge and let’s do some things.

You’ve gotten some of that this week by being here, so you can be more empathetic with her desire to go forward, and I think there’s a beautiful orchestra—a beautiful piece of music—that’s going to be played between the dance between the two of your styles as you move forward, as you use your cautionary side and your detailed-driven, due diligence side to hold things back until they’re reasonable. Then she uses her energy and passion to pull things forward until they freaking get done and we don’t analyze them into oblivion.

There’s this dance that happens there. It happens at my house with my wife. She’s wired exactly like you are, and I’m wired more like your wife in terms of personality style. I think that’s good. One of the reasons I went broke was I was disconnected from Sharon in my 20s. We were married, but she’s at home with the kids, and her answer was to everything, “Whatever you want to do, honey.” Well, I did—whatever I wanted to do. I ran the car off a cliff. When we’re pulling the car out of the water after it goes over the cliff, she goes, “I was going to tell you those construction signs were blinking back there—bridge out—but I didn’t want to bother you.”

And I’m like, “Bother me would be a good idea considering you were in the car.”

That’s kind of the thing I love about this discussion of family and family business and real people in the business being authentic, being real, and not being plastic and process-driven and let the thing have the organic mess that is life be part of the art of you all pulling this off together.

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