Dear Anna, What’s your advice for a woman who owns her own company and needs a man who is secure enough to handle her success, independence, and ambition?

Dear Boss Babe of the Lake,

First of all, let’s celebrate the fact that you’ve built something of your own. Success, independence, and ambition are not things to tone down or apologize for — they are exactly what make you magnetic. The right partner will see your fire and fan it, not try to dim it.

When it comes to dating, look for a man whose sense of self isn’t tied to competing with you, but to complementing you. A secure partner won’t feel threatened when you’re winning; he’ll be cheering the loudest from the dock. You’ll recognize him by his actions: he celebrates your milestones, respects your time, and steps up with his own purpose rather than pulling at yours.

And remember, the lake teaches us something important — calm waters run deep. Confidence and security don’t always shout. Sometimes they show up quietly, with steady presence, reliability, and respect. Hold out for the man who rows alongside you, not against you.

Signed,

Anna

Jen Bailey

Hi! I’m Jennifer Bailey and I partner with entrepreneurs who have massive ideas that could change the world. Most marketing is meaningless. Filled with empty promises, its only job is to bring in new traffic, new leads, and new customers. But I’ve drawn a line in the sand, and I’ve learned that marketing can do so much more than reach business goals and build profit. My methods give businesses the fire and soul they need to reach the right people, set the groundwork for sustainable relationships, and offer true value to the people on both the giving and receiving ends of marketing.

Read more about me here