5 Business Lessons Learned Over Wine with My Radio Sales Squad

There's nothing like a gathering of good friends to lift you up and add perspective. Radio brought us together. Friendship has kept us together for 30 years. We used to see each other daily, hear each other's phone conversations, cheer each other on, console one another in the low moments. We've traveled together, traveled to see one another. We've weathered and championed moves, marriages, kids, career changes, business launches and challenges.

We don't see each other nearly enough now, but when we do, it's like a moment hasn't passed. New stories weave together effortlessly with memories.

Among us is about a 10-year age span. Some of us are having life experiences now that others had decades ago, and others are leading the charge of what's to come. We had dinner together the other night (missing our friend Paula Beadle). We all left corporate to pursue other things, and most of us are small business owners.

As the evening unfolded, I realized something powerful: while we all have different personalities and have ventured into different lines of business, our collective themes aren't just friendship gold—they're business gold. Here's what I learned:

1. "I've always wanted to, and now I am" We're actualizing dreams at a faster rate. What we want for ourselves and our families has changed over the decades, and I see the rate at which we're making decisions has accelerated. One friend took a part-time gig so she can see all the concerts and sports events she wants. Another is on her way to Italy. I recently transformed the growth planning I do with clients into an online course to make it accessible to solopreneurs.

While we all possessed a "make it happen" attitude in radio sales, now we're making it happen for us—for what we want, for the experiences we want to have in our lives.

2. "I'm not doing it" Being clear on what you're no longer willing to do is a powerful declaration. Whether it's the type of work, who you're doing it with, tasks that others can handle, or where you're willing to live—boundaries create freedom.

This hit home when one friend shared how she finally fired a client after doing everything possible to help them achieve the outcome they said they wanted, only to watch them reject the very solution they'd asked for. Another talked about how she started delegating more to her assistant, reclaiming hours of her week for higher-value work.

3. Family is the core When we first met, many of us didn't yet have families of our own. Now I get it. We do what we do so we can do what we want for those we love…and help others do the same. The why is more powerful than the what. This clarity of purpose drives every business decision we make.

4. Laughter is key We are flipping hilarious, and over the decades we have laughed our way through loss, transitions, blunders, and victories. Business requires a sense of humor. I don't think you can be a business owner without it. When everything feels heavy, laughter lightens the load and keeps perspective in check.

5. Our futures are informing our present We're all making decisions today based on dreams we have for our future. It looks different for all of us, but we're all building the lives we want, and our business decisions help actualize them. This long-term thinking shapes everything from client selection to investment choices.

The Radio Connection It struck me during dinner why radio sales was the perfect precursor to entrepreneurship. Radio is 100% commission—you eat what you kill. You work with a breadth of industries, learning business intimately across sectors. It's professional services at its core. You encounter every possible personality and dysfunction imaginable, building resilience and adaptability. It's a solo sport, but you're in it together.

Just like entrepreneurship, you never truly succeed alone.

Your Turn What lessons are hiding in your closest friendships? Sometimes the best business advice doesn't come from a boardroom—it comes from people who've known you long enough to see your patterns, celebrate your growth, and remind you of who you really are.

What's one "girlfriend lesson" that's shaped how you do business?

#Entrepreneurship #WomenInBusiness #RadioSales #BusinessGrowth