Realizing My Sugar Baby’s Leadership Skills

I’ve been told I’m a bit of a control freak. But, in my defense, you kind of have to be when you’re a woman in business, especially if you have kids, and double especially if you’re a single mom. If I hadn’t been an absolute terror to work with, at least sometimes, and a strict as heck boss to my team, my media business never would have gotten off the ground.

That’s not to say that I’m a total nightmare. I have a good relationship with my daughters and their husbands, and I’ve had the same core team of employees for many years. I take care of my people, and I go to bat for them when the occasion calls for it.

The thing about being in a leadership position is that it makes dating hard. The only men that I really felt could handle it were so busy with their own projects that we were never able to form a long-term relationship. This point has been made ad nauseam, but if you’re a successful man in business, you’re a hot commodity. If you’re a successful woman in business, well, good luck to ya.

My workaround has always been sugar babies. I didn’t necessarily know that I was a sugar momma at first. It started with some innocent flirting with my landscaper. Then I had a steamy fling with the private chef of a friend of mine. In other words, dating younger guys is something that started organically. I happened to cross paths with young professionals who also didn’t have time for a traditional relationship. We would spend a few months together, in which I would treat them to nice dinners, trips around the country, and spa days. And then, we would move on amicably.

Stanley is the only one who seemed determined to stick around for the long haul. And I have to say, I was skeptical at the beginning.

So, Stanley, I should explain, was the younger brother of a friend of mine. That’s to say, he came from a rich family, but then they cut him off when he was in his mid-twenties because he had dropped out of college, picked up a drug habit, and managed to escape every rehab his family had put him in.

When I met him, he was two years sober and just barely starting to get his life back together, starting with monthly dinners with his sister, my friend Janice. Jan invited me to one of these dinners. She was always trying to get Stanley to mingle with high-powered people, to, I don’t know, motivate him to do something with his life. And I guess, you could say that he did do something with his life the night we met: he became my sugar baby.

Again, the whole thing happened organically. We were sitting together at the table, and we fell into easy conversation. Stanley had a really unique way of seeing the world, and even though he was only a few years older than my daughters, he was wise beyond his 28 years.

Fast forward a week, and Stanley and I were getting to know each other more intimately over dinner, one-on-one. He was explaining his plans for taking over the contracting business he had been working at for the past three years. He didn’t like to take orders from anybody, he explained. And of course, I could understand that.

“How do you feel about taking orders from a partner?” I asked, half-jokingly. I was used to calling the shots in my relationship, and I felt like it was probably important to establish the dynamic early on.

Stanley laughed.

“How do you feel about letting go of the reins a little bit? Letting someone else be in the driver’s seat?” he shot back.

I laughed too, but I felt like he had no idea what he was getting into.

Over the next few months, my relationship with Stanley was more or less conflict-free. He was okay with me making decisions in terms of when we could meet and where (and what he would be wearing), and I forced myself to stay silent when he chose the table where we would sit at the restaurant and ordered another round of drinks without asking. I figured this was me allowing someone else to take on some of the leadership role.

Of course, being in a relationship isn’t only about going out to eat. And eventually, an opportunity came up at my work that I would be traveling to Los Angeles to meet with a few existing and potential clients. It was a big deal, and the week would include long, tiring days of meetings and commuting and virtual check-ins with my team back home.

I was talking to Stanley about it one night, and he could tell that I was tense.

“Why don’t you let me come with you?” he asked casually.

Immediately, I tensed up, and Stanley chuckled in response.

“Relax,” he said, giving my shoulders a pat. “I just mean that I can be helpful, you know. Drive you to your meetings. I’m an excellent driver. I can do all the annoying stuff, like get dinners and coffees and schedule massages and fight with the hotel about making the wifi faster. I accept payment in first-class plane tickets and room service,” he added with a wink. “Okay, fine, I’ll fly coach. But I want a cocktail at the airport.”

I had to admit that the idea was appealing. But I was worried that this would take our relationship to a whole other level, and I wasn’t quite sure I was ready for that. Did I really want him to see me in my most stressed moment? Did I want him to see me without makeup? Did I want to risk snapping at him, bossing him around, pushing him away?

In the end, I said yes. If things went sideways, I could always send him home early.

Have you ever had one of those trips when nothing seems to go right, from the jump? That was what this trip was like. We were late to the airport, which was actually fine because the flight was rescheduled for a few hours later, but that meant that I had to rearrange my meetings. Then, when we got to LAX, one of my bags was missing. The small details don’t matter, but you get the gist. Everything was going wrong, and my nerves were frayed. Not a great start.

But let me tell you that things would have been so much worse had Stanley not been there. He was an absolute rock star, making sure that I was staying hydrated and ordering Ubers before I even had a chance to think about it. When it became clear that my bag was not coming out on the conveyor belt, he immediately said, “Don’t you worry about that. I’ll call the airline. Let’s get to the hotel and get you ready for your client dinner.”

And that’s how it went the whole week. He was awake before me, heading downstairs for coffee. He knew exactly when to be present and when to make himself invisible. He knew what I would want to order from room service before I even realized I was hungry. He made my bag miraculously appear within 24 hours, and he went to retrieve it while I was in a meeting. He was better than any assistant I had ever hired.

The real test came when we got into a fender bender on the way to one of my most important meetings. It wasn’t Stanley’s fault at all. The other guy had been on his phone. But it was severe enough that we had to pull over and deal with it.

I was furious. I started yelling at the other guy and threatening legal action. Stanley immediately took out his phone, and I wondered whether his go-getter attitude over the last couple of days had finally worn out.

But after just a minute, Stanley stepped in and took over. He told me a car was on the way to take me to the meeting, so I should get my stuff ready and let him handle it.

“You go,” he said firmly. “I’ll stay here and deal with this and then meet you after. I’ll be waiting downstairs when you come out.”

I told him absolutely not. I had to deal with this myself. But there was something about Stanley’s resoluteness that made me back down. Very few times in my adult life has someone made me back down like that.

Later, back at the hotel, I apologized for snapping at Stanley. I told him how much I appreciated him stepping up and fixing everything for me, again and again, over the week.

“You’re a real leader, you know that?” I told him.

“It’s good training for running my own business,” he laughed.

When we got back home at the end of the week, I had decided that I wanted to help Stanley move forward in his goal of buying the contracting business. I knew that it would mean that we had less time to be together, but I could see how much he deserved to be the boss.

To my surprise, he rejected the idea when I told him.

“I appreciate the offer, but I want to do this my way,” he said. “Anyway, I’m almost there already, myself. All I need from you is maybe some advice from time to time.”

I gave him a wink, “Oh, I’ve got plenty of advice. But I get a feeling you won’t be needing much of it.”