What Sixteen Years of Building Teams Taught Me

This post is a companion piece to episode 153 of the Beautifully Whole podcast. You can listen to the full episode here if you would rather hear the story in my voice.

This week I want to tell you a different kind of story than the ones I usually tell here. Not about food, not about supplements, not about how to run your morning at 55. About what has actually built the shape of my working life for the last sixteen years, and what I have learned along the way that I think would be useful to anyone quietly wondering what a second chapter in their own career could look like.

Eight years in corporate sales. Fifteen more building something of my own after that. That is my working life in the shortest possible summary. And the story of how I got from one to the other has some pieces in it that I have never sat down and written out before. So I am going to walk you through it. Because I think a lot of women in midlife are asking themselves the same quiet question I was asking when I made the pivot. What if there was another way. And if that is a question you have been carrying, I want you to have my version of the answer.

I Was an Accountant Before I Was Anything Else

I know. Look at me. I know. But I went to school for accounting, and my first working years were in bookkeeping and accounts receivable. Which means my job was to call people, mostly dentists, and ask them politely to please pay their bills. Which means my job was also to be hung up on, professionally, most days of the week. That was my introduction to what I later learned was really the same skill under a different name. Talking to human beings. Absorbing their reactions without taking them personally. Getting back on the phone and doing it again.

Then I met John. John was a sales guy. Long-career, deeply talented enterprise sales guy. And within about a month of knowing me, he was looking across the kitchen table saying, you have too much personality for spreadsheets. You should be in sales. And I looked at him like he had lost his mind. Because I had exactly the mental picture of sales that most people have. Icky. Pushy. Manipulating people. Talking too much. Selling water to a fish. I told him no about seventeen different ways for the first two years we knew each other. He kept mentioning it anyway.

The Pizza Joint That Almost Broke Me

In 2003 I finally took a shot. I was working the customer side of a large payroll company at the time, and I asked if I could try the sales side. They said yes. Which is how I ended up with a territory in northern New Hampshire and a list of businesses and a job description that was more or less, go find out who does their payroll, and then convince them to let us do it instead. Which was hard. And which I hated. And also loved.

The worst day of that job, and the one I still tell the story about, was the pizza joint. I had knocked on the front door of a pizza place, and I could see the people inside, and I could see them deciding to just not look at me. So I walked around back to the kitchen door. To knock again. To not be ignored. And I got to the back of that building, standing between a dumpster and a delivery door, and I heard myself think, oh honey, what are you doing. LeeAnne. Go take a rest. The sale of a pizza joint payroll account is not more important than your dignity.

And that was the beginning of the actual education. Not just how to handle a no, which I learned to do a hundred different ways over the years. But how to notice when I was working from panic instead of strategy. When I was hunting instead of connecting. When I had stopped seeing the people on the other side of the door as human. The pizza joint was a small moment. It taught me the whole thing.

What Happens When You Actually Get Good At It

I switched companies not long after that and landed in a different kind of sales role. Bigger companies as clients. More strategic conversations. I was helping business owners look at what they were spending on benefits and health insurance for their employees, and figuring out how to pool them into a larger group to reduce costs. Real problem-solving work. Real math. Real relationships built over months, sometimes years, before a deal closed.

That is where sales made sense to me for the first time. It was not about talking people into things. It was about listening to what a company actually needed, understanding it deeply enough to speak their financial language back to them, and then, if there was a fit, offering something that would make their business better. If there was not a fit, saying so and moving on to the next conversation. I got good at it. I stayed in the top one percent of my company. I made the incentive trips. I hit the numbers. I felt for the first time in my career like I had found something I was actually built for.

Which is what makes the next part of the story surprising, even to me.

How I Accidentally Walked Through a Different Door

Right around the time I turned forty, I got serious about fitness. I had always been an athlete, and I had always loved the gym, but I decided I wanted to compete. I found an international team of about seven hundred women who competed in the same category, and I got connected into that community. We trained together. We supported each other. We showed up for each other at competitions.

One day someone in the group sent out a note saying, here are the supplements we are all going to use for this next round of prep. I said, great, tell me what to send you, I will use whatever you recommend. Straightforward. A few weeks later that same person sent another note. It said something like, hey, did you know you can get your supplements paid for by telling a few friends about them. And I looked at the note, and I thought, that seems doable. So I told a few friends. And a few friends told a few friends. And my products started being paid for, and then I started to see a small check appear that was more than the products themselves.

I was not looking for a new career. I had a great job. I was making great money. I was, at that specific moment in my life, entirely uninterested in doing something else with my time. But I had a small thing going that seemed to be building on itself in a direction I had not expected.

The Event I Did Not Want to Go To

The team I was on decided to host a training event in New Jersey. My leader kept asking me to come. I kept saying no. I have a real job. I do not want to take a vacation day to sit in a hotel ballroom and learn about a side thing. It was one of those situations where the invitation kept getting warmer and I kept getting more resistant, until finally I gave in and went. Just to be a good sport.

I sat in that ballroom in a folding chair with a friend on either side of me, expecting nothing, and I watched people I had never met walk across the stage as recognition for what they had built. Some of them were women who had left corporate careers not that different from mine. Some had built substantial businesses. All of them looked like people who had chosen their own lives. And somewhere in the middle of it, sitting there in that hotel ballroom, something clicked in my brain that I have never been able to unclick since.

I understood, for the first time, that the small thing I was doing in the corners of my week was the same shape as the sales work I was doing full-time. Same skills. Same relationships. Same problem-solving. Except this version paid me on the momentum of everyone I helped, not just on the deals I closed personally. This version had no quota that got raised every January. This version, if I built it right, would keep paying me even when I was not actively selling that week. I got on the plane home from New Jersey with a specific plan in my head.

Telling John

I walked in the door and I said, honey. I am going to leave the corporate job and go do this full time. John, who is one of the most steady, supportive men I have ever known, looked at me like I had proposed selling the house and moving to Bolivia. There may have been a few sentences that included words I will not put in this blog post. He reminded me, correctly, that we had kids about to enter college. He reminded me, correctly, that my income was significant to our family. He reminded me, correctly, that my corporate job was one of the good ones.

And I said, I hear all of that. I am not asking your permission. I am telling you I am doing this. I set a specific milestone with a specific date. I told him that if I hit that milestone by that date, I would leave the job, and if I did not hit it, I would stay. That was the deal I made with him, and with myself. And I reminded him, gently, of the years earlier when he had taken enormous professional chances himself, back when his boys were small, and how those chances had paid off. And after some silence, and some more sentences, he said, okay. If you can do it, we go.

I did it. I hit the milestone. I gave my notice. I have been building what I built ever since.

How I Actually Built It

Here is the piece I want to give you, because it is the piece I think most people miss. What I did to build my team was the same thing I did to build a sales territory. I treated the people around me the way I had treated the businesses in my corporate portfolio. I looked at each individual and asked, what does this person actually need. Do they need help with their health. Do they need a second income to pay off debt or send a kid to college. Are they looking for community. Are they looking for a career pivot. And then I built a plan around the person, the same way I had built plans around businesses. If there was a fit, I offered something. If there was not, I let it go and moved on. That was it.

The people I built teams with became some of the closest friendships of my adult life. That part surprised me. I was not expecting the momentum of a group of people growing together, calling each other on hard weeks, showing up at each other’s events, celebrating when someone hit a milestone. It felt more like a professional community than any job I had ever had. Nine years at that first company. About twelve thousand people on the team I led at its peak. That is what happens when you keep showing up and keep serving the people in front of you.

Somewhere in the middle of that run, I got a call I did not expect. Tyra Banks was launching a beauty and wellness line, and she was picking a small founding-team of women to help build it from zero. I was one of the first two hundred women selected. I said yes because it was a chance I could not walk away from, and because I love the beauty and wellness space and I saw a real opening. I built that team to about eight thousand people over the following two and a half years. And then that company closed its doors, which is a real risk when you build with a startup, and I want to name it clearly. Not every venture works. That one did not.

What saved me during that particular season, and what saved me later during a much harder one, was residual income. Real income that kept arriving because of the customers who kept reordering from the first business I had built. I did not have to worry when that company closed. I did not have to worry when I was diagnosed with hereditary cancer risk and had a major surgery and a long recovery. My team quietly kept moving. My income quietly kept coming. That is not a promise you can make about most kinds of work.

What I Wish I Had Known Sooner

If I were sitting across from the version of me who left corporate that first time, here is what I would tell her. The income you can build in this kind of business is real. But real income has to be treated like real money. Meaning some of it needs to be saved, some of it needs to be invested, and some of it needs to make more money on its own while you sleep. I did not do enough of that. I paid cash for my daughter Jessica’s college education, which I am proud of and would do again. We traveled. We enjoyed the seasons when the business was growing. All of that I would keep. But I would also, if I could go back, put more away. I would invest in real estate. I would invest in other businesses. I would set up the compound work that some of my friends did, whose money is now making money for them every month while they build the next thing. I am doing more of that now. It took me too long to start.

Why I Am Building Again

A few years ago, I stepped away from active team-building because I was focused entirely on the ostomy community. I love that community. I am a spokesperson for a major medical brand in that space. I will always be a part of that work. But I quietly missed the other piece of who I have been for most of my adult life, which is a builder of teams. So a year and a half ago, I came back to it. I am part of a team called Heritage Club, which is a community of women and men who are choosing to be intentional about their health and their finances at midlife, together. It is stable. It is growing quickly. It is being done in a way I feel really good about. And it is where I plan to spend the second half of my working life.

Here is why this matters, and why I am telling you this whole story on a Friday morning. Some of you reading this are in a season of your own where the quiet question keeps coming up. What could my next chapter look like. Do I stay where I am. Do I lean into something new. Am I too far into my career to build again. And I want you to hear from a woman who has built two teams from scratch, who has survived a startup closing, who has survived a major illness with an income stream still intact underneath her, that starting a new chapter at 40, or 50, or 55, is not a wild idea. It is one of the most common quiet turning points of an adult life. And you do not have to walk through it alone.

If Any of This Is Speaking to You

I am an open book on this. If anything I have said in this post makes you want to know more about what building something looks like at midlife, whether the specific opportunity at Heritage Club could be a fit for you, or just what my working days actually look like now compared to my corporate years, come have the conversation with me. There is no pitch waiting at the end of it. Just a real conversation, one professional to another, to see whether there is anything here that would serve you.

You can hear a little more and get on my list for the conversation here: Learn more about Heritage Club

If you are here for the health side of my work and would rather stay in that lane, that is completely fine. The next blog will be back on that ground. This one was for the woman who is quietly asking the bigger question.