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A Funny Thing Happened on the Way to My Undoing: Life Lessons from Mary Kay, a Dusty Trombone, and Old Man Rogers

By Phil Glasgow

Mary Kay never thought it was a good idea. Now, hustling through the snowy streets of Chicago, desperate to find a music store, I was starting to agree with her. What kind of dummy would stand in front of 2,500 women with a clunky trombone and perform a song he’d never played in front of anyone before?

In those days, long before the internet radically changed the way people bought and companies sold, I was the vice president of sales for Mary Kay cosmetics. It was a woman’s world, run by one of the most successful female entrepreneurs the world would ever know, but I had a place in it, and that place was to tell our vast grassroots salesforce that they could succeed at something most of them had never done before. They could sell cosmetics to their friends and family and maybe, just maybe, find themselves driving around town in a pink Cadillac.

But in the early 1980s, two of our top sales directors said to me, “Here’s the problem, Phil. The girls love you, but you can’t identify with what they experience. A newly recruited wife who has never been in business, has never sold anything, and is scared to death, is discouraged by her husband. He tells her she can’t sell anything. And her friends tell her, ‘They’re just making money off of you. I know a lot of people who have failed at that.’ They see someone who has cleaned the same room year after year, and now she thinks she’s going to become a businesswoman and build a company. You don’t know what it’s like for her.”

I couldn’t disagree.

It was nearing the time of our big Jamboree, when we would welcome all these women from the Northeast Division to Chicago. I had six months to figure out how I might relate to them. And then I remembered that trombone.

When I was a college student, paying my way selling books door to door, I got into the funny habit of trading my customers for things in their houses. It started with an archer’s bow that I traded for a set of drums. The drums became a trumpet and the trumpet became a banjo. In the end, I wound up with an old valve trombone. No slide, just valves, but a trombone all the same. I had no idea how to play it.

Now, planning to address all those women with whom I “could not relate,” I thought of that trombone. I asked the sales directors, “What if I took my old broken down trombone and learned to play ‘Let the Sunshine In’?” I knew I’d be scared spitless—which is never good for a horn player—but that was the point. If I put myself in a position where I was completely out of my comfort zone, doing something I had never done before, maybe I could convince all those women to do the same. The sales directors loved the idea.

But for all the times I had taught that procrastination is the enemy of success, I forgot all about our plan.

Three months later, and not long before the Jamboree, I got a call from one of the sales directors. “Phil! The girls are so excited about what you’re going to do!”

This was the first time I started to panic. I took the trombone to a shop for repair, hoping the shop owner would tell me it was beyond fixing. But he said, “Sure, we can do it.” So my gig was still on.

How could she miss me? I was carrying a decrepit old case held together by duct tape and a leather belt.

Then Mary Kay got word of what we were planning. She said, “They tell me you’re going to play a horn in Chicago.”

I said, “Yeah, I am. It’s going to be part of my speech.”

“No, Phil, it’s not. Let’s you and I do what we do best. We hire these professionals to come in and play music. So, let’s not do that.”

Initially I thought, Oh, man. But then I realized, You know what? That makes a great part of the speech: Mary Kay herself said don’t do it.

I didn’t say anything else to her about it all the way up to the meeting. But as we were getting off the plane, Mary Kay saw me moving quickly through the aisle. Actually, how could she miss me? I was carrying a decrepit old case held together by duct tape and a leather belt.

“Phil, what’s that you’re carrying?”

“Well, uh, that’s, uh… that’s a trombone.”

She said, “I thought we talked about that.”

Of course we had, but the best defense at the moment was to fib. “It’s just a hobby, Mary Kay.” But I had learned that one song, and thought, If I’m going to do this, I’m going to do this.

Ninety minutes before my speech, I pulled out the trombone backstage to silently practice the fingering positions, because if I screwed up, boy, I’d had it. And the valves started sticking!

With a friend covering for me, I ran out into the street with my trombone and started begging for directions to a music shop. Someone pointed me to one upstairs two blocks down. The shopkeeper was positive enough and started working on those valves. Then he asked me what I needed this for. I said, “In about an hour, I’m giving a speech for 2,500 people and I’ve never played a horn before and I’m scared to death.”

“Oh, yeah? What are you going to play?”

“’Let the Sunshine In.’”

“Well, let me hear it,” he says.

“Right here? In front of your customers?”

“I thought you told me you were going to play it in front of 2,500 people.”

Some people are just too insightful! So, I played it, and he said to me, “I think you’ll be great. Do you mind if I come and watch?”

I said, “Come on. Having one person believe in me would be awesome.” That shopkeeper and I hit the snowy streets together and ran all the way to the convention hall.

When it came time for me to give that speech, I was still plenty nervous. But I asked the women, “What do you have broken that you can’t get fixed? Has procrastination, unexpected circumstances, or lack of experience, or the opinion of others kept you from the success you deserve?” I even asked them what they would do if Mary Kay herself told them they couldn’t do it. But then I said, “We can all overcome fear and gain confidence when one person believes in you and says, ‘I think you’ll be great.’” Then I did two things. I introduced them to the shopkeeper who was watching and believing from the back of the room. And—after an emergency drink of water—I started playing, “Let the Sunshine In.” Every single person in the room rose and started cheering.

I wish I could say that cheers and accolades have been the story of my life. There was a time after Mary Kay and later, while building and then selling Network Security Corp, when I began to speak before groups and incorporated humor. I loved seeing people laugh and admired stand-up comedians. So, I decided to give comedy a try myself. It took several years of hard work, but I was able to perform in hundreds of clubs in 26 different states.

As a comedian, I was OK but not great. Never a headliner, only a feature act. But I got booked because I had something better to barter than old musical instruments. Thanks to past relationships and business success, I was a member of several different golf clubs, including Muirfield Village in Ohio. I could get club managers and other comedians on virtually any golf course in America, from Pine Valley to Augusta National. Voila! Another gig! Eventually I opened for Gary Shandling, Tim Allen, Ray Romano and Jay Leno.

That was the beginning of buying my way into my next business. I’d spent some time around Branson, Missouri, where entertainers built their own theater. That way, they didn’t have to travel; instead, the audience did. They just had to get audiences in the building. I planned on building a theater in Branson until Lee Greenwood called and said, “Let me show you what’s happening in Pigeon Forge.”

Pigeon Forge is a beautiful spot in the mountains of east Tennessee. If you’ve ever been to Dollywood, you’ve been to Pigeon Forge. After visiting, I thought I could build a Comedy College and Theater in the Smoky Mountains that could be the Southern connection to Jay Leno’s Tonight Show.

I was wooed. Between the land, building, and operating capital, it was about an $8.5 million-dollar project. In Dallas, I had joined numerous investments with friends and now they, including Roger Staubach and Troy Aikman, put in a little over $1 million. The rest was on me. Well, that’s not fair. It was on me and Carol, my wife. And she was the one I leaned on heavily in the years to follow, because we lost it all when the theater failed.

It was the hardest thing imaginable, at least when it comes to business. I’d never failed at anything in my life. I was up there in Tennessee, my friends were in Dallas, and I felt shame and despair. But my friendships were strong and didn’t break. People were more concerned with me than any investment.

I grew up in Oklahoma, the son of a poor Baptist preacher. He believed that preachers should not be seeking out bigger and better churches. He took a lot of pride in that, but he also made a lot of trips to Old Man Rogers. Mr. Rogers owned the hardware store in town, and he was willing to loan my daddy money. We would pay it back over time, but not long after it was all paid back, my father would have to go back for more. We were always short.

I loved my dad, but I didn’t want to live like that. Although the baby of the family, I was going to go to college. When a schoolteacher asked my major, I had no clue. But then he asked me what I liked doing, and when he found out I loved math and was good at drawing, he said, “To me, it sounds like you could be an architectural engineer.” I began to dream.

My college experience was a long one—eight years—because I had to stop and work to get the money I needed to keep going. I was getting two educations: one from studying books and the other from selling books.

But the lesson I had gained growing up in that little church in Oklahoma and the lesson I was learning in and out of college was that people matter. Honestly, my life has been shaped by some people in high places. They have been influential mentors for me, and I thank God for them all. But when there have been challenges in my life—as a kid, in college, selling books door to door, and when I lost all that money in Pigeon Forge—the people who came around are people you have never heard of. Just friends. But faithful friends, who really cared about us when we needed it most.

After losing the theater, Carol and I started over in Knoxville, Tennessee. I took the advice of some of these caring people and got started again in financial services in 2000. It was difficult at first, touch and go, but with Carol right there in the office with me, and the blessings of God, we’ve experienced a wonderful comeback. Our clients are like family and our business is amazing.

One of the pleasures that has come out of that is that we have been able to connect again with a local country club, Fox Den. And for several years, a number of men have come together there for a Links Fellowship. It has been a place where we have seen lives change.

I gained a heart to tell others about my faith in Jesus back when we were living in Texas and I started traveling to try my comedy. I saw amazing changes there, too—changes that brought me to tears because of what God did in people’s lives. But in our Links Fellowship, we spend so much extended time together that we have an opportunity for all this to take root in our hearts.

Another Links Player and I played with one guy in a member-member tournament and invited him to join us for our weekly Bible study. He came as a courtesy, but he’s still with us. He said, “I remember when I was a kid becoming a Christian. Don’t know how I did it, but I became a Christian. I have never lived that life and I surely don’t live it now. Haven’t been to church in I don’t know how long. Never picked up a Bible.”

But then he said, “What I’m learning here is changing my life.” He stood up in front of a whole lot of men at a Fox Den gathering and he said, “Guys, I want to tell you something. If you are not coming to this, I started out of courtesy, but now I arrange my travel schedule around it because it has changed my life. If you are not coming, you are an idiot.”

That may be an unusual form of encouragement, but it came straight from this guy’s heart.

That’s what happens when you hang around with people and Jesus is in the picture. You get to see how he takes people’s broken lives and, beginning with their hearts, puts them back together again.

You might be wondering if I still have that old trombone of mine. After 35 years, hidden in the back of some closet, I took it out, planning to do a reprise of my Mary Kay speech for a friend who asked me to speak to a group of sales reps in her company. The poor trombone was falling apart. There was no chance I could play it, but I stood on stage and held it up to tell the story of the day when that old thing had “let the sunshine in” for a big crowd in Chicago.

Afterwards, I took the trombone home and started examining it closely. You could barely make out the engravings, but after online research, I found that what I had in my hands was a 1911 King trombone. An heirloom. Priceless.

I’ve since sent it off to a place in Oregon, which I am told is the only place it can be restored to its original condition. I hope so—it’s been there almost three years now! They’ve told me it should be done any time, but I’m still waiting, because they’ve run into all kinds of problems.

That’s the story of our lives, you know. All kinds of problems. But God considers us priceless and he’s willing to go to work on every sticky valve or tarnished bell tube that has become a part of us. He’ll take us through highs and lows to do his work, but in the end, we can trust him. He is faithful.

Links Players
Pub Date: March 16, 2020

About The Author

Articles authored by Links Players are a joint effort of our staff or a staff member and a guest writer.

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