Avocationist header image 2

Leaving the Barber to come home

© 2008 Avocationist · May 21st, 2008 · No Comments

David Chilton is the author of “The Wealthy Barber” – the multi-million-selling financial planning guide. At the peak of his success, he literally walked away to spend 3 years home-schooling his kids. In his entrepreneurial career, he has also been a broker, financial planner, and cookbook publisher.

Avocationist spoke to him in March 2008. The second of a three-part interview.

“In my whole career, the common denominator is communication.”


  • Pay attention to positive recognition: Dave got praise from an experienced source for one of his early speeches. It gave him confidence he was on the right track.
  • Be willing to question a career that’s not working, especially in times of success: Dave found that his enormous success brought new challenges and demands. His decision to take a break from his speaking career gave him the time to explore other uses for his passions.
  • Find “common denominators”: Dave has used his communication skills in every role he's had: from writing to speaking to teaching his kids. Take a look back to find skills you constantly use.
  • Read the full interview:

    Avocationist: Were any of the career transitions you made particularly difficult?

    “When ‘The Wealthy Barber’ sales went ballistic, selling almost 100,000 copies a month, it brought a whole new set of challenges.”

    Dave: I think the only one was when the book first boomed. You hear a lot about people saying that handling success is challenging; I think that is true. In 1991 when “The Wealthy Barber” went from doing fairly well to all of the sudden going ballistic, selling almost 100,000 copies a month, it brought a whole new set of challenges and I had to learn to say no, which I did extremely ineffectively. I was doing too much. I was traveling almost all the time, which from a fathering perspective is not very prudent, and I was overtired. It is interesting that when I look back at from 1991 to 1993, I have very few memories of those three years because I think I was suffering from sleep deprivation constantly.

    “The PBS show on 'The Wealthy Barber' is an interesting example of how you never know what will happen in life.”

    The PBS show on “The Wealthy Barber” is an interesting example of how you never know what will happen in life. We thought they were going to be modest shows, but they went nationwide and were huge hits. They were on for years and years. That wasn’t really the original intention. They were not supposed to be that big. But that led to a lot of opportunities and it also led to a lot of touring with PBS to help them to raise money. Again, I didn’t strike a very good balance in those days. It hit me out of nowhere and I think I made some bad judgment calls and it took me away too much from my home. I did straighten it out quite quickly, but handling that kind of super-charged, all-of-the-sudden, holy-smokers success is tough. I wasn’t expecting it and I certainly had never been through it before, and again, I was tired. I remember being constantly tired, and I was a young man then.

    Avocationist: It is really interesting to hear you say that because I think from the outside, people think, “That is what I want and why I am working so hard; if I could just be like him.”

    “There is nothing that looks more glamorous that’s less glamorous than traveling.”

    Dave: I think you are right. People only see the glamorous part, and you have heard this a thousand times, but there is nothing that looks more glamorous that’s less glamorous than traveling. You are switching cities every single day and nowadays with the security and having to be there as early as you do and the delayed flights and the hub system; especially stateside, traveling has become worse and worse. So if somebody calls me now and says, “Do you want to come out and give a speech in San Diego and then fly to one in Boca Raton?” I say, “Honestly, not really.” At my age I would rather spend my time doing other things, because you are going to leave for five days and be on stage for a total of about 4.5 hours. I don’t see that as the most productive use of my time anymore. Would I love the 4.5 hours? Absolutely. But the other 100 hours, that is not really a fun trip. Back when I was younger, I was taking a tremendous amount of red-eye flights, and that is another judgment call which was quite flawed. If I had to do it over again I would have done way less of that, because those red-eyes are killers.

    Avocationist: Of all of the jobs that you have done so far, which has been your favorite?

    “There is nothing I enjoy more than getting in front of the audience and using humor.”

    Dave: I think I still like speaking the best -- there is nothing I enjoy more than getting in front of the audience and using humor. The downside of speaking is getting there, as I just mentioned. I think at some points in my life, that has been fine. But when you have kids, that is a challenge; that is a compromise I am not too keen on, which is one of the reasons I scaled back on my speaking. But I do still love giving the speeches, and I’ve had a really great career. The only thing I ended up not liking was the interviews, and that is only because I did too many. For 10 years I did interviews literally every day about “The Wealthy Barber,” and after a while, answering so many questions about 401(k)s and paying off mortgages, it just got over the top.

    Avocationist: You just tired of saying the same thing again and again?

    Dave: Yes, I really did. Certainly you give some different answers, but for the most part, you are saying a lot of the same thing, and most authors go through that when they tour. But they don’t tour for 10 years and that was the difference, and I really think I hit a point back in the late ‘90s where I said, “Holy smokes, I just can’t do this anymore.” Now, funnily enough, if I wrote again, and I may on finance, I would be fine again. I have taken a long respite from the interviews, and I think at that point, taking a break is very healthy. I think it is hard to walk away from something right at its peak. But interestingly enough, it didn’t bother me too much.

    Avocationist: Was there one defining moment, or had things built up over time that made you decide to do that?

    “I’m finished. I am not going to speak anymore.”

    Dave: It had been weighing on me in the back of my mind, but there was definitely a trigger event in that I went on a very extended tour. I gave about 30 or 40 speeches in a 30 to 40 day period. As I was flying back in I literally made the decision on the flight. I remember my secretary saying, “You are kidding, right?” I said, “I’m finished. I am not going to speak anymore. I am going to take several years off and do other things.” She thought I was kidding, but I stuck to it. I think I came out and did two or three paid speeches in a number of years and I stopped when I retired. I did a few charity speeches, but for the most part, I didn’t do any.

    Avocationist: How did your kids handle it when you were around all the time? Did they enjoy it?

    “I liked the challenge and I like the puzzle of figuring out the most effective way to communicate and how we all learn differently.”

    Dave: I think they liked it better. My daughter didn’t love homeschooling because she missed the social aspect of conventional school. My son was able to gain access to that socializing through sports, so he loved it, and I really enjoyed it. I think it was very positively impactful on both of them, but especially on him. I am really glad we did it because it brings you closer together. It is challenging because you have to have a lot of patience and that is something that I am not normally very good at, but you are forced to grow that way, and you are forced to mature a little bit. But I liked the challenge and I like the puzzle of figuring out the most effective way to communicate and how we all learn differently. In fact, we all learn different things differently. Sometimes Scott would learn best through oral presentations and other times it would be through drill work and other times it would be through combining a lot of different things.

    Avocationist: Have you found a thread to your life, like your interest in helping people learn in different ways? That seems to be the theme.

    “In my whole career, the common denominator in everything is communication.”

    Dave: Absolutely. In my whole career, the common denominator in everything is communication. From speaking to writing the book and the unusual format of the cookbooks, to homeschooling; in everything I have done, that has been the common thread. It has all been around trying to communicate more effectively with different styles of communication. In a lot of cases it is involved using a tremendous number of stories, often wrapped in humor. That is the case with the cookbook, as well as with the homeschooling. I was using all kinds of different communication techniques to get through to people.

    “Our entire system, unfortunately, is set up where mistakes are frowned upon, but the way you learn is to make a lot of mistakes.”

    It is interesting when you are trying to deal with a young man and teach him better math and writing skills; a lot of it is helping them get out of their own way. Kids get in their own way through nervousness or a lack of confidence or through pattern thinking. You have to get them out of the box and creatively going and trusting themselves and not being afraid to make a mistake. Our entire system, unfortunately, is set up where mistakes are frowned upon, but the way you learn is to make a lot of mistakes. So not doing well on a test is a great way to learn and you learn best in life by asking questions, but our entire education system is based on answering them. I think when you get into the homeschooling situation, you are able to try a lot of different things that conventional educational approaches don’t embrace, partially because they can’t in that environment. I think it is amazing how much kids can grow. I was just blown away just by how much Scott improved in certain areas, especially math.

    Avocationist: Yes; my brother is a high school math teacher and has gotten really excited in the last year about using new methods of teaching. He is really reenergized with that as well.

    Dave: It is a naïve thought that we are going to have one teaching system work best for every child in the classroom. When you do the conventional lecture style with rows of seating, it will work well for lots of kids, but it is naïve to think it is best for all. That being said, from a cost and organizational perspective, tailoring a different approach to every child is not going to be effective or realistic, but can we strike a middle ground where we try a number of different things? Yes, and it sounds like people like your brother are.

    Avocationist: Definitely. Have there been particular people in your career who have been helpful to you, like mentors or people came along at the right time?

    Dave: I can’t think of any conventional mentors I followed, but there have been a couple of incidents in my life that have been very helpful. Certainly Andrew Tobias, a well-known American writer; his first major book was “The Only Other Investment Guide You Will Ever Need.” His breaking down the subject with humor really helped me. After reading it, I thought most people would prefer that. So that was a big influence for me.

    “I still to this day remember where he was when he said that to me.”

    I caught a really interesting break once when I was just starting out. I had not written “The Wealthy Barber” yet, but I just got involved in speaking and a local financial company brought in John Simpson, the President of Fidelity Canada. I was going to basically be his warm-up act. I was going to speak for a half an hour on basic personal finance using the humor and then he was going to talk about current market conditions. I gave my speech, and as I walked off stage, John came up to me and said, “I’ll tell you right now, if you never change that speaking style, if you stay with it exactly as is, you are going to be very famous someday.” I still to this day remember where he was when he said that to me at the Waterloo Motor Inn. I thought, “You know what? To hear that from somebody that high up - the President of Fidelity” It gave me a lot of confidence that I was on the right track. I also think my parents have been very positively influential. They have been very supportive and they did a great job of raising us where we had a lot of confidence and were not afraid to make mistakes and take chances.

    Tags: Career Advice · Entrepreneur · Mid-Life Career Change · Teaching

    0 responses so far ↓

    • There are no comments yet...Kick things off by filling out the form below.

    Leave a Comment