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Career advice: Make mistakes and ‘Cheer Up’

© 2008 Avocationist · May 28th, 2008 · 1 Comment

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 final of a three-part interview.

“I don’t know if I will ever fully retire.”


  • Start making mistakes, now: Dave’s entrepreneurial experiences began while he was in college. Starting early gave him lots of room to try things and learn.
  • "Steal" ideas from others by reading: Dave is a voracious reader. Many of his successful book marketing campaigns began with ideas from others’ books.
  • Appreciate what is good in your life: Dave nurtures his positive outlook through gratitude for the advantages he has and by using humor to keep things in perspective.
  • Read the full interview:

    Avocationist: Based on what you have learned and experienced, what advice would you give to people in their 20’s who are starting out and trying to figure out what to do next?

    “I think the younger you start, the more learning you go through.”

    Dave: A lot of this is going to seem trite, but I think some of the most old-fashioned, cliché advice is also bang-on. You can’t be afraid to make mistakes. I think a lot of people who are drawn to entrepreneurialism should get started as soon as possible. A lot of times starting in your 20’s allows you to get involved before you have a tremendous amount of other financial responsibilities like mortgages, spouses, and children. You also have more time to dedicate to the entrepreneurial venture. You can still take some risks. I think the younger you start, the more learning you go through. I hate to say this because I am a big proponent of formal education, but when I started my first small company at the age of 20 and 21, when I was an honors economics student at university, I learned more running that business in a year than I did the four years at university. I am a big believer in university; I am just giving you the truth.

    “The other piece of advice I would give is to read voraciously.”

    The other piece of advice I would give, and I don’t think you hear often enough, is to read voraciously. I think a lot of my inspiration has come from stealing other people’s ideas and customizing them and tinkering with them and making them applicable to my situation. We got about 90 percent of our book marketing approaches from other people; we “stole” them, in essence, from their books and applied them to our own situations. Experience is a great teacher, but it is a lot less expensive and you can leverage a lot more if you can learn from everybody else’s experiences. I read a tremendous amount in my early 20’s and I still do today. I think it played a very positive role in my life.

    “I think having a good disposition is the key to success in life.”

    The third thing I would say, and again it sounds very corny, but if you are going to go into business for yourself, or for that matter facing whatever challenges you are taking on in life, I think the most important thing you have to do is have a good disposition. You have to be a cheerful person. You are going to have your ups and downs. If you are going to be an entrepreneur, you are going to have a life full of challenges and tough days and setbacks and everything else, and you have to almost enjoy that. That has to be looked at as just a part of the process; it is a puzzle you must put together. The setbacks are all a part of it. I find over and over again, a lot of the most successful people I meet – and I mean with well-rounded success, not just financially, but they are good family people and enjoy their lives -- have a naturally upbeat disposition. They tend to be optimistic and see things positively, and I don’t mean with rose-colored, unrealistic glasses, but they see things positively, and I think having a good disposition is the key to success in life.

    Avocationist: Yes, and it also makes life more enjoyable along the way.

    “We are very blessed and life is full of opportunities, and I think people should see life for what it is.”

    Dave: It sure does. And I think for a lot of us it is a conscious choice. I talk a lot on stage now about people who complain way too much. They are constantly voicing negative thoughts and complaining about nothing. We are all so spoiled relative to what people have led their lives like throughout history, or for that matter lived their lives like now in Africa and Iraq and Iran. We are very blessed and life is full of opportunities, and I think people should see life for what it is. For most of us, though not all of us, it is very good, indeed.

    Avocationist: It is clear just from talking to you that you feel gratitude in a lot of ways, and that goes a long way in helping you stay in-check with what you are doing and staying positive. Do you have any regrets?

    Dave: You know, I really don’t have many. You are always going to make some bad business calls and sign some contracts you wish you hadn’t, but even the ones I have signed, where financially I don’t think it’s ended up being a very prudent move, I have usually enjoyed the partnerships and the processes and the learning experiences. There is almost no contract I can think of where I wish I hadn’t done it. There are a few I wish I hadn’t done financially, but they have all ended up being pretty good experiences and I can’t complain. I have been lucky to do well and I think you meet a lot of interesting people and I have traveled to a lot of good places and I have good kids. I don’t have a lot of regrets, frankly.

    Avocationist: How would you like to be remembered?

    “I could leave people with a message, the fundamental message I would drive home to people would be ‘Cheer up’.”

    Dave: It’s interesting because I get asked that in interviews a lot for whatever reason, and they always think I am going to say, “Save 10 percent” or “Pay yourself first.” But if I could leave people with a message, the fundamental message I would drive home to people would be “Cheer up.” I just meet too many people who are stressed out, negative and gloomy for the most bizarre and ridiculous reasons, whether it be a long line at the Starbucks or the fact that their car is not running smoothly. They can spin into bad moods for hours if not days, and I think people have really lost perspective and again, they don’t realize that for the most part, our lives are very good indeed.

    Avocationist: So you would like to be remembered as someone who helped people cheer up?

    “I think I would like to be remembered as a guy who pushed a lot of common sense.”

    Dave: Yes, I would be. That is something I am trying to focus more on going forward, and certainly on the finance front, I think I would like to be remembered as a guy who pushed a lot of common sense. I think people make a lot of this too deep. The fundamental message on personal finance is still “spend less than you make.” People just don’t save enough. They ask you how best to invest it and you have to look at the different opportunities, but the fundamental message is that you’ve got to save money. Americans in particular have really drifted away from that core message over the last decade. Because they had rising home values, they felt they could get away with saving less and less.

    Avocationist: I bought a book by a former monk who has written a book along the lines of gratitude you are talking about. I followed his ideas for 21 days and it was amazing how different I was and how different people reacted to me. People were just attracted to me because I was not falling into the gossip and the negativity. It was astonishing.

    Dave: Yes! I bought the book and it is excellent. I am a huge believer in that. You don’t have to act ridiculous, but you have to stay away from the trite negativity that we have gotten so involved in. I say on stage, next time you are in a restaurant, eavesdrop on the conversations on the table beside you. They are almost exclusively negative.

    Avocationist: Dave, what do you think you will do next?

    “I don’t know if I will ever fully retire. I think if I am even slowing down, I will still keep speaking.”

    Dave: I don’t know. I still have a major project with marketing the sisters’ cookbook in the States and I think I may write one more book after all of these years. I think those two things I am almost sure to do, but after that, I don’t know. After that I would like to do one more thing completely different from anything I have ever done. I want to start a business that doesn’t relate to the other ones and then sort of head towards retirement. I am 46 and that is probably 10 years down the road. I don’t know if I will ever fully retire. I think if I am even slowing down, I will still keep speaking.

    Avocationist: It sounds like you really love that. Is there anything you wanted to talk about that we didn’t get to?

    Dave: No; it was all good. It was a good interview.

    Tags: Career Advice · Entrepreneur · Personal Growth

    1 response so far ↓

    • 1 Sinoun // Sep 3, 2009 at 2:50 pm

      I really enjoyed reading this interview. The best take-away message was definitely the "cheer up" aspect, because not only do I encounter too many negative people, but I myself can sometimes be one of them.

      It's nice to be reminded that our worries and stressors are often very trivial. It's important to step out of the "moment" and expand our perspective - to look at the current situation relative to the bigger picture.

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