The truth behind the confidence of wildly successful people


Confidence is a key ingredient to success, but a lot of business owners try to develop it the wrong way. Ben’s inability to find true confidence had stalled his brand consulting business for years. It was actually a mentor of his, another brand consultant named Deidre, who wisely pointed this out to Ben. She tried to help him with his confidence, but to no avail. That’s when Deidre, who I had coached, sent him to me.

Blowing it

When I first got together with Ben a few years ago, he explained his frustration. He’d been out on his own for a few years and the only clients he seemed to ever get were small ones. Anytime he got a shot at acquiring a decent-sized client, he blew it.

Deidre, who had subcontracted Ben to help out with a couple of big projects, recognized his lack of confidence straight away. To help Ben, she advised him to act confident—keep his head high, give straight answers, use a firm tone of voice, etc. He did all that, but getting his own big clients still eluded him.

Wildly successful people

During our first meeting, I told Ben that while Deidre meant well, she’d given him a bum steer. Deidre’s own confidence didn’t come from acting confident, it came from a trait that is common to wildly successful people.

When Ben pushed me to tell him what the trait was I shifted the conversation in another direction, asking him what he’d studied at school, whether he went to industry conferences, what he read and how much. He’d studied marketing and advertising, and he’d been to a few conferences, but none since leaving an agency he’d worked at before flying solo. As for reading, he did a little for pleasure and occasionally checked out industry stuff online. The last time he read a full book on branding was during school.

Trade-show revelation

“Ben,” I said, “what’s the first thing you notice when you step into Deidre’s office?”

After naming a few furnishings, he finally gave me the answer I was looking for—the hundreds of books that lined her shelves.

I then told Ben about a revelation I had when I was about thirty. I was at a trade show for financial advisors selling a couple of business books I’d coauthored. When the speaking sessions broke out the trade-show floor would fill with financial advisors—young ones, those in the middle of their career and successful veterans. Milling among the crowd were the speakers, who were all among the world’s top advisors.

“Ben,” I said, “of those groups, who do you think bought more of my books? I should add that our books were geared to the junior entrepreneur.”

“I want to say the junior advisors, but you’re going to tell me I’m wrong, right?”

Bags full of books

As I explained to Ben, very, very few junior advisors bought any books. Some of the middle career folks bought, but a much larger portion of the veterans bought. But what surprised me most was that every single speaker who walked by—literally every single one of them—bought our books. In fact, their bags were filled with books from all the other vendors too. That made no sense to me.

I even advised one of the speakers not to buy our books. I was worried he was going to be disappointed because he would already know everything in the books. He looked at me and said, “I’ve never read a single book that didn’t have at least one great idea.”

Never stop learning

Ever since then I’ve noticed that—almost without exception—whenever I’m in the office of a very successful person I find shelves full of books. Seth Godin, one of the world’s leading marketing and branding gurus has said, “It’s not an accident that successful people read more books.” Most successful people never stop learning, and most successful people are extremely confident. The two things—confidence and knowledge—aren’t unrelated.

The ignoramus effect

There is however an ironic relationship between confidence and knowledge, because they don’t always go hand in hand. Ignorant people often overestimate their abilities—don’t we all have a relative like this?—while those with more knowledge sometimes suffer from a lack of confidence. It’s called the Dunning-Kruger effect. Another phenomenon is that the more you know, the more you realize you don’t know. I remember having that experience when I reached university—the sudden and massive exposure to how much there is to know. It was daunting, and it made me feel small.

Blowhards and masters

In business, the kind of false confidence that comes from ignorance doesn’t fly. Most clients are savvy enough to know they have a blowhard in the room. Fortunately that wasn’t Ben. He fell into that middle ground where many of us linger—an awareness of what you don’t know, leading to doubt. For those in this category, there’s hope, because you can get over that doubt by developing mastery of an area of knowledge. Deidre developed mastery of branding by continuously reading about branding, putting her knowledge to work in the real world and seeing positive results. It’s her mastery of branding that has given her confidence. She’s not acting confident, she is confident, and that genuine confidence is what earns her the trust of high-powered clients.

As I told Ben, if you want to move up market and start working with the big clients, you have to move out of that muddy area of doubt and acquire the kind of confidence that comes from mastering a subject area.

Three super confident words

Oddly, three words that Deidre and many successful people use to inspire confidence are: I don’t know. This phrase shows that you’re comfortable with what you know and what you don’t know. What you don’t know isn’t some monstrous cavern that you’re trying to hide by pretending you know more than you do. People can see through that. By the way, Deidre follows up “I don’t know” with “but let me find out.”

Camp confidence

Ben took our conversation to heart and immediately started a program of self-education that involved picking the brains of his mentor Deidre, going to conferences and reading and reading and reading. As he learned new branding strategies he would try them out on his smaller clients. He would frequently see great results, which would make him feel more confident about his new knowledge. After a year of some solid study and practice he felt an immense sense of confidence. It made him realize how much doubt he used to carry inside. Around that time he got a meeting with the head of a large summer camp, and closed the deal. It was his biggest to date. Over the years since, as his knowledge and confidence have grown, he’s gradually built a clientele of solid organizations.

The big takeaway

Confidence isn’t something you can fake. It’s a byproduct of mastering knowledge, which—as the speakers at that financial trade show have proven—isn’t so much a destination as a lifelong journey. But if you don’t set off on that journey the doors to big clients will likely remain closed to you. If you’re not a natural learner, somebody who pursues knowledge out of habit, you may, like Ben, need to push yourself.

If you want to share your own story about how increasing your knowledge has helped build your confidence, please let us know in the comments section below, or shoot me an email at donald (@) freshbooks (dot) com.

Author’s note: this post is based on business owners I have coached. I’ve changed their names and some telling details.

For other stories like this step into The Cowper Files.

Donald Cowper is a Small Business Writer at FreshBooks. He’s a successful entrepreneur, an experienced coach and the coauthor of two bestselling business books—Mega-Selling and The 8 Best Practices of High-Performing Salespeople. He is also the coauthor of Breaking the Time Barrier, the popular book on how to charge what you’re really worth.

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  • globalmagnet

    Great points made above Donald…all i would add is use all the various sources available to learn. I.e. CDs, Tapes, Videos, YouTube, Blogs, Forums, Networking Events etc etc. It concerns me when people fixate on reading ‘books’ i actually think that reading a book is one of the most ineffective ways to learn. Why? Because you miss what is important amidst all of the drivel used to make the book 200 or whatever pages….Its a slow process and its difficult to remember much of what is read. Also by the time a book has been written, edited, re-edited, released, and re-released. The material contained in it, is almost always out of date.

    • FreshJustine

      I completely agree with you about the different ways we can learn – I really enjoy video courses and membership programs myself. However, I think that it depends on what you’re learning too – for me, videos are great for improving my tech skills, but I definitely prefer books when I need to absorb a complex concept.

      • globalmagnet

        each to their own i guess. i actually think that paper books days are numbered myself for the reasons mentioned above…they are going and will go the same way as newspapers…ebooks will take over, because they can be updated easily, are searchable, commentable, discussable etc etc

        • FreshJustine

          Totally agree re: eBooks, they’re fantastic! You’re probably right about paper books but perhaps that’ll only happen to certain genres… I personally wouldn’t want to read my kids eBooks at story time :)

          • globalmagnet

            I hear you, paper book are still great, i love them too, but sadly i thnk the next gen wont have the love that we oldies have…i also read my kids ebooks all the time :) try “Theres a monster at the end of this book’ or most of the Disney (Peter Pan) or Cat in the hat books, the kids love em. Its good that they can ‘interact’ with the story too, it really brings the content to life and engages their minds.

    • Donald_FreshBooks

      Thanks for adding all the other ways to learn. It’s great advice to go with what works best for you, because everyone has their own unique learning style. I personally get a lot out of mixing things up, like listening to a webinar, watching a show and reading a book on the same subject. Each medium has its own strengths and weaknesses. I remember one time watching a history documentary and feeling like I learned a lot, but later, after reading a book on the same subject, I realized that a documentary simply can’t go into the kind of complexity a book can.

      • globalmagnet

        good points once again Donald. Thanks

  • Andre Yeu

    Unfortunately, the blowhards can often get away with it in the consumer world, where a very confident phoney, “faking it”, can pull the wool over the eyes of enough consumers to grow a business. Lots of those with Dunning-Kruger in fields like personal training, therapy, and in my industry, dog training.

    • Donald_FreshBooks

      Hi Andre – sadly that’s true. And of course there are some pretty impressive fakers in the B2B world too. Sometimes they eventually get their comeuppance though. And I like to believe that real expertise wins in the end.

  • LynnP

    From the very start of your career, tithe or set aside 10% for your own professional development. This is especially essential when you are your own boss. No one is going to provide it for you so make it happen for yourself. Even if you make very little, set aside a few dollars to buy good books, attend conferences, and subscribe to great resources. Commit to keep expanding your knowledge without breaking the bank and develop a professional habit that will last a lifetime.

    • Donald_FreshBooks

      That’s fantastic advice, Lynn. In my book, that 10% investment in oneself is the best investment one can make.

      • CynicFan2

        lets see: 10% emergency fund, 10% professional development, 35% debt load payments, 35% taxes, leaves 10% for everything else from eating to paying utilities.

  • Matthew Greener

    Brilliant post! I immediately thought of another (and seemingly related) problem and that is focus, or the lack thereof. You can study every day, but if you do not have a specific focus you will not become an expert!

    • Donald_FreshBooks

      Very astute, Matthew. You’ve actually hit on a key aspect of Ben’s success that I plan to cover one day. So you kinda scooped me here :)

  • Kathy

    Great article. You can have confidence and lose it. I agree that you should continue to develop and grow. The real key to maintaining confidence and success. Thank you.

    • Donald_FreshBooks

      Kathy, quite true that you can lose confidence. I know the feeling, painful when it happens. It’s also more of a challenge these days to stay confident because the pace of change is accelerating … but, as you say, the way to get it back is to continue to develop and grow… and remain relevant.

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  • Stephen Dunn

    As somebody who isn’t confident in my area of “expertise” I found this article very informative and I can personally relate to being over whelmed by the amount of knowledge there is to attain, I’m fully aware of how little I know but never took the obvious step to “solid study” it seems obvious that the more I know in my field the easier it is to provide firm straight answers thrus increasing my confidence.

  • j

    Seek Jesus and HE will solve all of your problems, nothing else will. God Bless.

  • satheesh wilson

    nice advice!

  • Paul – Golden Financial Servic

    The truth is that it starts with mentally visualizing. Without seeing yourself reach your goals, inside your mind over and over again, the reality is that your goals will remain goals and you will not accomplish them. The confidence can be built by seeing yourself in your brain, accomplish the task at hand. You can visualize anything from seeing yourself close a big deal, to visualizing yourself doing gymnastics. If you put in the work and time, but don’t visualize, then you will be missing a key ingredient. You have to physically do whatever you need to do to reach your goals, but you also need to spend time every day visualizing.

    • Donald_FreshBooks

      Thanks, Paul — you’ve outlined a powerful combination of strategies – forming a great recipe for success!

  • Paul – Golden Financial Servic

    99% preparation, and 1% execution, equals success. If you properly prepare mentally, you can execute much easier, and you will have the added confidence that you built up in your mind. Mind over matter.

  • UberOnTime

    Learning constantly will lead you to grow in different areas of your career. Understand than you can’t know too much, so being open to new ideas can give you new meaning in your career as you develop new skills.