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4 Professional Speakers Share Their Biggest Business Mistakes and Missteps


I don’t know anyone in business, myself included, who has not made business mistakes. As we all know, some mistakes are more costly than others but all can leave us feeling somewhat defeated and set back on our journey to success. I recently reached out to four professional speakers and business owners and asked them to share their biggest business mistakes and missteps so we can use each as a lesson on what to think about in our own businesses.

On the Kolbe Index, an assessment that helps you understand your natural instincts and behaviors, I rate a nine (9) on Quick Start. This means that I have a tendency to dive right into a project before mapping out the entire strategy (I can hear my team laughing as I divulge this). Now that I know this, I can stop myself before diving in so I can avoid mistakes, blunders, and missteps.

Despite being cautious, the reality is that sometimes you are going to spend time and money on things that don’t pan out. Here are four stories of mistakes and missteps from real folks that will hopefully allow you to pull back the reigns and check in with some of your strategies before hitting the “GO” button.


Joe Calloway is a very successful speaker who helps great companies get even better. He shares this story on how he got caught in the web of ‘everybody’s doing it.’

joe calloway“A few years ago I spent a few hundred dollars to be listed on some website that was designed to give exposure to speakers. Usually, I do not look twice at scams like that, but I saw that a number of well-respected speakers I knew were doing it, so I jumped in. Total waste of money. It turns out that we all took a chance on it because others were taking a chance on it. Big mistake.”

I suspect Joe is not alone. Many of us become swayed and make decisions based on the fact that “everybody’s doing it,” so here’s a question to help you think about it.

COACHES QUESTION: Even if others are doing it, is this strategy right for me?



Greg Hawks is a corporate culture specialist. Here’s his story on misspent advertising:

Greg Hawks“Generally speaking, when it comes to marketing, I am relatively frugal. I spend money in two ways: Building a website and speaking at select SHRM Conferences that I pay travel/lodging expenses to be there. Since speaking is my best marketing, doing non-pay sessions to audiences that are potential clients has worked out for me. However, in January of 2016, I thought I would try utilizing Facebook ads. I created six 1-2 minute videos of me talking about what we do, how we do it, some of our messages and philosophy.

Fortunately, my son is gifted with a camera and editing. There were no production costs unless you count the years of investment I have made in him as a human and the 27” Mac, Adobe Creative Suite, Canon 70d and 50 prime lens we already owned.

I enlisted a local marketing firm to put a 6-week campaign in motion. We targeted Meeting Planners, HR Pros and CEO’s in a couple of areas I would be speaking in the near future. The whole thing was a bust. I spent $1250 for the marketing company and $750 on the Facebook ads and generated zero leads. The only new Facebook likes/friends we gained were scary people. It was disappointing.”

No doubt Greg is not the only person to dive into Social Media spending as it is becoming more and more popular. However, we have to wade in slowly.

COACHES QUESTION: Have I tested my idea and strategy before going all in financially?



Linda Miles is a successful businesswoman, speaker, and consultant who operates a Tele-Consulting & Coaching business. Here is her costly story about getting caught by not paying attention to details.

Linda Miles“I have had several mistakes including leaving our book price off the brochure to market my first book (20,000 copies). Later, we accidentally scheduled a Sun Fun Seminar for dentists and teams at a fabulous resort in South Carolina only to learn another big NC/SC Convention we did not know about was the previous weekend. The penalty: $12,000 Cancellation fee and about $20,000 marketing costs down the drain (brochures design and printing, postage and ads in dental journals).”

Linda’s mistakes were more costly because she had a larger operation. Ouch!

COACHES QUESTION: How can I stop and think through my project from all different angles before putting any investment on the line.



This is my own story about the price I paid by taking on a client who I knew wasn’t going to be a good fit.

It is never a good idea to take on a client who is not a perfect fit. I, however, had to learn this lesson twice on the same client.I had briefly worked with the client years ago, and it just wasn’t a good fit, so we cordially ended the relationship and went our separate ways. When the same client circled back the second time to join one of my groups, I was aware and was cautious, but thought perhaps things had changed and decided to give it a chance. It was too late by the time I realized I had made a mistake.

For speakers, this might look like you realizing that you are in front of the wrong audience while standing on the stage in front of them. I realized my mistake during the live kickoff event for my group, gave the client a full refund of $14,000, and we parted ways. It was a lesson that I hope I never have to learn again.

COACHES QUESTION: Is this client or idea the right fit for me (really) or am I being swayed by the income?


Have you made a big mistake in your speaking business that you’d like to share? Please do so in the comments below so we can all learn!

See you soon, Wealthy Speakers!

Jane Atkinson

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