My First 5 Mistakes as an Entrepreneur


I rarely tell the story of one of the most embarrassing moments of my life, but I think I’m far enough removed from it that I can share a good chuckle without wishing I were dead. When I was about 19 years old, I went to a high school football game with a friend whose boyfriend was on one of the teams. She naturally knew quite a few people and was introducing me around when one guy said something to me that I interpreted as, “Can I have your phone number?” Six words, seven syllables. Since I had a boyfriend at the time, my circa 1990s reply was, “I already got a man.” After an awkward pause in the group, she pulled me aside and informed me that all he said was, “Hi.” One word, one syllable.


“Oh, I’m so embarrassed!”

Since jumping into the entrepreneurial pool, I’ve continued to make mistakes that – while much less mortifying – have made me shake my head and think, I can’t believe I did that. Jane Porter of says that “pointing out your own missteps…can be illuminating for readers,” so thinking back, here are five early mistakes that cost me in time and lost productivity.

1. Not having a clearly defined niche. Yes, I know that all the books and blogs and articles and experts say that this is one of the first things you should do when starting a business. I only knew what industries I didn’t want to focus on, but I felt that defining a niche would put a wall up and limit potential business. Well, let me tell you –you want that wall. You need that wall.

One of my first trips out to promote my business was at a general networking meeting. While I met some supportive entrepreneurs who were further along in their small businesses, most people had the same agenda – to sell their services but not be sold to. Plus, the range of represented industries was so varied that the one person who seemed partly interested in my services was from an industry that I had no knowledge of. Listening to him explain his business nearly sucked the marketing enthusiasm out of me. I just couldn’t wrap my mind around what he was saying. Huh? Are you asking for my phone number?

In his book, How to Start a Home-Based Web Design Business, Jim Smith illustrates how being successful in his particular industry requires access to a diverse set of skills, whether you possess them yourself or have access to a large talent pool. If not, you should focus on one niche market and become an expert in that area. Smith notes, “This will allow you to concentrate on a smaller market while building your skills in sales (or insert your own deficient skillset).”

2. Not making a “real” version of my business plan. My first business plan was all fluff. I drafted it while taking a continuing education course at a local college, and instead of treating it like the business roadmap it’s supposed to be, I wrote it like an academic assignment. Again I’ll reference Smith who details how to write an honest, navigational business plan to keep yourself on track. He then advises readers to have a second, more upbeat (but still honest) version if you need to sell your idea or secure financing.

3. Cold calling. I’ve done some cold calling in corporate environments that didn’t just entail dialing for dollars but actually dropping by prospects’ places of business with no prior appointment. So I took this sophisticated Fortune 500 training with me in my own business attempts. The good news is that the humiliation was never as bad as that high school football game, but it was counterproductive to effective lead management and to maintaining the level of confidence I needed to keep pushing forward.

I realize that cold calling is sometimes necessary, but do some prep work beforehand. Research your prospects to get an idea of their needs, and be prepared to manage concerns and objections. Some people are just naturally gifted at cold calling and sales, but if you don’t have that alpha personality, find your strength in a related task such as building and nurturing relationships. You should also add it to your IMC mix so that your prospects already have a general idea who you are.

cold calling cartoon

4. My first client. While this was technically a practice job, I was overzealous in agreeing to build an ecommerce site when I had never done an ecommerce site. I didn’t realize that such a task involves more than just figuring out the technicalities. There was the 200+ inventory that would change every season, and the shopping cart and batch upload method I chose was too complicated to hand off to the client. Plus, I found out through a third party “buffer” that the client didn’t understand most of what I was saying. I didn’t know how to turn off the jargon. I didn’t know I was speaking jargon. It was a mess, but I’ve since learned about managing the process (versus just the work) through some of the readings and discussions in IMC courses like Visual Information Design and Creative Strategy and Execution.

keep calm and try again

5. Fear of failure. Once in another life, a friend and I went to a Prince concert, and one of the stage crew asked her to go up on stage to dance alongside The Artist. She replied that she would only go if I could go with her. The crewmember agreed, and then they both looked at me as if to say, “Alright, let’s go.” I don’t know how many actual seconds went by, but I completely froze as a series of random what if thoughts ran through my mind. I finally managed to shake my head to say “no,” and the moment was gone. (As a side note, I don’t regret that decision because every girl who went up there was completely star struck and could barely move anyway.)

What was surprising was that I could actually be paralyzed by fear. Since starting my business, I’ve read and heard many encouraging articles and messages that remind me not to let fear paralyze me with inaction. I’ve mostly tried to heed this advice, but the mistake I have made is sometimes allowing fear to bubble just underneath the surface. By doing this, I was able to function, but when obstacles arose, I would get discouraged and give up. Be aware of this type of fear – it may not paralyze you but will set you up as a straw house that will crumble at the first sign of trouble.

In 7 Key Lessons from The $100 Startup, Chris Guillebeau says, “Failure is overrated. Many of the unexpected entrepreneurs I met had experienced numerous false starts and made plenty of mistakes….In event of initial failure, they were able to regroup and give it another go.”

Let’s let failure be part of the process. Get out there, make mistakes, fail, learn from it, and begin again.

What mistakes have you made in business? I don’t want to be the only one oversharing, so I’d love to hear some other examples of mistakes made and lessons learned.

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4 Responses to “My First 5 Mistakes as an Entrepreneur”

  1. Kevin G. Hart Says:

    Fear of Failure is my biggest challenge to overcome and if I’m not careful it will stop me dead in my tracks. Thanks for the excellent advice.

  2. Kristi Hansen Says:

    Love the candidness! One of my fave books, “The Icarus Deception”, speaks all about failure and the art of embracing it in order to find your niche. “It’s unlikely that you’ll create something scarce without doing something risky to get there.” – Seth Godin

    As for me, I haven’t tried anything yet. But I will…

    • Kris Prendergast Says:

      I just read a preview on Amazon. Wow. Here’s another great line – “Maintaining the status quo and fighting to fit in no longer work, because our economy and our culture have changed.” – Seth Godin.

      This looks like a must read. Thanks for the recommendation!

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