16 Entrepreneurs Discuss on Whether Mistakes or Failure Have Affected Their Success

Business fails are the best form of learning. Hiring an expert or a coach to walk you through establishing your business can help you minimise the chances of failure but some entrepreneurs will prefer walking alone. Whichever path works best for you, you’ve got to be comfortable with failure and most importantly learn how to improve or deal with it. Don’t be too hard on yourself for the failures and don’t give up yet.

We asked entrepreneurs and business owners on whether mistakes or failure have affected their success and here are the responses.

#1- I've learned more from my mistakes

Photo Credit: Jason McDowell

You can't run a business without making mistakes. Sometimes those mistakes are bigger than we care to admit, but we make them all the same. While big mess-ups in business can be discouraging and sometimes result in large setbacks, you have to push forward. I've learned more from my mistakes than my successes, and truthfully would not be as successful today without them. While it is possible to make mistakes large enough to run your business into the ground, this situation is unlikely. True failure, that is, giving up on your business is almost always a choice the owner makes. In those moments, it's crucial to check your reasoning and make sure you aren't quitting because its the easy thing to do.

Thanks to Jason McDowell, Wayzata Dental!

#2- Taught me how to live lean

Photo Credit: Phil Strazzulla

One of my biggest failures is that I was laid off from my very first job out of college when working at an investment bank during the recession.  It took a year for me to get another job.  But, that year taught me how to live lean, a requirement when getting a new business off the ground – something I've done twice.

Thanks to Phil Strazzulla, SelectSoftware!

#3- Powered my level of connectivity

Photo Credit: Kent Lewis

The first error I made in building my business was focusing too much on process and tools and not enough on the people. As a result, I became disconnected from my team as far back as 2010. It took a few years to manifest, but a wall began forming as trust and respect eroded on both ends. As I took on the account management role recently, attitudes began to change immediately. Working directly with my employees provided me insights into their brilliance, struggles and perspective. I was able to appreciate their commitment and craft and the feeling was reciprocated. My team appreciated my ability to manage client expectations while supporting and protecting the team. After my first client call as account lead a few months ago, I received a compliment from a coworker that set the tone: Kent, you accomplished more in that one call than the previous account person did in the past year. Thank you. That single compliment erased all of my reservations about my new role and inspired me to take our account management capabilities to new levels. The experience was similar for our other two executives relatively new to their roles as account leads. Suddenly, there was a new and powerful level of connectivity, respect and admiration amongst the account team and discipline experts at Anvil.

Thanks to Kent Lewis, Anvil!

#4- Taught me a lot of things

Photo Credit: Chhavi Agarwal

As a blogger, it is important to have different streams of income – ads, affiliate marketing, digital product etc. While i was still learning affiliate marketing, email copy etc, I rushed into launching my first digital product.It was a disaster. For 2 months, no one bought a single copy! After a few days, I received an email from a reader informing me that the payment gateway does not work and she is unable to buy. I rushed to fix it but in the next 2-3 weeks, I took it off the shelf. This fiasco taught me a lot of things. For example, need of segmented list, the importance of having conversations with your subscribers, testing out the entire funnel, etc. I am working on all of this and next month, plan to launch a couple of products. This time around, all is planned and well thought out. As an entrepreneur, you need to remember that every failure or mistake has tonnes to teach you. Do not waste your mistakes – learn from them and move ahead with a corrected plan.

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Thanks to Chhavi Agarwal, Mrs. Daaku Studio!

#5-  Made a way to my best years ahead

Photo Credit: Meredith Atwood

In 2017, I experienced the worst year of my life—both professionally and personally. I had leapt out of the legal profession as an attorney to be an entrepreneur. I watched, helplessly, as things completely out of my control caused utter destruction to my best-laid plans. I was left sitting with nothing. I had given up my lucrative paying legal job—for what was now gone. I didn’t sleep for weeks and then months. During these dark times, though, I learned that I had to build, start over, ask myself the right questions—and not look back. It took great restraint not to go back to the law(what I knew), but to continue on the path forward (what I knew I needed)even though I had to start over. Now, almost two years, a booming podcast and not one–but two!–book deals later, I know with all of my heart that the destruction was the best thing that could have happened to me. In the theme of Ryan Holiday’s, The Obstacle is the Way, I often say—that worst year of my life was completely the way to my best years ahead.

Thanks to Meredith Atwood 

#6-I took most mistakes and failures as indictments against me

Photo Credit: Terrell L. Strayhorn

As a business owner, I once operated in a way that mistakes and failures negatively affected my performance and success, not just individually but even company-wide. For instance, I used to let small mistakes–tardiness to a meeting, being double-booked, a typo on a company flyer, or small turn-out for a company event–negatively affect my mood, motivation, and mindset. I wouldn't just beat myself up (although I did that a lot), but I would also let minor mistakes and disappointments become major frustrations and near-global threats to our productivity, success, and existence. At that time, a single email from one client complaining about not getting a call back from a staff member would drain my attention, cause me to issue a company-wide email, call a staff meeting and stress the importance of timely communication with all clients. In such settings, however, my staff would ask me questions that revealed the problem with my approach: Who did they call? Was it the right number? What did they need? Why didn't you acknowledge the 100's of other calls that we did return? Usually I didn't know the answer to these questions because I did not ask or investigate–I took most mistakes and failures as indictments against me and my leadership, my team and their abilities, the company and our capacity to compete. I was leading with the wrong mindset, one that gave little room to mistakes, failures, growth, and development. With help from books like Carol Dweck's Mindset and other experiences, I replaced that approach with a growth frame that saw mistakes and failures as opportunities to learn, grow, and change for the better. This has helped me now see how mistakes/failures positively affect my success–they help make me and my company better.

Thanks to Terrell L. Strayhorn, PhD, Do Good Work Educational Consulting!

#7- Pushed back my success

Photo Credit: Lucy Harris

When I was first writing up my business plan, I made a mistake with filling in a few areas simply because I didn't take the time to read and acknowledge the section properly. I had to restart the plan and pay closer attention the second time around so I wouldn't make the same mistake again. This didn't affect my success too badly, it only pushed it back as I had to take the extra time to refill in the plan. Another time, I failed and it impacted my success for a while. I was looking into expanding my horizons and I failed to meet the requirements of one of my clients that were going to help me do so. This affected my self-esteem a lot as it prevents my expansion, as well as impacted my overall potential. However, I was able to overcome it over time and look where I am at now. Everything happens for a reason and taking your failures and mistakes as a grain of sand is the best way to handle the situation because everything will continue to evolve over time, in the end, you might be surprised.

Thanks to Lucy Harris, Hello Baby Bump!

#8-Learned on hiring well the first time

Photo Credit: Paige Arnof-Fenn

Mistakes make you smarter and teach you lessons in a deep way that success never can. I started a global marketing and branding firm 18 years ago and my biggest mistake was not realizing sooner that the people you start with are not always the ones who grow with you. The hardest lesson I learned when I started my company is not getting rid of weak people earlier than I did in the first few years of my business. I spent more time managing them than finding new customers. I knew in my gut they were not up to snuff but out of loyalty to them, I let them hang around much longer than they should have. It would have been better for everyone to let them go as soon as the signs were there. They became more insecure and threatened as we grew which was not productive for the team. As soon as I let them go the culture got stronger and the bar higher. A team people like to be surrounded by other stars. It is true that you should hire slowly and fire quickly. I did not make that mistake again later on so learned it well the first time. I wish I had known it even earlier though but lesson learned for sure!

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Thanks to Paige Arnof-Fenn, Mavens & Moguls!

#9-Created real conversations

Photo Credit: Lauren McManus

My biggest failure in business resulted in my biggest success. When I first started my business with my partner Alex in the health and wellness space, we made the fatal mistake of making it all about us. The good thing about that mistake is that even though it leads to zero product sales and more expenses than income, it created real conversations. We started to get to know our audience, and see what was really resonating with them. The posts on our website that were getting the most traction helped us nail down our ideal clients, and develop a monetization plan that actually worked. We figured out the needs of our audience, and then gave them exactly what they wanted. Before we knew it, we earned that elusive six figures within the span of 12 months. These days we make that or more every single month, and we do it by continuing to listen to our audience and delivering the products they need. We're so grateful for our massive failure because it showed us how important it was to make our business about our audience. Now we have two websites that serve two very different audiences, but the goal has always remained the same. Ask people what they really want, and then
give it to them. That truly is the biggest key to success.

Thanks to Lauren McManus, Create and Go!

#10- Hit rock bottom

Photo Credit: Carlos Hidalgo

The biggest mistake I made in my first business, is that I made it the most important thing. I was obsessive about the company growth and it truly became the center of all things at the cost of my relationships, my marriage and my personal health. As a result, I hit rock bottom and ended up leaving the company I co-founded 12 years prior. Since that time, I have been able to learn and began a second company with a different focus and purpose and am happy to say we are thriving, my relationships and marriage is better than ever and I have a better balance and healthy focus. While I never want to make that mistake again, I am glad to know I have learned from it and have a chance to build a company the right way and help others do the same.

Thanks to Carlos Hidalgo, VisumCx!

#11- I've learned two things

Photo Credit: Matt Secrist

Mistakes and failures have undoubtedly affected my success as an entrepreneur/business owner. In fact, some of my regrets in business are just that I didn't make certain mistakes sooner! That being said, making mistakes is only half the equation. Without the drive to learn from and prevent those mistakes from happening again, you're just setting yourself up for future disasters. Use your failures to literally make your business better. For every mistake I make, I've learned to double down and created processes/policies/procedures to avoid making those mistakes going forward. Also, there's a lot of wisdom in learning from the mistakes of others. Take time to read business books and reach out to other entrepreneurs for help. You'd be surprised at how many people out there are happy to share their experiences and spare you some stress, headache and potential revenue loss.

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Thanks to Matt Secrist, BKA Content!

#12- Significantly improved my business over the years

Photo Credit: Andrew Hansen

I'm someone who can confidently say that mistakes have significantly improved my business over the years. I have better accounting procedures only because I got accounting wrong once, and paid the price. I have a great business partnership only because I managed a previous partnership poorly. I find failures not only give you the information about what not to do next time but the pain that motivates you to avoid the same scenario next time. If you compare it to sports, where success or failure can be decided in a split second, results in business happen in slow motion. You always have time for deliberation in business, and so a storehouse of information from past failures is a tremendous asset that can always be drawn upon.

Thanks to Andrew Hansen,!

#13- Halted the growth of my company

Photo Credit: Tara Smith

Being a small business owner there will always be times when one makes mistakes. The biggest mistake I've made was thinking that I could do all things in my business. I was everything from the baker, cashier, accountant, social media manager, janitor, etc. As a result of this mindset, it halted the growth of my company tremendously. I have since learned to allow creatives that specialize in certain areas of my business to assist me and I've seen things change for the better. Now I am free to focus on what I do best…creating baked goods, which brings in the money to aid in the continued growth of my company.

Thanks to Tara Smith, The Cupcake Queen!

#14- We now see the warning signs much earlier

Photo Credit: James Lloyd-Townshend

My mantra for success is pretty straightforward: grab every opportunity, but take measured risks. A few years ago we decided to pursue a new recruitment market using our incubator brand, FRG Technology Consulting. Twelve months on, we realized the market just wasn't working for us. It just didn't tick enough of the boxes. The product had a partner channel, which was incredibly important to us. It was a candidate-short market, which is also a big win for us as it means there's a clear demand for a recruitment agency. But crucially, the product wasn't ‘mission-critical' for businesses, and, in turn, neither were our services. We now see the warning signs much earlier, allowing us to refocus on what we're good at and work towards our mission statement. Running a company is about having a clear vision of your destination and knowing when to innovative without trying to boil the ocean. Always lead from the front but listen to your employees and the market around you.

Thanks to James Lloyd-Townshend, Frank Recruitment Group!

#15- I believe in learning from the mistakes

Photo Credit: Michael Stahl

I am fortunate to lead and work with a tight-knit team and we celebrate our wins and learn from our mistakes. And we do make mistakes – and that's okay. I am not the kind of leader who yells at someone if they do. I believe in the ‘Edison process, whereby we might try one hundred things and see if just one will work. That's how we learn, grow, adapt and improve.

Thanks to Michael Stahl, HealthMarkets!

#16- Hindsight is always 20/20

Photo Credit: David Reed

In looking back, I recognize that my strength is networking and building connections. But one of my weaknesses is the administrative and clerical side of the business. It was a big mistake to not consider hiring a part-time administrative assistant or a virtual or assistant to help me keep my contracts and organized. If I would've had that assistant, I could have been a lot more organized. Even to this day, two years into my business, we're still trying to get a lot of our contacts and our contracts organized, especially now that my business is growing so fast. I feel like we’re still playing catch up with even our initial deals. Overall, I don’t feel like we’ve made a lot of mistakes in our business, but not hiring someone for administrative work is one of them.

Thanks to David Reed, Assured Senior Living Solutions!

Has mistakes or failure affected your success? Tell us in the comments below. Don’t forget to join our #IamCEO Community.

Mercy - CBNation Team

This is a post from a CBNation team member. CBNation is a Business to Business (B2B) Brand. We are focused on increasing the success rate. We create content and information focusing on increasing the visibility of and providing resources for CEOs, entrepreneurs and business owners. CBNation consists of blogs(, podcasts, ( and videos ( CBNation is proudly powered by Blue16 Media.

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