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The Fast Company Executive Board is a private, fee-based network of influential leaders, experts, executives, and entrepreneurs who share their insights with our audience.

13 leaders share the biggest mistakes they’ve made (and learned from)

Every professional story includes some mistakes and missteps—including the stories of successful entrepreneurs and business leaders.

13 leaders share the biggest mistakes they’ve made (and learned from)
Members of Fast Company Executive Board share their expert insights. [Image: Courtesy of the individual members.]
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Mistakes are an unavoidable reality of everyday life, including in the business world. The key to success is not perfection but bouncing back from mistakes and learning from them for the future. Some of today’s most successful entrepreneurs faced significant stumbles and setbacks before striking gold.

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The members of Fast Company Executive Board have also overcome their share of obstacles during their professional journeys. Below, 13 of them reveal their biggest missteps on the road to success. The lessons they learned from them are among the many reasons they’ve gotten where they are today.

1. NOT TRUSTING MY INTUITION

One of the biggest mistakes I have made in my professional life is not trusting my intuition. One example is when I knew it was time to move on from a career but I kept trying to fix something that was not going to change. I should have trusted my gut and known that exiting was the only option. Looking back, I wish I would have done it sooner. – Karolina Hobson, Radd Interactive

2. NOT PAYING ATTENTION TO ALL ASPECTS OF THE BUSINESS

My biggest mistake was neglecting one side of the business in favor of another. For a time, 100% of my focus was on getting to market. It wasn’t until my (incredibly amazing) co-founder had to step away due to a family death that I realized how far behind R&D was on hiring. We quickly course-corrected, and I learned that the CEO must always be deeply connected to every area of the business. – Melanie Fellay, Spekit

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3. NOT CONSIDERING COMPANY CULTURE

I once joined an organization where I was super excited about the role but did not sufficiently assess and weigh whether the culture was the right environment for the challenge and for me. Now, I coach all my mentees to do thorough due diligence on any culture they are considering joining and ensure the work they are being hired to do has sponsorship, is resourced, and has thoughtful metrics attached to it. – Amy Radin, Pragmatic Innovation Partners LLC

4. NOT PRIORITIZING MY PERSONAL LIFE

I think my biggest mistake was not having enough of a work-life balance. It’s extremely difficult to run a startup without wanting to handle all things at all times. I think I could have been better about setting a time block on my calendar in order to minimize people contacting me outside of work hours unless it was an emergency. – John Hall, Calendar

5. NOT DELEGATING

A mistake of mine has been not letting go of tasks soon enough. As the leader, it is your job to spend more time working on the business rather than just working in the business. Focus your attention on how to build and grow your enterprise and hire smart, capable people to take care of the daily grind. – Alex Husted, HELPSY

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6. NOT UNDERSTANDING THE IMPORTANCE OF FINANCIAL STABILITY

I didn’t recognize the urgency of creating financial security until I was handicapped by financial insecurity—and I was professionally and personally miserable as a result. Your goal should be to fast-track optionality so you have the ability to work and live on your terms. – Todd Miller, ENRICH: Create Wealth in Time, Money, and Meaning

7. NOT SEEKING EXPERT ADVICE

One mistake I made that could have had awful consequences was trying to save money by not hiring legal and accounting professionals. Experts in the fields of law and accounting save you money by helping you protect your business and by helping you reduce what you owe for taxes and other fees. It’s critical to get an expert opinion on legal and accounting matters, no matter how small your company is. – Syed Balkhi, WPBeginner

8. NOT BEING READY FOR EXPANSION

I underestimated how quickly my company would grow. It was difficult keeping enough inventory to fulfill customers’ orders. I also had to move three times in six months because I lacked sufficient warehouse and office space. It is important to consult an experienced analyst who can accurately track your company’s growth trajectory, even during the early stages. Also, always leave room for expansion. – Kelley Higney, Bug Bite Thing

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9. NOT PUTTING MY MENTAL HEALTH FIRST

In my early career days, external circumstances that were out of my control used to cause me a lot of stress. I have learned along the way that not only was this unhealthy but that there was so much more to gain and to learn if I focused on things that I could control, including my internal reaction to external circumstances. I am now more “Zen,” joyful, focused, and in flow, no matter what emerges. – Andreea Vanacker, SPARKX5

10. PASSING THE TORCH TOO EARLY

No one else can replace your passion as a founder, so don’t hand over the reins too early. I began an innovative educational company, and as it began to rapidly grow, I began having challenges balancing work and personal demands. I hired a replacement and breathed a sigh of relief—only to watch the financial support crumble. You can hire support, but you can’t replicate your passion and vision. – Dianne Dain, World Humanitarian Forum

11. TRUSTING TOO QUICKLY

I have sometimes been too trusting of people who didn’t have a long track record with me personally. The experiences I have had related to this situation taught me that no matter where a new contact comes from, you always have to vet anyone and everyone in some capacity. – Brad Burns, Wayne Contracting

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12. NOT TRUSTING MY GUT

We offer free migration and implementation services for new customers, which is unheard of in our industry. Years ago, I was told this was unscalable. I questioned myself and cut the service. It hurt our retention, so we reinstated the practice. Our retention jumped up and my company has grown year after year, proving that the practice does scale. – Jason VandeBoom, ActiveCampaign

13. WAITING TOO LONG TO BUILD MY TEAM

I didn’t focus on hiring and building the right team soon enough. Hiring the right team takes time and effort, and if you don’t start early, it will suck away a lot of time just when you don’t have it. – Anju Mathew, LynkCare Inc d/b/a OncoLens