The Worst Career Mistake I Ever Made: 10 Leaders Tell All and Share What They Learned

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Let their lapses from the past be your own learning opportunity.

We could all use a little advice sometimes.

When you’re dealing with a puzzling professional problem like how to have an awkward conversation with your colleague or how to ask for more money, talking to someone wiser and more experienced, who’s probably been there more than once, never fails to provide a little direction.

But just as valuable as what they would do in any given situation is what they would never do again. Some of the most significant lessons in life and work come with making a misstep and realizing what you did wrong. So we checked in with 10 super successful business leaders — from tech to healthcare to food and beyond — about the memorable mistakes they’ve made in their careers and what those experiences taught them about themselves.

Not negotiating for more

“My first job offer out of college, I was just so glad to get accepted right away. A friend in HR clued me in to the fact that they always expect you to negotiate, so leave room for that — and if it’s not salary, you could ask for more paid time off, professional development opportunities, or a commitment on a promotion schedule. Always ask!” – Kaylin Marcotte, founder and CEO of JIGGY Puzzles, a jigsaw puzzle brand promoting the work of emerging female artists

Succumbing to imposter syndrome

“There were many times I let being the least tenured professional in critical discussions drive me to second-guess myself — and keep my suggestions to myself. As a workforce, we’ve now coined this as ‘imposter syndrome,’ and I’m here to say it’s real and everyone has it. After enough times hearing experienced executives share perspectives consistent with my own thoughts, I’ve checked that instinct at the door and haven’t looked back.” – Kari Dixon, chief financial officer at air purification company WellAir

Making the easy decision instead of the right one

“In my first management role, I was tasked with building a team of nine. Unfortunately, after months of non-stop interviewing, I hired a candidate — even though I had additional questions for them. Within the first month, I realized my mistake and had a difficult conversation to terminate the employee. I learned two valuable lessons: Haste makes waste, and it’s better to spend the time sourcing the best candidate than to rush a hiring decision that may have a negative impact on your team. And once you realize you’ve made a mistake, act quickly and have the tough conversations in a timely manner.” – Quita Highsmith, VP and chief diversity officer at biotechnology company Genentech

Trying to grow too fast

“Building my first startup, I attempted to grow too fast, and it ultimately hindered the company’s growth. My team and I were building a business across four large cities, and my mentor, Marc Lore, always warned me not to expand before we worked out the economics in our first city. But I didn’t listen. I was eager to grow to block out any copycats, and I was confident my team would figure things out. But that approach drained a lot of capital and resources, leaving us very constrained. As a result, we lost some focus on the core business model in the name of hyper-growth.”– Katerina Mountanos, founder and CEO of Kosterina, a high-quality, organic brand of extra virgin olive oil

Pursuing a path without passion

“I grew up in a Persian family, which means you had three paths in life: lawyer, doctor, or engineer. But when I graduated law school at 21, I knew it wasn’t for me. As much as I loved law, I wanted to be challenged in new ways. I learned that taking a leap of faith on something you’re authentically passionate about is visible in the way you show up. Hair is personal for me — it inspires confidence — so I started Bellami Hair when I was 23 with about $10,000 and a big idea. It was just me and my co-founder at first, and I did everything from customer service to packing shipments to filing for trademarks. Today, we’ve built a multimillion-dollar business, and we’re the world’s largest hair extension brand. I’ve learned so much about the space that I’ve broadened my investments into other ventures that support women and diverse founders of purpose-driven brands.” – Nikki Eslami, founder of Wild Elements, a purpose-first platform that aims to restore symbiosis between humanity and nature

Not asking for help

“Asking for help from friends and family who have expertise in what you need for your business is so important. Now I know it’s a sign of strength to ask for help — it’s the furthest thing from weakness. I learned this after trusting my finances to a business manager who didn’t do what was needed. After just six months, my finances were in shambles. My mother has studied accounting and worked as a bookkeeper, so I swallowed my pride and enlisted her help. She quickly swooped in and guided my business back into harmony. Today, she’s on payroll — and I know I can trust her more than anyone.” – Rachel Krupa, founder of socially-conscious convenience store The Goods Mart

Picking the wrong partner

“When I decided to create my very first digital product, I shared my ideas with a client of mine, and she immediately suggested that we become business partners and create it together. I didn’t truly believe I was capable of writing, developing, and selling a product on my own, so I went all-in on this partnership. Cut to a few months later: I was doing 80% of the work and paying my partner 50% of the proceeds. When I tried to open a dialogue about a more equitable agreement, I received a response from her newly hired attorney. Ultimately, she stole my intellectual property. I had no choice but to sue her. Three years and six figures in legal fees later, we finally settled, and I got 100% ownership of my product. I learned that I need to trust myself, that I am absolutely capable of creating and launching products on my own, and that I will never let imposter syndrome push me into an unfair partnership again.” – Rachel Rodgers, CEO of Hello Seven, a coaching firm for female entrepreneurs looking to take their business to the million-dollar mark

Trying to do too much

“As an entrepreneur starting out, you have to do a little bit of everything and wear many hats. While growing my business, letting go and delegating is one thing I wish I did more of — and earlier on — as opposed to getting to an almost burnt-out point, where work no longer becomes enjoyable. Asking for help is OK, and you don’t have to (and can’t) do everything yourself.” – Elisa Marshall, owner of the French bakery Maman

Not recognizing valuable feedback

“During your career, you’ll frequently receive feedback on your communication and leadership style. In a male-dominated industry, it was sometimes difficult for me to understand if the coaching was meant to encourage me to be more like my male counterparts versus making me more effective and allowing me to be authentic as one of the only female leaders on a team. As I gained experience and confidence, I realized the feedback was valuable, especially in terms of effective communication. While I remain authentic, I wish I had incorporated some of the feedback earlier in my career.” – Jeannette Bankes, president and general manager for global surgical franchise at eye care company Alcon

Not standing firm in my beliefs

“All of my memorable mistakes have been characterized by the same thing: I tried to ‘go along to get along’ rather than holding to my beliefs. I’m much better now at pausing and challenging myself to think of how I’ll feel the next day if I compromise too willingly.” – Marna Borgstrom, CEO, Yale New Haven Health and Yale New Haven Hospital