Failures as Stepping Stones: 18 Business Leaders’ Lessons Learned in Early Career
We asked eighteen professionals, including CEOs and founders, to share the most valuable lessons they learned from early career mistakes or failures. Their insights range from the importance of delegation as a key to avoiding burnout to the necessity of discernment to prioritize quality over quantity. Dive into these profound lessons that have shaped their professional growth.
- Delegation as a Key to Avoiding Burnout
- Effective Communication Preventing Misunderstandings
- Planning for Success in Business Ventures
- Authenticity Over Flattery in the Workplace
- Mastering a Skill Over Spreading Thin
- Recognizing Your Worth in Salary Negotiations
- Open Mind and Trust in the Process
- Company Culture as a Business Imperative
- Clear Communication for Successful Projects
- Protecting Team Culture Over Toxic Clients
- Persistence and Timing in Startup Success
- Scaling Business Sooner for Growth
- Waiting for Great Opportunities, Not Forcing Growth
- Using Judgment and Taking Responsibility
- Authentic Leadership Gains Trust
- Charging Your Worth from Client’s Perspective
- Confidence and Poise in Communication
- Discernment for Prioritizing Quality Over Quantity
Delegation as a Key to Avoiding Burnout
In the early stages of her career, I made a significant mistake: I spread myself too thin. As an enthusiastic entrepreneur, I wanted to do it all—marketing, sales, product development, and customer service. I believed that being hands-on in all aspects of my business was critical to its success.
This approach led to burnout and affected the overall productivity of my business. The valuable lesson I learned was the importance of delegation. Recognizing the strengths of my team members and trusting them to carry out tasks allowed me to focus on my areas of expertise and strategic planning.
This shift not only improved the business operations but also fostered a culture of trust and empowerment within the organization. This experience profoundly shaped my leadership style and continues to inform my decisions as a business owner today.
Caroline Bogart, Founder, Writer, Course Researcher, Health Enthusiast, Tech Expert, The Carol Report
Effective Communication Prevents Misunderstandings
Early in my career, the most invaluable lesson that greatly shaped my professional growth was realizing how critical effective communication is. There was an instance when, while caught in a mountain of tasks of different urgency levels one week, I failed to communicate project statuses and delegate responsibilities clearly to my team members. This resulted in misunderstandings on task progress, task ownership, and significant delays that hindered another team’s progress on other projects.
I’ve since learned from my mistake and have actively worked on improving my communication tactics by making communication channels transparent and efficient. For example, I got into the habit of creating a task sheet for all involved parties to access, with broken-down tasks and deadlines, as well as setting a general reminder weekly about what needed to be accomplished by a particular date.
I must admit I’m still working on honing this skill, but it has since become central to my success.
Sebastian Morgan, Senior Content Specialist, CV Genius
Planning for Success in Business Ventures
Let me tell a story that still makes me wince to this day.
Early in my entrepreneurial journey, my friend and I caught the “get-rich-quick” bug and thought a dumpster rental business was our golden ticket. With stars in our eyes and a bank account brimming with enthusiasm, I threw down $27,000 on a diesel truck. Here’s the kicker: I knew zilch about diesel trucks, and $11,000 went into immediate repairs after the purchase.
We were so eager to dive in, and our game plan was, embarrassingly, to “learn as we went.” Now, don’t get me wrong, I’m all for doing and not being a “wantrepreneur.” But there’s a saying I’ve come to cherish: plan for success. Sure, planning isn’t doing, but if you’re shooting for the stars, you’d better have a roadmap (that you can adjust along the way).
The loss from that impulsive venture? It stung. But it reshaped how I approach every subsequent business move. I learned to marry my passion with prudence.
Dive in, but with a lifejacket of preparation.
John White, MBA – Owner, White Fox Cleaning, White Fox Cleaning Services
Authenticity Over Flattery in the Workplace
I was a newbie in the organization, trying hard to fit in. I noticed some employees paying a lot of personal and professional compliments to this one manager, who seemed to enjoy the attention a lot. I thought this was how things were done, and I must learn to pay compliments, too.
The first time was great. The second time was fine too. But keeping this up three to four times a week was hard. I couldn’t do it. It didn’t feel genuine, and my compliments started to feel shallow. One day, a senior colleague, who had observed me, told me not to try so hard to get on anybody’s good side.
She said paying compliments might help me in the short run, but over time, it would destroy my character and reputation. She advised me to put my head down and work hard. The right people, the people who truly mattered, would notice me. She asked me never to do anything that made me uncomfortable.
I had my first lesson on authenticity and the importance of being yourself. A lesson I never forgot.
Swetha Sitaraman, Thought Leadership, Vajra Global Consulting
Mastering a Skill Over Spreading Thin
Early in my career, I was so obsessed with being successful that I ended up spreading myself too thin across too many projects. In other words, I was trying to prove myself to all my colleagues and managers by always taking on more responsibility.
However, I realized over time that I wasn’t really developing any skills or expertise, and that I was continually falling short on projects because I was constantly overextending myself. Instead, I learned that in order to be successful; you need to focus on one particular skill or category and really master it.
That is how you truly flourish in your craft. You need to be focused and develop an expertise in a particular niche or category that makes you valuable to your organization.
Mathias Johansen, Co-Founder and COO, Guide2Fluency
Recognizing Your Worth in Salary Negotiations
Early in my career, I learned a valuable lesson about self-worth. I used to be naïve enough to think that companies would at least “show” that they had my best interest at heart. But as we all know, the reality was and is different. Despite having the same qualifications as a colleague, I learned they were getting a higher salary. I learned that companies don’t always act fairly unless you try to force their hands.
I spent too much time second-guessing myself, unintentionally giving my employer leverage over me. The true turning point came when I received an offer with a better salary and improved work-from-home conditions. Only when I handed in my notice did my current employer counter with a competitive package. This was when I realized I hadn’t recognized my own worth until I had another offer to confirm it.
The lesson here for me was always to know your worth and never settle for less. Your value isn’t determined by one employer but by the market and, most importantly, by yourself.
Andreas Grant, Founder, Networks Hardware
Open Mind and Trust in the Process
The most valuable lesson I learned was the importance of keeping an open mind; there is more than one way to reach your goals. I vividly remember the disappointment of not matching at my number-one spot for anesthesiology training. It was a tough pill to swallow.
As life unfolded, I found myself becoming a parent during my training, which wasn’t planned. Where I ended up for my training was a far better place to raise children than my top choice. The program was not only excellent but also located in a more family-friendly and cost-effective area. It became clear that life had a different, more suitable path for me.
This experience taught me that when life doesn’t go as expected, it’s vital not to be discouraged. In retrospect, I realized that everything was happening for my benefit, even if I couldn’t see it at the time. This valuable lesson has since shaped my professional growth by instilling in me the importance of resilience, adaptability, and trust in the process.
Elisha Peterson MD, MEd, FAAP, FASA, Anesthesiologist and Pain Medicine Physician, Elisha Peterson MD PLLC
Company Culture as a Business Imperative
In the early days of EchoGlobal, we overlooked the importance of a robust company culture. We were hyper-focused on metrics, often neglecting the human element that’s crucial in the recruitment industry. This approach led to high employee turnover and suboptimal performance.
The lesson was eye-opening: culture isn’t an HR checkbox; it’s a business imperative. That experience significantly shifted our approach, making us prioritize people equally with performance. Today, our culture is one of our most potent competitive advantages, driving both employee satisfaction and client success. This was a foundational lesson that I consider invaluable in my professional journey.
Lou Reverchuk, Co-Founder and CEO, EchoGlobal
Clear Communication for Successful Projects
A mistake taught me to communicate clearly. Early in my career, I was handed a small project to manage. I was enthusiastic but naïve, diving right into the tasks at hand without thoroughly discussing the project’s objectives and expectations with my team. The fallout from my oversight became apparent when the project deviated from its intended course, culminating in a final delivery that missed the mark with the customer.
This mistake was a harsh but invaluable tutor. It highlighted the critical importance of clear communication and a thorough briefing before embarking on any project. I realized that the zeal to get things moving should never overshadow the need to ensure everyone is aligned. The absence of a shared understanding led the project down a rocky path, a predicament that I could have avoided with clear communication.
Zames Chew, Co-Founder, Repairs.sg
Protecting Team Culture Over Toxic Clients
I was leading a small team to produce a project for a toxic client—the warning signs were there, but we didn’t have the experience to recognize them. The final work was being completed by a colleague and, upon delivery, that team member received the most insensitive and offensive feedback.
My response was to mediate and keep both sides amicable; after all, the income for the business had to be protected. However, this only empowered the toxic client, while negatively affecting the confidence and work life of my colleague. It wasn’t long before that colleague left the company in fear of a repeat situation.
Ultimately, this made me realize that your team and the company culture is more important than appeasing a toxic client. I am now very sensitive to how clients speak to my colleagues, and we are less tolerant of negative language. We need to show our colleagues that they are protected, and this, in return, bolsters confidence and a positive work culture.
Ryan Stone, Founder and Creative Director, Lambda Films
Persistence and Timing in Startup Success
I had two failed start-ups early in my career. While their failure was frustrating and demoralizing in the moment, I look back at them as crucial experiences that taught me valuable life lessons. I learned the hard way about the importance of persistence and timing. I learned how to put myself out there and take calculated risks.
On the more tangible side, I learned how to create long-term business strategies that are sustainable and pursue an aggressive strategy for early growth. These are lessons that I carried while founding my current company, which has, in turn, found huge success and that I recently sold for about $1.1 million.
Adam Shlomi, Founder, SoFlo Tutors
Scaling Business Sooner for Growth
The biggest mistake I made in the beginning of this company was not hiring and scaling sooner. I was in a routine that was easy to manage because I was the sole person responsible for everything that wasn’t outsourced.
It was comfortable. However, I was booked six months in advance for a couple of years, and regularly turned down work. I could have hired and scaled the business two years earlier than I did. Comfort is overrated. Do the uncomfortable thing. It’s the only way to learn.
Rick Berres, Owner, Honey-Doers
Waiting for Great Opportunities, Not Forcing Growth
One of the biggest mistakes I made in my professional career was forcing growth, not permitting myself the time to think through decisions, or even letting “good” opportunities pass by in order to wait for the great ones.
One example is when I moved a business location rather than shutting the underperforming store down entirely. The amount of effort and resources allocated to this move cost our company dearly, and the store performed nowhere near our expectations.
Jason Vaught, Director of Content, SmashBrand
Using Judgment and Taking Responsibility
I picked up this lesson in my first month on the job. It’s all about using your judgment, even when you lack experience. It stems from my early job experience, where I strictly followed a given template.
In my first week using that approach, I made a costly mistake for the company. While it did uncover flawed processes that needed discussion, I realized that at that moment, despite everyone else’s assurances, I had a gut feeling that something was amiss.
Regrettably, I trusted my more experienced colleagues more than my instincts. This experience later taught me that some people prefer an easier way of doing things, which may not be right for you. It’s vital to draw your own conclusions, analyze situations, make decisions that you believe are correct, and take responsibility for them.
Nadia Katrich, CEO, Appska
Authentic Leadership Gains Trust
When I first stepped into leadership, I was told, “Adjust your style to suit those who report to you.” Twelve months later, I had terrible ratings as “a leader that treated everyone differently,” and therefore wasn’t trusted. I quit leadership as a result of this devastating feedback but was slowly drawn back into it, this time determined to be myself—always.
This lesson was really hard, but really important. Be authentic, or be untrustworthy. As a leader today, I adjust my expectations—but never my style.
Rebecca Houghton, CEO, BoldHR
Charging Your Worth from Client’s Perspective
Charging my worth from the client’s perspective. As a new freelancer, my major priority was getting clients. This meant working with their budgets and maintaining an “hourly-rate” mentality. This worked well at first because it gave me enough momentum to quit my day job. But over time, I realized I was leaving thousands of dollars on the table by not recognizing the value I brought to my clients’ businesses.
Today, I approach pricing from a place of value, not just what I need to make per hour. This means thinking about what the project is worth to the client, especially if I’m saving them time and money or helping them gain new clients.
Alli Hill, Founder and Director, Fleurish Freelance
Confidence and Poise in Communication
In my third year of college, I qualified for a summer internship with a major Fortune 500 company. I worked hard and learned a ton in those three months. On the last day of the internship, however, the entire group of interns met in Dallas to give a 15-minute presentation about our accomplishments over the summer.
It should have been very easy. But when I walked into the room, I recognized the other interns. Each of their bosses was also in the room—and their bosses’ bosses. A couple of vice presidents from the corporate office were also in the room. My nervousness shot through the room.
My nervousness caused me to race through the presentation at breakneck speed. I had sweat pouring off my palms and forehead. As I sat down, mortified, I realized that no one in the room saw me as a potential future leader. They saw me as a scared kid.
People judge our competence by our confidence. So, you can’t just work hard. You also have to communicate with poise to get ahead.
Doug Staneart, CEO, Fearless Presentations
Discernment for Prioritizing Quality Over Quantity
Early in my journey with Ignited Results, I made the mistake of chasing every potential client and opportunity, believing that volume equated to success. I recall one instance where we onboarded a client without thoroughly assessing the alignment between their needs and our expertise. The result was a mismatch in expectations, leading to dissatisfaction on both sides.
This experience taught me the invaluable lesson of discernment. I realized that not every opportunity is the right fit, and it’s essential to prioritize quality over quantity. From then on, I became more selective, ensuring that we took on projects where we could genuinely add value and make a meaningful impact.
This shift in approach improved our client relationships and allowed us to deliver work we were genuinely proud of. It reinforced the importance of understanding our strengths, setting clear boundaries, and ensuring alignment from the outset. This lesson has been instrumental in shaping the.
Jon James, CEO, Ignited Results
