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20 Examples of How Leaders Overcame Significant Challenges in Their Careers 

Elita Torres

We asked twenty professionals from various fields to share their personal stories of overcoming significant challenges in their careers and the lessons they learned. From creative and marketing directors to attorneys, their experiences range from fixing the work culture after rapid growth to finding work-life balance through prioritization. Dive into these insightful narratives and learn from their experiences.

Fixing the Work Culture After Rapid Growth

About six years into our business journey, we experienced a period of rapid growth and subsequently doubled our team. On the surface, this felt like an achievement; however, what we didn’t expect was how this growth affected our culture and structure. 

Unfortunately, we quickly found that communication and personal relationships between team members broke down, and we lost our close-knit, supportive culture. It took us about two years to work with our team to regain that positive workplace culture and rebuild the trust between the business leaders and staff. This experience ‌changed how we perceive growth and our people. 

We aim to stay as small a team as possible and invest instead in professional development, freelance support, and perks to protect our employee welfare. We also prioritize the emotional well-being of our employees and have instigated regular one-on-one meetings outside of appraisals—to talk about their personal and professional lives.

Ryan Stone, Creative and Marketing Director, Lambda Films

Adapting Leadership for Generational Shifts

Over my 40-year executive management journey, one of the most profound challenges I faced was the changing nature of the workforce. I began my career practicing transformational leadership, aligning perfectly with the aspirations of my Generation X and Y team members. 

They excelled when presented with high standards, open communication about our vision, and encouragement for innovation. But as Generation Z started dominating our team, a shift in leadership style was imperative. 

These younger professionals yearned for collaboration and genuine interactions. Thus, I transitioned to servant leadership, putting their needs first and creating a collaborative decision-making environment. This experience taught me the essence of adaptability in leadership: understanding, valuing, and responding to the unique needs of each generation.

Fred Winchar, Founder and Certified HR Professional, MaxCash

Boosting Sales Through Collective Brainstorming

I remember one evening staring at the sales figures and feeling that weight of responsibility. It would’ve been easy to blame the market or external factors, but deep down, I knew I had to pivot our strategy.

So, I gathered my team for a brainstorming session. We spent hours dissecting our approach, from marketing angles to client feedback. It was during this session that a junior team member, fresh out of college, suggested a unique promotional angle we hadn’t considered. It was bold, but it had potential.

We rolled the dice, and within a month, our sales figures started to climb. By the end of the quarter, we had not only met but exceeded our targets.

What did I learn from this? Two things: First, never underestimate the power of collective brainstorming. Every voice, no matter how new or junior, can offer invaluable insights. And second, as a leader, it’s crucial to be adaptable. The business world, much like life, is unpredictable. But with adaptability, you can overcome it.

John White, MBA, Sales Manager, and Golf Instructor, John Carlton White

Solving Project Delay Problems Through Initiative

Early in my career, I faced a major project delay that risked losing a key client. The challenge was daunting, but I took ownership and gathered the team to find a solution. It required long hours and creative problem-solving. 

This experience taught me the value of teamwork, adaptability, and taking initiative during tough times. We met the deadline and strengthened client trust. This incident taught me that challenges are opportunities for growth and that being proactive in finding solutions can turn setbacks into success stories.

Ann Young, CEO, Fix The Photo

Fostering Team Collaboration Through Meetings

During a complex growth-strategy development project, I faced a significant challenge in fostering effective team collaboration. With diverse expertise and personalities, our team struggled to communicate clearly and coordinate efforts. 

Recognizing this, I introduced regular cross-functional meetings where each member could openly share their progress, concerns, and ideas. This initiative transformed our dynamics. 

We learned to value each other’s contributions, leading to improved communication, streamlined workflows, and a sense of unity. I realized that nurturing a collaborative environment isn’t just about tasks, but about building relationships and mutual respect, which ultimately drives success.

Khanh Tran, Growth Manager, Villa-Ibiza

Navigating the Emotional Impact of COVID-19

The hardest part of my career was the pandemic. I was working my way into marketing as a writer and social media manager and was absolutely thriving. I loved my team; I loved the work we did, and I was eyeing a leadership position. 

I was ready to ride out the lockdowns and did some good work at home, but I was sharing a small apartment with my girlfriend, who was also working remotely. We both caught COVID in the fall of 2020. I took almost a month off while I recovered, more emotionally than from COVID. I was just burnt out. 

Learning to forgive myself for struggling during that time was really hard, but I’m finally in a good place with it. I’ve learned when it’s time to work hard and when it’s time to take care of myself.

Nick Valentino, VP of Market Operations, Bellhop

Overcoming Burnout During the Pandemic

The most significant challenge I’ve faced in my career came about during the pandemic when healthcare workers were being stretched to our workload limits. Many PAs (myself included) took on extra hours for what we thought would be a short-term arrangement, but that turned into months straight of overtime in incredibly stressful conditions. 

As a result, I ended up very burned out, to where I contemplated leaving the profession more than once. Eventually, I could take a vacation, and afterward, I could get back to a more reasonable workload, although it still took several months for me to get back to 100%. 

What I learned from this experience is to listen to my body and respect my own limits. I’m a person who always wants to contribute as much as possible, and it’s hard to say “no” when you know people are depending on you. Sometimes, though, that “no” is necessary so that you can be there for people in the future, and I learned that from my experience.

Carlos Da Silva, Physician Assistant, PA Career Hub

Revamping a Complex Legacy System

During my early career as a software developer, I faced a daunting challenge when tasked with revamping a complex legacy system. The codebase was convoluted and lacked proper documentation, making it hard to comprehend.

I felt overwhelmed initially, but broke the task into smaller chunks. I focused on understanding one module at a time, meticulously untangling the code, and documenting each step. This methodical approach made the task more manageable and helped me uncover hidden patterns. 

I learned the importance of patience and perseverance, as well as the value of breaking down seemingly insurmountable challenges. This experience honed my problem-solving skills and taught me to embrace challenges as opportunities for growth. 

In the end, the revamped system improved efficiency and boosted my confidence, showing me that tackling challenges systematically yields fruitful results.

Jay Toy, General Manager, 88stacks

Learning New Software Through Help

I remember the first time I was given a challenge that seemed insurmountable. It was the summer after my first year of college, and I had just been hired as a research assistant. The problem was that I had never used Excel before.

I was so afraid of messing up that I didn’t sleep for three nights straight while trying to figure out how to use it. The next day at work, when my boss asked me what I did the night before, I told him about my lack of sleep and how terrified I was about the task at hand. 

He laughed and said he knew what he wanted done in Excel but wasn’t sure how to do it himself either. So, together, we spent half an hour working through the problem—and then he gave me another one!

That experience taught me two things: first, there’s no shame in asking for help when you need it; second, there are always people around who will help if you ask them nicely!

Jaanus Põder, Founder and CEO, Envoice

Handling Client Dissatisfaction Proactively

A defining challenge in my career was navigating a major client’s unexpected dissatisfaction with our service. Despite our best efforts, they were unhappy with certain aspects of our product. This setback led to a moment of introspection and action. 

I visited the client’s office to understand their concerns firsthand. This showed our commitment and allowed me to empathize with their situation. Through open conversations and collaborative problem-solving, we devised a tailored solution that addressed their specific pain points. 

This experience taught me the importance of proactive communication, listening deeply, and adapting swiftly. By embracing challenges head-on and using them as opportunities for growth, I learned that sincere engagement and customized solutions can turn a difficult situation into a transformative partnership, ultimately strengthening our commitment to customer success.

Travis Willis, Director of Customer Success, Aspire

Launching a Competitive Plan Against Rivals

In 2018, I faced a daunting challenge in my career. We observed newer competitors offering fewer features but at a more attractive price, appealing to our price-sensitive customers.

It stung—seeing our leads opt for these alternatives. However, instead of panicking, we reflected, strategized, and, after six months, launched the ZenMaid Free Plan. 

This plan not only matched the competition but surpassed it in value. It cleverly sets our customers up for success within our ecosystem. And the best part? When they’re ready to access more features, it’s just a click away. 

This experience taught me the power of adaptability and listening to market needs. It reaffirmed that, with the right strategy, challenges can turn into opportunities.

Amar Ghose, CEO, ZenMaid

Searching the Job Market Post-Graduation

One of the biggest challenges that I faced in my professional life—one that I didn’t expect—was the difficulty of actually getting my career off the ground post-graduation. I got my degree and even gained some valuable work experience during that time, but when I graduated and was ready to take on the workforce, it seemed like nobody would take a chance on me. 

I had the qualifications and credentials, but still, I struggled to even get interviews. So, after quite some time, I realized that I somehow needed to gain more professional experience in order to be a better candidate. 

I ended up getting an internship and worked exceptionally hard to prove myself—then that internship turned into a full-time position. I learned that sometimes career paths aren’t traditional, but taking a different path can still get you where you want to go if you just work hard.

Brittany Mendez, CMO, FloridaPanhandle.com

Integrating New Technology Into Systems

One of the most significant challenges I’ve faced in my career was integrating new technology effectively into existing processes and systems. When I started at my current company, we were only using a few basic software applications that weren’t able to support the growth of our business. 

After researching various options, I implemented an enterprise-level system that provided cross-functional support. It was a long process of integrating the new technology into existing systems, and I had to be patient and creative as I worked to find solutions to the various problems that arose. 

I learned an important lesson from this experience: that, while change can be difficult, it is sometimes necessary to pursue it in order to ensure our success. I also learned the value of being patient and creative when facing a challenge. If we don’t look for innovative solutions, we may never get the results we want.

Amira Irfan, Founder and CEO, A Self Guru

Resolving a Job Offer Dilemma

Many moons ago, I was a trainee solicitor (in England and Wales) and about to qualify as a solicitor—I was on Cloud 9. I was offered a newly qualified solicitor role by the law firm that trained me, but the pay was awful. 

Should I accept the job offer, look for a better-paid job, and then move once the higher-paid job is secured? Or should I ask for a pay raise or tell the firm I am considering my options? The previous trainee solicitor did the former. I chose the latter option – something about honesty and integrity. After two weeks, the job offer was pulled by the law firm. 

I was two months away from qualifying as a solicitor—with no job. Ouch—I thought to myself. The managing partner told me he had to do what was best for the law firm. That was my first real lesson in employment.

I found another job and spent three years at the firm. Now I’m a legal director. Loyalty to your employer? Is the grass greener on the other side? The grass is greener where YOU water it.

Usman Anwar, Legal Director, Anwar Legal

Aligning Work With Personal Values

As an entrepreneur, I’ve gone through several periods of burnout. The last time this happened in a significant way, I had grown my marketing agency too quickly, and then several things went wrong at once. 

I took two years off to figure things out, and what I realized was that I lost my sense of purpose because I was so busy trying to drive revenue. I wrote the Amazon bestseller, “Back After Burnout,” to share the lessons I learned and a few anecdotes. The major lesson is that your work needs to be purposeful. 

If your mission isn’t clear, then spend some time working through what you value most, and what activities and outcomes bring you the most joy, both personally and professionally. Whenever you start feeling burned out, go back to your mission and values and compare that to how you spend your time. If they’re not in alignment, then it means you need to change something.

Dennis Consorte, Digital Marketing and Leadership Consultant for Startups, Snackable Solutions

Turning Job Loss Into Opportunity

What better way to get fired than by an infamous CEO who wasted billions of dollars?

Our small Amazon FBA company was purchased by Adam Neumann to head WeWork’s retail ambitions.

After about 11 months of disarray, they fired us all to avoid us vesting our shares.

To be honest, the company was such an absolute disaster that even in the meeting with the HR lady, my boss didn’t even show up. As if calling them the “People Team” made anything better, I was elated.

Working for such a disastrous and disorganized company was stressful ‌ and hardly fun.

I probably would have never quit since that was too scary, but being fired from WeWork was the best thing that ever happened to me.

The lesson? Getting fired CAN be the best thing that happened to you. Most people will never leave a comfortable job.

It took me less than 9 months to double my previous salary, and 6 years later, I am running a seven-figure online coaching company.

Hayim Pinson, Founder, Muscle and Brawn

Managing Problem Employee Through Training

Push for the training you need in order to exceed.

Even though I was‌ a manager as editor of my high school and college student newspapers, being a manager in the “real world” was much different. 

Lacking specific management training, when my first management position was foisted upon me, I lacked the skill set needed to cope with a problem employee successfully. Being a people-pleaser and giving her what she wanted only made the situation worse.

The whole affair soured me on being a manager until five years later, at a different company, when I was offered the opportunity to manage three team members. Wanting a promotion, I agreed to take the position only if the company paid for management training. They agreed, and when one employee presented a challenge, I knew what to do to guide them to a solution and improve their morale.

Michelle Robbins, Licensed Insurance Agent, Clearsurance.com

Taking Risks and Trying a New Career Path

After teaching English for almost five years, I became increasingly unsatisfied with my job. The symptoms, such as apathy, irritability, and poor performance, were growing, and there came a moment when I realized I was experiencing professional burnout. 

It was an overwhelming sensation that, at some point, made me unable to continue. I knew it was time for a change, but the problem was I needed an alternative professional path in mind. I had never been one of those people who dreamed of starting a business based on their passion.

I took a risk and searched for a job aligned with my competencies, but in a field I had not explored. It quickly turned out that working in digital marketing gave me a tremendous amount of pleasure and‌ a feeling of professional fulfillment. 

This experience showed me that sometimes it is vital to try an unknown professional path that might be just waiting around the corner for you to master it.

Martyna Szczesniak, Community Expert, MyPerfectResume

Addressing Workplace Conflicts Logically

One of the significant hurdles I faced throughout my career involved overcoming the challenges associated with managing workplace conflicts. 

As I progressed in my professional journey, changes in location and shifts between different companies played a crucial role in my development, alongside the invaluable support provided by my parents. During this journey, I honed the skill of leveraging logical thinking over emotional reactions in various scenarios.

In instances where unpleasant conflicts arose, I adopted a strategic approach. Rather than impulsively firing off emails in response, I cultivated the habit of composing these emails, sending them to myself, and revisiting them the following morning. 

This practice allowed me to recognize the extent to which emotions were influencing my communication within the workplace. Another strategy I adopted was consciously disconnecting from work, either by logging off or taking a rejuvenating walk, before crafting a response rooted in emotion.

TK Morgan, Founder and Visionary, Tuesday At 1030

Finding Work-Life Balance Through Prioritization

One of the most significant challenges I’ve faced in my career is finding the right work-life balance. It’s still a work in progress. When I started my company, I made the mistake of trying to do everything myself. 

I wore every hat in the office, from records clerk to receptionist. I don’t regret this, as it gave me a good insight into each aspect of the business. However, it certainly wasn’t sustainable. I realized I needed to recruit, which I duly did. Even then, I found it hard to fully let go and found myself interfering. 

This wasn’t conducive to a harmonious workplace. Without intending to be, I was heading towards micromanagement territory. I was still taking on too much, and this was affecting my energy, efficiency, and, worst of all, my employees. 

I had to relax my grip, delegate, and properly prioritize. Once I did this, my team gained confidence, and my work-life balance improved. I learned that just because you can do it all, doesn’t mean you should.

Martin Gasparian, Attorney and Owner, Maison Law

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