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How to Overcome Challenges in Career Development: 10 Personal Stories to Learn From

In this article, ten seasoned professionals, including CEOs and VPs, share their personal experiences and lessons learned from significant challenges they faced in their career development journey. From transitioning industries by embracing the learner’s mentality to career breakthrough from seizing new opportunities, these leaders provide valuable insights into overcoming obstacles and achieving success.

  • Transitioning Industries: Embrace the Learner’s Mentality
  • Assertiveness: Key to Leadership Ascension
  • Pivoting Roles: From Technical Expert to Team Leader
  • Entrepreneurship: Perseverance Pays Off
  • Discrimination and Politics: Standing Firm Against Them
  • Overlooked for Promotion: A Catalyst for Change
  • First Case Triumph: Driven by Justice
  • From Programmer to Entrepreneur: Online Learning
  • Maintaining Motivation: Embracing New Challenges
  • Career Breakthrough: Seizing New Opportunities

Transitioning Industries: Embrace the Learner’s Mentality

After working in the healthcare sector for eight years and becoming familiar with it, transitioning to the FinTech space was challenging.

At first, I struggled with imposter syndrome and believed I needed to deeply understand the industry before I could sound credible to potential clients. However, I later learned that it’s essential to approach new jobs or industries with a learner’s mentality and dive right in.

You don’t need all the answers or knowledge immediately, but you will eventually gain competence over time. I discovered that often, we are our biggest obstacle and need to trust ourselves more. With the right attitude and approach, anyone can progress and thrive in a new industry.

Daniel JorgeDaniel Jorge
Senior Consultant, EC1 Partners

Assertiveness: Key to Leadership Ascension

My first leadership position occurred when I was promoted above my current boss and peers. As a young woman systems engineer in the ’90s, I was frequently called upon to look good, but not necessarily do much.

Because of my upbringing, challenging authority, questioning “why,” and asking for more, was not in my wheelhouse. But I finally had enough, and, unbelievably to me, I actually approached our VP, telling him to please fire me or use me. To this day, I have no idea what sold him, but it worked.

He promoted me. No skills, no training, no mentoring, no idea, but there I was, a leader! And believe me, not the best. But this one instance started my lifelong journey and love of the potential of self-leadership, as well as becoming a great leader of others.

Along the way, I’ve uncovered my secret to assertiveness, human-centric, inclusive leadership, and above all, what we don’t understand about self-awareness that hinders each of us in our career journey.

Cheryle HaysCheryle Hays
Founder and CEO, InPower Strategists

Pivoting Roles: From Technical Expert to Team Leader

A pivotal challenge in my career journey was transitioning from a technical role to a leadership position. Moving from hands-on technical tasks to managing teams brought a host of unexpected hurdles.

The initial hurdle was adapting my mindset. As a tech enthusiast, I was accustomed to solving problems directly. Shifting to a leadership role required embracing a broader perspective, focusing on team dynamics, and understanding the intricacies of human interactions within a professional setting.

To overcome this, I immersed myself in leadership literature and sought mentorship from seasoned leaders. Learning from their experiences provided invaluable insights into effective leadership styles, communication strategies, and the art of delegation.

Sai BlackbyrnSai Blackbyrn
CEO, Coach Foundation

Entrepreneurship: Perseverance Pays Off

In my mid-twenties, I decided I wanted to strike out on my own and become an entrepreneur. So, I started a business—or rather a few—on the side, while still working full time.

And… it was tough.

I didn’t have the advantage of knowing other entrepreneurs who could guide me. In fact, my family thought I was crazy about leaving a career in engineering to start my own thing.

But despite that, I stuck with it. And my perseverance paid off big time because I ended up scaling my business to seven figures.

So, here’s a big lesson I learned from my experience: If you believe your goals are possible, it doesn’t matter what other people think. Don’t let others tell you what you can or can’t do. Stay focused on your vision, and you’ll eventually get results.

Luisa  ZhouLuisa Zhou

Discrimination and Politics: Standing Firm Against Them

I have experienced various types of discrimination throughout my career journey, as well as office politics in regards to really being able to do what my job entails, and keeping things consistent and legal for companies. I have always stood firm in my beliefs and work ethic, even if it meant disagreeing with key leadership, by backing up my stance with four key pieces of evidence: internal policy, state/federal law, history of the issue within the organization, and research. I have learned it’s difficult to argue with evidence.

Shoneizi LangShoneizi Lang
Executive Director of Human Resources, Clear Rate Communications

Overlooked for Promotion: A Catalyst for Change

I’ve been fortunate in my career, but the biggest lesson I learned was to have faith in myself. When I worked for a division of a large corporate company, I was the number two in a group business and was overlooked for an internal promotion.

I raised my frustrations and concerns with the group CEO, saying that I didn’t think I would have gotten the role, but I would have liked the opportunity and experience. He said he was grateful for letting him know and that they would consider me for the position if it became available again.

Around 18 months later, my boss was removed and replaced with a new one. When I raised my concerns again with the group CEO, he said, “Rob, you make a great number two, but you’ll never make a number one.” I resigned the same day, put the wheels in motion to set up Aaron Wallis, and never looked back.

Rob ScottRob Scott
Managing Director, Aaron Wallis Sales Recruitment

First Case Triumph: Driven by Justice

Taking on your first case as an attorney is a significant challenge and milestone in the career development journey of any lawyer—and my experience was no exception. Motivated by an unwavering drive to achieve justice and success for my client, I felt immense pressure to perform. Fueled by this, I sank everything I could into thoroughly preparing for the trial. My efforts were rewarded in achieving an eight-figure verdict—a record-breaking result for Brevard County.

This experience taught me a key lesson: when driven by the right motivation—in my case, justice for my client—people have the power to achieve great things. Rather than let the pressure hinder my performance, or have any first trial nerves place self-doubt in my abilities, I constantly reminded myself of my “why.” Knowing my purpose armed me with the determination to step into the courtroom with confidence and give it my all.

Riley BeamRiley Beam
Managing Attorney, Douglas R. Beam, P.A.

From Programmer to Entrepreneur: Online Learning

For me, this was making the jump from being a programmer at an established company to becoming an entrepreneur. I knew the product, and I knew the technology, but I had extremely little clue about how to run a business or actually sell and make money. Luckily for me, there are very few things you can’t learn about online these days—and quite quickly.

I actually ended up taking a sales class online for the first year I was in business on my way to my first million in revenue. It taught me everything I needed to know, and I still find it an invaluable bit of learning a decade later.

Dragos BadeaDragos Badea
CEO, Yarooms

Maintaining Motivation: Embracing New Challenges

One of the hardest things for me has always been maintaining interest and motivation after I’ve been doing the same thing for too long. Call me a novelty-seeker, but I tend to mine out roles and leave for something new and challenging. This is not always easy, especially the further you go in your career when you get more pigeonholed.

For me, however, this meant that I needed to take a leap of faith when I jumped from my long-time role as a telecommunications director in a major multinational to the CEO of a tiny content-creation startup. A wildly different situation, but one where I can feel the passion to learn, grow, and keep moving.

Onno HalsemaOnno Halsema
CEO, Contentoo

Career Breakthrough: Seizing New Opportunities

The hardest part of managing my trajectory in my marketing career wasn’t getting my foot in the door—that was easy. I found work as a copywriter and social media account manager immediately after graduation. I was just stuck there for the next five years or so. I got raises, I went from part-time to full-time to salaried, but I was still stuck. I didn’t see a way to make it into management from where I was, and management-track jobs like project management seemed to want more diverse experience from me.

My breakthrough came when I volunteered to get our biggest client started on TikTok. Our agency had never worked on that platform before, and I took the lead on the project. Long story short, it was successful, and I ended up piloting my agency’s entire TikTok department. My big takeaway: Find what needs doing and do it.

Nick ValentinoNick Valentino
VP of Market Operations, Bellhop

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