Every career path has obstacles. Even the most accomplished leaders have faced moments where their goals felt out of reach. What separates the people who moved forward is how they responded—by adapting, learning, and finding new ways to progress.
Below, 17 members of Fast Company Executive Board share the challenges that once stood in their path and the lessons they drew from those experiences. If any of these roadblocks sound familiar, apply their expert advice for working through them.
1. TAKING THINGS PERSONALLY
I used to take every loss personally. I was rejected from Cambridge, I lost my first three boxing matches, VCs passed, deals collapsed. And I’d lose control, trying to figure out what I did wrong. As time passed, I learned that the world doesn’t punish you; it reveals you. A setback says, “something’s not aligned—yet.” Now I see setbacks as course corrections. You’re not being punished, you’re being prepared. – Aron Alexander, Runa
2. BEING TOO AMBITIOUS
Early in my career, my ambition often clashed with my career goal timeline. I thought I was ready for a promotion, but I hadn’t yet learned that the business also needs to be ready for you to step into a new role (not just the other way around). As I grew into the executive level, I found balance in the following: keep driving forward, but recognize that not everything will follow my timeline—and that’s okay. – Irina Soriano, Seismic
3. FAILING TO BALANCE TECH WITH GENUINE HUMAN CONNECTION
I once believed that the right tools, dashboards, and processes would drive innovation. But I learned the hard way—innovation is a team sport. Without a genuine human connection, even the best tech fails. That experience taught me to lead with relationships. I see this mistake repeating with AI—chasing efficient systems over trust and collaboration. That’s a recipe for disaster that I hope others avoid. – Alex Goryachev
4. STRIVING FOR PERFECTION
Early in my journey, I let perfectionism delay progress. I wanted every detail to be flawless before taking the next step. But I was taught magic lives in momentum. I overcame it by embracing imperfection as part of the story. My advice? Start before you’re ready. Let passion lead, and polish as you go. Progress, not perfection, opens the door to your purpose. – Sudhir Gupta, FACTICERIE
5. CONFUSING DREAMS AND GOALS
Learning how to set a goal with honesty was transformative. Recognizing the difference between a dream, a goal, and an objective helped me give myself adequate time and grace. It takes work to evaluate your personal and environmental readiness, and sitting with myself in truth was often the first and most difficult obstacle. Check yourself, check your resources, check your allies—then go. – Joynicole Martinez, The Alchemist Agency
6. DOING IT ALL ALONE
Trying to do everything myself slowed my progress toward key goals. Like many entrepreneurs, I believed no one could match my pace or standards. Over time, I learned to delegate and build a team I trust. That shift allowed me to scale faster and focus on what really moves the business forward. The takeaway: growth often starts when you stop doing it all alone. – Boris Dzhingarov, ESBO ltd
7. FEARING ‘NO’
Early in my career, fear of rejection stopped me from pitching big ideas. I overcame it by reframing “no” as feedback. Practicing small, low-risk pitches built confidence. Others can adopt this mindset shift to turn setbacks into growth. – Gianluca Ferruggia, DesignRush
8. LACKING BALANCE BETWEEN VISION AND EXECUTION
In the early days of my career, it was not that easy to balance vision and execution. It took some time for me to create a structured approach to taking ideas to action. To find a solution, I started to think about small, manageable tasks with the approach of using my mentors to guide me. My best advice is to focus on small iterative progress rather than trying to hit a perfect presentation. – Asad Khan, LambdaTest Inc.
9. BEING A ‘JACK OF ALL TRADES’
Early on at our agency, we struggled with being a “jack of all trades,” trying to do everything instead of focusing on our strengths. It was hard to let go of potential opportunities, but narrowing our focus to what we do best led to greater success and growth—proving that specializing can be more rewarding than trying to do it all. – Martin Pedersen, Stellar Agency
10. LACKING CONFIDENCE
Lack of confidence held me back early in my career. I overcame it by leaning into small wins, seeking feedback, and focusing on progress over perfection. Building self-trust made a real difference. My advice: don’t wait until you feel 100 percent ready—take action, learn as you go, and growth will follow. – Maria Alonso, Fortune 206
11. KEEPING COMPANY THAT IS AFRAID TO BRANCH OUT
My biggest setback came from sticking with a circle that valued stability over innovation. Once I sought out peers who weren’t afraid to disrupt norms, my career accelerated rapidly. Your network sets your ceiling, so build relationships with people whose bold ideas push you beyond your comfort zone. – Eddy Vertil, Vertil & Company
12. THINKING SUCCESS IS LINEAR
Early in my career, I believed that career success followed a linear path: do X, get Y, and you progress. I couldn’t have been more wrong. What it really took for me was quite the opposite: embracing risk, raising my hand, and pursuing unexpected opportunities to truly move forward and eventually achieve my goals. – Jani Hirvonen, Google
13. DISAGREEING WITH CONSTRUCTIVE FEEDBACK
I would sometimes get feedback that I didn’t accept (it wasn’t always accurate). I needed to learn that it didn’t matter if it was true or not—I had to address the feedback of that person. If 99 percent of folks thought I was a good communicator, but the one percent was an influencer, it was up to me to help that one percent see me differently. Reframe yourself because one size doesn’t fit all. – Sabrina Farmer, GitLab
14. STAYING COMFORTABLE
The biggest obstacle was my comfort zone. Chasing perfection sometimes paralyzed me. Instead of overthinking, I embraced imperfection and took bold, imperfect actions. I didn’t reach the goal right away, but I learned to celebrate small wins. Failure can be the best teacher. Instead of aiming for a perfect path, be willing to stumble. It’s in those mistakes that true growth and creativity happen. – Shawn Galloway, ProAct Safety, Inc.
15. CHASING EVERY OPPORTUNITY
As a classic achiever, I passionately chased almost every opportunity. As a result, I spread myself thin and was often behind the wave, not my best self. Learning to get altitude wasn’t just shifting perspective; it was knowing which priorities deserved my focus and would energize me. I am slower to jump, more selective, and happier. – Dr. Camille Preston, AIM Leadership, LLC
16. CARING WHAT OTHERS THINK
My ego stood in the way. I was too focused on how others perceived me, which ultimately hurt my progress. Real growth came when I prioritized purpose over image. Letting go of that mindset ultimately allowed me to move forward, making smarter decisions and building a successful company. – Toni Pisano, PortPro Technologies, Inc.
17. FAILING TO PRIORITIZE GROWTH
Prioritizing the work over growth is a very common challenge for emerging leaders. There are always competing priorities, and there will always be “something else” to do, but you have to make the time to prioritize your growth. – Monica Hickey, The Evoke Agency
