Rising Above: Overcoming Challenges on Your Passionate Journey

September 18, 2023
September 18, 2023 Terkel

Rising Above: Overcoming Challenges on Your Passionate Journey

In this article, thirteen professionals, including founders, CEOs, and directors, share their personal challenges faced while pursuing their passions. From overcoming fear of initiating new projects to managing time while pursuing passion amidst work, these insights offer a deep dive into the struggles and triumphs of passion-driven careers.

  • Overcoming Fear of Initiating New Projects
  • Learning New Skills in Real Estate Investing
  • Balancing Work and Home Life as an Entrepreneur
  • Navigating Competition and Detachment in Coaching
  • Introducing Innovation in Traditional Corporate Environments
  • Combating Self-Doubt and Fear of Failure
  • Conquering Fear of Rejection in Photography
  • Breaking Through Educational Barriers in Business-Building
  • Surviving Industry Downturn While Building Company
  • Managing Fear in Group Horse Riding
  • Battling Self-Doubt as a Professional Artist
  • Tackling Stage Fright in Public Speaking
  • Managing Time While Pursuing Passion Amidst Work

Overcoming Fear of Initiating New Projects

One of the biggest challenges I encountered while pursuing my passion was the fear of initiating a new project or venture. Overcoming this hurdle necessitated adopting a proactive mindset, embracing a trial-and-error approach, seeking mentorship, engaging in continuous self-improvement, and leveraging the power of self-belief.


By reframing failure as an invaluable learning opportunity and recognizing that success often stems from multiple attempts, I gradually developed resilience, bolstered my confidence, and cultivated the determination to persevere.

Through unwavering persistence and a steadfast commitment to learning and personal growth, I successfully conquered this challenge and forged ahead on my path to achieving my ambitious goals.

Ivan RadonjicIvan Radonjic
Senior SEO and E-Commerce Expert, Digital Marketing Consultant

Learning New Skills in Real Estate Investing

As an aspiring real estate investor, I had to learn a lot of new skills on the job. One of the most challenging aspects was learning how to analyze a property and understand the real estate market. I read countless books, articles, blogs, and watched many videos in order to understand the basics—but this wasn’t enough.

With an apprenticeship program, I could gain access to experienced real estate professionals who could provide me with the mentorship I needed to become successful. Through this program, I could gain valuable knowledge and experience in analyzing deals, understanding market trends, and making sound investments.

With their help, I could overcome the initial challenge of learning how to invest in real estate and now have a full-time career as an investor.

Keith SantKeith Sant
Founder and CEO, Sell My House Company

Balancing Work and Home Life as an Entrepreneur

Probably the biggest challenge for me to overcome was balancing work and home life as a serial entrepreneur. I love my career, but it’s extremely difficult to balance all of the business ventures and other responsibilities. I have a child, and my husband is my long-term business partner through various ventures, so finding a way to disconnect from work is a constant struggle. I need to find ways to power through.

Doing this has allowed me to pursue my passions. However, with a string of successful businesses behind me, I wouldn’t trade it for anything. You can, in fact, have it all if you find a way to make the puzzle pieces fit together.

Kate KandeferKate Kandefer
CEO, SEOwind

Navigating Competition and Detachment in Coaching

When launching a holistic coaching and consulting practice, two challenges are often faced. The first is the intimidating competition. Everywhere one looks, voices echo similar philosophies and approaches. However, it’s important to realize that even if the messages might be similar, everyone brings unique skill-sets and ways of using them, including distinct ways of bringing a message across. Skills can be refined and approaches tailored, ensuring the ability to offer something authentic and distinct.

The second challenge is more introspective. The profound care felt for clients occasionally makes it hard to detach. It’s natural to want them to thrive, but one must accept a fundamental truth: A coach can guide, advise, and support, but the choices clients make, using the insights provided, are ultimately theirs. This realization isn’t just about setting boundaries—it’s about respecting clients’ autonomy and trusting the process. Embracing these lessons can carve a path to success.

Mona Kirstein, Ph.D.Mona Kirstein, Ph.D.
Digital Strategist, Holistic Coach and Consultant, The Wholehearted Path

Introducing Innovation in Traditional Corporate Environments

In the early stages of my career, I was driven by a passion for revolutionizing how businesses approached their internal processes, particularly in the HR domain. However, introducing fresh, disruptive ideas in traditionally rigid corporate environments was an uphill battle. I frequently faced skepticism and reluctance from senior management, which often made me question the viability of my vision.

Overcoming this required a blend of resilience, continuous learning, and strategic relationship-building. Instead of getting disheartened, I took feedback seriously, refining my proposals to address concerns while maintaining the core of my innovative ideas. I invested in upskilling, attending workshops and seminars to bolster my credibility. Additionally, I sought mentors and allies within organizations who shared my vision and could vouch for the potential of my ideas.

In time, with persistence and a commitment to excellence, I managed to transform naysayers into advocates, proving that wit

James McNallyJames McNally
Managing Director, SDVH [Self Drive Vehicle Hire]

Combating Self-Doubt and Fear of Failure

In my own life, one of the biggest challenges I faced while following my passion was fighting self-doubt and the fear of failure, which kept me from going after my goals with all my heart.

To overcome this, I sought advice and mentorship from more experienced people in my field and used their guidance to boost my self-esteem. I also adopted an approach where I set small, achievable goals to build my confidence over time. Facing my fear of failure head-on, I reinterpreted it as a chance to learn instead of a setback.

Adopting the attitude that mistakes are important steps on the path to success gave me the confidence to take calculated risks, which helped me make significant progress on my journey.

Leonidas  SfyrisLeonidas Sfyris
CTO, Need A Fixer

Conquering Fear of Rejection in Photography

I have been passionate about photography since I was a child, but for many years, I kept my passion to myself because I was afraid of being rejected. Even though deep down inside I knew that my photos were good and worthy of sharing with others, I was still scared of the possible feedback I could receive.

Finally, after a lot of self-reflection and determination, I decided to take the plunge and share my photos with the world.

Shaun MartinShaun Martin
Founder and CEO, We Buy Houses In Denver

Breaking Through Educational Barriers in Business-Building

My passion is business-building. I love creating jobs and, frankly, the challenge of it. But business-building isn’t easy. I’ve faced the issue of being a high-school dropout and not having the formal education necessary to acquire investors and other forms of startup capital, as well as questioning myself if I really knew what I was doing.

I overcame it by sheer force of will. I worked harder to build my own capital reserves, studied on my own the areas of business, marketing, and accounting that I needed to know, and pushed through. Now I own four successful businesses and employ over fifty people.

Christopher OlsonChristopher Olson
CFO, Surfside Services

Surviving Industry Downturn While Building Company

One challenging period I faced while building my company was a steep downturn in our industry. As revenue dried up, we had to make difficult changes to survive. This meant reducing staff and slashing budgets – tough moves emotionally.

Staying focused on our mission of empowering customers fueled me through the dark days. I refused to compromise on our core values, despite the hard choices needed financially.

Keeping spirits up was critical too. I communicated transparently with employees and celebrated even small wins. We got creative with contests and virtual events to maintain camaraderie despite job losses.

With relentless persistence, we managed to stabilize. When conditions rebounded, our culture was stronger than ever thanks to the shared struggle.

Pursuing one’s passion is rarely a smooth path, but determination and care for people help weather the storms.

Ankit PrakashAnkit Prakash
Founder, Sprout24

Struggling with Fear in Group Horse Riding

My passion is horse riding. I love everything to do with horses. However, I used to struggle when riding in a group. My horse would get more excitable, and I’d panic that I would lose control.

Several years ago, I traveled to the Camargue and had the opportunity to ride a beautiful Camargue horse. The stunning gray horses have roamed the Camargue region in the south of France for hundreds of years, and the chance to take one to a local beach for a gallop was a dream come true.

There were no options for a private ride, so I swallowed my fears, joined a group, and rode out to the beach. All my nerves evaporated as we galloped along the surf. I had never felt so free or so confident in my entire life. Even when the horse sped up, I was able to bring him back.

Now, whenever I ride in a group, I force myself to remember that feeling of confidence. I remember that I was able to control my horse that day and that I have the knowledge to handle myself and my horse, even when things go wrong.

Rebecca WebberRebecca Webber
Head of Content, World Meters

Battling Self-Doubt as a Professional Artist

During my journey to become a professional artist, I faced the challenge of consistent self-doubt, comparing my work to others’. This hindered my creativity and drive.

To overcome it, I distanced myself from social media, focused on personal growth, and sought constructive feedback from mentors. Embracing my unique style and continuous learning, I transformed challenges into stepping-stones, driving my passion forward.

David BuiDavid Bui
Director and Business Specialist, Schmicko

Tackling Stage Fright in Public Speaking

A major obstacle I experienced while pursuing my passion for public speaking was terrible stage fear. Fear of speaking in front of an audience incapacitated me, limiting my capacity to successfully share my thoughts and connect with others.

To overcome my stage fright, I used a progressive-exposure technique. I began by speaking in small, comfortable groups before graduating to larger crowds. This assisted me in desensitizing myself to the nervousness that comes with public speaking. I also sought professional instruction from a seasoned public-speaking trainer, who gave me specialized advice on conquering my unique phobias and refining my delivery techniques.

In addition, I used mindfulness and relaxation techniques to assist me in controlling my nervousness on stage. Over time, with consistent effort and a willingness to confront my fears head-on, I overcame my stage fright and acquired confidence in my public speaking skills.

Timothy AllenTimothy Allen
Sr. Corporate Investigator, Corporate Investigation Consulting

Managing Time While Pursuing Passion Amidst Work

One significant challenge I faced while pursuing my passion was a lack of time due to a demanding job.

To overcome this, I adopted a structured time-management approach. I prioritized my passion by setting specific, achievable goals and dedicated consistent, focused time to it, even if it meant sacrificing leisure activities. By creating a well-defined schedule and eliminating distractions, I maximized my productivity during limited free hours. Additionally, I sought support from friends and family who understood my dedication, which helped me stay motivated.

Ultimately, this disciplined approach allowed me to make steady progress in pursuing my passion despite a busy work life.

Sarah PolitiSarah Politi
Founder and Managing Director, Jade & Sterling

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