For a long time, work was central to my identity. I obsessed about my job, making it the cornerstone of my life.😬 I've now learned the art of balance and appreciate other facets of my life; but I don't regret my workaholic streak. It drove me to demand more from myself and my employers. It taught me to question whether my job helps me become the person I aspire to be, both in terms of skills and values.

No matter how uncomfortable and socially tortured you feel, the moment will pass and you’ll survive. It helps to prepare. It helps to practice.

This led to a fair amount of job hopping, with at least 13 positions under my belt, all of which were swirled with immense learning and confidence building. The cherry on top? Meeting absolutely wonderful and inspiring people along the way.

Out of the 13, I want to share the three jobs that scared me the most, yet have also been the most transformative in building my confidence. These three careers pushed me beyond my comfort zones, tested my limits, and ultimately made me a more resilient and self-assured professional (and human!).

Career Challenge 1: Find the Confidence to Speak as a Myx VJ

I've always been hesitant to speak in front of crowds. In class, I'd think once, twice, five times before raising my hand to ask a question, let alone share my thoughts. When I’m surrounded by familiar faces, my outspoken persona makes an appearance; but among strangers, I retreat into my shell.

How I came to be a video jock for Myx Music Channel, introducing music videos and hosting live concerts, is another story. (Curious? Ask me about it!😅) Today’s story is about my struggle with public speaking. I admit that I was comfortable in front of a camera. But live events were terrifying!

One defining moment was during a massive concert with thousands in the crowd. Technical glitches called on my shaky hosting powers, demanding that I “stretch” my segment. The pressure was intense! I recall a wide-eyed kuya Miko with his headset on the frontlines mouthing, “Streeeetch,” while making those dreaded hand signals. This meant something was wrong and I had to keep talking up the crowd until they gave me a thumbs up.

Oof! That will live in my traumatic memory vault forever. Right next to it, though, is the memory that I survived the longest 10 minutes of my life. Lesson learned! No matter how uncomfortable and socially tortured you feel, the moment will pass and you’ll survive. It helps to prepare. It helps to practice.

Over time, I learned to manage my nerves and speak comfortably in front of crowds, even embracing the occasional blunder with humor—after I get over the cringe.😮‍💨 To this day, I feel insecurity seep in because of my lack of eloquence. But I’m pushing myself to the uncomfortable spotlight through my own personal project: I Suck (at Smalltalk).

Interested in leadership and world of work topics? You might enjoy these conversations I had with amazing people leaders on the Employee Experience Experience podcast!

Career Challenge 2: Communicate and Negotiate with Top Executives for Global Media

This job redefined my belief in myself and what I could achieve. I’m forever grateful to mentors Franco Verona and Brian Banta. I would have shrivelled up in front of CEOs without their exceptional guidance and training. They remain invaluable sources of business advice and networking opportunities. (I appreciate you, senseis!)

With Global Media, my responsibilities as project director included researching a country’s economy and top industries, creating prospect lists, arranging meetings with top executives (Cold calls still give me the chills!), flying to and finding suitable living arrangements, conducting interviews, meeting sales quotas, writing reports, and a lot of coordination. Rinse all that and more, then repeat!

Our remote work setup—even before the term was coined!—was ahead of its time, utilizing Google Docs and weekly update meetings before it became commonplace. The reports I produced with the GMI team in Dubai, Doha, Japan (Former Prime Minister Shinzo Abe wrote the introduction!), the Netherlands (I interviewed then Foreign Minister Frans Timmermans who later became the Vice-President of the European Commission!), and more, all serve as lasting reminders of my ability to tackle daunting tasks in foreign soil. The secret sauce is a mix of great training, research, support, and sheer determination.

In hindsight, a career in sales wasn't my calling, but with the guidance of mentors like Franco and Brian, I found invaluable lessons in resilience and adaptability. Those years taught me how to conquer my fears and the world!

Explore some of the reports I produced and authored published in the Foreign Affairs magazine.

Career Challenge 3: Lead a Team to Shape a Senator's Voice for Former Senator Bam Aquino

By this time, I was no longer daunted by addressing large audiences and engaging with influential individuals. My initial role in the Senate was as a speechwriter, and transitioning into this sphere didn't scare me; I was excited! It was the unexpected leap into the position of Communications Director that brought my fears to the surface. Leading a team for the first time felt daunting, and self-doubt crept in as I questioned my capabilities.

What helped me overcome this was my commitment to honesty and clarity. I openly shared my concerns with the team while remaining steadfast in goals. Together we crafted both our values and objectives, even designing large stickers for our office so we’re constantly and subconsciously reminded of how we want to work. Together, we transformed words on the wall to reality.

Equally helpful was a supportive team who truly believed in my potential to lead. Senator Bam and fellow directors who I looked up to and respected served as the best examples and guides. Thanks to them, I know to strive to lead by example, to empower my team rather than micromanage, and to recognize that allowing others to shine is the best reward.

I may not have been the best manager, but I kept us aligned in a shared vision, message, and brand. More importantly, I empowered a collaborative work environment built on trust; one that we all loved. My time with this incredible team remains a source of pride—an experience I'll cherish forever. I look forward to sharing more stories from this journey in my future writing.

Here’s a small pocketbook we put together with some of our favorite articles.

Embrace Challenges, Ignite Confidence, and Thrive

As I reflect on my journey of confronting and conquering career challenges, I'm reminded that our professional paths are not just about what we achieve, but how we grow along the way. Embracing challenges isn't merely a necessity; it's an opportunity to ignite your inner confidence, fortify your resilience, and emerge as a stronger, more empowered professional and individual.

From trembling in front of audiences to orchestrating international projects, each career hurdle has been a transformative step towards self-discovery. Through these experiences, I've learned that it's not the absence of fear that defines us but how we confront it head-on.

So, if you find yourself standing at the precipice of a daunting career decision or facing a seemingly insurmountable challenge, remember that you have within you the capacity to overcome. Challenge by challenge, you'll not only develop the skills and knowledge you need but also the unwavering belief in your own abilities.

As you navigate the twists and turns of your professional journey, consider this: Your career path is a canvas, and each challenge you encounter is an opportunity to paint a masterpiece of growth and achievement. So, embrace the unknown, lean into your discomfort, and watch as you transform self-doubt into unwavering confidence. You've got this!

If you have your own stories of career challenges and triumphs or if you'd like to share your insights, please feel free to do so in a comment. Let's continue this empowering conversation together. Shy? Message me on LinkedIn!

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit janinayramirez.substack.com

Overcoming Career Challenges: My Journey to Confidence