Perhaps you’ve raised your children, and now they’re forging their own paths. Or you’ve left a career that no longer excites you. Maybe you’ve relocated to a new country, lost a loved one, or simply decided it’s time to live a more meaningful life. Whatever brought you here, one thing is certain: you are not alone.

In the Algarve, this story is familiar. Research by the Algarve Women’s Network reveals that nearly 80% of women who relocate must pivot their careers. Many find themselves in fields they never imagined, drawn to opportunities that align with their values and the local lifestyle. But how do you begin when you feel like you’ve lost your identity?

To explore this journey, I spoke with Maureen Gilbert, a coach who specialises in navigating these transitions and reflected on my own “Year of Yes”—a transformative chapter that reshaped my life in Portugal.

The Year of “Yes”

When I moved from the UK to Portugal in 2021, I envisioned a slower, simpler life. After years of burning the candle at both ends, I was ready to retire and dedicate myself to family and leisure. For a time, it was blissful. Golf, hiking, and swimming became part of my daily routine. Yet, as my teenage sons began to assert their independence, I found myself with too much time and too little purpose.

Turning 50 only heightened this restlessness. For decades, my identity had been tied to my career and family. Who was I without them? With an open calendar and an undefined future, I decided to embrace uncertainty. I embarked on what I called my “Year of Yes,” committing to saying yes to any opportunity that sparked curiosity.

  • I volunteered as a school representative, mentoring young people in entrepreneurial skills.
  • Experimented with real estate (and quickly learned it wasn’t for me).
  • Enrolled on a Sustainable Leadership postgrad course at Cambridge, where I graduated top of my class.
  • Led a local women’s networking group, which grew into a thriving hub for international women seeking professional growth in the Algarve.

Through these experiences, I discovered what many of us already know but hesitate to admit: transformation isn’t about finding yourself. It’s about creating yourself.

A Conversation with Maureen Gilbert

When I spoke with Maureen, she echoed many of my feelings about the challenges and opportunities of midlife transitions.

Me: Maureen, why do you think so many of us feel stuck during this phase of life?

Maureen: Because for years, we’ve followed a roadmap. We’ve ticked the boxes: education, career, family. Then suddenly, we find ourselves at a stage where the road ends. The structure we’ve relied on disappears, and we’re left asking, “What now?” It’s unsettling, but it’s also an invitation to start living on your own terms.

Me: But what about the fear of making the wrong choice? That’s what held me back for so long.

Maureen: Waiting for the “perfect” choice or the universe to guide you is often just fear in disguise. Life isn’t a straight line; it’s a series of experiments. Think of it like a GPS. It can’t guide you unless you’re moving. You might take a wrong turn, but you can always recalibrate.

Maureen’s wisdom resonates deeply. During my “Year of Yes,” I often found myself second-guessing my choices. Was pursuing sustainable leadership the right move? Should I have focused on something less complex and local like real estate? Yet every step, even the missteps, brought me closer to clarity.

Finding Meaning in the Journey

One of the most impactful moments of my year came last summer when I conducted research within the women’s network I had helped to grow. The results were eye-opening. These women—intelligent and driven—were navigating their own reinventions. They weren’t content to retire or slow down. They were pivoting careers, launching businesses, and seeking ways to contribute meaningfully to their new communities.

Their struggles mirrored my own. They, too, were questioning their identities, wondering how to balance ambition with lifestyle, and seeking ways to make a difference. That’s when my path became clear: I could use my experience in business development to guide these women through their transitions.

Lessons for the Road Ahead

If you’re at a crossroads, here are a few takeaways from my journey and Maureen’s insights:

  1. Start Moving: Don’t wait for the perfect plan. Action creates clarity. Each step, even the wrong ones, will teach you something valuable.
  2. Focus on Experiences: Instead of obsessing over the “right” choice, ask yourself what you want to experience. Adventure or stability? Connection or solitude? Growth or peace?
  3. Embrace Experimentation: Your next chapter doesn’t have to look like your last. Try new roles, hobbies, or studies. You’ll learn what resonates and what doesn’t.
  4. Trust Yourself: The universe isn’t withholding answers. Sometimes, silence is a reminder that you’re in charge now. Your choices define your journey, not fate.

Your Turn to Choose

The beauty of this stage in life is that you get to write the script. Whether you’re looking to rediscover purpose, launch a business, or simply find balance, Portugal offers a vibrant community of like-minded individuals navigating similar paths.

So, who are you now? The answer isn’t waiting for you out there. It’s something you’ll discover along the way.

If you want to read more of Maureen’s reflections, sign up to her Notes from a MidLife Crisis on Substack.com

Author

Kamila is a dedicated advocate for entrepreneurial community development and women’s empowerment. She helps women build remote-first businesses that align with their passions and support a lifestyle of freedom, inspiring them to seize opportunities and create their dream lives.


Community Lead Portugal | Multi-Award-Winning Entrepreneur | Bestselling Author | Founder of HerFreedomBusiness.com | Co-Founder of Algarve Women’s Network

Kamila Laura Sitwell