Empower Your Executive Encore: Boldly Relocate and Thrive Abroad

emotional intelligence - self actualization executive encore self-trust travel and relocation Mar 28, 2025

Are you dreaming of a new chapter that involves relocation to another country, continent, or hemisphere? Are you feeling unsure about where to start? Whether you're an expat preparing for your next move, a senior executive seeking a fresh chapter after stepping away from corporate life, or a woman entrepreneur exploring new horizons and global business opportunities, the thought of relocating to a different country, continent, or even hemisphere can feel both thrilling and unattainable. It can feel surreal, like a dream that is too distant to pursue. It can be a transformative journey to reconnect with yourself on multiple levels.

Helen, a senior executive who transitioned from Toronto, Canada, to the vibrant streets of Buenos Aires in 2018, shared her inspiring story as a guest on a recent Executive Encore video podcast. Helen's move wasn’t just a change in a postal code. It was a leap into the unknown with the courage to do what was important to her while ensuring each step was in her best interests.

Helen is a shining example that it’s never too late to make a bold move and embrace change.

Discover how Helen embarked on her journey toward self-actualization, the valuable lessons she gained along the way, and practical tips to help you plan your transition and relocation.

Why Move? It’s Your Encore Stage

After several trips to Buenos Aires, Helen knew exactly why she kept returning: the city’s vibrancy, rich culture, and lively energy had captured her heart. Enchanted by its atmosphere and the warmth of its people, she made the bold decision to pack her belongings and embark on a life-changing move that was aligned with the life she wanted to live. Later, she discovered that there was even more to love: wine, the tango, and a strong social network for newcomers.

Her biggest lesson? “It’s never too late to take a bold step. Whether it’s writing your first book or moving to a new country, your encore is what you decide it will be.”

This is your reminder that your next chapter is your encore. What you choose to make of it doesn’t need to conform to conventions or society’s expectations. Like many, we've been there before. It might not have served us well, as it may not have been in our best interests, and it’s not something we need to repeat.

It is now your story to write and your stage to own. Your next chapter and your encore.

How to Prepare for Your Move

Dreaming of a new life abroad is exciting, but a successful relocation requires careful planning. Helen emphasized that her decision to relocate was not based on a whim and that preparation is key for such a bold move. Helen stressed the importance of preparation and broke it down into key steps.

1. Do Your Research 

Start by learning everything you can about your potential destination, your dream location:

  • What language is spoken? Are classes available at home or where you plan to relocate?
  • What’s the climate? Will it suit your lifestyle?
  • How accessible are professional opportunities, coworking spaces, or industry events?

Understanding cultural nuances, legal systems, transportation, and local customs is also critical. Knowing these details will make your transition smoother and more rewarding. You will also avoid disillusion, disappointment, and regret, which can be devastating emotionally and financially.

2. Pick the Right Location 

When choosing where to live internationally, Helen recommends focusing on your lifestyle, the activities you love and what you might miss when you leave your current location and lifestyle behind. Dig deep into the needs, wants, and consequences of making this decision.

  • Will you need a bustling city for networking opportunities, or do you prefer a quieter town rich in cultural experiences?
  • Will you miss getting together with people who are important to you, such as family and friends? How easy or difficult would it be to return "home" if you wanted or needed to?
  • Will you miss activities or the day-to-day conveniences that you have come to enjoy?

In my Encore Lifestyle workshops, I have met people who had not considered the effects of relocating. Here are a few examples of choices and potential consequences:

  • One couple had never discussed their individual needs, desires, or expectations. One partner enthusiastically announced plans to move back to their family home in another province, only to be met with shock and strong opposition from the other, who was adamantly against the idea.
  • In another case, someone expressed that he could never live in a place without access to pizza delivery or a reliable internet connection.
  • Yet another example highlighted a fear of isolation in a snowbound region, where winter lasted for months. Winter activities such as skiing and snowmobiling were abound, but the person's interests and plans for her choice of enriching activities had no connection to snow or cold-weather hobbies.

Every country and city comes with its unique and endearing rhythm—find one that matches yours.

3. Test Before You Commit 

Helen didn’t move to Buenos Aires on impulse. Before making the move, she made several visits to assess its suitability. You can be infatuated by the "vacation" experience, but this won't be a long vacation. Could you live there?

"If possible, immerse yourself in your destination ahead of time. Spend a few weeks or months there to see if it truly aligns with your vision," Helen suggested.

This trial period can give you a realistic sense of what it’s like to live there. Vacation accommodations often create a misleading portrayal of local living conditions.

4. Plan Financially 

Moving to a new country is an investment. The investment is not just emotional but financial.

  • Develop a realistic budget for relocation costs, such as housing, flights, and visas.
  • Understand currency exchange rates and cost-of-living differences.
  • Research healthcare and insurance options for expatriates and their families.

As you embrace the journey ahead, take steps to ensure financial stability, creating a foundation for a flexible and sustainable future and lasting peace of mind.

Before conducting business or starting work in a new location, it’s essential to thoroughly assess your rights and obligations, as well as the potential tax implications.

5. Build a Support System 

“You can’t do it entirely alone," Helen shared. "Find support systems and give yourself grace as you adjust."

Here’s how to start building your network:

  • Join local expat communities or attend meetups.
  • Connect with industry contacts or professional groups online.
  • Look for cultural and professional mentors who can help guide you.

A strong community can help you settle in and feel at home faster.

6. Understand Legal and Immigration Rules 

Your dream move can hit a snag without fully understanding the legal requirements:

  • What type of visa will you need?
  • Are there residency requirements or restrictions on property ownership?
  • Will you need to transfer certifications or licenses to continue your career?

Consulting an immigration lawyer specializing in your desired destination can save you valuable time, money, and unnecessary stress. It’s crucial to thoroughly research and prepare if you plan to work or conduct business in a new country. Proper planning can help you avoid complex immigration and tax-related issues.

Beyond Practicality – The Emotional Journey

Helen shared personal insights about adapting to cultural shifts, navigating emotional ups and downs, and rediscovering herself in a completely new environment.

“The transitions weren’t seamless. I had to be patient with myself. But looking back, I wouldn’t change a thing. Every challenge taught me something new about myself and the world.”

Helen's advice? “Life transitions are challenging, but they’re also opportunities to grow and rediscover who you are. No matter where or who you are, if you’re dreaming of a change, don’t dismiss it. It’s probably your calling.”

Get Started on Your Next Move

Do you feel like life is calling you into a new chapter, onto a new stage, in a new country? Or simply a change that gives you a new and perhaps profound perspective? Whether you're relocating to a new country, crossing continents, venturing to another hemisphere, or simply moving 200 miles to a different town, it’s more than a change in geography. It’s an opportunity to embrace growth, challenge your limits, and live with bold intention.

Take Helen’s advice:

  • Do impeccable research.
  • Start planning the logistics, even if your move is years away.
  • Ask for support: Legal, financial, cultural, and social.
  • Move forward with trust in your capability and capacity to do what's best for you and in pursuit of self-actualization. Transform your knowledge and experience into wisdom, and let it become a source of joy.

Your encore destination is waiting. All it asks of you is to take the first step.

Remember, this decision might just become one of the most rewarding chapters in your life. Maybe you will write your memoir.

Connect with Helen

Your next chapter is waiting. Schedule an Executive Encore Complimentary Call with me. Ask and learn about the two-hour program Master Your Approach to Goal Setting for Transition from Employee to Entrepreneur.

Resources

Rare Steak, Red Wine, Hot Tango. A Rollicking Memoir of Argentina by Helen Wilkie, Executive Book Coach and Ghostwriter.

Video Podcast Links: Unlock Your Story: Writing a Book to Make an Impact in Your Executive Encore. Guest: Helen Wilkie

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