Kach’s Journey

A woman sitting on a green couch, holding a microphone and speaking, in a setting with stage lighting and metal scaffolding in the background.

“From OFW beginnings to becoming the first Filipina to visit every country in the world, this is Kach’s story of courage, resilience, and global mobility.”

Every milestone carries a story. Below, you’ll find the full chapters of Kach’s journey - told in detail, with the struggles, lessons, and triumphs that shaped who she is today.

2009–2013: Breaking the Cycle

A young woman with long dark hair, wearing a black tank top, denim shorts, and bracelets, smiling at the camera while standing near a river with boats and a row of palm trees in the background.
Certificate of completion awarded to Katrina Medina Umandap by the Philippine Overseas Labor Office in Kuwait, dated June 16, 2009. It features the Philippine flag, an official seal, and ornate gold border design.

Born into an OFW family, Kach followed the familiar path after graduating with an Economics degree from UP Los Baños. She worked at the Philippine Embassy in Kuwait and later for an oil company in Iraq, witnessing firsthand the challenges faced by Overseas Filipino Workers. Meeting backpackers passing through the Middle East sparked a new idea that travel and work could exist together.

At 24, she chose courage over convention. With only a backpack, she began traveling across Southeast Asia, teaching English in Vietnam, training in yoga and Ayurveda in India, and volunteering along the way. These years became her foundation, showing that Filipinos could embrace resilience and adaptability while breaking free from traditional expectations.

2014–2017: Building Two Monkeys Travel

Collage of various news article headlines about travel, backpacking, and expat lifestyle, including titles like "Love on the Road," "Dreams do come true: Pinay backpacker," and "Why I’m proud of my Philippine passport."

In 2014, Kach co-founded Two Monkeys Travel, a blog that grew into one of the Philippines’ pioneering travel platforms. Through it, she shared raw stories of bus rides, border crossings, and cultural exchanges, showing the realities of a digital nomad’s life.

Her writing and storytelling reached a wider audience when she began writing for Rappler, leading to global features in TIME, BBC, Forbes, Al Jazeera, and more. By 2017, she had traveled to 100 countries across 7 continents, transforming her adventures into proof that Filipinos could build careers through mobility and creativity.

2017–2019: Life at Sea

A woman with long hair, wearing sunglasses and a black dress, smiling on a sailboat named 'EMPRESS' during sunset.

Kach’s journey took to the ocean when she and her partner lived aboard a sailboat in the Caribbean. Days were dictated by tides and winds instead of clocks, while her “office” shifted from cafés to the boat’s deck.

During this time, she embraced off-grid living, resourcefulness, and community reliance, all while connecting with OFWs in the islands she visited. Her life at sea was more than an adventure. It symbolized how Filipinos could thrive in spaces often seen as unattainable, expanding her message of courage and adaptability.

2019–2020: Building an Anchor in Montenegro

Smiling woman with long braided hair and sunglasses on her head, wearing a black dress and jewelry, raising her right arm near a waterfront with an island and buildings in the background.

After years of constant movement, Kach decided to create an anchor by settling in Montenegro. She invested in a villa and became the first Filipina to secure a digital nomad residency visa there, proving Filipinos could access opportunities usually reserved for citizens of wealthier nations.

Even with a home base, her travels continued. She explored Central Asia, Pakistan, Iran, Mongolia, and other regions often overlooked by mainstream tourism, reinforcing her advocacy that Filipinos with limited visa power could still cross borders and thrive globally.

2020: Setbacks and Resilience

Bold pink banner with text, cartoon illustration of a girl with long hair holding a phone, and a photo of Kach Umandap smiling, promoting a presentation on becoming a digital nomad.

The pandemic abruptly halted her global journey. Borders closed, flights stopped, and Kach faced personal challenges including health issues and PTSD. Instead of stepping back, she turned her focus toward helping others navigate remote work.

She launched the Facebook group “How to Become a Digital Nomad,” which quickly became a lifeline for thousands. At the same time, she published guides on home-based jobs and virtual assistance opportunities. This period of stillness transformed her message. Freedom was not only about traveling, it could also start from home.

2022–2023: Expanding Platforms and Advocacy

A smiling woman in military camouflage uniform holding a Philippines Air Force plaque that reads 'HABAGAT'. She is surrounded by other uniformed personnel standing in formation or socializing, with a backdrop of banners bearing military insignias.
Promotional poster for the 'Travel with Kach' event on June 24 at 9 PM, featuring a smiling woman with braided hair, wearing a red coat and a smartwatch, promoting travel tips and visa guidance on FYE channel.

As the world reopened, Kach launched her lifestyle and travel show Travel with Kach on ABS-CBN’s TFC and co-founded FilipinoPassport.com, a platform guiding Filipinos through visas and relocation. She also joined the Philippine Air Force Reserve Command as Sergeant Katrina Medina Umandap, a recognition that grounded her journey back home.

She shared her advocacy on global stages, speaking at the Management Association of the Philippines Fellowship, the Siargao Digital Nomad Summit, and leading the Digital Nomad Barangay Project in El Nido. These initiatives connected her personal journey to real opportunities for Filipinos, linking tourism, mobility, and remote work.

2024: Championing Global Mobility

Four people standing outdoors, holding a banner that says "We are FWT," with a PTV People's Television banner and logo behind them.

Kach’s role shifted from personal trailblazer to systems builder. She was named the first Ambassador of Filipino World Travelers and returned to the Philippines to speak at the 2nd Digital Nomad Summit in Siquijor.

At the same time, she embarked on her most challenging expedition, traveling through 26 African countries. Beyond personal milestones, her journeys became demonstrations that Filipinos, even with visa limitations, could carve a path across the globe.

2025: Completion and Legacy

Group of five Filipinos standing together at an indoor event, with a Filipino flag and a logo in the background, one person holding a pamphlet titled 'gala'.
Group of Indigenous children and a woman in traditional colorful attire, smiling, at a cultural event or gathering in an outdoor setting.
Group of six women and one man posing with a welcome sign for Kach Umandap, with traditional Filipino costumes and feathered headdresses, in an airport or terminal setting.

On January 6, 2025, Kach achieved history as the first Filipina to visit all 195 countries using only her Philippine passport. She was honored by President Ferdinand Marcos Jr. at Malacañang and celebrated across national media, from GMA and ABS-CBN to Eat Bulaga and Rated Korina. Her homecoming in Cebu symbolized a collective Filipino victory on the global stage.

Her focus now turns from personal achievement to collective empowerment. Through Mission #1642, she is visiting every municipality in the Philippines to bring digital work opportunities to local communities. With projects like the Student Nomad Club, she is shaping the next generation of Filipinos to thrive as global citizens. Her journey is no longer just about crossing borders but breaking them for others.

More about #Mission1642