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Black Women Leading


DATES: May 25 - June 1, 2024 | 8 Days, 7 Nights

PRICE: $4,900

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We believe that driving innovation and amplifying your voice at your organization is not just a goal, but a necessity. For Black women, navigating the professional world is tough and can lead to feelings of frustration and being overlooked. But we know that you have the talent and potential to create new career possibilities and drive change.

That's why we've designed this program specifically for Black women who are ready to take their careers to the next level. Through a unique combination of group coaching, speaker sessions, and social activities led by Black women who have started their own initiatives and businesses, we will guide you towards success. Our leaders will share their stories, experiences and offer expert advice to help you feel empowered, prepared and ready to tackle any challenge.

Throughout this learning, work, and travel experience, we will cultivate a culture of curiosity, support, and inspiration. Our participants will not only gain new skills and knowledge but also expand their professional network and feel energized for future career growth. Plus, we'll be doing it all in beautiful Lisbon, Portugal!

Join us for a week of discovery, growth, and adventure. Let's unleash your full potential and create a brighter future together.

The Program.

Our Experience Leaders.


Lauren Chesley

Head of Industry, Retail & Restaurants, SXM Media

Lauren Chesley is currently the Retail & Restaurants Head of Industry at SXM Media where she leads strategy and development for the retail and restaurants categories across SiriusXM, Pandora, SoundCloud and Stitcher.

 Lauren has held positions as a creative strategist, talent brand and marketing manager, experiential event planner, influencer marketer, and a trend/consumer/media insights lead at other companies like Target and Squarespace. Passionate about cultivating diverse and inclusive cultures and conversations, Lauren has also led efforts to integrate the multifaceted aspects of identity into all she does in and outside of work.

In addition to her corporate work, Lauren is certified as a coach from NYU and is a photographer, and author of STREET SPEAK, a book that showcases the power in street art to motivate, inspire and ignite passion every day. 

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Margo Gabriel

Journalist & Culinary Experience Creator

Margo Gabriel is a journalist, author and associate producer from Boston, MA. She is based in Lisbon, Portugal. She is the author of The Expat Kitchen cookbook. She has been featured in the New York Times, HuffPost, Sweet July, Conversas Ao Sul, and Time Out Lisboa. Her words have been published in Boston Art Review, Cuisine Noir, Culinary Backstreets, Fodor’s Travel, and Refinery29. She is a contributing writer at Cuisine Noir magazine. She is also the Food & Drink columnist at Time Out Lisboa. As a culinary creative, Margo partners with chefs and restaurants around the world to increase the visibility of minority and locally owned businesses on global platforms. Her partnerships include media features, private dinners, restaurant debuts, and more. 

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Day by Day Itinerary

Each program will vary slightly based on time of year, weather, and cultural events in Lisbon. This agenda provides an overview of what to expect throughout the program.

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Day 1

Arrival Day

Make your way to your apartment and rest and recharge from travel. 

Due to many flight arrival times throughout the day, there are no planned activities. Take some time to settle and relax in the evening and get to know your new city.

Day 2

In the morning, we will introduce you to the city with a 4-hour historical walking tour of Lisbon and some of our local secrets.  This tour of the city will set the stage for your cultural, professional, and personal learning experience.

After you take a rest from the walking tour, it’s time to officially kick off the program!  Dinner with us at one of our favorite spots in Lisbon and we will show you what eating in Portugal is all about. We will stroll past the crowds and sit down to feast on Portuguese culinary delights and, of course, good Portuguese wine.

Day 3

We start Monday in our work space. The opening leadership session establishes the leadership theme for the week in an inspiring and provocative way. We will pause for lunch from the Second Home cafe and finish the worskhop early afternoon. The rest of the afternoon is yours for individual work time if you need to attend to things for your job back at home.

In the evening, we have a special community event with Black women from around the world.

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Day 4

Tuesday is an open day for you to explore the city or individual work time at the office space. Wake up on your own time, sip coffee and your breakfast on a sidewalk cafe before taking on the day. You may choose to visit the famous Feira da Ladra - a large flee market in the old town or stroll along the water near the Tower of Belém. Our local guide will help you plan the perfect day.

Day 5

We are back at the workspace to continue our personal and professional journey from morning to mid-afternoon.

In the evening we will come together for a cultural event.

Day 6

Thursday, we take a day trip out of the city to visit the fairy tale land of Sintra, Portugal.  During this one-of-a-kind experience, we will travel to the mountains to see some of the best spots in the area. We’ll get great views of the palaces and Castle of the Moors as well as spend time in Quinta da Regaleira and wander through the charming streets of the village.


Day 7

This closing session will wrap up the week’s professional development. We will take the time to reflect on our experience and make personal commitments. We’ll conclude the official program with a fun dinner where we can all reflect on our experience and end the week Lisbon-style!

Day 8

Depart Lisbon

Important Program Notes & Details

What's Included?

7 nights accommodation in Lisbon, Portugal; participation in leadership development courses; workspace access at program office; welcome and closing dinner; 3 lunches, private tours with local guides, cultural activities; support from program leader pre and during your trip.

What's Not Included?

International airfare and personal travel insurance. We strongly suggest participants to have personal travel insurance that at minimum covers medical emergencies and cancellations. We don't cover expenses during your free time, transportation to non-program events (like an Uber ride), damages to your apartment, food & beverages not included in the official itinerary. 


This program includes some walking tours where the ground may be uneven such as cobblestones, stairs, or hilly, you may be on your feet for several of hours at a time and should be comfortable walking 1-2 miles (2-3km). Many buildings and sites in Portugal do not have elevators.

Booking Terms & Cancellation

This program has a non-refundable deposit of $1500 (USD) that must be paid immediately in order for a participant to be officially registered. This shows your commitment to the program and allows our operations team to start working on your arrival. Full payment of your program is due 90 days prior to your program start date.


You may cancel on or before March 25, 2024 and receive a refund minus the $1500 deposit fee. Any cancellations after March 25, 2024 is 100% non-refundable. 

If the program is cancelled by Workbreaker, you will be refunded the entire program fee and deposit.

More FAQs

You can read more details and FAQs HERE. If you have more questions about this program, we're very happy to answer!


We can wait for your to join our next cohort in 2024!

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What They've Said

Changed the way I look at the world

"Workbreaker for Black Women was a uniquely curated experience that took me on a personal and collective journey for myself and the brilliant women that I met on this cohort. This was such an amazing growth experience that has forever changed the way I look at the world!


Great blend of curated cultural experiences

"Workbreaker was a great blend of curated cultural experiences, free time, and introspective work. Lisbon is amazing! Great food, friendly people, and a haven for handmade goods."

Experience I will never forget

"The Workbreaker Black Women Leading experience was like none other I have experienced. Being able to learn, live, and work in another country with like-minded women is an experience I will never forget!"


Gave me the chance to dream

"I loved the opportunity to experience Portugal and the essence being embedded in a community and the opportunity for Black communities to have access to quality foods, services, and work spaces all in walking proximity. This opportunity gave me the chance to dream!"

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