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CARIBBEAN EDITION - September 2022

A Portrait of Affluent Giving in the Caribbean

Watermark releases new study aimed to grow philanthropy in the region

The Caribbean may be your home, a home away from home, or a loved travel destination, or you may have clients with Caribbean interests.  New research sheds light on the giving practices of generous people across the region, and offers a practical roadmap for philanthropists, nonprofits, governments, and private sector partners. 

The first study of its kind, A portrait of affluent giving in the Caribbean: Experiences, barriers, and the future of philanthropy was produced by Dr. Sharilyn Hale after confidential conversations with more than 30 philanthropists across eight jurisdictions in the region, including nationals, non-nationals, and members of diaspora communities. 

Highlights include:

  • Givers in the Caribbean share many characteristics and concerns with their philanthropic peers around the globe
  • In spite of some barriers to giving, 60% plan to give more over the next three years 
  • Generational succession within family enterprises offers new potential for philanthropy
  • Private sector partners have a unique opportunity to encourage more giving 

With a long connection to the region, Sharilyn is happy to share these findings with the hope it will spur new conversations about giving among all those who care about the Caribbean. 

Download your free copy

Early responses to the report:

"I learned a lot and enjoyed seeing how our challenges are similar to other Caribbean countries. I hope it is widely distributed and that it contributes to the charitable efforts in the Caribbean. I am honored to have been included in your research." 


"The report is beautifully produced, and contains such valuable data and insights."


 "An excellent report...very readable...I hope it will encourage more philanthropy."

"I can really relate to many of your findings. I like the way you have been able to show the local donors' views as well as the non-nationals. It reflects well on humanity and on the culture of the Caribbean people."

All things philanthropy:

BNN Bloomberg Smart Wealth with Thane Stenner

In a wide-ranging and good-humored conversation, Sharilyn recently joined host Thane Stenner to talk philanthropy, and answer questions you may have been too polite to ask (like how a philanthropic advisor is paid!):  

  • Living a life of purpose
  • Why public libraries are so cool
  • How philanthropic advisors help and tips for selecting one
  • Caribbean connections
  • How major fundraising campaigns really work
  • Giving trends; giving globally, and more. 
Watch Sharilyn & Thane here 

Shared with Watermark Matters subscribers before public release on September 28, this episode is part of the Smart Wealth podcast series featuring industry and community leaders in Canada. 

Check out past episodes here, including conversations with business luminary Michael Lee-Chin, wealth coach and family enterprise expert Patricia Saputo, investment entrepreneur Som Seif, and economic consultant David Rosenberg.  

Giving visibly, under the radar: Considerations and options for those who don't love the limelight

There is value in being able to see the generosity swirling around us, and the ways in which it makes our individual and collective lives better, safer, and healthier.

Yet, a major theme from A Portrait of Affluent Giving in the Caribbean: Experiences, barriers, and the future of philanthropy is privacy. Philanthropists in the region prefer giving quietly, driven by factors such as culture, religion, and security. This discretion seems to contribute to perceptions that giving is limited.

In other parts of the world, public naming and recognition for charitable giving are more common, making philanthropy overt and visible, and many philanthropists enjoy being highlighted in this way. However, an increasing number of affluent donors desire greater privacy in their giving, to avoid undue scrutiny in these digital and polarized times. 

If you are a donor on the fence about how visible you want your giving to be, Sharilyn offers some questions to consider, no matter where you live or give.

Caribbean countries rate favorably in 2022 Global Philanthropy Environment Index

How easy is it to give where you live?  Ease of giving allows generosity to flow and make an impact...and not all countries are the same.  For the first time, two Caribbean countries have been included in the Global Philanthropy Environment Index (GPEI), indicating Barbados has a 'highly favorable' environment, and Jamaica a 'favorable environment', for philanthropy. 

An initiative of the Indiana University Lilly Family School of Philanthropy, the index evaluates more than 90 countries and economies on a five-point scale, across six key factors that measure philanthropy: (1) ease of operating a philanthropic organization; (2) tax incentives on giving; (3) cross-border philanthropic flows; (4) political environment; (5) economic environment; and (6) socio-cultural environment for philanthropy. 

Sharilyn served as regional editor for the Caribbean, collaborating with experts Jane Armstrong (Barbados) and Karen Johns (Jamaica), with the hope to include more Caribbean nations in future releases of the index.  

Curious how your country compares globally? Explore the index here.  

Strategy ~ Family Engagement ~ Governance

Serving leading philanthropists, generous families and social purpose organizations in Canada and the Caribbean, Watermark offers customized expertise to help those who give, give well, engage their families, and channel their wealth and influence for good.

Contact Dr. Sharilyn Hale for a confidential exploration of your needs.
Watermark Philanthropic Counsel
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