Five lessons in five years

Over the past five years, I have written 60 monthly “On Philanthropy” columns for Sunday’s Denver Post.

These columns covered a broad range of topics related to individuals, families, businesses and foundations — and how they can approach their philanthropic initiatives with strategy, thoughtfulness and effectiveness. In my role as a philanthropic strategist, I’ve gained additional experience working closely with individuals and organizations in Colorado and across the country.

A lot has changed over the past five years. The field of philanthropy has become more sophisticated and complex. The opportunities for philanthropists to make a difference — for themselves and the causes they care about — have become better defined.

Although philanthropy is a deeply personal and highly individualized endeavor, here are the top five broadly applicable lessons I’ve learned:

1.  Look through two lenses

When determining philanthropic goals, look through both internal and external lenses.

The internal lens examines one question: What am I hoping to achieve for my family, business or self by donating hard-earned money or precious time to charity?

Personal giving may be inspired by many reasons, including theology, gratitude, desire to create or repair relationships, ego, fear, recognition, legacy creation, power, compassion, and tax and estate planning.

Businesses hope to enhance employee recruitment, retention, engagement and productivity; customer loyalty; regulatory approval; investor value; and a deeper social license to operate.

The external lens examines a different question: What am I hoping to preserve or change in my community, country or world?

By looking through both internal and external lenses, an individual or organization can develop a solid philanthropic strategy.

2. Engage others

When possible, engage those around you in the examination of internal and external questions and the design and implementation of your philanthropic strategy.

Families should include all generations in meaningful and ongoing conversations about what matters — with openness to diverse opinions based upon different generational experiences. Ideally, every adult member of the family should have a place at the table, a voice and a vote.

In business, engaging stakeholders such as employees, customers, community leaders, investors and others in answering internal and external questions has been shown to significantly improve the return on philanthropic investments.

3. Go deep, not wide

Many donors adopt the “peanut butter” approach — spreading their charity thinly across the surface of a wide variety of nonprofits. It is much better to focus deeply (and with impact) on a smaller number of carefully selected key issues or causes.

4. Deploy all philanthropically committed capital for mission

The money — nearly $1 trillion — sitting in foundations and donor-advised funds is committed to a mission, has received a tax deduction and cannot be returned. Annually, only 5 to 20 percent of that amount is distributed to nonprofits. The rest is usually invested for the sole purpose of financial growth.

The goals of these investments may not match your philanthropic priorities and objectives. Make sure these investments advance — not contradict — your charitable mission and that all of your philanthropic capital is being used to achieve your charitable goals.

5. Give boldly; start now

Giving today — when you can see the results — is much more satisfying than giving from the grave. Guaranteed.

Rarely do people donate so much to charity that they can no longer provide for themselves or their loved ones. Without sacrificing quality of life, many of us can give far more than we currently do.

Consult with your financial adviser to determine what you can really afford to direct to worthy causes — and then start today. Your community needs your help now.

In my first column, back in 2010, I wrote: “Philanthropy is like love. The more you make philanthropy a cornerstone of your life, the more you find the joy, meaning and satisfaction in living.” The more people I see incorporating philanthropy in their lives, families and businesses, the more those words ring true.


Nonprofit of the month: Colorado Criminal Justice Reform Coalition

Since 1999, the Colorado Criminal Justice Reform Coalition has worked to halt the growth of the state prison population by advancing community health, safety and justice. The group advocates for drug policy and sentencing reforms, investment into treatment and community development, ending the use of private, for-profit prisons, and reintegration services. CCJRC also leads grassroots efforts to increase health care access and civic engagement by justice-involved people.


Bruce DeBoskey, J.D., is a Colorado-based philanthropic strategist working with The DeBoskey Group to help businesses, foundations and families design and implement thoughtful philanthropic strategies and actionable plans. He is the president of the Colorado Philanthropic Advisors Network, a teaching fellow with Boston College’s Center for Corporate Citizenship and a frequent speaker at conferences on philanthropy.