Getting serious about philanthropy is like embarking on a voyage. It is exciting to explore your beliefs and aspirations, learn from experts and practitioners, and experiment with different types of grants and organizations.

But the journey can also quickly become overwhelming; the social and environmental needs are so great that it can be hard to know where to start! What's more, the pressure to "do philanthropy really well" is higher if you're giving very large sums of money, and planning to give for a long time.

It’s important to realize that every philanthropic journey is different. You may be an experienced donor in one area, while still exploring your interests in another. So it may be helpful to think of three broad stages for your philanthropy, with each stage containing a unique set of activities that will help you get the best results.

Stage 1 - Exploring

In the early stages of your philanthropy, you likely have a wide variety of causes that you care about. That’s OK – many donors start by writing checks to different types of organizations. However, some philanthropists decide they want to get even greater results by "being strategic" in their giving. So your first task must be drawing some rough boundaries. Which causes will you especially target?

There’s no single right answer. But a good way to get started is to ask yourself a few questions: What people, problems, places, pathways, or philosophies do I care most about? Based on my experiences so far, what do I know I like/dislike, and where do I want to learn more? For my first set of intentional grants, what’s in and what’s out? How much do I want to spend on each particular issue? You will likely revise your answers over time, so nothing is set in stone. But it’s important to have a starting point. What are the watchouts at this stage? At one extreme, it’s easy to get too wrapped up in trying to define the perfect approach or strategy before making any grants. At the other extreme it may be tempting to stay in check-writing mode and support too many causes without picking a few to really learn more about. This shotgun approach is unlikely to tell you a lot about where you can really help accelerate results.

How to get started? One way to navigate these two extremes is to take a portion of your grantmaking and experiment with a small handful of investment “pilots.” Pilots allow you to learn about areas you care about while generating results – by intentionally selecting a handful of exciting grantees in a related space, partnering with a funder or two in that space whom you admire, and researching the issues you care about. Pilots also allow you to learn about what you personally enjoy funding, a critical step in developing your philanthropic interests.

For now, it’s important to recognize that you are not deciding on a big strategy; you’re learning about what it really takes to get results. You are also learning more about how you really want to “do” philanthropy. Your pilots may last a year or two, and as long as you’re respectful of setting expectations among grantees, you can learn a tremendous amount about how to deepen your philanthropy going forward.

Read more about Stage One: Exploring

Stage 2 - Experimenting

Some individuals spend most of their philanthropic life exploring. Others, however, want to deepen their commitment to a few key areas. With some grantmaking experience under your belt, you may have found an area that you want to delve into further. Or, you may have added to your “let’s not do that again” list. Either way, you will have gained information that will sharpen your priorities. You may also have started to identify the results you seek, and what role you can best play in getting there. At this stage, you may start asking yourself: Given what I’ve learned from my prior grantmaking experiences, what is in and what is out going forward? What results could I imagine holding myself accountable for? What resources (money, time, influence) am I personally willing to invest? What interventions are likely to yield better results, given my resources?

What are the watchouts? At this point, you’re starting to define a strategy. It is important to define what “success” looks like, but beware the trap of getting overly wedded to too many metrics. Work with grantees and other partners to identify the few indicators that really matter. Figure out how you (and your grantees) will know whether things are working, and how you will use this knowledge to make better investment decisions next time.

Another common trap is getting so wrapped up in a highly-engineered grant selection process that you miss the forest for the trees. You want to focus on ensuring that your grants really do add up to your greater vision of success. Finally, beware overconfidence and the urge to “fly solo.” In the quest to aim high, some philanthropists become overly optimistic about what their limited resources can realistically accomplish. Consider how your philanthropy fits into the context of the field, and how your efforts, together with others’, might drive even greater change.

Read more about Stage Two: Experimenting

Stage 3 - Swinging for the Fences

Some philanthropists stay in the experimenting phase with the bulk of their resources. Others become frustrated with the results they’re seeing, or get excited by the small-scale results they have facilitated, and decide to pursue change on a larger scale. Such a move requires a well-informed strategy (deeply informed by grantees and others in the field), a clear sense of what works and what is being tested, the right set of aligned partners, and realistic assessments of your progress against the results you want to see achieved. The more you listen and use what you’ve learned to adjust your course, the more likely you are to achieve the change you hope to see in the world.

At this stage, you may start asking yourself: What have I learned about what works, and where I can best invest my resources? What do my grantees and their beneficiaries really think about my approach? How can I improve as a funder?

What are the watchouts? A common trap in this stage is failing to solicit outside perspectives and help. It’s important to seek feedback about your efforts, because you are unlikely to hear bad news and receive constructive input unless you explicitly ask for it. Excellence in philanthropy must be self-imposed because philanthropy is exempt from the kinds of accountability imposed on businesses and government. There are no “markets” or customers responding to your actions; there are no voters pressuring you to change your approach.

Another challenge in philanthropy, even with a solid strategy, is knowing when to stay the course, and when to adjust. It is difficult to stay on track, and refuse to be distracted. One way to guard against this trap is to review your decision-making process; it should help align with what you are trying to achieve, while also allowing you to be flexible to incorporate new information as it arises.

Read more about Stage Three: Swinging for the Fences