You Can’t Fail

Philanthropists are in the enviable position of determining their own bottom line. On the one hand if you are trying to achieve something, then by definition you may not achieve it and therefore “fail”. On the other hand, if you are giving money away you are only able to fail the people you hope to help. You can’t personally “fail”.

So if you can’t fail why aim low? Why not strive to do the impossible? Why not make mistakes and then try again tomorrow?

One of the reasons that philanthropy is often compared to venture capital, is because venture capitalists make lots of long shot investments with the expectation that most will fail but some will wildly succeed. Of course a VC really can fail because if they have too few wild successes they will run out of money an not be able to make any more investments. Most philanthropists don’t plan on their philanthropic investments achieving any financial return and so they are not dependent on “successful” grantmaking to make more grants in the future.

In the end, I think the biggest risk to a philanthropist is the risk of playing things too safely. The fallout of playing things too safely is that you end up with a long list of nice things you’ve done for other people, but nothing really to show for it.

Since you know you can’t fail, what are you going to do?


  1. Crossroads says:


    Really enjoying your blog.

    I am managing several SE/ NGO operations in China, and advising donors as well,.

    your post is spot on, and it is a common phenomenon I find here. Donors are very hesitant to work with some groups as they fail to understand the environment which they are operating in. That somehow their own ignorance makes the benefactor risky, and in the end they chose the safe option which may not actually be the best option.

    On the other side of the coin, as an NGO manager, I can see where NGOs choose the more conservative route. It is easy, safe, and perhaps there is security in staying small. For those looking for growth though, I focus their efforts in understanding that investing in a scalable platform will pay out long term, and that by doing so they will attract more investment.

    At the end of the dy though, getting people out of their comfort zones is always difficult, but for those that do I feel the lessons are important regardless of their short term success… it is the long term than we all need to be focused on.

    Keep up the good work.


  2. Thanks so much. It is a funny paradox that sometimes the biggest risk is deciding to not take a big enough risk!

    Good luck with your work.

  3. @gkccf says:

    What would you attempt to do if you knew you could not fail?

  4. @gkccf says:

    What would you attempt to do if you knew you could not fail?

  5. @gkccf says:

    What would you attempt to do if you knew you could not fail?