We need to practice to improve our skills.
It’s going to take time, effort, and a little sweat. Sometimes we workout with others, and sometimes alone. We’re going to stumble along the way, but that’s how we learn. What matters is that we show up, even on days that we don’t really want to.

If I were starting a new workout regime, I might go to the store (or clean out my closet) to find a new outfit, schedule time in my calendar to workout two or three times a week, chat with my spouse or partner and close friends about my new goals, and sign-up for an event a few months from now to give myself a stretch challenge to aim for. For example, I’m currently attempting to train for a 100+ mile cycling event in June, which has encouraged me to make time for biking in my week.
Still, most of us don’t really have intentional conversations or plan strategies for our philanthropy or even set goals.
Instead, we respond to year-end mailings from organizations we’ve supported in the past. We call in to the local public radio station when they do their twice / year annual fundraising drives. Sometimes we sign up for a monthly auto deduction when a natural or political disaster happens, and we are moved by the recent news we consumed. We might hire a babysitter so we can attend a local gala for an organization that our friend serves on the Board of and personally invited us to attend. We might make a family activity out of volunteering for a morning of trash clean-up hosted by a local environmental organization. And most of us call all these types of one-off actions “philanthropy.” Sound familiar?
To be clear, we are engaging in philanthropy when we do these things. Just like I am exercising when I run through an airport hoping to not miss a connection or sign up for a local 5k race with a group of gal pals.
What if exercising our philanthropic muscles also included things like:
- Conducting a giving audit of who I’ve given to and volunteered with over the past five years;
- Developing a personalized mission statement to guide my philanthropic decisions going forward;
- Engaging in conversations with my spouse, adult children, or other decision-makers about how we give away money, evaluate impact, and continue to deepen our own learning and reflection about giving away money;
- Listening and asking for feedback from organizations to hear more about their challenges and how I might best show up as a partner;
- Proactively shared with my advisors (wealth planner, financial advisor, estate attorney, tax person) what philanthropy means to me and how I want it to show up in our conversations; and more.
Unfortunately, when it comes to philanthropy, we often go at it alone. Giving money, time, and expertise makes a difference, of course. And imagine what impact could look like when we step it up a notch with a professional coach / advisor / accountability partner. Like working with a supportive physical trainer, sometimes working with someone to expand our comfort zone gets better results than doing something solo.
A philanthropic advisor is someone who can walk alongside you on your journey. Aristotle is credited as saying “to give away money is an easy matter and in any man’s power. But to decide to whom to give it, and how much, and when, and for what purpose, and how, is neither in every man’s power nor an easy matter.”
And just like exercising, we can’t let perfection be the enemy of the good. I recently saw a fleeting chat from someone on a well-attended philanthropy webinar: “Moving money to good is better than doing nothing while looking for perfect.”
I immediately jotted it down on a post-it note and hung it on the bulletin board behind my computer screen because it felt so pointed to me – for both my approach to philanthropy and exercising.
I’m not trying to train for an Iron Man event or try-out for the Olympics. I just want to keep up with my five-year old and have fun riding my bike, do a little cross-country and downhill skiing in winter, and enjoy an occasional hike in the woods with my family. But I also make time to sprinkle in a little yoga and strength-training, so I don’t throw my back out (I am in my 40’s now after all).
If you’re in a similar place with your philanthropy … wanting to be a little more strategic and impactful, but not looking to be the next MacKenzie Scott or Rockefeller or Carnegie, let’s connect.
-Kileen
