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Get comfortable with being uncomfortable...

Making the Ask

I have a passion for running and have been doing it for a long time.  Some days it’s easy to put on my running shoes to head out and other days I don’t feel like I have the energy, but I do it because I know the benefits.  Sometimes it can be raining, too hot or even snowing and it is uncomfortable, but I miss the benefits if I don’t do it.

It’s probably a simple analogy but asking people for money can be the same way.  There are days that you would rather check email and stay in the office rather than go out and see one more donor.  And there are days where you can be so excited about seeing someone new or a friend who has been generous to your organization.

Fundraising is something that most people are not comfortable doing.  In fact, most people would tell you they don’t like it for many different reasons.  What I tell my coaching clients (leadership and/or staff) is that they have to get comfortable with being uncomfortable.  Someone has to set up the appointment, someone has to be making the ask because the work will pay off.  It would be easier to have a meeting without a planned next step but are you being a good steward of your time or your potential donor’s time?

Do the hard work and get used to making the ask.  Each time you do it will get a little easier.  It may never be effortless, but all things worthwhile never really are.

The summer will be ending soon so lace up your running shoes because fall is always a busy season for fundraising – no matter where you live in the country.


“Chase the vision, not the money, the money will end up following you.”

—- Tony Shieh, CEO Zappos


Written by:  Paul D’Alessandro