Being willing to be uncomfortable

December 22, 2025

Filed under: Board Development,Fundraising,Leadership,Volunteers — Tags: , — jonathanpoisner @ 3:03 pm

This is a follow-up to an article I wrote more than a decade ago entitled: “Step Out of your Comfort Zone.”

I was recently talking to a board member for a nonprofit and they used the exact phrase I wrote about then. “I’m not comfortable approaching my friends to ask for donations.”

To which I asked, with some attempt at diplomacy, “I hear you, but are you not willing to be somewhat uncomfortable if that means the organization can better help people?”

Here’s my paraphrase of what the board member really was saying:

“Our mission is vitally important to the community. Which is why I’m unwilling to make myself uncomfortable to support it.”

Of course, the board member would clearly balk if phrased that way. Yet, this is the disconnect we often hear.

Great passion. Only willing to do things that are emotionally easy.

Now if someone is uncomfortable with a request because they have ethical or legal qualms, that’s a different story. But if it’s emotional discomfort, people need to recognize that change in our world rarely happens only by people being comfortable.

Organizations that fail to create a culture where its leaders get past this disconnect are likely to putter along doing some work, but they are unlikely to thrive.

Why does this disconnect between belief in the cause and unwillingness to be uncomfortable?

What are the consequences of this disconnect?

And how can a nonprofit overcome it?

Why the disconnect?

The level of discomfort people expect to feel when talking to a friend or acquaintance about supporting an organization is based on two cultural taboos:

  • A taboo against talking about money
  • A taboo against pressuring people

It’s not that people aren’t sincere about their belief in the cause. It’s that taboos are strong, especially when combined with fear of the unknown.

Both taboos are cultural. Young children don’t have them. They’re constantly asking their parents for money. And have no qualms about using pressure tactics.

Our parents and others teach us not to talk about money or use pressure tactics and most of us (though not all) absorb those lessons by the time we are adults. For example, we learn that it’s rude to ask someone how much money they make.  Or to be viewed by others as someone who is “pushy.”

What are the consequences of the disconnect?

You may be thinking, so what?

Almost always, the consequence is the organization winds up on a lower trajectory with less ability to accomplish its mission.

A focus on comfort is a recipe for complacency, inaction, and inertia. Any organization seeking change (whether global, national, or local in scope), is rarely likely to succeed without people routinely stepping outside their comfort zone.

The biggest practical impact: fewer resources (both money and volunteer time).

Many people may be aware of and even like the organization from afar, but few wind up in a relationship with the organization in ways that make a difference.

Foundation grants may give the appearance of organizational health for a while.

But the long run prospects are rarely good.

How do you overcome this disconnect?

There is no silver bullet you can produce that instantly will make this disconnect go away. But there are some strategies that work over time.  Here are four you may wish to try.

  1. Name the taboo.

Often times, the first step towards getting past a fear of being uncomfortable is to name the taboo behind it. Talk about it. Recognize it for being the cultural artifact that it is. A cultural taboo that is learned can be unlearned.

With regard to the concern about being perceived as pushy, do an exercise where you name all the more positive synonyms for pushy (e.g. assertive, dynamic, persistent, strong-willed). These are characteristics of strong leaders who are most likely to generate followers to a cause.

  1. Recognize the difference between imagined discomfort and actual discomfort.

Many times the discomfort people expect to experience dwarfs the actual discomfort they will feel when doing it.

Indeed, for the vast majority of board and staff who I’ve worked with as fundraisers, their expectation of discomfort turns into the opposite: a positive experience both for the asker and donor. The asker feels validated. The donor is happy to invest in an organization that will accomplish things in the community the donor values.

“Try it, you may like it” isn’t just a phrase for parents trying to get their kids to taste something new.

  1. Find a cheerleader.

Cheerleading works. Find someone who’s “been there, done that” and who can talk about their fears of doing something uncomfortable and how when they tried it the experience was positive. Nothing is more likely to get board members willing to fundraise than hearing one of their peers talk about how they overcame their own reticence and now recognize that effective fundraising can be a powerful way to strengthen relationships.

If nobody within your own organization fits the bill, find someone else in the community. In any community there are organizations thriving. Get to know them and who is driving them forward. Ask them to provide a pep talk about what’s possible.

  1. Keep the cause front and center.

Sometimes organizational meetings are so stuck in the weeds of finances, programs, and action plans that those involved can become disconnected from what motivated them to get involved in the first place.

They’re unwilling to be uncomfortable in part because they’ve lost passion for the mission. If you fear this is happening, set aside 10 minutes at every board meeting for a round-robin where everyone shares one thought about why they are passionate about the work being done. This may seem like a waste of 10 minutes, but when I’ve used this technique it makes a palpable difference in the quality of the remaining meeting time.

When it comes time to get out of the comfort zone, remind people about their passion for the cause.


So for those of you reading this prior to New Years, recognize that the last few days of the year are the very best days to ask people to make donations to your nonprofit, so challenge yourself to step beyond your comfort and make at least one bold ask!

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