How Many Bridesmaids Dresses Are You Wearing At Work

I love rom coms; they bring joy, hope and good feelings.

This past rainy Saturday I watched 27 Dresses, ready for a relaxing feel-good movie.  When suddenly, my nonprofit brain kicked in. As I watched Jane say yes to being a bridesmaid again, and again, and again I realized she wasn’t just wearing bridesmaid’s dresses. Every dress represented another responsibility she’d quietly picked up. 

Years ago, I too was wearing too many bridesmaid dresses at the office.  If something needed to be done, I'd often do it myself because it felt easier than showing someone else. I told myself I was being helpful, keeping things moving, and making everyone's job easier. I avoided uncomfortable conversations because I didn't want to upset anyone. Looking back, I thought I was protecting the relationship and being a great team player. What I was really protecting was my own discomfort.

While watching the movie I realized that many nonprofit leaders have closets full of bridesmaid dresses, and they are wearing them all to work every day. One more committee meeting, one more proposal, one more donor call, one more board conversation, one more responsibility, and the list goes on. Before long they are carrying more than 27 dresses alone. 

The interesting thing is... the board has a closet full of dresses too.

A thank-you call. Sharing a story about the mission. Welcoming a new donor at an event. Introducing someone from their network. Inviting a friend to visit your organization. Helping steward a long-time supporter. Opening a door to a new community connection.

Those dresses are hanging in the closet every day. Except the board members don't know which ones to wear. 

The scene that stays with me is Jane is sitting in a restaurant with Kevin, the wedding reporter (an unlikely friend) who asks questions.   As the conversation unfolds all the frustration she's been holding inside finally explodes out. It isn't polished or graceful. It's an explosion because she's kept avoiding the difficult conversations she needed to have.

It dawned on me that 27 dresses wasn’t just about the dresses and many responsibilities, but also about the conversations we avoid. And every conversation we avoid is another dress we carry. 

I've sat around countless board tables and listened to executive directors wonder, "Why am I carrying this alone?" And listened to board members say "I want to help... I just don't know what that looks like."  Once upon a time I was one of those board members.

Neither side is trying to disappoint the other. They’re simply having different conversations in their own heads. The executive director assumes the board understands what's needed. The board assumes they'll be asked if they're needed. So, everyone waits. And while waiting, fundraising becomes one more responsibility carried by a few people instead of a shared responsibility embraced by the whole board.

One of the biggest myths in nonprofit leadership is that difficult conversations damage relationships. I’ve found the opposite to be true.

After working with many boards and leadership I know that when expectations are clear, communication is honest, and people understand the role they play, trust grows. Board members become more confident because they know where they can contribute. Leaders feel less alone because responsibility becomes shared.

Boards don't become fundraising partners because someone handed them a job description. They become fundraising partners because both board and leaders have the courage to create clarity, invite participation, and keep the conversation going.

Later Jane speaks up honestly, and now she does it with calm and clarity. She hasn't changed who she is. She's simply found her voice. She stops trying to make everyone happy and comfortable, and ironically, that's when her relationships become more authentic. She eventually stopped saying yes to a role that no longer fit her and started having conversations, instead of withholding them.  

Jane finally stops carrying what was never hers to carry alone. And of course that leads to her happy ending. 

Romcoms aren't just love stories, they're transformation stories. They're about ordinary people finding the courage to stop pretending everything is fine, to say what needs to be said, and to take the next imperfect step. Maybe that’s part of the reason I enjoy them and of course, the happy ending. 

Whether it's a rom com or a nonprofit, the best stories aren't about perfect people. Maybe that's the real happy ending. Not that everyone stayed comfortable. Instead they shifted out of their comfort zone and now possibly are only wearing 1or 2  dress instead of 27 dresses. 

How many dresses are you wearing? Which ones are you ready to shed? Which conversation will help you do that?

I'd love to help you start those conversations with your board. Sometimes all it takes is a fresh perspective, a little clarity, and someone to help everyone find the role that fits them best. Feel free to connect with me by email sonia@upliftingnonprofits.com or schedule a time to chat https://calendly.com/sonia-uplifting/1on1?