Stay - You won’t want to miss out.
God honors the nonprofit leader who shows up, builds relationships, and refuses to quit.
If you are in your first few years of nonprofit leadership, this is for you.
You are doing harder work than most people around you will ever understand. The funding is uncertain. The problems are complex. The wins are slow and the losses are loud. You are learning to lead in real time, with real people, and real stakes.
Before you are tempted to believe it’s not worth it — stay.
There’s a corner booth at a coffee shop I’ve been going to for nearly twenty years.
I’ve designed websites there and written grant proposals. Asked donors to partner with nonprofits I believed in. Met old friends. Made a few new ones.
It is a familiar friend — a place to retreat and connect with my community.
Saturday, I was back in that booth with my friend John. A few hours later, I sat with Nancy. Two separate conversations. Two people who chose to stay.
John has had a long career leading city parks and recreation services, then years shaping the next generation of nonprofit leaders in the classroom. Nancy is a board member of a nonprofit whose mission she knows not from a strategic plan — but from her own life.
By the time I drove home, I realized both conversations had landed in the same place.
Relationships.
Both of them taught me something I already knew but needed to hear again.
John and the creative conversation
When John was teaching, he devoted a section of his course to one of the hardest things in this work — asking people to give or partner financially. He called it “creative conversations,” and what he described stuck with me.
His students didn’t just love this part of the curriculum because it was interesting. They loved it because it was real. They felt like they were learning a skill, not reciting a fact.
And then they had to use it.
They took the methodology out of the classroom and into their week. The stories that came back were remarkable. One student went to his auto mechanic — just a real conversation, curious, unhurried, no agenda.
He walked out with $250 off his repair bill.
Two hundred and fifty dollars. From a conversation. Think about that.
It started with a conversation. It ended with a relationship.
That’s the difference, isn’t it? A creative conversation is solution-based. It starts with listening, not pitching. It treats the other person as a collaborator, not a target. The best asks I’ve ever made didn’t feel like asks at all. They felt like an invitation to do something meaningful together.
John has seen enough of this work to know: the fundraisers who endure are the ones who connect — not the ones who close.
Conversations lead to connections. Connections have magic.
When you start really listening, you can find yourself helping to create change that is more than a number or a dollar sign. It creates joy through grit with a bit of grace.
John saw it in a classroom. Nancy learned it in a waiting room.
Same lesson. Different place.
Nancy and the service that didn’t exist yet
Nancy told me about a season in her life when her husband was going through serious health challenges. There was a local nonprofit whose services, had they existed at the time, would have made an enormous difference for her family.
They didn’t exist yet.
Today, Nancy sits on the board of that very organization. She didn’t just advocate for what she once needed — she gets to help guide and fund it. That’s the kind of leadership that only comes from living in a community long enough to know its gaps, and seeing your efforts help people — not just a program — because you lived it yourself.
The most powerful advocates are often the ones who have lived the need.
Nancy understands something deeply true about nonprofit work: the relationship with your community isn’t a marketing strategy. It’s how you learn what actually matters and meet the people who are building the future.
Neither John nor Nancy set out to become the person their community needed. They just stayed. And staying has its own beauty. As a nonprofit leader, you will develop plans, hire staff, and raise funds. You do it long enough, and you will see the beauty of not just lives changed — but communities built.
What thirty years gives you
When you’re new to this work, you can only see the next hill.
The next payroll. The next funding cliff. The next board conflict. That’s not a criticism — it’s just where you are. You’re learning to survive.
But something shifts when you’ve been at it long enough. You start to see the future — not because you’re smarter, but because you’ve lived through enough present moments to recognize the patterns.
A few weeks ago, I texted a former donor out of the blue. He had been instrumental in giving to a nonprofit I led years ago, and I just wanted him to know I was still grateful. Ten years later. No ask. No agenda. Just a thank you.
His response stopped me.
He thanked me for the opportunity to make a difference.
That is the joy I have seen for decades. People love to show up with generosity, and many do so with quiet humility. They want to see lives transformed but find themselves with limited time, money, or skills. As a nonprofit leader and instigator, you get to see people come together to form a community.
Joy, grit, and grace
People like John and Nancy didn’t get here because they had better strategies.
They got here because they showed up — for years, sometimes thanklessly — with joy in the mission, grit through the hard seasons, and grace toward themselves and everyone around them.
That’s the currency of a long career in this field. Not a bigger budget. Not a better CRM. Three things that don’t show up on any grant report:
Joy. Grit. Grace.
Joy that they have seen lives transformed. Grit because so many people stood with them. And grace, because God has caused growth when people stay, when they help, and when they pray.
Who are the John and Nancy figures in your life?
If you’re early in your career, find them. Buy the coffee. Ask the questions.
If you’ve been around for a while — be them.
The corner booth is waiting.
And so is God.
He sees the conversations you are having. The relationships you are building. The days you showed up when no one noticed. He is not done with the work he started in you — and he is not done with the work he started through you.
Your grit is not wasted. Your grace is not invisible. The joy is coming.
Stay.
Dave Sena writes about nonprofit leadership at BoldLeading.com. The Bold Bulletin is published weekly for mission-driven leaders who want to lead with more clarity, courage, and staying power.