We'll Figure It Out But Maybe We Don't Have To Figure It Out Alone.
There is something about leading a nonprofit right now that feels different.
I have written before about the challenges of nonprofit leadership: funding, staffing, grant writing, contracts, reimbursement cycles, growing community needs, and the constant work of building something sustainable while responding to what is immediately in front of you. I say all of that while also acknowledging there is a lot to celebrate.
Assuming you're not new here—to our little piece of the internet—you know this work is personal to me as a CEO and founder. At Meryl’s Safe Haven, we continue to grow, develop new partnerships, expand housing opportunities, strengthen our programs, and plan for what comes next. I am incredibly proud of what we have built—although sometimes I don't realize how much we've built until I hear other people talk about us—and where we are going. But growth does not make an organization, or its leaders, immune to difficult moments.
In fact, sometimes growth introduces an entirely new set of challenges and while I love the opportunity to figure out something new... Y'all, I need a break.
At the same time, there is one thing people say to me often: “If anyone can figure it out, it’s you.” Or some variation of it.“You’ll figure it out.”...“If anyone can make it happen, you will.” I understand why people say it and most days, I believe them.
Over the last several years, I have watched this organization navigate challenges, seize opportunities, build partnerships, expand programs, and accomplish things that once existed only as ideas on paper. Actually, some never even made it to paper.
We have figured out a lot.
But lately, I have been thinking about what “figuring it out” actually requires from leaders—and whether we have created an expectation that strong leaders are supposed to do all of that figuring out on their own.
The Conversations Behind the Leadership Title
My informal “Who’s Who of Worcester” has continued, although in smaller and less structured ways. Sometimes it is a scheduled conversation. Sometimes it is a quick check-in. Sometimes it is simply two nonprofit leaders finding a few minutes to talk honestly about what is happening behind the scenes. Those conversations have reinforced something for me: This work is hard—even when the organization is doing well.
We talk about reimbursement delays, rising expenses, hiring and retaining good people, managing growth, funding cycles, boards, contracts, sustainability, and the constant balancing act of responding to today's needs while preparing for tomorrow. And yes, sometimes we talk about payroll.
When you are talking with someone who understands this work, sometimes you don't even have to finish the sentence.
There is the nod.
The look.
The “That!”
That immediate recognition that says, I know exactly what you mean.
Those moments are hard to hear.
They are also felt deeply.
Because they remind me that a difficult month, an unexpected challenge, or a moment when the timing of resources doesn't align neatly with the timing of obligations is not the same thing as failing. Sometimes it is simply part of leading. And sometimes figuring it out gets heavy.
When “Figuring It Out” Gets Heavy
The cost of everything has gone up. Housing. Food. Insurance. Utilities. Transportation.
Life.
And while I take tremendous pride in caring for others, I am also learning that sustainability has to include the people doing the sustaining—including me.
Last month, I had to type one of the most challenging text messages of my career: I had to ask for help.
Clutches pearls.
It wasn't challenging because of pride.
Okay.
Maybe there was some pride.
It was challenging because, in that moment, asking for help felt like failure.
Somewhere in the back-and-forth messages, the conversation became emotional. What followed was one of the most supportive exchanges I have experienced during my time as a CEO.
There was no judgment.
There was understanding.
Encouragement.
And a willingness to help me think through what might be possible. Somewhere in that exchange came perspective. Organizations encounter challenges. Leaders identify them. We assess the options. We make the calls. We use our relationships, resources, experience, and creativity. We make decisions. We adjust.
We figure it out.
And sometimes asking for help is figuring it out and maybe, just, maybe this is why people say: Check on your strong friends.
When someone develops a reputation for figuring things out, people naturally assume they will continue figuring things out. (And they probably will.) But strength doesn't mean never encountering a difficult moment. Leadership doesn't mean having unlimited resources. And organizational sustainability doesn't mean the absence of challenges.
Sometimes strength is recognizing a challenge early enough to do something about it.
Sometimes it is knowing who to call.
Sometimes it is changing course.
And sometimes it is being willing to say: I could use some help figuring this one out.
What If We Figured Some of It Out Together?
Those conversations with other nonprofit leaders have stayed with me.
The nods.
The “Thats!”
The moments when someone says something you have been thinking but haven't said aloud. My “Who’s Who of Worcester” conversations originally came from my desire to listen, learn, connect, and better understand the people who were doing this work before we arrived—and who might become allies as we did the work alongside them but maybe there is a next step.
Maybe we need to create a different kind of space for nonprofit leaders in our community.
Not another conference.
Not another networking event.
And not another panel. (Sorry. I think panels are great. Really, I do!)
But I'm thinking about something different.
Maybe we need a Nonprofit Leaders Support Group.
No PowerPoint.
No prepared talking points.
No expectation that anyone walks through the door with all the answers.
Just nonprofit leaders sitting together and talking about what this work actually looks like right now.
Unscripted. Unpolished. Honest.
A space to talk about what is working and what isn't. Growth and funding cycles. Boards and staffing. Fundraising and contracts. Cash flow and reimbursement delays. Burnout and boundaries. Difficult decisions and exciting opportunities, but I don't want it to simply be a place where we talk about what is hard.
I want us to talk about how we can support one another. What resources can we share? What introductions can we make? What lessons have we learned the hard way that another leader shouldn't have to learn alone? Where can we collaborate instead of compete? Who has already figured out something another organization is struggling to navigate? And perhaps most importantly: How do we make sure the people holding up our community organizations have somewhere to go when they need someone to help hold them up?
Worcester Nonprofit Leaders, This Is an Invitation
So, I'm putting the idea out there. If you lead a nonprofit in Worcester or Worcester County and this sounds like something you need—or something you would be willing to help build—I want to hear from you.
No panel.
No performance.
No pretending we have it all figured out.
Strong organizations aren't organizations that never face challenges. They are organizations willing to face those challenges, learn from them, adapt, build relationships, and keep moving forward.
Maybe leadership is figuring it out, but maybe part of becoming a better leader is recognizing that we don't always have to figure it out alone. I still believe we'll figure it out.
I'm just starting to think we might be better at figuring some of it out together.
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