The Reality of Leading in the Messy Middle
Marcia Beckner
Welcome to Nonprofit CEO SPARK, the podcast for bold leaders ready to navigate growth and change with energy and confidence.
I’m Marcia Beckner, nonprofit founder, former executive director, and culture strategist with nearly 20 years in the social impact world.
Each week I help nonprofit leaders stop spinning out, set boundaries, and design inclusive cultures where all staff can thrive.
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Welcome back to the Nonprofit CEO SPARK Podcast. I’m Marcia Beckner, your host.
Today, we’re talking about something that everyone listening right now will be able to relate to. I can promise you that.
Most leadership stories get told in two versions: the before and the after. Everyone loves a good makeover show, right?
Well, people talk about the breakthrough after the culture is stabilized, after the hard decisions work out, after the team rebuilds trust, and after the organization finds its footing again.
But very few people talk honestly about the middle, or what we’re calling the messy middle.
The part where you’re still leading while things feel uncertain, where you’re carrying pressure privately while trying to create steadiness for everyone else.
Where the staff dynamics feel fragile, communication is harder, and you’re making important decisions without fully knowing how they’ll turn out.
And the truth is, most nonprofit CEOs and executive directors are not living in the polished after version of leadership, right?
Most are leading in the messy middle every single day.
In this episode we’re having a real conversation about what leadership actually feels like during seasons of change, instability, and uncertainty, while you’re still trying to move the mission forward.
Because the messy middle is not a sign that you’re failing, it’s where your leadership is actually formed. So I really am excited to introduce you to my guest today, Annie Bacci. She is the CEO of TGTHER. And Annie, welcome to the show.
Annie Bacci
Great, thank you so much, Marcia. I’m really happy to be here with you today.
Marcia Beckner
Happy you’re here too. Thank you so much.
This is a really important conversation, so that people don’t feel so alone as they’re going through the messy middle.
And I can tell you, as someone who’s been an executive director before for 10 years, 10 years felt like the messy middle.
Like, what’s the clear beginning, what’s the clear ending, do those even actually exist? So let’s talk about reality today.
Annie, first tell everyone a little bit about yourself and your organization, and where you are today.
Annie Bacci
So, our organization is TGTHER. Our mission is to end youth homelessness, and I have been the CEO here for about two and a half years.
Before coming to TGTHER, I’ve spent my career working in homelessness and housing, really working mostly with communities, states, cities, counties, around how do you strategically address people experiencing homelessness in your community and find sustainable solutions.
I actually started my career as a case manager, working with youth who are experiencing homelessness in 2004 in Denver.
And so when I had seen this role come available at TGTHER as the CEO, I was ready to really start working locally again.
I had been working nationally with different communities, and I’d always had a passion for the youth work, and so it seemed like a great full circle moment to come to Together and lead this team and this mission forward.
Navigating Growth, Infrastructure, and Sudden Course Corrections
Marcia Beckner
That’s amazing. So you’re working with, you know, one of the most vulnerable communities here in the States, and thank you for doing this work.
You’re brave, you’re bold, you’re, you’re doing something that most people wouldn’t even know how to step into, and you’re doing it every day, and that’s so admirable.
So, thank you, Annie. I just wanted to pause for a second. Thank you. You started two and a half years ago, which was probably 2024 ish.
Annie Bacci
Yeah, late 2023.
Marcia Beckner
Yeah, late 2023. Okay, and then we had 2024 and 2025, which I don’t have to tell most people listening that there were massive changes last year and threats to our local communities.
Including, I’m sure, your organization.
So tell us, like, when there’s funding uncertainty… like, was that what happened to you last year? Like something dramatic that caused some significant turmoil?
Annie Bacci
Yeah, I think that TGTHER is really facing multiple headwinds, and I think what I’ve learned is that’s often the case.
It’s usually not as simple as, you know, funding uncertainty or one funding cut. It’s usually layered upon multiple vulnerabilities within an organization.
And so, you know, when I arrived at TGTHER in late 2023—and part of what really excited me about the role is that TGTHER was ostensibly in a period of growth.
We had been an organization based in Boulder, Colorado. We had just expanded to open new housing in Denver in 2024.
I was really excited about the expansion. We had grown our staff to really be able to serve young people in these growing programs.
And what I learned shortly after arriving at TGTHER and really digging into some of the financials and the operations is that, you know, and this is again not uncommon in nonprofits, there was expansion based on vision and hope without real infrastructure built behind it.
So you know, the organization had opened a lot of programs that we didn’t have long-term committed funding to run in perpetuity.
And you know, this was sort of a foundational vulnerability that was helped along by the PPP that came during 2024.
We also received quite a bit of ARPA funding from local and state governments, which really helped bolster the organization, and in a way kind of cover up or extend the period of operational stability.
That then, it felt like, very abruptly shifted in 2025 with ARPA and stimulus funds sun setting, the economy changing, the federal administration changing.
And so we did have then several inflection points, including a sudden and significant funding cut that threw us into a real reactive period of having to make some hard decisions very quickly.
Including closing programs and downsizing, having to lay off a significant number of team members, which was extremely painful.
And you know, we’re still living with what happens on the other side of contraction after a period of growth.
The Honest Difference Between Isolation and Loneliness
Marcia Beckner
Wow, okay, that is a lot, Annie. That is significant.
How are you? I always go to kind of the health and well-being of you leading through this time. How are you managing the stress that comes with those massive changes?
Annie Bacci
That’s a great question, and you know, I love your work, Marcia, because you talk a lot about, you know, how leadership can feel isolating at times.
And you know, I would say, I haven’t felt isolated in this period, but I have felt lonely at different periods.
Because you know, there’s a really limited number of people that you can lean on and really share kind of the details of the nuances of what you’re holding with decisions.
And you’re also carrying the awareness that your decisions have real impact on people’s lives.
I feel lucky that I had developed some great tools and practices before coming into this role around self-care, and how I have, like, a kitchen cabinet of folks that I know I can call and process things with, even if they’re not ready for public consumption. So I’ve been utilizing that.
I think that it really, it isn’t linear, so that’s, you know, something I want to say for other leaders out there, especially when you are in a turnaround or restabilization moment.
It feels like, oh, once the tanker starts turning, we’re going to hit our stride and find our footing, and every day will get easier. And that hasn’t been my experience.
I think you know I have weeks where I think, wow, things are clicking and the culture is feeling like it’s growing and getting stronger.
And then the next week, you know, two or three things will happen where it just feels like we’re back to square one, or you know, we’re still not out of the woods yet, even though we all really want to see it.
And so I think it’s coming back again and again to the tools, and knowing that it’s normal to have a path that isn’t linear. In fact, that’s usually how it is.
And so yeah, I think that’s important for other leaders to hear that again, when we tell stories—like you say, everyone loves a comeback story.
So when we tell the story, it can get reduced to, you know, these really hard events happened, hard decisions were made, things started to turn around, and off we go.
But in reality, it’s like the squiggly line graphic that I know a lot of leaders see, where it’s like my path, what I thought my path would look like, and what it actually looks like. Definitely living that in the day to day.
Marcia Beckner
Oh yeah, never a straight line, is it? I’m curious. You said you don’t feel isolated, but you feel lonely. Like, how do you define the difference?
Annie Bacci
I think isolated is where maybe, for me, you don’t really know who to call or who to talk to. And like I said, I’ve done a lot of intentional work to cultivate that for myself.
You know, I have colleagues and mentors and friends, I have a therapist… like, I have this sort of way to make sure that I don’t get isolated.
And at the same time, as a leader, there’s decisions that you have to make that you can crowdsource, you can process, you can weigh the pros and cons.
But at the end of the day, you’re the one who has to sit with that decision and make that decision, and it’s really you. And that can feel lonely, you know.
Sometimes I wish I had a co-CEO, so we made this decision together, and it’s been an important part of my leadership journey to know, okay, this is my decision to make.
And it’s really important, and I’m going to, you know, weigh everything in making that, and communicate as much as I can as soon as I can.
I’ve been thinking about… well, I’ve been really into the show The Diplomat. I don’t know if you’ve ever watched that.
Marcia Beckner
I haven’t watched it yet.
Annie Bacci
It’s a great leadership show.
But they were talking about, you know, in politics, when decisions get to the president’s desk, they’re often 49/51.
Meaning, you know, it could go either way, and there’s no great answer, and you have to choose. There’s a good argument for either way.
And that really is to me—not that I’m comparing myself to presidential aspirations—but that is what leadership is about.
Because if it were an easier, a more clear decision, it would never make it to your desk.
It would never make it to you, because some of your other amazing, more capable staff would have already made the decision.
And you know, we have a culture of really empowering leaders to make decisions on their own, and so those are the moments where it really does feel lonely.
Marcia Beckner
And with that 51/49, you’re just going to make half the people mad, no matter what you decide.
Annie Bacci
Right.
Marcia Beckner
And then you feel that’s where the loneliness comes in, where it’s just like you can’t make everyone happy.
Annie Bacci
Right. And a lot of responsibility, because it will have impact for…
Marcia Beckner
Yeah.
Annie Bacci
Young people we work with, and for our staff.
And so, you know, I just have this desire for folks to know, like, I do not take this lightly.
Like, I know my decisions have impact, and sometimes I can get into over justifying or over explaining.
And that’s when I know I’m kind of out of my integrity, because I really try to hold the process and share as much as I can about the process during the time in which I’m making a decision.
Defining Better: The Deep Dive into Team Transparency
Marcia Beckner
Yeah, and a lot of staff in the, you know, the organizations I’m working with, or my client organizations, are always asking for more transparency, more transparency.
And how do you handle that?
Because it’s, you know, like you said, some things aren’t ready yet to be shared because they’re sensitive issues.
How do you handle this call for higher transparency from your team when you want to give it to them, but you have to, like, wait for a certain point?
Annie Bacci
Oh gosh, I mean, I think so much of what you’re describing is like the human experience, right?
Like, we always feel like we’ll feel better if we have the information sooner or more of it, even if it’s bad news, and that actually, in my experience, hasn’t been the case.
And I’ve learned, I think, by sharing too much, too early, around, like, “well, here’s all the things I’m considering, and here’s all the possibilities that could happen…”
And then staff feeling like, oh my god, like something big could happen, and it could really impact me, but I’m not going to know what the outcome is for a while.
And there’s a lot of reasons that you can’t share, especially personnel-related decisions, HR related decisions.
And so I think that how I handle it is I try to make myself available, so going to like team meetings, staff meetings, and hear from staff, like what information do they feel they’re missing?
Because a lot of times you’re like, oh, I can actually answer that or share that.
And also just create opportunities where I can invite people to check assumptions with me or concerns with me.
Because sometimes the rumor mill will get going, and it’s not actually… you know, I can actually say, well, that’s not something on the table for consideration.
But I really think that what I’m able to share with staff is that we are working really hard to turn things around and restabilize.
And we’re going to have an all hands call every month, which is something new that we’ve decided to do, which has helped a lot for information sharing.
We’ve created processes like an anonymous feedback form that has a little QR code. My team loves a good QR code.
They can input questions, concerns, and it really helps just create that flow of information.
And sometimes I think when people want transparency, it’s that they don’t actually know how to get their questions in front of the leader, and so opportunities for that, and just, you know, being transparent.
You know, I say, like, I can share, I want to share as much as soon as I can, and I need you to trust me that, you know, I can’t share everything.
I think a lot about communication with you all, and it’s really important to me.
Marcia Beckner
That’s awesome. I think that what leaders can sometimes forget is, when staff are calling for transparency, they probably each have different questions to ask.
And it kind of, as you were talking, made me think about, like, parenting, where you know you can’t share everything with your kids as they’re growing up, it’s not age appropriate.
But they will ask questions, and when they’re ready to know, they’ll ask you a direct question, and if you can answer that, then that just continues to build trust.
So it’s almost like the call for transparency is way too vague, and you can kind of share back as executive director, and say:
“You know what I’ve seen in the survey, or what people are asking for, is more transparency, as you know, we’re navigating the messy middle right now. Please give me your questions, either directly in my office, or through this anonymous avenue or channel that you’ve set up.”
That is a really important, easy thing to do, and you will get more questions than you would have thought.
Because some people are afraid to ask questions for fear of being, I don’t know, misunderstood, or it will be used against them.
The anonymous feedback form is really powerful, and you know, put a QR code to it, and it gamifies the whole thing, makes it more…
Annie Bacci
Great. That’s a great point, Marcia, about the messy middle.
I think that, you know, sometimes you can just get in reactivity mode and react and go about solving problems where you’re actually not clear on what the problem is you’re trying to solve.
And transparency is a great example of, like, okay, well, staff said they need transparency, so we’re going to do A, B, and C, and then staff are like, that’s not what we wanted at all, and that doesn’t satisfy our desire.
And so really like taking that step, which is slowing down to say, what does better look like? Tell me what better would look like. Tell me what more transparency would look like.
We were getting a lot of feedback… I was getting a lot of feedback around staff wanting more leadership presence, which I think is common for nonprofits that have direct service programs.
And it’s really hard, that’s also very vague. What does that mean? Do you want me sitting like in your space for one day every month?
And so then we tried that, and staff were like, “I’m sorry, what are you doing here?”
And so really it was like, okay, tried that, now let’s have a conversation, like, what would actually feel meaningful?
And it was, I think it’s really them just having a chance to have informal conversations with me, to float questions, to give me feedback in an informal way.
And I learn a lot during these times where I’m hanging out with staff and programs.
Marcia Beckner
That’s cool. Do you have, like, a specific name for it or anything?
Annie Bacci
No, we don’t. That’s a really good… that’s something we should, because we also love a good, good branding, good name.
We call our all-hands meetings “one together” calls. No, but I should think about it a little more and ask them.
Marcia Beckner
Yeah, ask them to do a little competition.
Annie Bacci
I think we’re finding our groove with it more and more, and see young people over in our, yeah.
Small Anchors and Doing the Next Right Thing
Marcia Beckner
Yeah, yeah. And so you’ve told us about kind of like when you came in and where you started, which was, we’ll call that the beginning, for lack of a better word, because it was started way before you, but let’s say it was your beginning.
Now you’re in the messy middle, figuring it out on a day to day basis, and not at the end.
Do you have any advice for other leaders who are in this same kind of messy middle space, and the end feels a little bit too far or too vague?
How do you approach, like, your day-to-day life as you’re, you know, recalibrating towards that ideal future?
Annie Bacci
I think it really is breaking things down into smaller chunks.
And you know, one of the biggest pieces of advice that we say a lot, because we have to remind ourselves, is to celebrate the wins.
To really acknowledge when you see things shift.
Like when we first started doing these all hands, these monthly all hands “one together” meetings, it was kind of clunky and rough.
And staff were like, “what is this for? Like, do we get to have a conversation or do we have to air our questions, or we don’t really understand,” you know.
And we started to say, like, well, this is for information sharing and transparency.
And I said to the team, like, it’s like a podcast, not a talk show, like we’re sharing with you.
And this is because they were like, well, we don’t know what things are happening and shifting.
And then just, you know, the last couple times it’s felt like, wow, we’re really finding our groove, we have sort of a routine with these meetings.
And you know, we share wins and celebrations and birthdays and updates, you know, around the organization.
So you know, and it’s not perfect, but we’re celebrating, you know, that it’s better, and that it’s a place of community for staff.
And I also think, you know, when you’re in, you know, like you talked about the beginning, I would say the hopeful beginning, the messy middle, and yeah, we’re not through it yet.
But I would say that it is really, as a leader, identifying what are the things that you know you need to move forward regardless of the outcome of this period of time.
So for me, you know, I have like three things that I feel that I’m uniquely positioned to move forward.
And no matter what the outcome for TGTHER is, like getting these three big strategic things moving in a good direction will benefit the mission and the organization.
And so that really helps me as a leader to have a filter of what I say yes to, what I say no to.
And then it also helps with transparency and communication with staff, because you know, as an ED or a CEO, you’re getting a lot of feedback around the spaces that you are in and the spaces that you are not in.
And so I say to the team, like, this is what I’m basing my decisions around, you know, the spaces that I’m in and the spaces that I’m not in, and I think a lot about that.
Because people internally always want more of you, and people externally always want more of you.
So you have to not only make those decisions, but I think communicate the why behind them.
And we have an amazing staff. I love your work around, like, intergenerational work—a lot of Gen Z employees, and they really want the why, that’s really important.
And so communicating that, having your anchors as a leader, knowing what you’re working on…
And then I think, you know, sometimes it is just… another CEO told me when I was in a really difficult period, and I was just like, I don’t know what even to do next.
And she was like, “do the thing that’s right in front of you, and just keep doing that until you start to find more of a rhythm to your days.”
And so, you know, it’s like getting up and putting on your tennis shoes in the morning, which makes it easier to walk out the door and go for a walk, even though you can’t imagine going for a walk because it just feels too hard.
So, just like I think those small things of, how do you… what needs to be done today, and doing it, and it starts to create that momentum.
So I think don’t underestimate, like, the small things that you can do each day to move it forward. So, those are, yeah, some of my big pieces of advice for other leaders.
Marcia Beckner
Annie, thank you so much. I just needed all those reminders today.
And I hope everyone listening can really take this in and know that they’re not alone, and feeling lonely is part of the job.
It is normal, so there’s nothing wrong. But reach out and make sure that you have peer support.
On that note, I am launching a mastermind in the fall for a small group of executive directors and CEOs who want to feel a little less lonely as they’re going through this work.
We don’t have all the answers for how everything’s going to turn out.
But I love what you just said about: just do the next right thing in front of you.
And if you’re feeling alone and isolated a lot, please, you know, reach out to me, I can connect you with people, and we’ll make sure that leadership is less lonely than it should be.
Annie, thank you so much for sharing your story and your tools for success, and you’re doing an amazing job. Thank you for that, for the work you’re doing in the world.
Annie Bacci
Yes, thank you, Marcia, for having me, and for the work you’re doing in the world. That’s really important.
Marcia Beckner
Thank you. Thanks for listening to today’s episode of Nonprofit CEO SPARK.
If you’re ready to turn burnout into boundaries and build a healthy, happy culture where everyone, including you, can thrive, visit culturecares.com to learn how I support nonprofit organizations like yours.
If this episode brought you value, share it with a fellow leader navigating stress and overwhelm.
And remember, you are meant for great things, and you don’t have to burn out to prove it.
Until next time, keep leading with courage and confidence.