Don’t Be Afraid to Dream Big — Just Be Ready to Do the Math

I have two major failures in my professional career. And they both revolved around fulfilling a big dream. In this case, the dream was the same: to build a performance venue in my community to serve our performing arts organizations.

The first attempt failed. The second attempt failed.

The question that hung over my head was this: did I dream too big?

The instinct was to give up. To accept that perhaps we just didn’t have the capacity. Maybe the community wasn’t ready to support the idea. Clearly, this was never going to work.

Fortunately, I’m stubborn. Really stubborn. Ask my husband.

I wasn’t ready to give up. The need was there. The community did support the idea. My organization was the right one to steer the project.

So what was wrong?

The dream was not the mistake. The planning was.

We knew what we wanted. We didn’t know how to get there.

Many small nonprofits want to dream big. We have visions of expanded programs, better infrastructure, larger staffs, better space, bigger reach, more capacity. We want our mission to deliver big impact. We want to change the world. It’s why we work in the nonprofit sector. Unfortunately, many of those dreams die before they even get a vote in the boardroom. Our fear of “what happens if this doesn’t work” holds us back, causing us to scale down our ambition. The reality of how difficult it can be to meet current liabilities—let alone fund the cost of our dreams—stops us in our tracks.

And that’s not a bad thing.

The reality of what it will actually take to realize the vision should stop you. Or at least slow you down.

But stopping doesn’t mean giving up. It means taking a moment to move ahead thoughtfully. Having a good roadmap will get you to your goal—but the key is taking the time needed to make a truly detailed one.

As with everything, money matters, and cash is king. Any dream roadmap has to start with doing the math. When your organization is proposing a big project, it’s important to ensure you are able not only to pay for it, but that you can also afford the planning process, the fundraising needs, and any new operating costs after the dream becomes a reality.

Will you be able to afford the costs of the dream today, tomorrow, and next year?

Beyond money, those same questions should be asked about the capacity of your organization. Will your team have the ability to plan, execute, and manage this project? Will you be able to continue mission fulfillment while you work on the project—and after it’s completed?

And most importantly, will this project align with your organization’s mission? Will it support your vision? Will it strengthen and grow your organization? If the dream doesn’t fit the mission, you need to rethink the dream.

These are scary questions to answer. And often, after looking at all the data, we think, “We can’t do this.”

That is a natural reaction. When you have no staff, a small board, and an even smaller budget… how can you ever afford a dream?

While these realities should not be ignored, they shouldn’t stifle your ambition. If the dream fits your mission and will result in a stronger organization in the end, you can achieve it. You just have to plan it.

If the dream is so big it doesn’t fit who you are today, then create a plan that includes growing into it.

I’m a naturally impatient person. When I get an idea, I want to get it done today. My instinct, when an idea comes into my head, is to jump right out and start asking donors for money. I want to swing the hammer and get that new building started. I want to hire that new team we’ve always needed. I want to launch that new program immediately. I want to realize my dream now.

But that mindset is exactly what first derailed my ambition to build the performance center.

I didn’t have a feasibility study completed. I just knew we needed this project.

I had a location figured out, but no agreement with the owners in place. Once they saw the community interest, I assumed they’d be happy to hand over the keys.

I didn’t have a budget. I figured I’d raise the money first and work out how to spend it later.

I didn’t have an organizational plan to ensure we could afford to operate a performance center. We’d cross that bridge when we got to it.

We went straight to the public and started raising cash. And we were moderately successful, given that we had no clear plan. We raised $10,000 before we had even talked to the owners of the desired space.

And then it all fell through. We couldn’t reach a deal. We couldn’t acquire the building we wanted. We had no backup plan. We had failed. And I had to go back to my donors, tail between my legs, and give the money back.

This was the lowest I had felt in my entire career.

The problem hadn’t been the dream. It had been the planning.

The second attempt to build a new performance center felt like we were starting on the right foot. We had the building. We did the feasibility study. We had the numbers. We had a plan.

But we didn’t follow it.

The plan was written and stuck on a shelf. As the project progressed, we never revisited it or replanned when circumstances changed. Out of eagerness, we just reacted.

When a dream hits—when you see what you could be, when you envision a new future—the tendency is to get moving. This is especially true when your dream excites your board and donor base. The instinct is to think, if we don’t do this now, we’ll lose momentum and excitement.

The reality is, if the dream is a good one, your donors will want you to slow down, map it out, and revisit it often.

Strategic planning is stewardship.

The lesson from the first failure was clear: we needed a plan. But the second time, we stopped checking it to make sure we were still on track.

We had the documents. We had done the work. And we still failed—because we stopped using them.

Planning done right will also help keep the dream alive. Digging into a spreadsheet should excite you, not discourage you. Having a roadmap makes the dream real. Knowing how to get to the goal line turns an idea into a project.

The first step in this process is clearly defining what it is you’re trying to accomplish. The big dream doesn’t always have to be a multimillion-dollar capital campaign to build a new building. It could be increasing programming, hiring a full-time executive director, expanding your reach, or turning volunteer positions into paid ones. But each of these requires a clear path to get there.

Start by asking yourself these questions:

Will it advance your mission?

• Will your donors support this project?

• What are the actual financial implications?

• Will your team have the bandwidth to complete the project while also continuing to fulfill the mission?

• How long will the project realistically take?

• What will your organization—and its finances—look like when you’re done?

These questions should be examined before a final vote is brought to the board—and well before you start asking for money.

Note: the answers to these questions do not all have to be “yes.”

“I’m not sure” means we just need to do some research.

“No” means we need to ask whether the answer could become “yes” with some planning—or “yes” if we adjust the idea.

After you’ve thought through the above, write it down. Make a list. What do you want in clear objectives? Where are you today? And what steps do you need to get there?

This step leads you naturally into building a feasibility study, a strategic plan, and a budget.

A few notes on these plans as you get moving.

Feasibility Study

We’ve all seen plenty of nonprofit experts talk about hiring a consulting firm to do a feasibility study. For a small nonprofit with limited means, paying for a professional study often doesn’t fit into the current budget, and donors and grantmakers rarely want to help fund it.

That upfront cost is what stops many small nonprofits from pursuing change and growth. Or worse, it reframes the feasibility study as an unnecessary luxury.

The reality is you can’t afford not to do a feasibility study. If the money is not available to hire professionals, look for people willing to donate their time. Assemble a team of people with knowledge of your industry, your community, and what the project entails to form a feasibility committee. These people should not be current members of your organization. Your team needs an outsider’s perspective.

After the study is complete, your organization needs to be willing to accept its outcome—which can be difficult if the results contradict your assumptions. But feasibility studies are not about whether an idea is accepted or rejected; they’re about whether the idea is doable in its current form—or whether it needs to be reworked.

Strategic Plan

After the feasibility study, you should have a clear idea of whether you can do it. Now the question becomes: how do you do it? That’s where the strategic plan comes in.

I love strategic planning. Partially because I’m a strategy nerd. But mostly because when you take the time to write out how to reach your dreams, you start to feel their reality.

A strategic plan turns a dream into a project. It gives it life. By putting down how to get to your vision, you’re codifying the vision itself. You’re taking that dream and saying, “here’s how you get there.”

Take your time with this plan. Work with your team so you’re not missing any potential roadblocks.

The internet is full of templates for strategic plans, and they can be a great starting point. But don’t get hung up on the format. Focus on the path. Be realistic.

Make sure you have the capacity to reach each benchmark on the timeline. And make sure your organization and its mission are the guiding principles behind what you’re writing. If you have a $5,000 annual budget and five volunteers fulfilling the mission, your strategic plan is not going to look the same as the $1,000,000-a-year nonprofit with a full staff. This document is your plan. It should fit your organization.

Most importantly, keep it flexible. This is a working plan. As you move forward in the planning process, stop and make sure it’s still taking you in the right direction.

Use the feasibility study as a guiding principle as you review and re-review the plan. Remember, you create these documents not so they can sit on the shelf. You create them to guide you in your work. The lessons from a good feasibility study give you the right guardrails to ensure that when you do make adjustments, you can follow what’s actually feasible. It will ground you in reality as you strategize and re-strategize.

Budget

Now to the math—and perhaps the most daunting task. It can be hard to take emotion out of money, especially when you’ve taken the time to really think through the vision. It can feel like you’ve had the wind knocked out of your sails when you see the reality of what your dream costs.

But budgeting shouldn’t make you cry. It should ground you. It should create a realistic picture. And it gives you the data you need to make sure your plan will work. Because ultimately, when you create a budget, you’re creating data to help guide the project. Big numbers can be scary. But if you have a realistic plan, big numbers can be achieved.

I’m not going to go into the nuances of budgeting here. But I will leave you with a few pointers.

Budgeting for a project should not include revenue you are currently earning. A project budget shows you what new revenue you need to find. Current operating funds should not be used to fund the project.

Let me slow down here and say that again. Current operating funds should not be used to fund the project. This is about adding value to your organization. Don’t undermine your current work in the process.

Be realistic in your fundraising. Remember, you need to find the money to make the dream a reality on top of what you already need to continue your mission. You’ll be asking a lot of your donors. Make sure you’re not asking for more than you can reasonably expect to receive.

If the final number is too big for today, take a moment to restructure the plan into phases you can accomplish. Don’t give up. Break it down.

Follow the numbers. If the numbers don’t fit the plan, rework the plan. While you’ll want to wait to start budgeting until you have a basic roadmap, know that your budget may lead you back to revising your strategic plan. Build these together because they depend on each other.

Make sure you’re creating a diversified revenue plan. Your current donors won’t be able to shoulder this new initiative alone. Look for other funding strategies to close the gap.

Be realistic in the expenses. Remember, this process is meant to create data, and the golden rule applies: garbage in, garbage out. Don’t be afraid to look at the actual costs. Take out the emotion. Use the data to help you plan, not cause frustration.

Like the strategic plan, keep the budget flexible. Have check-in moments along the way to ensure you’re meeting (or exceeding!) your benchmarks. Don’t be afraid to adjust as you go.

Don’t make the same mistake we did when we ignored our plans for a performance center. Revisit often and replan when needed.

Running nonprofits is hard. Especially when your dream is big and your revenue is small. But nonprofits are all about dreams. When your organization was founded, it was because of a big dream. Your founders knew that your mission needed to be met, and they would make it happen. That’s a huge risk.

Growing your nonprofit should also be a dream. But it should also be done with intention and care. It’s easy to get excited when an idea hits, but don’t make my mistake. Don’t go to your donors without doing your homework. Use those documents and tools to get you there. Don’t be afraid to slow down and make sure you’re doing it right—while also protecting what you already have.

And most importantly, don’t give up on your dreams. Just be prepared to do the math.

Now go do some good!

Let’s Talk Failure

I’m going to say something you may have never considered: it’s okay to admit it’s not working.

As nonprofit people, we tend to lead with our bleeding hearts. And that’s a gift—it helps us show up, care deeply, and keep going when things are hard. But that same instinct can make it incredibly difficult to accept when something isn’t working and a project needs to be abandoned or a course correction needs to be made.

We become attached to the dream.

This is a common problem in the small business world, too. When you’ve put blood, sweat, and tears into something, admitting it’s not working can feel like admitting you failed.

In nonprofit work, failure doesn’t feel like a professional misstep. It feels personal. It feels like you failed your community—the very people you exist to serve. Staying the course feels necessary when your reason for existing is to support your neighbors. Persistence becomes a virtue. Mission-driven people know hard work and are not afraid of it. When it’s hard, we keep going—sometimes without stopping to recognize that it’s hard because it’s not working.

That kind of failure is difficult to digest. It’s difficult to accept.

I know. I’ve been there.

Recognizing failure isn’t giving up—it’s deciding to do it better. It’s admitting there’s a problem and choosing a different path.

I currently serve as the Executive Director of a regional symphony orchestra. During COVID, we went two full seasons without concerts, and our donations were cut in half. We survived on one-time grants from foundations and the government. Like many organizations, we were in survival mode.

When it came time to reopen, I made a huge miscalculation.

I believed our audience missed live music so much that the moment we opened our doors, they would come flooding back—even with mask mandates and vaccination requirements. We planned a full season—actually, the biggest and most expensive season we’d done in years—because we knew the audience would be there.

We couldn’t have been more wrong. During our first season after reopening, our audiences were a quarter of what they had been before the pandemic. Donations didn’t rebound at the pace we anticipated. We ended the season in a $50,000 hole.

The next season’s revenue then started being used to fill that hole—which meant the hole just got pushed forward into the next season’s budget. And then pushed again. For three years.

Our audiences slowly rebuilt. Donations slowly climbed. But while we had enough revenue to cover each season as it came, we never quite had enough to fill the deficit we dragged behind us.

This decision—to allow our mistake to haunt us for so long—is a common narrative for small community nonprofits. We often only define failure as complete collapse. But sometimes failure happens alongside success. In our case, we were pulling out of the pandemic. But our failure to correct the mistake continued to haunt us, and the uncorrected failure was hurting our ability to fulfill our mission.

Eventually, we had to stop and face reality.

We needed to understand what was happening—and make different decisions.

So we did.

We planned a season with fewer concerts to reduce expenses. We restructured staff hours. And our board fundraised like they never had before.

We filled the hole.

And for the first time in years, we started the next season in the black.

What’s more—that painful reset actually set us up for a stronger future. We built a more secure donor base. We stabilized our finances. And we ripped up our old strategic plan and fundraising strategies in favor of something far healthier than what we had before the pandemic.

That course correction allowed us to build something better.

Choosing to intentionally cut back on mission-fulfilling programming is difficult. We had plenty of patrons and musicians vocalize their disappointment in our reduced season of concerts.

But what sometimes feels counterintuitive—like cutting back on the very reason you exist—is the responsible move. Realigning, restructuring, and redesigning when your current direction isn’t working is stewardship—even if it doesn’t look like it in the moment.

So now that we’ve established it’s okay to admit something isn’t working—how do we get from failure to success?

Admit the failure—and take responsibility.

Admitting failure needs to happen at all levels of the organization’s management structure. Your board and management staff need to sit down together and define the problem and where it came from. This is not always easy. We all know how hard it can be to get your whole board and management staff on the same page about anything. But failure in a nonprofit is everyone’s responsibility—and everyone should own it.

The key is to take personalities out of the equation. Identify why something failed without pointing to people. This isn’t about blame. It’s about understanding. A bad decision is rarely a single person’s failure; it’s an organizational failure—whether that means not recognizing the decisions were leading down a path of failure, or failing to provide oversight and allowing a few to make decisions that led there.

I’ll say it again: don’t point to people. Point to actions.

Trace the decisions.

Go back to the beginning of the end. Identify the decisions that were made—the assumptions, the risks taken, the trade-offs accepted—that led you here.

Pick those decisions apart. Treat them like scientific data. Conduct a failure autopsy.

Learn from what you find.

Once you’ve mapped the road that led to the failure, analyze it.

What could you have done differently? Where was the last off-ramp? Why did those decisions feel right at the time? What information did you not have—or underestimate—or ignore? What would have been a better choice?

Failure comes in many forms, and the reasons are rarely simple.

But the point is this: accept that something went wrong, learn the lesson, and carry it forward.

Those lessons make you stronger. Smarter. Better equipped to take your next steps.

When something isn’t working—when you realize you’re going from one emergency to the next—start by taking a moment to ask yourself, and your organization, these questions:

• What is really going wrong?

• Where did this start going wrong, and what decisions led us here?

• How do we correct course?

• Are we willing to accept that sometimes course correction means cutting back or ending programming?

• How do we rebuild stronger?

• What lessons did we learn from the mistake?

Failure doesn’t end the work; refusing to face it does.

Now, go do some good.