Written by Heather Volchko, BCBA
Five years into entrepreneurship, I understand that leadership is not a title you earn once or a skill you master in isolation. It is a practice - shaped by uncertainty, strengthened through relationships, and refined each time leaders choose shared purpose over individual control.
Early in the founding of TLC Nonprofit, I wrote about what serving on a nonprofit board had taught me: the importance of servant leadership, collective decision-making, strategic thinking, stakeholder trust, financial stewardship, and agility. Those lessons remain foundational.
But building something from the ground up asks you to grow alongside the work. In the beginning, the organization often feels inseparable from the founder. Its ideas, risks, late nights, successes, and disappointments can feel deeply personal. Over time, though, leadership requires a shift from being the person who carries everything to becoming someone who creates the conditions for others to carry meaningful parts of the work too.
That shift has been one of the most challenging and, simultaneously, one of the most important lessons of my first five years as an entrepreneur.
Year One: Learning to Begin Before Feeling Ready
The first year of entrepreneurship was defined by beginnings: beginning before I had every answer, beginning without a perfect plan, and beginning with a vision that was clearer in terms of values than in logistics.
There is a particular vulnerability in starting something new. You are often making decisions with incomplete information, building systems while using them, and explaining a future that others cannot yet see. At times, entrepreneurship can feel like trying to assemble an airplane while already in flight.
In that first year, I learned that courage is not the absence of uncertainty. It is the willingness to act responsibly within it.
For me, that meant grounding decisions in mission rather than waiting for certainty. It meant asking questions like: What problem are we trying to solve? Who are we accountable to? What would it look like to build something that is useful, ethical, sustainable, and responsive to the people we hope to serve?
Those questions became an anchor. They did not eliminate the risk, but they helped me distinguish between fear that was asking for thoughtful planning and fear that was simply asking me not to grow.
The earliest version of my leadership was highly operational. It looked like writing, planning, troubleshooting, communicating, designing, revising, and handling the many small tasks that make an idea real. But even then, I was learning an important lesson: doing everything myself may be necessary for a season, but it is not a sustainable leadership strategy.
Year Two: Moving From Vision to Systems
By the second year, the effort began to ask different questions of me.
A vision can inspire people, but systems make it possible to deliver on that vision consistently. Entrepreneurship taught me that good intentions are not enough. If we want to create meaningful, lasting impact, we need structures that support quality, accountability, learning, and follow-through.
This is where leadership began to feel less like creating and more like designing conditions.
I started thinking more carefully about the systems behind the work:
How do we make decisions in ways that are clear and values-aligned?
How do we communicate expectations without creating unnecessary bureaucracy?
How do we document what we are learning so that progress does not live only in one person’s memory?
How do we build processes that are flexible enough to adapt but sturdy enough to support growth?
How do we ensure that our operations reflect the same respect, transparency, and care that we want our external work to represent?
In educational organizational change and nonprofit work, we often talk about implementation. A strong idea is only the beginning; what matters is whether people can use it consistently, adapt it thoughtfully, and sustain it over time.
Entrepreneurship made that principle personal. I learned that leadership is not only about imagining what could be. It is also about building the scaffolding that allows others to participate in making it real.
“A strong idea is only the beginning; what matters is whether people can use it consistently, adapt it thoughtfully, and sustain it over time.”
Year Three: Learning That Delegation Is an Act of Trust
One of the harder transitions in entrepreneurship is recognizing that being capable of doing something does not mean you are the only person who should do it.
For many founders, delegation can feel risky. When you care deeply about the mission, quality, relationships, and reputation of an organization, it can be tempting to hold tightly to every decision. You may tell yourself that it is faster to do it yourself, easier to revise it yourself, or safer to maintain control yourself.
Sometimes, in the short term, it will even be true.
But over time, holding too tightly limits both the organization and the people within it. It prevents others from bringing their expertise, creativity, and perspective to the work. It turns leadership into bottleneck management. And it can unintentionally communicate that contribution is welcome only when it mirrors the founder’s exact approach.
I have been learning that delegation is not simply distributing tasks. It is a very real demonstration of trust.
Trust says:
I believe you have something valuable to contribute.
I do not need you to do this exactly as I would do it for it to be worthwhile.
We can create enough clarity around the purpose, the boundaries, and the desired outcome for you to lead within your area of competence - even if you don’t have the confidence.
That does not mean stepping away from accountability. It means becoming more intentional about what leadership actually requires. Sometimes that means providing context, resources, feedback, and support. Sometimes it means making a difficult decision. And sometimes it means getting out of the way.
The goal is not to remove leadership. The goal is to make leadership more available throughout the entire organization.
Year Four: Making Distributed Leadership Real
The language of distributed leadership can sound aspirational: shared ownership, collective expertise, collaborative decision-making, and leadership at every level. But making those ideas real requires more than inviting people into a meeting or asking for input after the direction has already been determined.
It requires changing how power, responsibility, information, and opportunity move through an organization.
As our board and program leaders continue to strengthen our distributed leadership efforts, I have been watching what this means in practice. Distributed leadership is not the absence of structure, nor is it a vague belief that everyone is responsible for everything. In fact, meaningful shared leadership depends on clarity.
Distributed leadership asks us to be explicit about:
Which decisions fall under the responsibility of the board, of program leadership, and which should be shaped by officers, advisors, partners, and stakeholders
Where expertise should lead, even when that expertise does not sit in the most formal or visible role
How people receive the information they need to make meaningful contributions
How we create feedback loops so that concerns, ideas, and insights can move upward, outward, and across - not only downward
How we share credit, learn from mistakes, and hold one another accountable to the mission
For a young organization, this work matters because habits form early. If we want a culture where people feel ownership, where ideas are strengthened through different perspectives, and where leadership is practiced rather than protected, then we have to build those expectations into our systems now.
I am increasingly convinced that distributed leadership is not about making leadership less accountable. It is about making accountability more collective.
When people have genuine influence over the work, they are more likely to understand the larger purpose, identify emerging challenges, and help carry solutions forward. The organization becomes less dependent on one person’s capacity and more resilient because knowledge, responsibility, and commitment are shared.
That is especially important in mission-driven work. The challenges we hope to address are far too complex for one leader, one department, one board member, or one organization to solve alone.
“I am increasingly convinced that distributed leadership is not about making leadership less accountable. It is about making accountability more collective.”
Year Five: Leading Through Questions, Not Just Answers
By year five, I have become more comfortable admitting that entrepreneurship does not lead to a final moment when everything suddenly feels settled.
There are still hard decisions. There are still competing priorities, limited resources, unexpected setbacks, and goals that always seem to require more time than anticipated. There are still lots of moments when I wish I could see farther down the road.
But I have changed in how I meet those moments.
Earlier in the journey, I often felt pressure to have the answer - to be decisive, prepared, and certain. Now, I more fully understand the greater value in asking better questions.
Questions create room for collective intelligence. They help uncover assumptions. They invite expertise that might otherwise remain unheard. They make it possible to explore a challenge before rushing toward a solution.
Some of the questions guiding me into the school year ahead are:
What does our mission require of us in this moment?
Whose perspective is missing from this conversation?
What are we learning that should change our approach?
Are we solving the immediate problem? Or are we addressing the conditions that created it?
What should remain stable? And what needs to evolve?
Where are we relying too heavily on individual effort when we should be strengthening a shared system?
How can we make the next right decision while continuing to learn and adjust?
Leading through these questions has helped me understand that mature leadership is not about becoming less uncertain. It is about becoming more capable of leading responsibly amid uncertainty.
Innovative Leadership in an Increasingly Distributed Organization
Five years into entrepreneurship, I still do not believe leadership is about becoming the person with the loudest voice in the room. I know it is about helping create rooms where more people can contribute meaningfully.
It is about recognizing when to provide direction and when to invite dialogue. It is about balancing ambition with stewardship. It is about building systems without losing humanity. It is about holding a strong vision while remaining willing to revise the path.
Most of all, it is about understanding that organizations do not grow because one person works harder than everyone else. They grow when people are connected to a shared purpose, equipped to lead from their strengths, trusted with real responsibility, and supported by structures that make collaboration possible.
The first five years of entrepreneurship have reinforced that leadership is not a destination in my life. It is a continual process of becoming more reflective, more courageous, more collaborative, and more willing to let the work rest with more than one person.
I am deeply grateful to every board member, collaborator, partner, and supporter who has helped shape this work so far. This is the kind of leadership I will keep practicing - nothing that centers a single founder, but leadership that expands capacity, invites ownership, and makes lasting innovation possible.
The next chapter will not be defined by having all the answers, but by continuing to learn together, lead with purpose, and build the conditions for ideas - and people - to move from visioning possibility to collective impact.
Cheers to the first five years of TLC.
“The first five years of entrepreneurship have reinforced that leadership is not a destination in my life. It is a continual process of becoming more reflective, more courageous, more collaborative, and more willing to let the work rest with more than one person.”
