How Margot Toppen Builds a Village for Entrepreneurs, Educators, and Young People

When Damien Howard invited Margot Toppen onto Village Talks, he wasn’t just bringing on another guest. He was bringing on someone he already trusted with his own ideas, doubts, and next steps.

Margot calls herself a social impact entrepreneur. For more than two decades, she has worked at the intersection of education, creativity, and innovation — launching ventures in social-emotional learning, edtech, and the arts; leading at a global nonprofit; and most recently serving in an AI-enabled mental health startup.

Today, she’s shifted her focus toward coaching and mentoring others — especially people in transition who feel “there’s more in me” and want their work to matter.

Underneath all of that is one simple idea:

“It just all feels lately like it's really all just about showing up for your community, a.k.a. your village.” – Margot Toppen

This conversation with Damien on Village Talks is a window into how Margot thinks about purpose, preparation, risk, and the loneliness young people are facing — and what it will take to rebuild real, intergenerational villages.

What a Social Impact Entrepreneur Really Does

Everyone seems to call themselves an entrepreneur these days. Margot is careful with the term — and even more careful with the phrase social impact entrepreneur.

Damien asked her to break it down, especially the “social impact” part. Her answer was simple, but not simplistic:

“A social impact entrepreneur is a person who aligns purpose and passion and kind of uses a framework or benchmarks of how is what I do impacting the greater good.”

For Margot, entrepreneurship isn’t just about launching a product or stepping away from a traditional job. It’s about constantly asking:

• Does my day-to-day work connect to something bigger than myself?

• Who is helped by this work — beyond my own satisfaction or income?

• How do I know if I’m still serving that larger purpose?

That lens shapes how she coaches others. Many of the people who come to her are:

• Educators leaving the classroom or administration

• Professionals navigating mid-career transitions

• Emerging founders trying to design ventures that actually help people

A common thread: they’re not just chasing a new role. They’re trying to align their next chapter with a deeper sense of meaning and contribution.

Big Picture and Details: Why Preparation Matters

One thing Damien has always noticed about Margot is how she shows up prepared. She watched previous Village Talksepisodes. She reflected on what “village” means to her. She thought through how to connect her story to what listeners need.

That’s not accidental.

“Something that I've been praised for a lot throughout my life is this really great balance between big picture and details.”

For Margot, preparation is not about perfectionism. It’s about alignment.

“If my greater purpose right now is to share my life experiences as an entrepreneur with other entrepreneurs, how can I make sure that how I show up for the types of questions that Damien might ask me are in alignment? I don't want it to just be random.”

That’s a useful frame for nonprofit and youth-development leaders:

• Big picture: your mission, theory of change, and “why.”

• Details: how you spend your time this week, the questions you ask in meetings, who gets invited into the room.

When those two match, people feel it.

When they don’t, frustration grows — and as Damien noted during the conversation, frustration often signals broken systems.

Using Values as an Everyday Assessment Tool

Damien shared his own practice during the conversation: a color-coded calendar to see where his energy goes — purpose-aligned work, revenue generation, family, rest.

He asked Margot how she checks whether she’s living in alignment with her purpose.

Her answer was grounded and practical:

“About once a year, I try to make some space to just really reflect on what are my core values right now… and then think about how do these values map to different aspects of my well-being.”

Margot doesn’t treat values as a poster on the wall. She treats them as an assessment tool.

Her process:

1. Revisit core values annually

2. Map those values across life areas like

   • Family and friends

   • Health

   • Work and intellectual life

3. Look for gaps between values and behavior

If she values relationships but her schedule shows no time for family or friends, that’s data.

Then comes the difficult step: letting something go.

“If I feel like a value to me is spending time with family and friends, but I notice that that's not really happening as much as I want or need, then I need to make space in my schedule for that.”

For organizations, the same lesson applies.

Values aren’t just about what you add.

They must guide what you stop doing.

Drawing the Line: A Practical Method for Saying No

Damien named something many leaders feel: saying no is hard.

Margot shared a tool she learned during a Chicago Innovation Women’s Mentoring Co-op session:

“Make your list. And then after the top four or five things, draw a line and say, these are the things that I can get done. And these are the things that I'm okay with letting go of.”

The power isn’t the list.

It’s the line.

Without a line, leaders and organizations drift into overcommitment:

• Too many partnerships

• Too many initiatives

• Too many meetings that don’t move the mission

Drawing the line creates clarity — and protects energy for the work that matters most.

From Founder to Coach: Walking With People in Transition

After years of launching ventures and leading organizations, Margot is now spending much of her time coaching people in transition.

Many of the people she works with are asking questions like:

• What comes after my current role?

• Should I start something of my own?

• How do I align my career with purpose?

Damien described the experience of working with her this way:

“If you're going to take Margot up on her offer, you better be prepared to be asked all of those questions that Simon Sinek says are necessary in order for us to crack the nut and get to the depth of the why.”

Margot sees this season of her career as an opportunity to lift others up.

“At the moment, I'm more about empowering other people and lifting them up so that they can achieve that greater impact.”

The Loneliness Epidemic Facing Young People

When Damien asked Margot what she sees as the most pressing issue facing young people today, she answered immediately:

“Loneliness, self-isolation, and the loss of a willingness to be vulnerable and take risks.”

She worries that technology — especially AI — may unintentionally reduce experiences that build confidence and resilience:

• Struggling with a problem long enough to find your own answer

• Asking another person for help

• Taking social risks and sharing ideas

“Technology is almost removing the confidence to make a decision for yourself or come up with your own solution.”

The concern is not technology itself.

It’s what happens when technology replaces human connection.

Technology and Village: It’s Not Either/Or

Margot is clear that she’s not anti-technology.

But she believes we must be intentional about how we integrate it.

“We need to be thoughtful about how we're integrating it and making sure we're not allowing it to replace those developmental milestones.”

Today, building a village requires intentional effort.

“Right now, we have to make it a proactive choice to make those connections. It's not just happening.”

Her hope is that leaders will strengthen the connective tissue between generations — creating spaces where youth, educators, technologists, and community leaders learn from each other.

The goal is simple:

Keep people connected.

Practical Takeaways for Leaders

Margot’s insights translate into practical actions for youth-serving leaders.

1. Revisit your values

Block time annually to:

• Clarify your core values

• Compare them with how time and energy are spent

• Close the gaps.

2. Draw the line

With your team:

• List your priorities

• Circle the top 4–5

• Draw a line

• Let the rest go.

3. Design for connection

Measure programs not only by outputs but by relationships:

• Are youth forming trusted relationships?

• Are mentors connected to the mission?

• Does technology support human connection?

4. Build intergenerational collaboration

Create spaces where:

• Youth voices shape decisions

• Adults listen as well as lead

• Generations problem-solve together.

Margot’s vision isn’t a new program.

It’s a stronger web of relationships.

If you’re curious how organizations are integrating human mentoring with technology to strengthen their village — rather than replace it — you can learn more about how mentoring programs are scaling support through technology at:

https://www.sel-plus.com/selvieai