Village Talks — Pam Schilling on Mentorship, Nonlinear Careers, and Preparing Young People for What’s Next

What is up, Village—Damien here.

You know I come into these conversations easily excitable, but this one really hit home. I got to sit down with my friend Pam Schilling, someone I met through the edtech/entrepreneurship space here in Chicago. She’s one of those people who carries a quiet depth—decades of experience, real scars from the grind, and a deep commitment to seeing people thrive in their careers.

In this episode, Pam pulls back the curtain on what it means to:

• Build a career across five different chapters

• Tell the truth about how hard entrepreneurship really is

• Live inside a culture where mentorship is the norm, not the exception

• Build a company, Archer Career, to help students and early-career talent navigate all the invisible rules no one teaches them

“The career is what you make of it. I’ve had five careers in my life. It’s a journey.”

Meet Pam: First-Gen, Five Careers, and a Different Kind of “Success”

Pam opens by sharing something that always surprises people at the universities where she speaks:

• She is first-generation college—her dad grew up very poor and never went to college; her mom didn’t get to go because she was a woman.

• Despite that, in her home, college was never “if” — it was always “when and where.”

As a kid she wanted to be an astronaut… until she realized you can’t fly the shuttle if you wear glasses. Then she thought about law… until she met a tax attorney and decided that wasn’t it either.

So she studied accounting, went on to get her MBA from Chicago Booth, and did what a lot of MBAs do:

• Consulting

• Tech

• Strategy and operations work

What she couldn’t have imagined back then is that she would become:

• A founder,

• A career strategist,

• And someone helping students and early-career professionals navigate a world her parents never had access to.

“I’ve had five careers in my life. I think I have one more before I’m done.”

Entrepreneurship: Not Sexy, Just Hard (and Worth It)

Pam keeps it all the way real about entrepreneurship:

“I don’t think it’s sexy. I think it’s the hardest job I’ve ever had—and I’ve had extremely hard jobs. But it’s the best job I’ve ever had.”

She points out:

• It’s easy to bring a product to market, especially now with AI.

  “A 10-year-old can do it.”

• What’s hard is persisting:

  • Building and improving the product

  • Getting customers and keeping them

  • Handling customer problems

  • Raising money

  • Leading a team

  • Doing 100 things you’ve never done before

What makes it survivable for her?

1. Context. She’s got 20+ years of business experience behind her, so she has a reference point for “hard.”

2. Purpose. The work is deeply connected to her “why,” which helps absorb the difficulty—not erase it, but contextualize it.

“On my worst days now, it’s still not as tough as some of my days in consulting… and because I have a different purpose for the work, it absorbs some of the toughness.”

For any of us in the Village trying to build something, that perspective matters. The grind is real—but so is the purpose.

Mentors and the Village at Work

You know Village Talks is built on this conviction: we don’t get where we’re called to go by ourselves.

Pam’s story is a case study in that.

Formative Mentors at 21

Her first job out of college was at Sprint in the early ’90s, in a department that was transforming from traditional accounting/audit into internal consulting. They brought in senior leaders from places like:

• GE

• General Dynamics

• PricewaterhouseCoopers

• EY

These were companies known for leadership development. And with those people came a culture:

• Mentorship wasn’t a side dish.

• It was built into the way people worked, developed, and interacted.

She shares a moment that changed her:

• She was a smart, driven 20-something who believed,

  “If I work really hard and say intelligent things, I’ll get promoted.”

• A senior leader, Alan, pulled her aside after some friction and a tough performance review and said:

  “You’re pushing too hard. You’re not coming off the right way. Think instead about enabling the success of everything around you.”

She didn’t like hearing it at the time—but it reshaped how she thought about leadership and contribution.

Apprenticeship and Intentional Networks

Later, in consulting, she experienced an apprentice model:

• Traveling with senior consultants

• Long dinners full of stories and lessons

• Informal but powerful mentoring built into the work

Then Chicago Booth reinforced the message:

“Day one, they tell you the network is important—you’re now part of this family.”

That gave her the confidence to keep asking for help, seeking guidance, and learning on the edges of innovation.

So when she became a founder—even with 30 years of experience—she knew she needed mentors again.

• She reached out to celebrity entrepreneurship faculty at Booth.

• She reached out to classmates now serving as senior executives.

• She slowly built a network in edtech, AI, and startup land.

“At the zero stage, you need people around you who can speak truth to you. You’re fueled by passion and you don’t always see clearly. You need the voice of truth. Those are mentors.”

Takeaway for Our Village

As I reflected back to her, one big lesson for all of us:

• Leaders have the power to normalize mentorship.

• Build cultures where mentorship isn’t “extra,” but part of what it means to belong.

• Help people understand:

  “Here, we receive help and we give help. We grow together.”

Why Archer Career Exists

So what does Pam’s company, Archer Career, actually do?

“We recreate the career experiences I had the good fortune to have.”

Archer focuses on improving employment outcomes for early-career talent by:

• Working primarily with universities

• Offering e-learning, career programs, and specialized tracks (like grant writing for PhDs)

• Helping students navigate the unwritten rules of the pathway to employment

In short:

Mission: Help people achieve their career ambitions and the ROI on their education.

Pam’s conviction was born out of frustration and compassion:

• She was good at job searching (five jobs in seven years after her MBA).

• She sat on hiring teams, and one day interviewed a Booth student whose interview was going terribly—until she shifted into “coach” mode.

• She was stunned that even at a top business school, students were struggling with the basics of interviewing and positioning themselves.

“It befuddled me. If this is happening here, what’s going on at every other school in the country?”

That question became fuel for Archer.

Resumes, Basics, and a System Failure

Pam doesn’t mince words:

“I don’t know if you’ve ever read resumes. They’re often terrible.”

For her, it’s not about shaming students—it’s about calling out a system failure:

• We manage to teach millions of people how to drive cars.

• But we don’t systematically teach millions of students how to write a solid, readable resume.

She dreams of a world where:

• Every college student leaves school with a strong resume.

• Employers aren’t forced to judge someone’s potential through a “crappy document,” but can see the human being and their capacity.

Archer channels that energy into:

• Basic, rigorous foundations (like resumes, interviews, job search strategy)

• Delivered at scale, so it doesn’t depend on “happening” to meet the right mentor like she did.

The Magic Wand: Jobs for Motivated Talent

When I handed Pam the “magic wand” and asked what she would change for young people like Omarion—the 20-year-old I’ve known since high school who’s struggling to find work—she got very concrete.

“High-performing companies should have some kind of job for someone who is purely motivated.”

Her vision:

• Certain companies create roles or bootcamps where:

  • You don’t need a resume.

  • You don’t need to have gone to a particular university.

  • If you show up, demonstrate motivation, and make it through a structured bootcamp, you get a real job.

Why?

Because we both know there are diamonds in the rough—young people who:

• Are motivated

• Have raw talent

• Just haven’t had access to the right school, credentials, or polished documents

A good bootcamp-plus-job model could:

• Catch people like Omarion

• Give them structure, training, and income

• Redirect their trajectory away from the “abysmal things” that can happen when you’re idle, broke, and disconnected

Village Action Steps

Pam’s story and work stirred up some very practical invitations for our Village:

For Employers & Companies

• Build mentorship into your culture, not as an extra.

• Consider piloting bootcamp-to-hire pathways for motivated talent without traditional credentials.

• Treat early-career development as an investment, not a favor.

For Educators & Nonprofit Leaders

• Normalize asking for help and offering feedback.

• Teach the basics: resumes, interviews, networking, career storytelling.

• Partner with organizations like Archer to support students beyond graduation.

For Mentors & Community Members

• Think long-term. Many of “our kids” are now 19, 20, 21. The mentoring doesn’t stop at high school graduation.

• Ask the employment question: Are you working? What are your barriers? How can we help?

If you see yourself anywhere in this story—as a first-gen professional, a mentor, an entrepreneur, or someone trying to shepherd young people into stable, meaningful work—I hope this episode encourages you like it did me.

We don’t build careers, companies, or communities alone. We build them through village.