The Messy Parts with Maryam Banikarim

Episode: Debunking Myths About Careers, Generation Gaps, and The Power of Side Hustles (with Sam DeMase)
Date: September 22, 2025

Episode Overview

This episode features Sam DeMase—a career coach, author, consultant, and creator of the “Power Mood” platform with a vast following on TikTok and Instagram. Host Maryam Banikarim dives into Sam’s unconventional career journey, how generational divides shape workplace expectations, and actionable advice for negotiating, dealing with toxic bosses, pivoting roles, and harnessing the power of side hustles. The conversation is candid, encouraging listeners to embrace the “messy parts” of their professional and personal development.

Key Discussion Points & Insights

1. Debunking Generational Myths in the Workplace

[00:00]

• Boomers & Gen X Misconceptions:
  Sam identifies that older generations often view Gen Z as “lazy” and “entitled.” She counters, “It’s a very different time now...young people now...don’t want work to be their entire life, because making work your entire life doesn’t get you where it used to.” (Sam DeMase, 00:11)
• Lack of Empathy:
  Sam adds, “Boomers used to work hard and get a house...Gen Z and millennials, we cannot have that. Reality is different. That understanding does not exist right now between Boomers and Gen Z.” (Sam DeMase, 00:29)
• Reverse Perceptions:
  When asked if Gen Z misunderstands older generations, Sam quips, “No, no misperceptions. I think they have it correct.” (Sam DeMase, 00:45)

2. Sam’s Origin Story: Embracing 'Messiness' and Leadership

[01:42–07:47]

• Background:
  Born in Queens, raised in Long Island, passionate about writing and literature.
• Gallatin at NYU:
  Appreciated Gallatin’s interdisciplinary approach, “We call it the school for gay misfits...I did food studies, jazz voice, music theory, business, entrepreneurship.” (Sam DeMase, 02:47)
• First Job in Food Service:
  Quickly moved from manager to general manager, leading a 70-person team.
• Entrepreneurial Spirit:
  Brought confidence and a willingness to take risks, influenced by strong women in her family.
• Reframing ‘Bossiness’:
  Grew up called “bossy,” later realizing it was early leadership. “Looking back, I was a leader, but I felt ashamed about it at the time.” (Sam DeMase, 05:06)
• Learning to Say ‘No’ and Advocate:
  Outlines the challenge for women raised to comply. “My business is founded on self-advocacy.” (Sam DeMase, 07:02)

3. Leadership & Authenticity at Work

[07:58–10:25]

• High EQ & Empathy:
  Sam explains her leadership edge came from empathy and authentic connection with staff: “I could connect with them in ways other managers weren’t.” (Sam DeMase, 08:33)
• Show Up Authentically:
  Instead of focusing solely on tasks, she built relationships: “What’s going on with your grandma?...Work isn’t the be all, end all of our lives.” (Sam DeMase, 09:05)

4. Career Pivots: From Operations to People Work

[10:25–15:34]

• Recognizing Strengths:
  Pivoted to HR/Recruitment, leaning on her “superpower” in people operations.
• Situational Mentors:
  “Situational mentor is somebody who helps you through a specific time because their skill sets relate.” (Sam DeMase, 10:53)
• Parallel Pivoting:
  Sam coined the phrase for leveraging transferable skills: “Know your superpowers and tell a powerful story about your experience.” (Sam DeMase, 11:38)
• Defining Your ‘Superpower’:
  “If you’re not confident, have a chat with your bestie, your mom, your grandma…ask what you do better than anyone else.” (Sam DeMase, 13:58–14:33)
• Identify Patterns:
  Maryam suggests reviewing performance reviews to discover recurring themes and strengths.
  “Ask your best friend to write your biography.” (Sam DeMase, 15:06)

5. Startups, Challenges, & Return to Fast Food Leadership

[15:21–19:01]

• One Fine Stay Experience:
  Describes startup life as “its own brand of chaos…goals constantly shifting, priorities changing.” (Sam DeMase, 15:35)
• Building Culture on a Budget:
  Used direct conversations with employees to improve culture despite no funding for perks.
• Returning for Growth:
  Accepted a role with global travel—“The best. I made some of the best friends of my life.” Experiences ranged from glamorous (Japan, Korea) to “less glamorous” (Sarasota, FL). (Sam DeMase, 17:41)

6. Navigating Workplace Stress and Organizational Conflict

[19:03–21:46]

• High Responsibility:
  “Most stressful time, in addition to being the most fun…You don’t know if the electricity is going to be out...there was a lot of communication struggles.” (Sam DeMase, 19:07)
• Friendships at Work Can Be ‘Messy’:
  Managing friends after getting promoted is complex, especially when you disagree with organizational decisions.
• Letting Friends Go:
  “It’s difficult to look someone in the eye and be like, I’ve given you five chances...I would always give people that heads up.” (Sam DeMase, 20:19)

7. Bridging Generation Gaps—Advocacy & Empathy

[21:17–24:07]

• Frequently acted as generational translator: “Advocating for younger generations and explaining that to the older generation.” (Sam DeMase, 21:17)
• Younger employees demand “the why” behind mandates, not just orders: “Gen Z...will not accept a return to office mandate…They need to know the why behind it.” (Sam DeMase, 23:24)
• Suggests some Boomers lack empathy due to unresolved trauma (22:32).

8. The Birth of the Side Hustle – “Power Mood”

[24:11–29:58]

• Side Hustle Genesis:
  Started giving advice on TikTok/Instagram as “A Power Mood,” driven by witnessing inequity and lack of advocacy in corporate worlds. “I’m the advice giver…the person everyone comes to.” (Sam DeMase, 24:59)
• Employer Backlash:
  Company objected, despite no conflict-of-interest. She received a formal write-up: “I felt kind of betrayed, to be honest, by them…I felt singled out.” (Sam DeMase, 27:14–28:28)
• Choosing to Leave:
  Book deal enabled leap to full-time entrepreneurship: “When I got the book deal, I was like, bye.” (Sam DeMase, 28:29)

9. Advice for Job Transitions, Negotiation, and Side Hustles

[30:08–41:40]

• When to Leave Your Job:
  “If you’re asking the question, be done, get out.” (Sam DeMase, 30:08)
• Job-Hopping is Normal:
  “It’s really easy to move jobs. Doesn’t matter how long you were there, it just matters the impact that you made.” (Sam DeMase, 30:35)
• Low-Risk Side Hustle Launches:
  Advice to start while employed: “Start working on something that brings you joy in small doses…and that can help you see the light and move forward from where you’re at in the dark place.” (Sam DeMase, 31:43)
• Dual Path Strategy:
  “Lean into the things you like about your job…You’re going to produce better results.” (Sam DeMase, 38:24)
• Handling Toxic Bosses:
  Document everything and start with a conversation: “The first thing HR is going to say to you: Did you talk to them?...It’s about the work at the end of the day.” (Sam DeMase, 38:52 & 39:49)
• Negotiating Offers:
  “You can express gratitude and ask for what you’re worth in the same sentence…Ask for more.” (Sam DeMase, 40:09–40:28) Companies expect negotiation. If an offer is rescinded, “it’s extremely rare. And you just dodged a bullet.” (Sam DeMase, 41:16)
• Elegant Resignations:
  Be brief and gracious: “I’ve appreciated learning from you, I’m ready for my next opportunity. My last day is [date].” (Sam DeMase, 41:40)

10. Owning an Authentic, Public-Facing Brand

[32:12–35:58]

• Explaining the Job:
  “For the older generation, I’ll say: I’m a consultant. But I also show up authentically on the Internet and give advice to strangers.” (Sam DeMase, 33:17)
• Mental Health & Rest:
  “You don’t always have to be on your power mood 24/7…If I need to rest, I need to shut things down, I’ll do it.” (Sam DeMase, 33:59)
• Sharing the Messy Parts:
  Coming out publicly was nerve-wracking but positive. “The response was overwhelmingly positive, ended up being my most liked post of the year.” (Sam DeMase, 34:48)
• Lesson:
  “The more authentic I became, the more I liked my work and the more I found my authentic clients.” (Sam DeMase, 35:20)

11. Mental Health Journey

[35:58–37:06]

• Anxiety and Depression:
  “I think like a journey of experiencing anxiety and depression...I did eventually get into talk therapy and medication.” (Sam DeMase, 36:06)
• Physical Manifestation:
  “For me, it showed up as insomnia, or as physical stress, like, oh I can’t breathe.” (Sam DeMase, 36:48)

12. Career Expert and Brand Partnerships

[37:19–38:01]

• ZipRecruiter Consultant:
  “I represent them as career expert on behalf of job seekers…We talk about how job seekers can carve a path forward even in these current times.” (Sam DeMase, 37:19)

Notable Quotes & Memorable Moments

• On Flattening Generational Stereotypes:

  “Gen Z and millennials, we cannot have that. So our reality is very different to theirs. And I think that’s an understanding that does not exist right now between Boomers and Gen Z.”
  — Sam DeMase, 00:27

• On Self-Advocacy:

  “My business is founded on self-advocacy.”
  — Sam DeMase, 07:08

• On Job-Hopping:

  “It’s really easy to move jobs. Doesn’t matter how long you were there, it just matters the impact that you made.”
  — Sam DeMase, 30:35

• On Negotiating Offers:

  “You can express gratitude and ask for what you’re worth in the same sentence.”
  — Sam DeMase, 40:09

• On Authenticity:

  “The more authentic I became, the more I liked my work and the more I found my authentic clients.”
  — Sam DeMase, 35:20

• Final Rapid-Fire Advice:

  “Ask for more.”
  — Sam DeMase, 42:46

Timestamps for Key Segments

• 00:00 — Generational myths about work ethic
• 01:42 — Sam’s background, upbringing, and education
• 03:25 — First job experiences and early leadership
• 07:58 — Developing empathy as a leadership asset
• 10:25 — Pivoting careers and “parallel pivoting”
• 13:58 — How to discover your “superpower”
• 15:34 — Startup chaos and culture-building on a budget
• 17:04 — Accepting a high-travel, high-stress, high-reward role
• 19:03 — Messy realities of travel and responsibility
• 21:17 — Bridging generational divides in management
• 24:11 — Starting a side hustle and employer pushback
• 28:29 — Book deal as the catalyst for entrepreneurship
• 30:08 — How to know when to leave a job
• 31:43 — How to start a side hustle with low risk
• 38:24 — Staying high-performing (and sane) while side hustling
• 38:52 — Handling toxic bosses
• 40:09 — Salary negotiation strategies
• 41:40 — How to gracefully resign
• 33:59, 35:20 — Owning your authentic self publicly
• 36:06 — Mental health, anxiety, and the necessity of support

Overall Tone & Takeaways

This episode is candid, practical, and deeply empathetic. Sam DeMase and Maryam Banikarim tackle the complexities of modern work with humor and encouragement. The openness about “messy” moments—whether that’s being written up for a side hustle, pivoting careers with no map, or sharing mental health battles—underscores that there is no clean path to success, only honest evolution.

Resonant Message:

“You don’t always have to be on your power mood 24/7.” (Sam DeMase, 33:59)
And, most importantly:
“Ask for more.” (Sam DeMase, 42:46)

For Listeners Short on Time:

If you haven’t listened, this episode offers a blueprint for navigating modern work life with courage, adaptability, and authenticity—fitting for anyone reconsidering their work, relationships, or path forward. The practical advice for navigating toxic workplaces, negotiating offers, and launching side hustles is especially actionable.