What if the pressure to “have it all figured out” is the very thing holding you back?

In this episode, I sat down with Erin Halper for a refreshingly honest conversation about entrepreneurship, consulting, and what it really looks like to build a sustainable business over time.

Erin shares her journey from early entrepreneurship to private equity, consulting, and eventually building The Upside — a global community for independent consultants and business owners. Along the way, she breaks down some uncomfortable truths we don’t talk about enough: nobody has all the answers, “overnight success” is mostly fiction, and slow, steady work beats flashy metrics every time.

This episode is for anyone who’s tired of pretending, tired of chasing vanity milestones, and ready to build something real.

What you’ll get from this episode

• Why even experienced entrepreneurs are still figuring it out
• The myth of overnight success — and what actually creates momentum
• How to spot bad advice and unhealthy business role models
• What sustainable success really looks like behind the scenes
• Why curiosity, humility, and patience matter more than hype
• 
  

If you’ve been questioning your pace, your progress, or yourself — this conversation will feel grounding.

Get to know Erin:

Erin Halper is a former private equity professional and entrepreneur who founded The Upside, a high-caliber community connecting experienced consultants and senior leaders to meaningful, flexible work. After more than a decade advising businesses, Erin set out to build a better way for top talent to collaborate as colleagues, not competitors. Her journey into entrepreneurship became deeply personal when her first son was born with a heart defect, reinforcing her belief in autonomy, flexibility, and sustainable success. Today, Erin helps seasoned professionals level up their impact, income, and control over how they work without sacrificing excellence.

Connect with Erin:

LinkedIn: https://www.linkedin.com/in/erinhalper/

Instagram: https://www.instagram.com/erin.halper/

Website: https://betheupside.com/

Website: https://talentdevelopmentnerds.com/

LinkedIn: https://www.linkedin.com/in/candicemitchelltdnerd/

Instagram: https://www.instagram.com/talent_development_nerd/

YouTube: https://www.youtube.com/@candicemitchell.TDNerd

Talent Development Academy: https://talentdevelopmentnerds.com/tda

Original music composed by: Paul DeHaven

pauldehavenmusic.com