Cut The Tie Podcast with Thomas Helfrich
Episode 285

What does it take to leave a steady government career and build something of your own? In this episode of Cut the Tie, Thomas Helfrich sits down with Shane Silsby, a former public sector leader turned founder of Silsby Strategic Advisors, to talk about cutting ties with stability, embracing ambiguity, and redefining success on your own terms.

After two decades serving in government leadership roles—including as a director at the sixth-largest county in the U.S.—Shane walked away from a reliable career path to build a business rooted in flexibility, impact, and freedom. But the transition wasn’t easy. From navigating the unknown to confronting financial pressure and family fears, Shane shares the mindset shift that made it all possible.

About Shane Silsby:
Shane is the CEO and founder of Silsby Strategic Advisors, where he provides fractional executive services to local governments and strategic guidance to private sector clients seeking to work with public agencies. With over 20 years in government leadership and now years in entrepreneurial consulting, Shane blends insider knowledge with a deep understanding of both operational and policy complexity. He’s also the author of Managing for Meteors, helping organizations prepare for disruptive change before it strikes.

In this episode, Thomas and Shane discuss:

• Why cutting the tie to a steady paycheck is terrifying—and necessary
  Shane reveals the internal battle of leaving security behind in favor of more meaningful, high-impact work across the country.
• How corporate life wasn’t the answer either
  After a brief stint in the private sector, Shane realized real alignment came from doing things his way, not chasing profit-first mindsets.
• How to get comfortable with ambiguity
  From family pressures to financial uncertainty, Shane opens up about the daily mental challenges of solopreneurship—and how to navigate them.
• The silent tie no one talks about: spousal pressure
  In a rare moment of vulnerability, Shane shares the honest conversations with his wife about uncertainty, money, and chasing an unclear dream.
• Why 2025 requires a pivot mindset
  Whether you serve local governments or the private sector, Shane explains how agility and awareness of federal and global changes will define the next wave of entrepreneurship.

Key Takeaways:

• Ambiguity is the price of freedom
  Solopreneurship means betting on yourself—even when you don’t know the odds.
• Don’t wait for certainty—act anyway
  The right time never comes. Move forward, even in the fog.
• Corporate doesn't always mean comfortable
  Sometimes, the “safe” move turns out to be just another box.
• Your spouse is part of the journey
  If you’re making big career changes, bring your partner into the conversation. Often.

Connect with Shane Silsby:
📘 LinkedIn: Shane Silsby
🌐 Website: silsby-sa.com
📧 Email: [email protected]

Connect with Thomas Helfrich:
🐦 Twitter: @thelfrich
📘 Facebook: Cut The Tie Community
💼 LinkedIn: Thomas Helfrich
🌐 Website: www.cutthetie.com
📧 Email: [email protected]
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