You've sold the business. You've left the successful career. You finally have the freedom to choose what comes next.

So why is it so difficult to figure out what you actually want?

For many founders, executives and accomplished professionals, life after success brings an unexpected challenge. After decades of pursuing goals, building businesses and making important decisions, they're suddenly faced with a question that seems almost impossible to answer: What do I really want to do with the next chapter of my life?

In this episode of What's Next After Success, Kevin Simcock explores why having unlimited possibilities doesn't necessarily create clarity, and why the pressure to find your next purpose can actually keep you stuck.

In this episode, we explore:

• The paradox of freedom: Why having more choices after leaving a successful career or business can make deciding what comes next harder.
• The trap of past success: How we unconsciously evaluate new possibilities using the same expectations, ambitions and definitions of success that shaped our previous careers.
• Curiosity before purpose: Why finding something worth exploring may be more useful than trying to identify your life's next great mission.
• Building a possibility portfolio: A different way to explore potential directions without immediately committing to another business, career or identity.
• Experience creates clarity: How small, real-world experiences can help you discover what genuinely interests, energizes and fulfils you.

Whether you're figuring out what to do after selling your business, finding purpose after leaving a successful career, or simply wondering what you really want from life now, this conversation offers a different way to approach the question.

Maybe you don't need to know what you want to do with the rest of your life. Maybe you just need to discover what's worth pursuing next.

Follow What's Next After Success for more conversations about life after success, finding meaning, exploring possibilities and building a next chapter that's genuinely your own.

Purchase Kevin Simcock's Book: Whose Ladder Is This?

Available on Amazon Kindle, paperback, and hardcover

Barnes & Noble | Indigo Books

Contact Kevin at kevinsimcock.com

Check out more episodes of What’s Next After Success on YouTube: https://youtube.com/@kevinsimcock

Host: Kevin Simcock

LinkedIn: https://www.linkedin.com/in/kevin-simcock/

You've spent years building, leading, and achieving. Now that you've stepped away, why does deciding what comes next feel so urgent?

For successful executives and business owners, doing nothing can feel unbearable. The temptation is to jump straight into another venture, accept another leadership role, or fill your calendar with new commitments. But what if rushing forward simply recreates the life you wanted to leave behind?

In this episode of What's Next After Success, Kevin Simcock explores why taking time to pause after a business exit or major career transition might be the most productive decision you make.

Drawing on his own experience, Kevin challenges the instinct to keep moving and explores three important considerations for navigating your next chapter:

• The art of doing nothing: Why giving yourself permission to decompress creates space to see new possibilities.
• The power of better questions: How understanding your evolving values, motivations, and priorities can reveal what's genuinely worth pursuing.
• Rethinking your timeline: Why your next chapter isn't a destination to reach, but a direction that develops through exploration and experience.

Whether you've recently sold your business, stepped away from an executive career, or are questioning what success should look like now, this episode invites you to reconsider what it really means to move forward.

Before deciding what to do next, discover what makes it worth doing.

Purchase Kevin Simcock's Book: Whose Ladder Is This?

Available on Amazon Kindle, paperback, and hardcover

Barnes & Noble | Indigo Books

Contact Kevin at kevinsimcock.com

Check out more episodes of What’s Next After Success on YouTube: https://youtube.com/@kevinsimcock

Host: Kevin Simcock

LinkedIn: https://www.linkedin.com/in/kevin-simcock/

AI is making it easier than ever to research an idea, test a business, and build something new. At the same time, it is changing how companies think about roles, headcount, and the future of work, raising a bigger question for accomplished professionals considering a career transition or next chapter.

So what happens when AI gives you more possibilities, but no better answer about which one is actually worth pursuing? Kevin explores how AI can help you investigate and validate new directions, why the falling barriers to starting something create a new kind of decision problem, and why judgment, self-knowledge, and discernment become even more important as technology gets more capable.

AI may help you build almost anything, but the harder question is: what should you build?

Purchase Kevin Simcock's Book: Whose Ladder Is This?

Available on Amazon Kindle, paperback, and hardcover

Barnes & Noble | Indigo Books

Contact Kevin at kevinsimcock.com

Check out more episodes of What’s Next After Success on YouTube: https://youtube.com/@kevinsimcock

Host: Kevin Simcock

LinkedIn: https://www.linkedin.com/in/kevin-simcock/

Research referenced in this episode

• Challenger, Gray & Christmas - Challenger Report: March Cuts Rise 25% From February, AI Leads Reasons: https://www.challengergray.com/blog/challenger-report-march-cuts-rise-25-from-february-ai-leads-reasons/

• Gallup - U.S. Workers Continue to Report Downsizing: https://www.gallup.com/workplace/711287/workers-continue-report-downsizing.aspx

• TechCrunch - Monday.com is the latest tech company to blame AI for layoffs - here are 20 others: https://techcrunch.com/2026/07/25/the-running-list-major-tech-layoffs-in-2026-where-employers-cited-ai/

• Government of Canada - Research summary: Artificial intelligence and automation in Canada’s labour market: https://www.canada.ca/en/employment-social-development/corporate/reports/research/summary-ai-labour-market.html

• Gusto - 2026 New Business Formation Report: How AI Is Reshaping Who Starts a Business in America: https://gusto.com/resources/gusto-insights/new-business-formation-2026

• JPMorganChase Institute - Small Business in the Age of AI: https://www.jpmorganchase.com/institute/all-topics/business-growth-and-entrepreneurship/small-business-in-the-age-of-ai

• International Labour Organization - Changing landscape of skills in the age of AI: https://www.ilo.org/publications/changing-landscape-skills-age-ai

• Thomson Reuters - Future of Professionals Report 2026: https://www.thomsonreuters.com/en/institute/future-of-professionals-2026/report

• Business Insider - Anthropic's AI fluency chief says the best AI users know when to do the work themselves: https://www.businessinsider.com/anthropic-ai-fluency-chief-discernment-tax-work-2026-9