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On Courage Podcast
12. What to Do at a Career Crossroads
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12. What to Do at a Career Crossroads

The first step is to recognize that your career crossroads is really a life crossroads; then use this proven process to help you move forward

After concluding the 3-part Purpose Series, I'm excited to be planning a group coaching experience tailored for 5-10 people eager to connect to their purpose and integrate it more profoundly into their lives. If this interests you, I’d love to hear from you! Please take a moment to share your thoughts in this brief 2-minute survey. Thank you.


In this episode, we look at the challenging—and common—terrain of a career crossroads.

Many of us have been there. Some of us are likely at one now.

I’ve certainly been there.

Back in 2022, I had just laid myself off and started a sabbatical. I had no idea what was next for me professionally. That’s when a friend recommended the book, “Designing Your Life”, which offered a structured approach to explore my options.

In the photo below (taken this week), I’m holding a worksheet from that book that I completed at a coffee shop a few weeks later. That worksheet played a pivotal role in clarifying my next steps.

Having experienced its effectiveness firsthand, I now use this process with many of my clients facing similar crossroads. In this episode, I delve into this process and share ideas for you to turn your career crossroads into a moment of powerful transformation.

Key Episode Takeaways:

  1. Becoming Aware of It: A career crossroads is different than a career decision or strategy. It’s when you really don’t know what’s next for you. Whether you’re employed or unemployed, take a moment to assess your feelings about your current situation and where you see yourself heading.

  2. What’s Beneath: Instead of solely viewing a career crossroads as a professional dilemma, consider it a broader life crossroads—an opportunity for holistic personal growth.

  3. Why Navigating It Is Hard: Attempting to solve life problems with career tools is ineffective and often leads to feelings of pressure and urgency. These factors hinder our ability to engage in a thoughtful exploration process.

  4. See the Opportunity: Prior to taking action, it's essential to cultivate self-awareness of your own crossroads. Zoom out to see the bigger picture and embrace the journey as a transformative experience.

  5. The "Designing Your Life" Methodology: Leveraging the principles outlined in the book "Designing Your Life" provides a structured and flexible approach. It helps you explore various life paths and gain clarity on your next steps.

  6. The “Odyssey Plan” Worksheet: This 5-step process can be completed in under an hour. It offers a powerful tool to imagine possibilities, address lingering questions, and move yourself forward. I share personal insights on completing the worksheet effectively.

  7. Tips for Success: To maximize the benefits of this process, allow yourself to dream freely and prioritize learning. Choose a stimulating environment to complete the worksheet, and consider setting a time limit to maintain creativity and focus.

These days, there are many people at a crossroads who need support. If you believe this episode can help them, I encourage you to share it.

- Elliot

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On Courage
On Courage Podcast
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