How to handle fears when making a career pivot with Paul Ollinger

Criticizing, judging, & attacking yourself, Disengaging and using safety crutches

One way in which we play-it-safe is by “discounting what’s important to us or minimizing our needs.” Of course, in relationships sometimes we prioritize the relationships’ needs versus our individual needs. And yet, if this playing-it-safe move goes unchecked we may end up living lives that are unfulfilling.

In this conversation, I chatted with Paul Ollinger, a nationally-touring stand-up comedian, podcaster, and former digital sales leader.

Key Takeaways

This conversation was a powerful one because:

– Paul shares in detail how he made a shift, twice, from having a career that looked perfect on the outside and was enjoyable, – great benefits, stable, great people to work with – to creating a career path that was meaningful and purposeful.

– Paul shared the key questions he asked himself when figuring out what gives him meaning in this career: What would happen if I gave it all that I got in this life? What is my day to day life going to look like when I’m into this? What’s success? What’s my stress going to be about? Who will I spend time with?

– Lastly, Paul shared his behind-the-scenes process when preparing for a standing up show, starting with idea collection and ending in his mindset when performing in front of an audience.

You have heard me saying this before, we all play-it-safe. The challenge is when we do it, how often we do it, and how we do it. Discounting what matters to use is just another playing-it-safe move and we better watch out for it!

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how to handle fears

Resources

Show notes with time-stamps

01:32 Paul’s Journey from Business to Comedy
03:46 The Shift to Comedy: A Deep Dive
06:53 Navigating Fears and Embracing Failure
13:56 The Creative Process and Life as a Comedian
30:12 Making a Career Shift: Insights and Advice
34:54 A Hypothetical Coffee with Donald Trump
 

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