Be the C.E.O. of Your Career: Discovery in Action with Jason Van Orden

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Written By Tammy Gooler Loeb

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Be the C.E.O. of Your Career: Discovery in Action with Jason Van Orden

Follow Your Curiosity: Discovering What's Next in Your Career

When a career path no longer feels right, it can be tempting to think the only answer is to start over. But sometimes the better question is simply, What am I curious about? In this episode of Work from the Inside Out, Tammy Gooler Loeb explores the second practice in her Be the CEO of Your Career framework: Discovery. Rather than allowing uncertainty to translate into  overwhelm or paralysis, discovery encourages people to ask questions, gather information, experiment, and remain open to what they can learn along the way.

Tammy brings this practice to life through her conversation with entrepreneur, strategist, and longtime podcaster Jason Van Orden, whose career has been shaped by following his curiosity. Jason began with an interest in computers and programming, eventually becoming an electrical engineer and software developer. But after several years, he recognized that working as an employee wasn't the right fit. His curiosity led him into real estate investing, marketing, teaching, and consulting, eventually helping him discover podcasting in its earliest days. He and a friend launched Internet Business Mastery, which grew into a Top 10 business podcast and became a major part of his career for more than a decade.

Jason's story also demonstrates that discovery doesn't necessarily mean throwing away everything that came before. After years of success with his podcast and business, he reached a point where he realized he was no longer energized by the work. Rather than abandoning all of his experience, he took time to explore what he wanted to carry forward. His technical knowledge, marketing experience, teaching skills, and years of working with entrepreneurs eventually came together in his work helping coaches and consultants grow their businesses and communicate their unique expertise. His journey shows how seemingly unrelated experiences can become valuable pieces of a much larger career story.

For Jason, curiosity has remained a reliable way to navigate uncertainty. He encourages people who are wondering what comes next to follow their curiosity rather than feeling pressured to immediately identify their direction or make a major career decision. Discovery can begin with something as simple as asking a question, talking with someone who has experience in an area of interest, attending an event, or experimenting with a possibility. Jason's own interest in artificial intelligence is another example of this approach, as he explores how new technology can support his work while still preserving his authentic voice.

Discovery is not something that ends once someone finds the "right" career. As Tammy points out, it can become an ongoing practice throughout a person's career and life, including during major crossroads such as retirement. The questions may change, but the process remains the same: stay grounded, get curious, engage with others, and gather real information rather than guessing or becoming overwhelmed. For this week's CEO of Your Career Move, listeners are encouraged to choose one thing they've been wondering about and talk to someone who knows more about it. One conversation, one question, or one small experiment can be enough to turn curiosity into discovery and reveal a possibility they hadn't considered before.

In This Week's Podcast, Learn More About:

  • What discovery looks like as an ongoing career practice

  • Why curiosity can be more useful than trying to "find your passion"

  • How to turn uncertainty into an invitation to explore

  • Recognizing the breadcrumbs that appear throughout your career

  • Using experimentation to learn what fits

  • Why discovery requires engagement with other people

  • How Jason transitioned from engineering to entrepreneurship

  • The unexpected path from real estate investing to podcasting

  • What Jason learned from leaving a successful business

  • How networking became an important part of his next chapter

  • Using your existing skills in new and unexpected ways

  • Exploring AI while maintaining an authentic voice

  • Why you don't need to have your entire next chapter figured out

Learn more:

Your CEO of Your Career Move:

Pick one thing you've been wondering about.

It could be a different role, a possible career direction, an industry, a business idea, a skill you want to develop, or simply a question about what might be possible.

Instead of researching it alone at your laptop, go talk to a person about it.

Have one informational conversation. Reach out to someone who has already explored that path. Ask an honest question. Talk to a librarian, colleague, former coworker, mentor, or someone you admire.

The goal isn't to make a decision.

The goal is to discover something you didn't know before.

That's discovery in action.

Interested in individual or group coaching with Tammy?  Learn more about her coaching service.

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Affiliate Links: Disclosure of Material Connection: Some of the links above are “affiliate links”. This means that if you click on the link and purchase the item, I will receive an affiliate commission. Regardless, I only recommend products and services I use personally and believe will add value to my listeners. I am disclosing this in accordance with the Federal Trade Commission’s 16 CFR, Part 255: “Guides Concerning the Use of Endorsements and Testimonials in Advertising.”

 

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About Tammy, host of
Work from the Inside Out

Before launching my coaching practice, I worked in mental health, higher education, public policy, and fundraising. Those experiences showed me how deeply our work shapes our sense of purpose—and now I help clients navigate change and growth so they can feel more fulfilled and aligned in what they do

More about Tammy
Tammy Gooler Loeb
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