Showing Up Online Without Losing Yourself | Jana Oman

What if the biggest thing holding you back online isn’t your skill — but your need to look perfect?

In this episode of Yes And Land, Ryan Gregerson sits down with Jana Oman to explore authenticity, personal branding, and the pressure to show up polished in a world obsessed with highlight reels. Jana shares her journey from learning to code in the early MS-DOS era at just eight years old to carving out a unique identity in real estate by embracing who she truly is.

Through the lens of Disney’s Encanto, they unpack the emotional weight of expectations, imposter syndrome, and the freedom that comes when you stop performing and start being yourself.

If you’ve struggled with confidence, overthinking your content, or wondering whether you’re “enough” to show up online, this conversation is for you.

Actionable Takeaways

• Audit where you’re performing instead of connecting.
• Rewrite your bio to reflect who you actually are.
• Share one honest, imperfect story this week.
• Stop copying industry templates and experiment with your voice.
• Choose clarity and alignment over polish and perfection.

Authenticity isn’t a branding tactic. It’s your advantage.

CHAPTERS

00:00 – Why Showing Up Online Feels So Hard

01:00 – Introducing Jana Oman

02:00 – Coding at Age Eight (MS-DOS Era!)

03:00 – Discovering College Was Possible

05:30 – The Pressure to Perform Online

10:00 – Lessons from Encanto

15:45 – Authentic Personal Branding

22:00 – Letting Go of Perfection

28:00 – Your Flaws Are Not Disqualifiers

34:00 – What Real Breakthrough Looks Like

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Your breakthrough may start with letting go of perfection.