<![CDATA[Founder by Design: Crossroads Conversations]]>https://founderbydesign.substack.com/s/crossroads-conversationshttps://substackcdn.com/image/fetch/$s_!Hhi6!,w_256,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F892f2907-256c-4f2a-ad24-bfab68dbf51f_300x300.pngFounder by Design: Crossroads Conversationshttps://founderbydesign.substack.com/s/crossroads-conversationsSubstackSat, 09 May 2026 23:39:24 GMT<![CDATA["Everything Was a Resume Move"]]>https://founderbydesign.substack.com/p/everything-was-a-resume-movehttps://founderbydesign.substack.com/p/everything-was-a-resume-moveTue, 28 Apr 2026 16:23:54 GMTHwei-Yi Lee spent the first two thirds of her career making every move count on paper. She earned a prestigious MBA. She took a strategic step down in title. Then she (almost) perfectly timed her corporate exit. She optimized everything for how her resume would be perceived by her next employer. The strategy worked until the linear career path no longer made sense.

In this conversation, Hwei-Yi talks about the motivations and market forces shaping her “third arc,” why she’s learning software development at 48, and how she’s treating this next chapter as a living sandbox, with a clear sense of purpose and the rigor to figure it out along the way.

If you’ve ever made a career decision based on how it would look on paper instead of how it felt, this one’s for you.

Are you navigating your own crossroads? I’d love to have you on the show.

Apply to be a guest

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]]><![CDATA[Crossroads Conversations]]>https://founderbydesign.substack.com/p/thought-experimenthttps://founderbydesign.substack.com/p/thought-experimentTue, 10 Mar 2026 14:14:19 GMT
Photo by Sage Friedman on Unsplash.

When the path to success is no longer mapped for you, how do you decide which direction to go?

Crossroads Conversations meets these moments head on and tackles the tradeoffs we make when the path forward isn’t clear and the outcome isn’t guaranteed.

Listen to new episodes

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]]><![CDATA[Episode #2: Doubt]]>https://founderbydesign.substack.com/p/episode-2-doubthttps://founderbydesign.substack.com/p/episode-2-doubtMon, 02 Mar 2026 15:14:12 GMT

Doubt isn’t your enemy. It’s a messenger.

We’ve been taught to push past doubt, stuff it down, keep moving. But what if that’s exactly the wrong approach?

In Episode 2 of Thought Experiment, I’m getting personal — sharing what came up for me mid-launch — and exploring why doubt is actually your brain doing its job. The real question isn’t how to get rid of it. It’s knowing what to do with it.

Give it a listen and let me know: where is doubt showing up for you this week?

Founder by Design is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

]]><![CDATA[Episode #1: Listening]]>https://founderbydesign.substack.com/p/how-well-do-you-listen-to-yourselfhttps://founderbydesign.substack.com/p/how-well-do-you-listen-to-yourselfSun, 01 Feb 2026 22:38:31 GMTHey Subscribers! I’m trying out something new. Every week(ish) I’m coming at you with Thought Experiment, an audio series where I contemplate the collective energy and offer perspective on how we can all move through the world a little differently.

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