BiB025: Don’t Forget the Boobs with Michael Smith

Giving himself permission to be who he wants to be, author/business owner and self-proclaimed ‘executive transvestite traveler’, Michael Smith had his fair share of experiences in his time in Thailand. Perceiving gender as something of a more fluid kind, he personally choose the box for ‘transvestite’ but won’t blame anyone who’d refer to him as a ladyboy.

With a Master’s Degree in Math from Cambridge University, Michael Smith is the owner of a custom software company and author of “Intuitive Leadership Mastery“, which is about using intuition in business and what it takes to reach your goals. With all of the chaos in the world, things cannot be done rationally. He suggests quieting down and listening to your intuitions. Also, keeping a “decision journal” that keeps track of your insights while using a scientific approach will help you achieve your goals.

Although, wearing high-heels and a bra aren’t the most comfortable, dressing as a woman makes him feel natural. Knowing that he wanted to cross-dress from an early age, Michael decided to “come-out” to his employees about 15 years ago. He told each person one-on-one, finally easing his anxiety.

Michael also mentions, that while entering the U.S. dressed as a woman is a little nerve-wracking, Thailand immigration is usually friendly. He recommends that if you are wanting to experiment with your gender, Bangkok; known for it’s diversity, is the place to test the waters.

Mentioned in this Episode


I had some help with this episode: Lou Pobjecky kindly helped me with a lot of the necessary audio edits to get the file in a listenable shape. Lou also put together the cover image and quick description for this episode.

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Lou is a podcast producer and audio engineer. He makes sure that the Brewed in Bangkok sounds as smooth as silk. You can find out more about him on LinkedIn.

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