Sail Loot Podcast 012: From Corporate America to Ottsworld with Sherry Ott

By on January 15, 2015

Sherry Ott was once living the good live in New York City. She had a great job as a project manager in the information technology sector.

Sherry was living the perfect American lifestyle. Perfect for what we’re told “The American Dream” is anyway. Perfect on paper for that resume that stated that she went to school, got a good job, and was working on building a good career that would help pay for all of the stuff that she could ever dream of.

For the next 35-40 years she would go to work every day, do an above average job, take her 2-4 weeks of vacation every year, and retire at the ripe age of 65 right? If that is your dream lifestyle, then I’m not going to tell you that it’s the wrong thing to do, but Sherry decided that it wasn’t right for her. She ran away from that corporate lifestyle to travel around the world.

This is the story of how Sherry made her dream of traveling come true, and how she has kept going.  She doesn’t need sailing money, but she does need to support her nomadic lifestyle. Some of the tips that Sherry includes in this amazing interview can be used to save your sailing money, and make some money while cruising.

Sherry has traveled around the world and back, and there is no end in sight.

A Few Things You’ll Learn About In This Episode:

  • What Sherry was doing prior to running away from corporate America.
  • Why Sherry decided to run away.
  • Sherry’s original travel plan.
  • The steps that Sherry took to start her adventures.
  • Where Sherry went and the number of countries that she visited in her first 16 months.
  • Can you guess where Sherry took her ESL certification course?
  • How Sherry started her Ottsworld blog.
  • How and why Sherry decided transfer Ottsworld to a self-hosted site and start monetizing it.
  • Where Sherry is now.
  • Starting Meet Plan Go and what inspired her.
  • Meet Plan Go’s Big Hairy Audacious Goal (BHAG).
  • How Sherry met Michaela Potter, her Meet Plan Go business partner.
  • The plan to monetize Meet Plan Go and their struggles.
  • What they try to teach at Meet Plan Go.
  • How Sherry works with Destination Marketing Organizations (DMO) and Tourist departments.
  • How new media – websites, blogging, podcasting – has revolutionized the travel and tourist industry.
  • Sherry’s top tips for taking a break from the corporate lifestyle to travel.
  • Sherry’s top tips for making a complete lifestyle away from.
  • And much more!

Links and Resources From This Episode:


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P.S. Sherry also shared some other great pictures, so I had to throw them in!

Sherry is a nomad. She has to carry all of her stuff somehow!

Sherry is a nomad. She has to carry all of her stuff somehow!

Sherry went to Patagonia and took some amazing pictures.

Sherry went to Patagonia and took some amazing pictures.

Sherry went to Patagonia and loved it!

Sherry went to Patagonia and loved it!


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About Teddy

I am a 37 year old that just wants to find a way to make a remote income, gather some Sail Loot and cruise the world! I have been sailing for a couple of years now, but mostly on 10 day trips as vacationing crew. I just recently took sailing to the next level by completing my Basic Keelboat, Basic Cruising, and Bareboat Cruising Certifications! I am also Vice President of a Medical Consulting Company, have a Mechanical Engineering degree from Georgia Tech, and have taken several Coding, Computing, and Online Business courses. It's time to share what I have learned!


  1. Sherry Ott

    January 17, 2015 at 8:49 am

    Teddy- thanks so much for having me on the show! Maybe one day I’ll actually put those sailing lessons to use in the world! Best of luck on the podcast!

    • Teddy


      January 17, 2015 at 10:20 am

      Sherry – The pleasure was all mine! Good times! Thank you for all the wonderful tips on how to escape, take a long break, and make a lifestyle out of it! Sounds like you’ll just have to travel to visit us on our sailboat someday – when we finally get one! On the hunt for one tomorrow.


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