Productive Flourishing
Productive Flourishing
Episode 39 - Be True to Yourself with Natalie Sisson

Episode 39 - Be True to Yourself with Natalie Sisson

Known as the Suitcase Entrepreneur, Natalie Sisson has been traveling the world and living out of her suitcase since 2006 while also running a successful online business from her laptop that generates a six-figure income. She is a number-one bestselling author, podcaster, speaker, and adventure and is on a mission to help entrepreneurs create true freedom in their lives by 2020. Natalie joins Charlie on the show today to discuss her adventuresome lifestyle, how she grew her business, upcoming changes, and much more.

Key Takeaways:

2:04 – How Natalie got started in entrepreneurship and what made her want to do it.

4:35 – Natalie’s first business and what ultimately led her to leave and move on.

8:37 – Challenges Natalie faced in the first years of Suitcase Entrepreneur and what she saw as the most challenging areas of business.

12:11 – Spark moments in the first years of Suitcase Entrepreneur that let Natalie know she should keep going.

13:20 – Something Natalie learned that she wishes someone had told her before she started.

18:25 – The balance between always talking about yourself and your experiences but using that to help teach others.

19:33 – The process Natalie took in writing and publishing her book.

25:27 – Getting over the fear of asking people to support your work and help you.

28:38 – Natalie’s views on freedom.

31:41 – New things and changes coming up in Natalie’s life and work and what led to making those changes.

36:33 – The most unanticipated challenge Natalie is facing right now.

37:36 – Be true to yourself and comfortable with whatever decision you make at the time.

Mentioned in This Episode:

Freedom Plan Program


Connection Point Systems


Seth Godin

Jonathan Fields

Fresh in Fifteen podcast



Pam Slim

The Art of Asking, Amanda Palmer

Tim Ferriss

Chris Guillebeau

Productive Flourishing
Productive Flourishing
Productive Flourishing (formerly the Creative Giant Show) explores how to do the work that matters to become your best self in the world. Host Charlie Gilkey and occasional co-host Angela Wheeler take listeners on a deep dive into the lives of leaders, changemakers, creatives, and entrepreneurs who are thriving in life and business by doing work that matters. Listen in to see how they cultivate meaning, success, and happiness as well as their approach to productivity, business, health, and the challenges (yes, even the deep, dark ones) that show up in their lives.