The Journey to Meaningful Work: Interview with Shawn Askinosie

At some point in life, most of us will go through a career transition. Maybe you get let go or it’s just not a good fit, but whatever the reason, as some level, you know something is missing and there is more you are meant to do.

The Journey to Meaningful Work: Interview with Shawn Askinosie

Our guest today, Shawn Askinosie, went through a challenging transition that led him from being an attorney to selling chocolate for a living. The journey was so significant that he wrote a book called Meaningful Work: A Quest To Do Great Business, Find Your Calling, And Feed Your Soul. I love this book.

Before reading his book or being introduced by our mutual friend Seth Godin, I tried Shawn’s chocolate at Jenny’s Ice Cream years ago. They offered an Askinosie chocolate flavor, created from ingredients provided by Shawn’s family-run company, and it was amazing. Without even realizing it, I was a Shawn Askinosie fan.

Eleven years ago, Shawn started Askinosie Chocolate after a twenty-year career as a defense lawyer. Using a bean to bar model, he sources the beans himself from all around the world. Askinosie Chocolate’s work toward community development locally and globally has been well-recognized. Oprah Magazine called him “one of 15 guys saving the world” and Forbes recently named the company one of the 25 best small companies in America.

On this episode of The Portfolio Life, Shawn shares the story of his journey from lawyer to chocolatier to author. His experiences have taught him how to navigate life, measure company growth beyond profit, and what practical step we can take today to find more meaningful work. I hope you enjoy it.

Listen to the podcast

To listen to the show, click the player below (If you’re reading this via email, please click here).

Show highlights

In this episode, Shawn and I explore:

  • What did a monastery teach him?
  • When do you know you are in the right place at the right time?
  • What does it mean to be resting in the presence of God?
  • What is his heart metric for his book?
  • Why did he write his story the way he did?

The best way to find ourselves is to lose ourselves in service to others.

Shawn Askinosie

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Shawn’s search for his next venture

  • What was a daily activity that helped him find his next passion?
  • Did he know anything about chocolate before starting his business?
  • What happened when he went to the Amazon?
  • Why did desperation actually make his discovery harder?
  • What did volunteering with palliative patients in a local hospital teach him?

Our greatest joy is our sorrow unmasked.

Shawn Askinosie

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Lessons from Shawn’s book Meaningful Work

  • What can you learn from the two parts of his business’ vocation?
  • What is farmgate and why is it important?
  • How to answer the question: how much is enough?
  • What happens if you don’t find the purpose of your work?
  • Why and when we should practice reverse scale.


What is one thing you’re going to do to bring meaning to your work after listening to Shawn? Let us know in the comments.