Jack Levitt's 91 years old. He's still a practicing lawyer in New York City. He takes daily walks of 2-3 miles and has a sharper intellect and fashion sense than most people I know. Here, he shares one powerful piece of wisdom for navigating life's big decisions—especially helpful for those prone to over-analysis, such as myself. Enjoy.

Cosette "CoCo" Leary recently published a book called “From Welfare to the White House”; she went from raising four children off $742 per month to getting a position on Capitol Hill. Now she has returned with a mission: to guide others on a similar journey—from simple existence to living out your deepest talents and passions.

I got my mind blown twice, brains splattered across the walls, with several mini-blows along the way. I came away a different person. Perhaps you will too.

Jelani Memory is founder and CCO of Circle Media.

Circle Media gained national attention when one of their products—Circle—was picked up by Disney after a failed Kickstarter.

Jelani lives a principled and focused life. He talks about what makes people reluctant to take risks (even when it could lead to deep fulfillment), as well as one of our biggest roadblocks: the illusion that we need permission to pursue the things we love.

How do we know we’ve found something we love? It’s not a conscious choice, or something we have to figure out - it’s just something you feel. This is behind Marcus’s love of photography, and just one small aspect of what make’s Portland’s top commercial photographer a very special and insightful guest.

Jamie Mustard is known professionally as "the Iconist" - he specializes in helping people "rise above the noise". He works primarily with artists, musicians and business executives, and has consulted for brands such as Intel, Cysco and Symantec.

What happens when you stumble upon a life-changing idea? It's now on you to develop it, sculpt it, and essentially execute. That can take time, though, years even, and it's a process filled with doubt, frustration, headaches. It's necessary though--'the blender', as Jamie calls it--as it paves the way for you doing the work you are ultimately capable of performing.

Emily Crumpacker is an author and chef--amongst many other things--here in Portland. Many credit her as being a main catalyst in turning the Pacific Northwest into the food mecca it is today.

Essentially, though, she's just a woman who wants to learn about the world and everyone in it. This has led to some fascinating career moves, like cooking for Leonardo diCaprio in Morocco and working with Julia Child in France. Her story is a great reminder of how fascinating the world can be, if you only give it a chance.

Tod Kelly - Writer by Harris Newman

David Hastings is a playwright and copywriter, so storytelling has been how he's made his bread for almost his entire life.

He and I sit down to discuss what makes a "compelling story", touching on the creative process, advertising, Trump, and something in theater called "the $64,000 moment".

Lucas Longacre is a filmmaker and producer. He's done several features, documentaries, tons of web video and also the PBS show, "Original Fare".

In this conversation, we talk about the reality of doing work you love, as well as the nature of human desire. He also shares some stories of how he was able to break out in a highly competitive industry.

Nancy Simon - Fashion Designer by Harris Newman