Ann Shen started her career as a grant writer and realized that the ladder she was climbing was leaning against the wrong wall. She then took the courageous step of going to art school and starting over again. Since then, with a combination of skill, grit, and newfound faith in herself, she’s gone a long way as a free agent. Click here to listen to Ann’s story on this week’s episode of Free Agents.

This episode of Free Agents is sponsored by:

• Hover: Show the world what you’re passionate about with 10% off your first purchase.
• FreshBooks: Online invoicing made easy.

On this week’s episode of Free Agents, Mike and I talk about why “eating your frog” is an important free agent survival skill. I talk through a pivot in my approach to book publishing, and Mike shares his struggles with “Imposter Syndrome” and how he overcomes it.

This episode of Free Agents is sponsored by:

• Squarespace: Make your next move. Enter offer code FREEAGENTS at checkout to get 10% off your first purchase.
• FreshBooks: Online invoicing made easy.

Mike Schmitz joins Free Agents as the new co-host. In this episode, we get to know Mike better, learn about his journey, and discuss the show format going forward.

This episode of Free Agents is sponsored by:

• FreshBooks: Online invoicing made easy.
• Casper: The Internet’s favorite mattress. Get $50 off select mattresses with the code ‘FREEAGENTS’

Family members with employment issues remind Jason about just how far he has come. I grapple with letting go of control and working with an assistant. And Jason hands in his resignation and participates in an “exit interview” with me. Join us for the latest episode of Free Agents.

This episode of Free Agents is sponsored by:

• Squarespace: Make your next move. Enter offer code FREEAGENTS at checkout to get 10% off your first purchase.
• FreshBooks: Online invoicing made easy.

Podcaster Merlin Mann joins Jason and me on this week’s Free Agents to discuss his long journey as an independent worker, during which he has pivoted from tech guy to productivity expert to a specializer in cult hits.

This episode of Free Agents is sponsored by:

• Timing: The automatic time-tracking app for macOS. Use this link to save 10% on your purchase.
• Squarespace: Make your next move. Enter offer code FREEAGENTS at checkout to get 10% off your first purchase.

There’s a lot to think about on this week’s Free Agents. I need to deal with some clients who aren’t paying me. Jason thinks about “taking a personal day” and how that’s different from going on vacation or taking a few hours off. I ponder creating a mission statement for myself. And Jason questions whether he’s unable to give himself credit for doing certain kinds of work.

This episode of Free Agents is sponsored by:

• Freshbooks: Online invoicing made easy.
• Warby Parker: Quality eyewear at a fraction of the usual price. Order your FREE Home Try-On kit today.

Longtime web developer, tech executive, start-up co-founder, inspirational speaker, and coach Jaimee Newberry joins us on this week’s episode to discuss her own journey, when to go out on your own, when to walk way from projects, and how to deal with unexpected success.

This episode of Free Agents is sponsored by:

• Timing: The automatic time-tracking app for macOS. Use this link to save 10% on your purchase.
• Freshbooks: Online invoicing made easy.

My home workspace gets invaded by teenagers, Jason reprises his old commute and learns to appreciate the ability to work from anyplace, and a listener reminds us of a classic technique: making promises that your future self has to keep. Join us for the latest episode of Free Agents.

This episode of Free Agents is sponsored by:

• Timing: The automatic time tracking app for macOS. Use this link to save 10% on your purchase.
• Freshbooks: Online invoicing made easy.

You might not realize it, but creative professionals in the entertainment industry are also free agents. In this episode, we talk to writer/actor/director David Wain of Wet Hot American Summer and The State about his life as a free agent, from hitting MTV right out of college to the lean times that followed. Turns out that juggling a busy schedule, learning to say no, and not being able to plan vacations far in advance are all features of his line of work.

Guest Starring: David Wain

This episode of Free Agents is sponsored by:

• Squarespace: Make your next move. Enter offer code FREEAGENTS at checkout to get 10% off your first purchase.
• Freshbooks: Online invoicing made easy.