
The Freelancer's Guide To Less Anxiety with Chris Brogan & Ada Calhoun
From The Anxious Achiever by Morra Aarons-Mele
March 26, 2026 · 48 min · Episode 306
About this episode
This episode explores the relationship between freelancing, mental health, and the challenges of entrepreneurship with insights from Chris Brogan and Ada Calhoun.
Is entrepreneurship making your anxiety worse, or is it actually revealing something deeper about how you work and cope? In this episode, I talk with entrepreneur Chris Brogan and writer Ada Calhoun about the complicated relationship between freelancing, mental health, and the illusion of stability. Chris shares what it’s really like to build a career while living with depression, why success and struggle can coexist, and how he’s learned to “negotiate” with his mental health instead of letting it define him. Ada also breaks down the emotional and financial realities of freelance life, and the fears many of us carry about money and security. Tune in to rethink stability, understand your patterns, and build a way of working that supports your life. Check out our sponsors: Northwest Registered Agent - Protect your privacy, build your brand and get your complete business identity in just 10 clicks and 10 minutes! Visit https://www.northwestregisteredagent.com/achieverfree Shopify - Sign up for a $1 per month trial, just go to http://shopify.com/anxiousachiever Talkiatry - Head to http://talkiatry.com/achiever and complete the short assessment to get matched with an in network…
People in this episode
Host: Morra Aarons-Mele
Guests: Chris Brogan, Ada Calhoun
Topics covered
- freelancing
- mental health
- entrepreneurship
- anxiety
- financial stability
- depression
Keywords
- freelancing
- mental health
- anxiety
- entrepreneurship
- depression
- financial stability
- success
- struggle
Sponsors
Northwest Registered Agent, Shopify, Talkiatry, Working Genius, Brevo
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