The Freelancer's Guide To Less Anxiety with Chris Brogan & 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 Shopify - Sign up for a $1 per month trial, just go to Talkiatry - Head to and complete the short assessment to get matched with an in network psychiatrist in just a few minutes. Working Genius - Take the working genius assessment today and get 20% off with code ACHIEVER at working Brevo - Meet brevo, the all in one marketing and CRM platform built to help you connect with customers, boost engagement and grow your business smarter. Go to brevo.com/achiever and use code ACHIEVER50 for 50% off. In this Episode, You Will Learn 00:00 Can you be successful while living with depression? 05:00 What it really feels like to work through depression day-to-day. 08:00 Why performance can feel easier than personal connection. 12:00 How to “negotiate” with your inner critic instead of fighting it. 16:45 How depression shows up in everyday work tasks. 18:45 What radical transparency about mental health looks like at work. 23:45 Is freelancing really riskier than having one employer? 26:15 What to do when your income drops or disappears. 30:15 Why freelance success doesn’t eliminate financial anxiety. 34:00 How freelancers manage mental health care. 38:00 How childhood experiences shape your fear around money. 42:45 Why does “enough” never feel like enough? Resources + Links Get a copy of Ada Calhoun’s book, Why We Can’t Sleep HERE! Learn more about Chris Brogan’s work HERE! Learn more about Adverse Childhood Experiences (ACEs) HERE! Get a copy of my book - The Anxious Achiever Watch the podcast on YouTube Find more resources on our website morraam.com Follow Follow me: on LinkedIn @morraaronsmele + Instagram @morraam Follow Chris on LinkedIn: @cbrogan Follow Ada on Instagram: @adacalhoun

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The Freelancer's Guide To Less Anxiety with Chris Brogan & Ada Calhoun is an episode from The Anxious Achiever by Morra Aarons-Mele.

This episode is 48:07 long.

This episode was published on Mar 26, 2026.

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