meta_pixel
Tapesearch Logo
Log in
The Anxious Achiever

The Freelancer's Guide To Less Anxiety with Chris Brogan & Ada Calhoun

The Anxious Achiever

Morra Aarons-Mele

Business, Careers, Management, Health & Fitness, Mental Health

4.7599 Ratings

🗓️ 26 March 2026

⏱️ 57 minutes

🧾️ Download transcript

Summary

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 psychiatrist in just a few minutes. Working Genius - Take the working genius assessment today and get 20% off with code ACHIEVER at working http://workinggenius.com 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

Transcript

Click on a timestamp to play from that location

0:00.0

Think of a workflow that you execute every week and you wish it could run itself.

0:09.8

Well, with Notion's new custom agents, consider it handled.

0:14.7

A status update agent can just automatically scan your progress each week, synthesize key updates,

0:20.8

compile them into a report,

0:22.3

and send it. So you don't have to. I love Notion. I use Notion. Notion is at AI-powered

0:29.7

connected workspace for teams. Try their new custom agents at Notion.com slash achiever. That's notion.com slash achiever, all lowercase to try their

0:42.3

custom agents today. And when you use this link, you're supporting the show.

0:48.5

Bravo is the all-in-one marketing and CRM platform built to help you connect with customers, boost

0:53.6

engagement, and grow your business smarter to help you connect with customers, boost engagement, and

0:54.8

grow your business smarter. And you can use Aura, the AI assistant that helps you create

1:00.5

smarter campaigns in real time. Get started for free today. Use code Achiever 50, and you can

1:07.6

save 50% on starter and standard plans for the first three months of an annual

1:11.8

subscription. Just head to brevo.com. That's b-revo.com slash achiever to take your marketing

1:18.8

further with Breva and ORA. I travel a lot and I need to protect my data. That's why I use

1:26.8

ExpressVPN to secure my online data. And

1:30.9

plans start at just $3.49 a month. That's only 12 cents a day. Secure your online data today by

1:37.9

visiting ExpressVPN.com slash Achiever. That's ExpressVPN.com slash achieverver and find out how you can get up to four extra months.

1:47.8

ExpressVPN.com slash achiever. Are you starting a business? Do you need compliance documents and

1:54.5

bylaws and an operating agreement and all of the paperwork you need to create a business identity?

2:02.7

Don't pay hundreds or thousands of dollars for what you can get from Northwest Registered Agent for free. Visit Northwest Registeredagent.com

2:08.8

slash achiever free and start using free resources to build something amazing. Get more with Northwest

2:14.8

registeredagent.com slash achiever free.

...

Please login to see the full transcript.

Disclaimer: The podcast and artwork embedded on this page are from Morra Aarons-Mele, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of Morra Aarons-Mele and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.

Copyright © Tapesearch 2026.