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

6 snips

Mar 26, 2026

Guest

Ada Calhoun

Guest

Chris Brogan

Ada Calhoun, writer who explores midlife work anxiety and freelance money fears. Chris Brogan, entrepreneur and content creator living with clinical depression. They talk about how freelancing exposes stability illusions. Conversation covers negotiating with inner critics, day-to-day effects of depression on work, cashflow and client diversification, and the emotional roots of financial fear.

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ADVICE

Thank Your Inner Critic Instead Of Fighting

Thank and acknowledge your inner critic instead of fighting it to reduce its power.
Use Dr. Matthew McKay's technique: verbally thank the critic and then proceed with your plan anyway.

ADVICE

Schedule Forty Percent To Avoid Overload

Structure work by scheduling only ~40% of your day and reserving low-density blocks to avoid overwhelm.
Brogan uses nine 20-minute checkboxes (three hours) for business growth that can move around the day.

INSIGHT

Helping Others As An Antidepressant

Helping others is Chris Brogan's fastest antidepressant and reliably lifts his mood.
He warns it's not a substitute for self-love but can accelerate recovery during down periods.

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