Earn & Invest · Jordan Grumet (Doc G)

673. Ten Things About Disapointment (Solo)

·32 min·2 clips

Doc G reveals the three types of disappointment: circumstances, people, and yourself—and why one dominates.

Ten things, one familiar ache. Doc G returns to the solo format after a Monday conversation with Ilana Golan from the Leap Academy about portfolio careers, the future of career, and a startup deal that went wrong. The topic is disappointment. The setup is simple: someone starts a startup with a friend, then gets cut out of the deal at the last moment. Doc G handles that hurt directly. He does not treat disappointment as rare, theatrical, or reserved for unusually brutal turns in life. Everyone runs into it, he says. The useful question is what to do with disappointment once avoiding it is off the table. His first claim is blunt. Disappointment is inevitable, so the work starts with giving up the fantasy that you can eliminate it. Then he names three kinds. A person can be disappointed in circumstance, disappointed in other people, or disappointed in oneself. The third one carries the most weight. Doc G argues that the first two often turn inward, becoming regret about poor risk mitigation or not protecting yourself well enough. That makes forgiveness practical, not soft. If self-disappointment is the dominant form, learning to forgive yourself becomes part of learning anything at all. Growth is the payoff he keeps pointing toward. The host links better self-forgiveness with the ability to keep building new business and keep learning after a setback. The structure is intentionally scaffolded. At the midpoint, he pauses, recaps points one through five, and resets the listener for the second half. The tone is coaching without getting syrupy. Disappointment is treated as real pain, but also as something you can sort, name, and use. The ad break pulls focus late. Still, the main argument holds: disappointment gets less destabilizing when experience improves judgment, self-protection, and recovery.

As heard by us

A practical framework for disappointment, self-forgiveness, and growth.

Doc G opens by framing disappointment through Ilana Golan's startup setback, then uses that story to shape a three-part view of disappointment in circumstance, in other people, and in oneself.

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Why you'd press play

When disappointment hits your plans, this gives you a steadier way to name it.

Read the full recommendation in PlayNext →

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