What if uncertainty isn’t something to escape but the space where reinvention begins?
In this episode of Gen X Crisis, Robert talks with journalist, podcaster, and Substack writer Jonathan Small, whose career spans the magazine heyday of the ’90s to today’s creator economy. From interviewing George Carlin as a temp to launching the hit podcast Write About Now, Jon’s story is about learning to adapt, create, and stay curious when the ground keeps shifting.
Rob and Jon explore the emotional terrain of midlife, the unease of not knowing what’s next, the quiet ache of fading relevance, and the paradox of finding freedom when the plan falls apart. They dig into how work, identity, and creativity evolve with age, and why embracing uncertainty may be the most honest way to live right now.
This one’s about letting go of control, trusting your instincts, and realizing that “not knowing” can be the start of something new.
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And check out Jonathan Small’s Substack, Small Talk, and his best selling book Write About Now, interviews with over 400 writers in journalism, fiction, non-fiction.
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