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Why Midlife Anxiety and Overwhelm Make Habits So Hard to Stick To S1 EP5
If you’ve been struggling with midlife anxiety, overwhelm, low motivation, or the feeling that you keep trying and failing at change, this episode is for you. In this conversation, Jody Brooks speaks with Roger Webb about why habits are so hard to stick to, why willpower and discipline are often overrated, and how the real block is usually deeper than behaviour alone.
Roger shares his own messy middle moment — a season of depression, identity loss, and burnout that left him feeling disconnected from himself and questioning everything. What followed was an unexpected reset: a new job in a pizza restaurant, a fresh sense of identity, and eventually a nomadic life that forced him to surrender, trust, and rebuild from the inside out. Along the way, he began creating Random Habit, an app designed to help people make change feel easier, kinder, and more human.
This episode explores the pain points so many midlifers know well: people pleasing, self-sabotage, emotional exhaustion, shame after “failing” again, and the frustration of doing all the right things without lasting results. Jody and Roger unpack how random reinforcement, small wins, and self-compassion can support real transformation — not by pushing harder, but by helping you show up for yourself differently.
If this conversation resonates, subscribe to Messy Midlife and visit authenticcoaching.me for show notes and resources.
Connect with Roger: https://randomhabitapp.com/
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