Fun First: The Big A## Calendar Episode with Taylor Prokes episode artwork

EPISODE · May 20, 2026 · 1H 1M

Fun First: The Big A## Calendar Episode with Taylor Prokes

from Maybe Running Will Help? · host Nicky Tamberrino

Discover how intentional planning with the Big A## Calendar can transform your year, boost your purpose, and reduce overwhelm. Listen to my conversation with Taylor Prokes, CEO of the 100 Mile Group, as she shares insights on setting meaningful goals, creating memorable adventures, and building habits that last.In this episode:How the Big Ass Calendar helps organize your year visually and intentionallyThe importance of starting small, like holidays and birthdays, for first-time usersThe story behind Jesse Itzler’s diverse career — from rapper to jingle writer and endurance enthusiastTips on how to leverage the calendar for big events and mini adventures throughout the yearThe power of habits and steady progress in creating a fulfilled, balanced lifeHow planning ahead increases energy and keeps you motivatedThe significance of shared experiences like races and collaborations in strengthening team bondsInsights on incorporating non-physical goals, like learning piano or exploring new hobbiesThe role of accountability and visual tracking in habit formationUpcoming launches and customized calendars for students and busy professionals15% off The Big A## CalendarTimestamps:00:00 - How the Big Ass Calendar simplifies annual planning02:05 - Starting small with holidays and birthdays for first-timers04:12 - Jesse Itzler’s journey from rapper to endurance racer and entrepreneur07:45 - Building habits with the calendar: consistency over perfection10:30 - The importance of shared physical challenges to foster team cohesion13:50 - Incorporating non-physical goals into your yearly plan17:20 - How visual tracking boosts accountability and motivation20:30 - The advantages of planning year-long adventures and mini goals23:50 - The impact of intentional scheduling on mental energy and happiness28:10 - Customizing calendars for students, families, and professionals31:50 - The importance of small, meaningful adventures and experiences35:45 - How the calendar system enhances reflection and memory-making39:15 - Practical tips for integrating planning into daily routines43:30 - Final encouragement: start planning now to make every year meaningfulResources & Links:Want to connect with Taylor?Let’s make your next year intentional, exciting, and memorable!

Episode metadata supplied by the publisher feed · Published May 20, 2026

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Fun First: The Big A## Calendar Episode with Taylor Prokes

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