The Planning Playbook jobs and careers

About The Planning Playbook

Most people know what they want in life — but few have a system to achieve it. The Planning Playbook was created to change that. Founded by Durelle and Samantha Bailey, The Planning Playbook is a simple yet powerful planning system designed to help people take control of their lives, set intentional goals, and create a clear plan to reach them. It started with their own story. With Durelle’s background in the military and Samantha’s decade of corporate experience, they combined what they learned about discipline, strategy, and execution to create a planning system for their personal lives. This system helped them build two homes before the age of 27, travel to over 15 countries together, save and invest six figures, complete six degrees between them, and build multiple six-figure businesses. In December 2023, a video of their Annual Strategy Meeting went viral, reaching over 20 million people worldwide. What began as a personal tradition quickly became a global movement — inspiring thousands to take planning seriously and showing what’s possible with clarity, structure, and action. Today, The Planning Playbook is more than just a system — it’s a community. It provides practical tools like a goal-setting and tracking spreadsheet, a budgeting tool, webinars, and an online course. Durelle and Samantha also offer one-on-one sessions to help people implement the system and stay accountable. What makes The Planning Playbook special is its flexibility. It’s designed for everyone — singles, couples, entrepreneurs, busy professionals, and families. No matter your income, age, or life stage, The Planning Playbook offers a blueprint for success that you can personalize to fit your goals and lifestyle.