Skip Cummins

Products and Services



Online Video Course

My failure to master my “origin challenge” cost me in large part my professional reputation, career, some $50 million of my net worth, and my marriage. If I only knew then what I know now and am sharing with you!

Now that I have your attention, let’s talk about what MASTERING YOU really means. Simply put, it is the process of discovering who and what you are, from whence you came, and what you need to do become the best version of you possible, personally and professionally. The MASTERING YOU process starts with mastering your “origin challenge.”

This course is designed to empower you with the knowledge and tools to understand, own and revise as appropriate your origin programming, namely the behavioral, social, emotional, intellectual and psychological “DNA” given to you by your parents and others during your first 18 years of life when you were the most open, most impressionable and most programmable. Then redefine and realize your full potential. By thoroughly planning, frequently measuring, frequently reporting and appropriately rewarding your mastery of your origin challenge.

Filled with thought provoking questions, practical exercises, worksheets, and resources, “HOW TO MASTER YOUR ORIGIN CHALLENGE” is your first step to mastering you from the inside out, personally and professionally. Free from all the powerful outside forces trying to define and master you from the outside in.

Are you ready to take a long hard look in the mirror?
Then hold yourself accountable to make the changes that the fully informed expert looking back at you tells you to make to realize your full potential?

If so, then this course is for you!

Available in print, eBook, & Audiobook.


Do you ever wish you had a been there, done that confidant who understood your personal and professional challenges, wouldn’t pass judgement, and would tell you things you needed and at times didn’t want to hear?

For many of us, utilizing the experience of others, not only their success, but also the tragedies they’ve dealt with, and how they’ve owned, embraced and learned from mistakes and failures, is the key to success.

Unlike most personal growth books, in MASTERING YOU I openly share with you not only my extraordinary accomplishments, but, most importantly my colossal mistakes, in candid, sometimes ugly detail. Everything I admittedly wish I knew then that I know now.

MASTERING YOU challenges and empowers you by providing tools to look deep inside yourself to:

  1. Understand the type of person you are and why.
  2. Identify what you want and need to change.
  3. Create and implement plans to MASTER YOU FROM THE INSIDE OUT and realize your full personal and professional potential.
The rest is up to YOU. This book helps YOU MASTER YOU.
It doesn’t MASTER YOU for you.

Whether you are trying to find a professional edge, improve your personal life and relationships, need feedback from an unbiased source, struggle to find happiness, or just want to find better life balance…



Live on location or live remote video conferencing.

Session Options:

  • One-hour keynote and Q&A + two total hours of workshops. (3/4 day)
  • One-hour keynote and Q&A + four hours of workshops. (full day)

Method: Live on location or live remote video conferencing.

Program personalized to the needs of the participants

General Topics
  • The Origin Challenge
  • Your Happiness Formula
  • The Integrity Principle
  • Live Your Life Plan
  • Boundaries Set You Free
  • Common Language, Vocabulary, and Experience Creates Communication
  • The Status Quo Conundrum
  • The Picking Your Battles Dilemma

  • How to Win When “Shit” Happens
  • Your Daring Greatly Recipe
  • How to Deliver on Your Promises and be a Hero
  • Selling and Buying Your Way to Abundance
  • The White Flag Victory Rule
  • Are You Scalable?
  • The Self Care Test
  • Mentors, Confidantes, building your team, and OPM


Intended for groups of 4 to 20 from a single company, this intensive is intended to provide participants with personalized, practical tools to reach their personal and professional potential.

Group Size: 4-20
Sessions: Two -hour introduction session.  60-minute weekly sessions for 3 months.
Method: Live remote video conferencing.
Topics: Program personalized to the needs of the participants.

Skip Cummins Private Coaching


Intended for the executive on the go, this program is works with individual one-on-one to identify your personal and professional needs and wants, identify what is holding you back, and provide the practical tools, exercises, and mentoring to help you master you and breakthrough your barriers.

Group Size: One-on-one.
Intro Session: Two-hour intro session, followed by (3) one-hour weekly sessions for a month.
Ongoing Sessions: one-hour weekly sessions.
Method: Live remote video conferencing.
Topics: Program personalized to the needs of the participant.

Skip Cummins Private Mentoring Intensive


Taking complete advantage of Skip’s experiential knowledge and coaching, this program is a uniquely personalized approach to help executives master their potential.

Group Size: One-on-one.
Session: Initial 3-day in-person shadowing and training. Weekly one-hour sessions. 24-hour access to Skip on an as-needed basis. 3-month initial engagement.
Method: In person and live remote video conferencing.
Topics: Program personalized to the needs of the participant.

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