24 Questions with Jason Goldberg

What does an award-winning entrepreneur, a TEDx Speaker, a bacon-atarian (thats a vegetarian who still eats bacon), a funky sock lover, a former rapper (who opened for the Wu-Tang Clan – YES, really!) and a previously 332lb man (who has since lost over 130lbs despite his affinity for bacon) have in common?

They are all the same guy!

Jason Goldberg (JG for short) is the King of Playful Sales, Success and Self- Leadership. He is a geek, turned entrepreneur, “Edu-tainer”, author of the #1 International Best-Seller “Prison Break” and creator of both the Playful Prosperity AND the Business UNusual System programs.


1. What does thriving mean to you?
Thriving feels like flow – it feels like putting in purposeful effort and feeling the fulfillment of that aligned action!

2. What’s the one domino that moves you toward thriving?
I gotta cheat here – its a 2-sided domino (LOL) Creation and Service! If I’m not doing both of those in some way, I just don’t feel the same!

3. What was or is your favourite way to sabotage yourself?
My BIG one was (and still creeps in from time to time) is that I’m not doing enough when anyone looking from the outside might say I was doing MORE than enough!

4. What gets you back on track?
Getting clear on the SOURCE of that not-enough-ness. The source is almost always (meaning ALWAYS) that I am taking my thoughts WAY too seriously – I am attaching to them as TRUTH instead of seeing them as fleeting and momentary misunderstandings.

5. What question should we ask ourselves?
In response to anything that feels stressful, confusing, heavy, or hard: “How can I PLAY with this?”

6. What did you learn recently?
That as terrified as I was, I AM able to ride scooters and navigate around the crazy streets of Bali!

7. Divide your age by half , who were you then?
I would have been 19 – I was the same man and a totally different one at the same time. I was still someone who cared about bringing joy to others, about solving problems, about being successful. BUT I was also someone who didn’t exactly know what his true gifts or genius zone was. I didn’t know (or more accurately didn’t think it was ok) to be fully self-expressed because that would make me unprofessional. I was a prisoner of circumstance and a victim of the world much more often then, where now I am much more of a Self-Leader, taking radical personal responsibility for the experience of life I am having, while also trying not to take things too seriously or make them overly significant.

8. What was one of your aha/breakthrough moments?
When I first saw the power of Self-Leadership – not only that I COULD but that I already always WAS in control of how I experience life and the lens through which I see the world. That seems like personal growth 101 to most people but to me, at that low point in my life, it was EVERYTHING!

9. Whats the one resource you would recommend?
The book “Reinventing Yourself” by Steve Chandler

10. What is your favourite quote?
“Don’t ask yourself what the world needs. Ask yourself what makes you come alive, and go do that, because what the world needs is people who have come alive.” -Howard Thurman

11. What are your top VALUES?
Enthusiasm, Integrity, Service, Mastery

11. What is your focus this year?
To continue optimizing the systems we have created for our business while simultaneously making sure that the services we offer are LIFE-CHANGING and SUPER fun for everyone who we serve!

13. You write a book for your grandkids, what principles do you want to pass on?
I’ve already written it, “Prison Break” 😉 – the principles are all about just how powerful we are in creating our moment-by-moment experience of life!  That we don’t have to be serious to be successful. That creativity, courage, calm, and curiosity are always worth cultivating and practicing. That people matter and we should care about how we show up in the world and be of service whenever possible!

14. Who is one of the people that made an impact on your life?
Steve Chandler

15. What are you thankful for?
My health, my home, my tribe, my mind, my heart, my soul, my struggles, and the opportunities that await.

16. If someone grew up in a dysfunctional/chaotic home what advice would you give them going forward?
Your past is data, NOT a diagnosis. Its information, NOT instruction. We are able to reinvent ourselves in ANY given moment; in seemingly small or massively large ways!

17. What is your favourite memory of this year?
Wow, that’s a tough one! So many great memories this year! I would say leading my private “Proximity to Greatness” group biz accelerator. There was something about the 6 of us spending a weekend together, sharing oxygen, energy, and possibilities that I just can’t shake the LIT-UP-NESS from!

18. Think 3/5 years from now, what is your hell if you don’t take action or self sabotage?
Hell for me would be not having my impact and reach grow. I want my message and my energy to impact millions every year so if I’m not doing what needs to be done to have a higher likelihood of success with that, it will feel like my heart, my mind and my creativity are constipated 🙂

19. What do you need to have LESS of in your life?
LESS attachment to disempowering thoughts.

20. What rule should we be breaking?
That we have to be SERIOUS to be successful.

21 . What’s the one thing you want to do before you die?
There is no ONE thing…but I do want to know that I have helped millions of people live lives that are full of self-expression, joy, and LIT-UP-NESS!

22. If i am just starting out to transform my life, what one week practice would you recommend?
A practice of Self- and Other-Compassion (start the day sending love to others and hoping that their suffering is significantly reduced or completely eliminated AND be gentle on YOURSELF as you are playing with transformation).

23. Who would you like to acknowledge by nominating them to be showcased @ THRIVEMASTERS?
Ashley Stahl

24. How can people connect with you?
www.BeCompetitionProof.com www.PlayfulProsperity.com www.TheJasonGoldberg.com