Episode #42: Jason Goldberg Speaks On Owning Your Obstacles & Leading Your Life

Posted by Top LIVIN on


Thanks for listening to another episode of It Ain’t Weak to Speak with Sam Webb. Please rate the podcast and leave a review if you enjoyed it. 

Click here to leave a review & rate our show

Jason Goldberg is an international bestselling author, transformational speaker and former rapper who opened shows for the Wu-Tang Clan. He joins us today to talk about how he radically turned his life around by the power of self responsibility. 

Raised by a single mother and having never known his father, Jason discovered as a child that making people laugh was a way to fill the void he felt inside. He talks about how humour became his shadow and that it was his way of avoiding his own internal pain. He shares how although comedy was born from a place of pain, he eventually learned how to turn it around to help other people.

Jason opens up about the low point in his life when his marriage fell apart and he was left obese, depressed, suicidal and alone. This was the moment he knew he had to reach out for help and start taking responsibility for where his life had ended up. He shares how it was the beginning of a radical transformation towards hope and a bright future ahead.

We talk about the power of being a safe place for others and that men in particular often fear that they will be a burden by asking for help. We discuss what it means to reframe our language from being a victim to taking self responsibility and Jason shares some of the strategies and questions he asks himself to move through the hard times.

Jason has an incredible insight into thoughts and emotions and talks about how we need to approach things from a binary and informational perspective instead of judging ourselves and going into shame and guilt. 



[3:30]: How Jason came to be the opening act for Wu-Tang Clan and how being on the stage for an audience fulfilled a deep desire in him

[4:50]: How Jason’s comedic spin was born from a place of pain but that he turned it around to make people laugh in order to make a difference and help 

[7:00]: How humour disarms us and allows us to connect on a deeper level and that there is a fine line between humorising and trivialising 

[8:15]: How people need to feel like they have a safe space to fall apart and that men in particular don’t feel safe to open up because of the way our society says a man should be

[10:00]: We all need to become a safe space for the people around us

[10:50]: How using humour can become a shadow if you use it to avoid your own internal pain and that Jason realised he can’t help others unless he’s first helping himself.

[12:40]: Jason talks about the day he realised he needed to take personal responsibility for his life and the fact that he was overweight, stressed, anxious and depressed.

[15:00]: How Jason began to research to learn the language of self responsibility instead the language of a victim

[16:15]: How we need to approach things from a binary and informational perspective instead of judging ourselves and going into shame and guilt. Ask yourself, is this effective or ineffective?

[18:40]: How we need to be able to feel what we’re feeling and let it be present but know that it doesn’t have to be relevant to your life. 

[20:30]: Heavy emotions are the early detection system that tell us that something is off. We don’t have to judge them or shut them out, but recognise what they’re trying to tell us.

[22:50]: How we all need help and the worst thing in the world is to isolate ourselves and feel like a burden. Jason realised this when he first split up with his wife and knew he couldn’t do it on his own.

[25:00]: We need to communicate what we’re feeling to our friends because they can’t read minds but it’s also a reminder to be a safe place for others so that it’s easy for people to reach out.

[28:00]: Jason’s #1 international best seller book, Prison Break, and that he often refers back to the chapter “Your intuition is drunk” to help rise above situations to gain back his creativity

[29:40]: Why Jason loves snow globes and how they are a beautiful analogy for life.

Everything is temporary and isolated, just like our thoughts.

[32:00]: How we need to give situations time to settle down. Jason talks about Prison Break Questions (PDQ’s) and how they are incisive, introspective questions that make the problem no longer problematic.

[34:00]: Jason shares a time he used a PDQ to work through a time of anxiety and depression by asking, “if i knew, what would i do?”

[35:40]: When we beat ourselves up, our minds aren’t clear but when we accept without judgement, we are calm and can find our way through.

[37:00]: Understanding how our thoughts and feelings work, observing and recognising them, can be really freeing

[39:20]: How Jason works predominantly as a mentor to other transformational coaches on how to build their businesses in an authentic way and truly serve their clients. He’s also working on some shows that combine hip hop, spirituality and comedy all around personal growth 

[41:00]: The best piece of advice Jason received in response to a 5 page email which made him realise that he is both the problem and solution for anything going on in his life



Website: www.thejasongoldberg.com

Instagram: @thejasongoldberg

Facebook: @thejasongoldberg


Thanks for listening to another episode of It Ain’t Weak to Speak with Sam Webb. Please rate the podcast and leave a review if you enjoyed it. 

Click here to leave a review & rate our show!


If after listening to this episode and you don't quite feel right or you want to reach out to someone to speak to, we have provided some useful resources below. 

For immediate support please call one of the following 24/7 hotlines. Someone will be ready to take your call. Remember, ‘It Ain’t Weak to Speak’

 If you are in Australia:


Emergency: 000

Lifeline: 13 11 14

Kids Helpline: 1800 55 1800

 If you are in the United States:


Emergency: 911

National Suicide Prevention Lifeline: 1-800-273-8255

Crisis Text Line: Text LIVIN to 741741 in the United States


If you would prefer to speak with someone face-to-face, we recommend visiting your local GP (doctor) who will be able to have a chat with you about what is going on in your life and refer you to a mental health professional if required.

For some tools to help you with things like stress, low mood, general worries, please check out our LIVIN tips and tricks here.

If you would like to learn more about LIVIN, join the movement, or help spread the word, please visit us at the links below:

Follow us on Instagram, Facebook, Twitter and Linkedin 

Shop Our Merch collection to support the cause and start a conversation that could save a life.

Get Involved in one of our upcoming events or book a program at your school or workplace.

Donate to support the mission and help us spread the message.

Join us on our Facebook Group to continue the conversation and to connect with our community so that we can help more people.

Subscribe to our Newsletter so you can follow our journey.