EPISODE · Feb 2, 2026 · 1H 19M
#103 - The Courage To Be Cringe - He Coached Me Live And Found My Blind Spot - Jack Tipper
from Awaken Out Of Context · host Jason Berry | High Performance
If you're a business owner who knows what to do but can't seem to do it, someone struggling with procrastination on the things that matter most, or a coach or creator battling self-doubt and fear of judgment - this conversation will give you practical tools to understand what's actually blocking you and how to shift it.Jack Tipper is an NLP Master Practitioner and business mindset coach who helps coaches and entrepreneurs break through subconscious blockers that keep them stuck. After years of struggling with anxiety, people-pleasing, and needing external validation, Jack discovered neuro-linguistic programming and rebuilt his own identity from the inside out. Through his Limitless coaching program, he helps clients close the gap between where they are and where they want to be - not through motivation, but by rewiring the beliefs that are running the show.In this episode, you'll learn:-Why procrastination isn't a laziness or time management issue - it's a symptom of deeper fears including fear of failure, judgment, and even fear of success-What NLP (neuro-linguistic programming) actually is and how your internal language shapes your identity, emotions, and external reality-How to spot subconscious blockers in high performers - the telltale signs someone is standing in their own way, even when they have the strategy and knowledge to succeed-Why "just do it" advice fails most people and what actually works - shifting your perspective first so the action becomes 100x easier-The courage to be disliked - why letting go of other people's opinions is one of the most powerful things you can do for your business and content-How micro decisions like putting the pasta packet in the bin build a chain reaction of discipline that bleeds into bigger actions-Why inaction between coaching sessions destroys self-trust and how the "continual push" is the prerequisite for lasting transformationThis conversation includes a live coaching moment where Jack identifies a limiting belief in real time - and the uncomfortable truth about why some clients don't get results.Chapters00:00:00 Trailer 00:00:49 Welcome, Background & Avoiding Clichés00:07:29 Beliefs & Identity Beneath Positive Thinking00:15:26 NLP & Why We Procrastinate00:28:10 Client Results & Self-Belief (Sophie Jones)00:34:24 Talent vs Discipline & Personal Brand in the AI Era00:41:40 Courage to Be Disliked, ‘Cringe’ Post & Live Coaching00:56:03 Pre-Breakthrough Signs & Drinking Choices01:05:23 When Coaching Stalls: Fear, Doubt & Inaction01:09:27 90-Second Message: Awareness, Basics & Next Step01:13:08 Action Over Entertainment & Micro-Wins01:18:04 Where to Find Jack & OutroIf you enjoyed this episode you will enjoy these:https://www.youtube.com/watch?v=5j4vnr_Xa3k&list=PLMebuClQRf08P0UXfiilUCQA9YN8m951D***LINKS***Jack Tipper Instagram: https://www.instagram.com/jacktipper_coach/Jack Tipper LinkedIn: https://www.linkedin.com/in/jack-tipper-b46a3a117/Sophie Jones Instagram: https://www.instagram.com/soph.jones__/NLP (Neuro-Linguistic Programming) - Wikipedia: https://en.wikipedia.org/wiki/Neuro-linguistic_programmingNewsletter signup: awakenoutofcontext.comJoin the indiip beta:indiip.com/beta15% Off Bare Bar (CODE: JASE):https://bit.ly/barejaseMY STUFF:awakenoutofcontext.comAwaken Out Of Context Podcast (YouTube & Podcast Links):https://bit.ly/3tk8FVvFollow Me On Instagram (@awakenoutofjason):https://bit.ly/3RAkKQj
What this episode covers
If you're a business owner who knows what to do but can't seem to do it, someone struggling with procrastination on the things that matter most, or a coach or creator battling self-doubt and fear of judgment - this conversation will give you practical tools to understand what's actually blocking you and how to shift it.Jack Tipper is an NLP Master Practitioner and business mindset coach who helps coaches and entrepreneurs break through subconscious blockers that keep them stuck. After years of struggling with anxiety, people-pleasing, and needing external validation, Jack discovered neuro-linguistic programming and rebuilt his own identity from the inside out. Through his Limitless coaching program, he helps clients close the gap between where they are and where they want to be - not through motivation, but by rewiring the beliefs that are running the show.In this episode, you'll learn:-Why procrastination isn't a laziness or time management issue - it's a symptom of deeper fears including fear of failure, judgment, and even fear of success-What NLP (neuro-linguistic programming) actually is and how your internal language shapes your identity, emotions, and external reality-How to spot subconscious blockers in high performers - the telltale signs someone is standing in their own way, even when they have the strategy and knowledge to succeed-Why "just do it" advice fails most people and what actually works - shifting your perspective first so the action becomes 100x easier-The courage to be disliked - why letting go of other people's opinions is one of the most powerful things you can do for your business and content-How micro decisions like putting the pasta packet in the bin build a chain reaction of discipline that bleeds into bigger actions-Why inaction between coaching sessions destroys self-trust and how the "continual push" is the prerequisite for lasting transformationThis conversation includes a live coaching moment where Jack identifies a limiting belief in real time - and the uncomfortable truth about why some clients don't get results.Chapters00:00:00 Trailer 00:00:49 Welcome, Background & Avoiding Clichés00:07:29 Beliefs & Identity Beneath Positive Thinking00:15:26 NLP & Why We Procrastinate00:28:10 Client Results & Self-Belief (Sophie Jones)00:34:24 Talent vs Discipline & Personal Brand in the AI Era00:41:40 Courage to Be Disliked, ‘Cringe’ Post & Live Coaching00:56:03 Pre-Breakthrough Signs & Drinking Choices01:05:23 When Coaching Stalls: Fear, Doubt & Inaction01:09:27 90-Second Message: Awareness, Basics & Next Step01:13:08 Action Over Entertainment & Micro-Wins01:18:04 Where to Find Jack & OutroIf you enjoyed this episode you will enjoy these:https://www.youtube.com/watch?v=5j4vnr_Xa3k&list=PLMebuClQRf08P0UXfiilUCQA9YN8m951D***LINKS***Jack Tipper Instagram: https://www.instagram.com/jacktipper_coach/Jack Tipper LinkedIn: https://www.linkedin.com/in/jack-tipper-b46a3a117/Sophie Jones Instagram: https://www.instagram.com/soph.jones__/NLP (Neuro-Linguistic Programming) - Wikipedia: https://en.wikipedia.org/wiki/Neuro-linguistic_programmingNewsletter signup: awakenoutofcontext.comJoin the indiip beta:indiip.com/beta15% Off Bare Bar (CODE: JASE):https://bit.ly/barejaseMY STUFF:awakenoutofcontext.comAwaken Out Of Context Podcast (YouTube & Podcast Links):https://bit.ly/3tk8FVvFollow Me On Instagram (@awakenoutofjason):https://bit.ly/3RAkKQj
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#103 - The Courage To Be Cringe - He Coached Me Live And Found My Blind Spot - Jack Tipper
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