Why Holding Goals Too Tightly Kills the Magic (And What to Do Instead) with Gregory Benedikt

Join Doug Bennett as he sits down with coach Gregory Russell Benedikt for a conversation about dreams versus goals. Gregory shares his journey from a 100-day rejection challenge, including asking strangers to jump in their pools, to landing a TEDx talk and meeting his girlfriend through bold action. This episode explores Gregory's perspective on holding goals loosely, his experience with goal apathy and his coaching approach where he becomes a "dream Sherpa," accompanying clients on their bucket list adventures. KEY TAKEAWAYS • A simple knock on a stranger's door asking to use their pool went viral and kick started an entire journey that led to Gregory's TEDx talk. • After years of hitting targets, Gregory discovered that achieving goals brought brief celebration but rarely the lasting fulfilment he expected. • The retreat Gregory has wanted to host for three years suddenly became possible when a community member offered her 40-acre Colorado ranch three days after he committed. • Gregory met his girlfriend by walking up to her in a crowded restaurant and handing her his name on a receipt after feeling an instant connection. • The dream sherpa concept emerged from Gregory wanting to do more than traditional coaching sessions. • Reading "Rejection Proof" twice sparked Gregory's 100-day challenge, proving that sometimes you have 10 seconds to act before putting the book back on the shelf. • Day 66 brought a complete breakdown where Gregory quit for a week, questioning why he was wasting time on ridiculous stranger interactions. BEST MOMENTS "It's moments like that, Doug, that just give me so much hope and excitement and awe and wonder." "We need to get started because if we're willing to take messy, imperfect action, you will learn the lessons you needed to learn." "Everything you need to know in order to achieve the goal, make the dream, become a reality. Everything you need to learn is learned through doing the thing. It's not learned before." "We've all got more time than we actually use. How, you know, check your phone. How long have you been on Facebook or, you know, screen time this week?” "I have a philosophy of yes. You know, if somebody asks me a question, it doesn't matter. Doug, would you like to, the answer's yes at that point." ABOUT THE GUEST Gregory Benedikt https://gregoryrussellbenedikt.com/ https://www.linkedin.com/in/gregoryrussellbenedikt/ https://www.youtube.com/watch?v=ezygvBTXeeQ VALUABLE RESOURCES Website: http://dougbennett.co.uk/ Email: [e-mail] LinkedIn: https://www.linkedin.com/in/financialdoug/ Twitter: https://twitter.com/FinancialDoug Facebook Wealth Tribe: https://join.dougbennett.co.uk/ Download Your "Ten-Step Guide To Financial Freedom" Here: https://bit.ly/Struggle-Success BOOKS: Goals Do Come True is now live and available to buy on Amazon: https://amzn.to/3phcy6Z Think Simple, Win Big is now live and available to buy on Amazon: https://www.amazon.co.uk/Think-Simple-Win-Big-Business/ Enjoy, and come back for the latest podcast each Wednesday. Thank you for listening.