Episode 780: The Ten Best and Worst Decisions of My Life - Part One (Worst Decisions)

Episode 780: The Ten Best and Worst Decisions of My Life - Part One (Worst Decisions)

Author: James Wedmore August 18, 2025 Duration: 28:03

What is a "bad decision" if not a lesson in disguise? And what do you do once you've learned that lesson? Today, I'm sharing the ten worst decisions I've made across my 18 years in business and life. From costly business partnerships and legal missteps to personal regrets and missed financial opportunities, I'm pulling back the curtain on my biggest screw-ups so you don't have to make the same ones. 

This isn't a conversation about regret; it's about reflection. Tune in now and to let us know which of these you can relate to the most, and make sure to tune in next week for Part Two, where I'll be revealing the best decisions I've ever made! 

If you haven't yet signed up for my free weekly newsletter for online experts, The Digital CEO Weekly, you can sign up now and get it delivered straight to your inbox every Monday morning at www.jameswedmore.com/newsletter

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Before you go, snap a screenshot of the episode playing on your device, post it to your Instagram Stories and tag us, @jameswedmore and @jeunejenni. 

In this episode you'll hear:

  • Why doing it yourself is sometimes the best option, and how I learned this lesson the hard way through multiple business partnerships

  • The crucial importance of getting every agreement in writing

  • Why you should invest in yourself sooner and the single decision that changed my business trajectory after years of struggling 

  • How the habit of investing, no matter how small the amount, is more critical to financial success than how much money you make

  • What I learned after selling Bitcoin and passing on real estate opportunities out of fear

  • Why the desire to "improve" something that's already working can lead to costly mistakes and how I learned this lesson the hard way 

  • The importance of keeping your guard up and not trusting easily 

  • Why a bad decision is only a true mistake if you don't learn from it and apply the lesson to future choices

For full show notes and links, visit: https://www.mindyourbusinesspodcast.com/blog/780 


There's a common thread running through the stories of many entrepreneurs who feel stuck despite all their effort, a sense that the relentless hustle isn't yielding the results they envisioned. The Mind Your Business Podcast, hosted by seven-figure entrepreneur James Wedmore, digs into that very gap between effort and outcome. James operates from a conviction that lasting success is less about copying another person's tactics and more about cultivating the right internal foundations. He argues that mindset ultimately trumps strategy, that there's an essential magic beyond mere metrics, and that your core attitude dictates the effectiveness of your actions. Each episode serves as a practical dialogue aimed at untangling the complex web of entrepreneurial psychology, moving beyond superficial tips to explore how mental frameworks directly influence business decisions and growth. You'll hear candid reflections on shifting from scarcity to abundance, the role of intuition in data-driven environments, and how to lead with clarity instead of fear. This isn't about discarding hard work, but about aligning it with a purposeful and resilient perspective. For anyone building a venture, this podcast provides a necessary counterbalance to the conventional grind narrative, offering a space to reconsider what truly drives a sustainable and fulfilling business life. Tune in for conversations that reorient your focus from just managing a business to thoughtfully minding it.
Author: Language: English Episodes: 100

The Mind Your Business Podcast
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