Overthinking Entrepreneur

Megan Brewster
  • 5.0 (20)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

Overthinking Entrepreneur is me and probably also you 🤣 My goal with the podcast is to get you out of overthinking and into action and we will talk about social media strategy, mindset, and building confidence in yourself to make decisions!

  1. JAN 8

    57. You don't have to do the New Year like everyone else

    The new year can feel equal parts exciting and overwhelming. So much possibility! But also so much pressure to do everything "right" In this episode, I’m sharing a different way to think about fresh starts, especially if you’re coming off a tough season, burnout, or a long break from your business. We talk about how to decide what actually makes sense for you right now, why repeating someone else’s plan (or even your own from a different season) doesn’t always work, and how to set yourself up for progress you can actually stick with! 🦖 Links & Things I Mentioned 🦖 Winter Retreat (Starts January 12) The cozy winter version of my Business Summer Camp! Find those details here! 🦖 The DINOmite Squad (My Membership) If what you really need is ongoing support, accountability, and a community that gets overthinkers, my membership might be a great fit. This is where I’m putting a lot more of my focus this year! Find those details here!

    29 min

  2. 11/25/2025

    56. How to choose the right investments for your business

    Black Friday has been getting out of hand for years, and this one feels like everyone is throwing 12 different deals with 7 bonuses at you, and it can be so overwhelming! In this episode, we’re talking about how to figure out what’s actually worth investing in when the voice in your head starts going “that's a great deal, maybe I should grab this… just in case” 🤷‍♀️ You’ll hear: 🦖 What to keep in mind during times like Black Friday or those random weeks where it seems like every person you follow is launching their program at the same time 🦖 How to tell if something is right for you right now 🦖 What to think about before you hit buy 🦖 How what can seem like just taking advantage of some great deals can accidentally turn into something that really hurts your trust and belief in yourself If you’ve ever bought something you swore you’d use “someday,” or you’re trying to make the smartest choices for your business without getting swept up in the hype, this episode will give you a clear way to think through it. p.s. I also share what I’m offering for Black Friday and how I made that decision without burning myself out. 🦖 Year of Prompts + PromptBuddy (50% Off for Black Friday!) If content is taking up way too much of your time and mental energy or you struggle to be consistent (or both!), this is for you! You’ll get an entire year of my Content Prompts + the Prompt Buddy GPT that makes applying them to your business easy and fun! You'll thank yourself each month when you get the next email! 💕 Click here to learn more and see a real example of the Buddy in action!

    23 min

  3. 11/11/2025

    55. Breaking the burnout cycle

    You know how you put way too high of expectations on yourself, push yourself too hard to get it all done, crash, swear you’ll slow down next time, and then somehow end up right back there again? That’s the burnout cycle! In this episode, I’m talking about what it looks like when you’ve been doing this to yourself for years, and why you can’t keep running on fumes forever. If lately even “easy” tasks feel heavy, or you’ve been wondering why rest never really feels restful anymore, you might even be in burnout right now! In this episode you will learn: Sneaky ways you get stuck in this cycle and what it can look likeWhat causes burnout compared to times you've been busy but fineHow to break the cycle with two specific changes 🦖 Learn more about my Squad membership here! 🦖 Browse everything I offer or join my email list so you don't miss anything here!

    46 min

  4. 10/28/2025

    54. What If You Stopped Being So Afraid to Mess Up?

    Do you ever get stuck because you don’t want to make the “wrong” move? It used to be a huge problem for me (and still can be!) Eventually I learned being stuck there will hurt your business WAY more than an actual mistake! In this episode I’m sharing two mindset shifts that helped me stop worrying so much, including: 🦖 How to actually define what failure means for you 🦖 Why “what if I mess up?” keeps you stuck way more than the mistake itself 🦖 Why successful people aren’t the ones who never mess up Mentioned in this episode: 🦖 Accountability Coaching – get voice message check-ins with me to help you stop second-guessing every move 🦖 The DINOmite Squad – my coaching community for overthinkers who want to take consistent action and make sales their own way

    18 min

  5. 10/21/2025

    53. What goes where? How to stop guessing and know where that content should go!

    Do you ever feel confused about what should go on your social media vs in your emails? Or even within your social media? What goes in stories vs your feed vs your group? 🤷‍♀️ This episode will help you finally make sense of it all! You’ll walk away knowing how to: 🦖 See where each piece of your business fits in the bigger picture 🦖 Simplify instead of trying to be everywhere 🦖 Finally post with intention (so all that posting can start getting you somewhere!)

    35 min

  6. 10/14/2025

    52. Stop trying to give 150%! A better way to think about balance

    In this episode, I’m sharing how I think about balance! You’ll hear: My pie chart analogy that might change how you see balance foreverWhy available time ≠ available energyHow to lighten your load without guiltA few ways to make business feel lighter The long-game moves that help you finally step off the hamster wheel If you’ve been feeling like you’re running at 110% and still falling behind, this episode will help you take a breath and start finding your own version of balance! 🦖 Come hang out in my free Facebook group 🦖 Join my membership 🦖 Join the Business Reset

    27 min

  7. 10/07/2025

    51. Unexpected things that get harder the longer you are in business

    You’d think that after years in business, some things would just get easier, right? Some things do, but others actually get harder! If you’ve been wondering how you could possibly still be struggling with your ideal client, your content, or how to talk about your offers, this episode will help you understand why and what to do about it! Mentioned: 🦖 Join me for Business Reset Week starting tomorrow! You’ll get the full workbook plus my new Business Reset Buddy GPT to help you make a plan that actually fits you! 🦖 October Prompt to Post Buddy 🦖 My membership, The DINOmite Squad

    34 min

  8. 10/02/2025

    50. Planning isn’t your problem, but sticking to it is!

    If you’ve been stuck in the plan → burnout → shame → start over loop, this one’s for you. In this episode, I share how I broke myself out of this cycle I see time and time again with my clients! 🦖 Why wildly ambitious “new me on Monday” plans set you up to fail 🦖 The sneaky mindset piece that keeps good plans from sticking 🦖 How to design a schedule that works for your brain and season of life 🦖 A way to rebuild confidence that actually works And if you want help breaking out, join my Business Reset Week happening October 8th-15th where we will create a plan you can actually stick to! Details and sign up here! 💕 https://shop.meganbrewster.com/products/business-reset-week

    42 min
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Trailer

5
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About

Overthinking Entrepreneur is me and probably also you 🤣 My goal with the podcast is to get you out of overthinking and into action and we will talk about social media strategy, mindset, and building confidence in yourself to make decisions!

Information

  • Creator
    Megan Brewster
  • Years Active
    2024 - 2026
  • Episodes
    58
  • Rating
    Clean
  • Copyright
    © Copyright 2026 Megan Brewster
  • Show Website
    Overthinking Entrepreneur