Overthinking Entrepreneur

Hosted by Megan Brewster

Business Entrepreneurship Education

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Latest episode

Mar 2026

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About the show

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!

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60 recent

March 24, 202615 min

60. If people aren't finishing, does that mean you did something wrong?

Have you ever created something you were really excited about like a challenge, program, product regimen, or even free content, and then felt discouraged when people didn’t actually follow through or finish it?It’s really easy to assume that means you did something wrong, or that you need to change everything. (And you might! 🤣) But what if there's something else you need to think about first?In this episode, I’m talking about something I’ve been noticing recently in my own business, especially after running challenges for years!People don’t always engage or complete things the way they used to. But that doesn’t automatically mean it isn’t helping!We’re talking about:why “not finishing” might not mean what you think it doeshow people are actually consuming and benefiting from content right nowand why you might be having more impact than you can seeIf you’ve been questioning whether what you are doing matters, I think this will give you a different way to look at it. 💕 Mentioned in the episode: Learn about my membership The Squad here!

March 10, 202623 min

59. What if you don't need more time or more discipline? Just fewer decisions!

It's way too easy to assume your problems with consistency and growth are because of you. You just need more discipline, more ideas, to be better and work harder.But what if the real issue is something much simpler?Decision fatigue.When every time you sit down to work you have to decide what to post, where to post, what you should work on first, your brain is already exhausted before you even start working!In this episode, I’m talking about why too many decisions can drain your energy and make it feel like you don’t know what you’re doing anymore, even if you absolutely do!In this episode: • Why decision fatigue might be slowing your business down • The difference between consistency and strategic consistency • Why winging it can eventually stop working • How simple “blueprints” can make your business feel manageable again • What it means to make the decisions once instead of every dayFind information about joining Decision Week live starting March 16th here: https://shop.meganbrewster.com/products/decision-week

February 26, 202613 min

58. What are your top 3 priorities?

We’re talking about something deceptively simple that has shifted the way I think about comparison and staying on track.Most of the things we envy in other people’s lives or businesses are probably just one of their top priorities.And if it’s not one of yours, of course you don’t have the same result.This episode is about:How priorities impact your resultsThe difference between “I can’t” and “I haven’t chosen to”And how to stop beating yourself up for things you didn’t even decide to prioritize🦖 Learn more about my Squad membership here!🦖 Browse everything I offer or join my email list so you don't miss anything here!

January 8, 202629 min

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!

November 25, 202522 min

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 yourselfIf 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!

November 11, 202545 min

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!

October 28, 202518 min

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 upMentioned 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

October 21, 202535 min

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!)

October 14, 202526 min

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 wheelIf 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

October 7, 202533 min

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