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Overthinking Entrepreneur

Overthinking Entrepreneur

Megan Brewster

BusinessEducation

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!

Episodes

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

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 day Find information about joining Decision Week live starting March 16th here: https://shop.meganbrewster.com/products/decision-week
23min•Mar 10, 2026
58. What are your top 3 priorities?

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 results The 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!
13min•Feb 26, 2026
57. You don't have to do the New Year like everyone else

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! This is where I’m putting a lot more of my focus this year!
29min•Jan 8, 2026
56. How to choose the right investments for your business

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!
22min•Nov 25, 2025
55. Breaking the burnout cycle

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 like What causes burnout compared to times you've been busy but fine How 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!
45min•Nov 11, 2025
54. What If You Stopped Being So Afraid to Mess Up?

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
18min•Oct 28, 2025
53. What goes where?  How to stop guessing and know where that content should go!

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!)
35min•Oct 21, 2025
52. Stop trying to give 150%!  A better way to think about balance

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 forever Why available time ≠ available energy How to lighten your load without guilt A 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
26min•Oct 14, 2025
51. Unexpected things that get harder the longer you are in business

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
33min•Oct 7, 2025
50. Planning isn’t your problem, but sticking to it is!

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!
41min•Oct 2, 2025
49. What Overthinkers need to know about AI (especially if you’re resistant to using it)

49. What Overthinkers need to know about AI (especially if you’re resistant to using it)

If you are an overthinker and you aren't using AI, you are missing out! It's become my new best friend for my overthinking brain to help me talk things out, brainstorm, and make decisions. And it's available when I'm in hyperfocus mode at 1am 🤣 I was resistant to AI myself and am so glad I decided to give it another try. I am by no means an AI expert, but I think that's kind of the beauty of this episode. You can hear my real experience as a real person a few steps ahead of you and how I am using it! You'll hear me cover: 🦖 Why your resistance to AI is totally normal and what changed for me 🦖 The surprising things AI can do that AREN'T writing things for you 🦖 How I use AI in my own business and lots of ideas you can try 🦖 Things you need to be aware of and watch out for when it comes to AI 🦖 And my own rules for ethical use of AI and how you can decide on your own
1h 11min•Sep 23, 2025
48. How to get lucky in business (without relying on luck)

48. How to get lucky in business (without relying on luck)

If you have ever looked at someone else’s success and thought, “must be nice,” this one is for you! I've been on both sides of this and I give my honest thoughts on what people call "luck" and the very real things that make it possible for opportunities to find you and actually stick. In this episode, we get into: Being discoverable: stop hiding in private spaces, make it clear who you help and what you sell, get in the rooms where people can find you Being operationally ready: simple systems for inquiries, orders, and follow up so a spike in interest does not make you panic Being personally ready: mindset and nervous system stuff, thicker skin, less people pleasing, more self trust, so you do not crumble when momentum hits Listen if you are ready to stop waiting for luck and start setting yourself up to get "lucky" 🦖💕
23min•Sep 16, 2025
47. Are there patterns to your procrastination?

47. Are there patterns to your procrastination?

Are you a procrastinator? Me too! Always have been, and always will be. I have made peace with that at this point 🤣 But I have noticed there are times I am really avoiding a task above and beyond my "normal" which usually means something else is going on. Figuring out that "something else" is the key to breaking through and finally checking that task off your to do list, so in this episode we dive into how to do that by noticing your own patterns! Links for stuff mentioned in this episode: 🦖 Click here to grab the September Content Prompts and try the new Prompt to Post Buddy GPT free!! 🦖 Click here to learn about my membership and the Accountability Coaching upgrade!
36min•Sep 9, 2025
46. Content Myths That Keep You Stuck, and how to break free

46. Content Myths That Keep You Stuck, and how to break free

This episode is for my overthinkers and perfectionists: content edition! I’m sharing the biggest content misconceptions I see keeping people stuck, and what to do instead so your posts actually work! We get into: The pursuit of “perfect” content Why you're spending too much time on your posts How to stop chasing what “they” do and write like you Fixed mindset vs growth mindset for content, yes you can get better I also share a peek at something new I made to help, Prompt to Post Buddy. A custom GPT that pairs my September Content Prompts with step by step guidance to help you brainstorm how to fit each prompt for your business, ideas for how to structure your post and your main bullet points, and then after you write it, it will audit if the post is set up for maximum engagement using my rules and make suggestions! This is NOT ChatGPT writing a robotic post for you, it's like having me in your pocket coaching you through writing the post yourself to take out the overthinking so you spend less time writing your content and actually feel confident that you got it "right!" Click here to grab the September Content Prompts and try the new Prompt to Post Buddy free!! If you’ve ever said “I have a prompt, how am I still stuck?!” this will help you get out of your head! Listen, then go write the post you’ve been avoiding today. 🦖💕
34min•Sep 2, 2025
45. The reason their post worked and yours didn't

45. The reason their post worked and yours didn't

Have you ever seen someone post or send an email that blows up with sales and engagement, so you try it, too? And then.. crickets. If you’ve ever wondered why it worked for them but not for you, this episode is for you! In this episode, I break down: The #1 reason “copy and paste” strategies usually flop What matters more than “magic wording” How to adapt inspiration so it actually works for YOUR personality and YOUR people To be clear this episode is NOT about bashing formulas, templates, or “swipe copy.” It’s about understanding what really drives results so you can stop spinning your wheels and start building long-term growth in your business. So the next time you’re tempted to copy someone’s post, listen to this first! 🦖💕
24min•Aug 26, 2025
44. I'm back! 9 Lessons learned from/during my [accidental] 9 month hiatus

44. I'm back! 9 Lessons learned from/during my [accidental] 9 month hiatus

I decided to take a break from recording my podcast that ended up lasting much longer than I expected. Here's what I learned about taking a break and coming back from your podcast or anything in your business you aren't enjoying. Since the break ended up being about 9 months, I came up with 9 lessons for a nice juicy first episode back! I can't wait to be back and share more of my tips, lessons, and perspectives on online business, sales, branding, and time management for overthinkers!
49min•Aug 19, 2025
43. Why you should post about your business more

43. Why you should post about your business more

There's a good chance you should be posting about your business more! I know you might be worried about annoying people, but it can actually annoy people less when you talk about it more, as long as you do it the right way! You might not believe me now, but I'm going to spend the whole episode trying to convince you and I bet you come around! 🦖 Browse my shop (use code PODCAST for 25% off your first order!) 🦖 Join my Facebook group (includes a free social media basics course!) 🦖 Download my free Engagement Guide and Checklist
29min•Oct 29, 2024
42. Listen to this one if you start things and don't finish them and then beat yourself up

42. Listen to this one if you start things and don't finish them and then beat yourself up

The title really says it all! Are you someone who starts things but doesn't finish them and then beats yourself up? Me too, or at least I used to be! A few years ago I had a mindset shift about finishing things that has helped me so much! In this episode I share what it is so you can stop beating yourself up, too! 🦖 Browse my shop (use code PODCAST for 25% off your first order!) 🦖 Join my Facebook group (includes a free social media basics course!) 🦖 Download my free Engagement Guide and Checklist
17min•Oct 22, 2024
41. What I Learned by Combining My Challenges—and Why I Decided to Split Them Again

41. What I Learned by Combining My Challenges—and Why I Decided to Split Them Again

The first time I ran my Get Your Face In Your Feed Challenges, I did them separately. The second time, I decided to combine them, and now this time I decided to split them up again. In this episode I share the story of why I did this and what I learned from it that you can apply to your own business!
34min•Oct 15, 2024
40. Why you need to "get your face in your feed"

40. Why you need to "get your face in your feed"

The phrase "get your face in your feed" was one of my best half asleep ideas. I found it written in my notes the next morning and it went on to inspire my favorite challenge I've ever created In this episode I share what it means to "get your face in your feed" and why it's so important!
20min•Oct 8, 2024
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