
Advertise on podcast: Overthinking Entrepreneur
Rating
5from
This podcast has
61 episodes
Language
EnglishPublisher
Megan BrewsterExplicit
No
Date created
2024/01/18
Latest episode
2026/03/24
Average duration
32 min.
Release period
15 days
Description
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!
Unlock Overthinking Entrepreneur podcast Email contact info,
Listeners & Audience details
Email contact information
Direct podcast contact details

Listeners
Audience numbers & engagement insights

Audience details
Podcast Insights

Podcast episodes
Check latest episodes from Overthinking Entrepreneur podcast
60. If people aren't finishing, does that mean you did something wrong?
2026/03/24
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 see
If 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!
59. What if you don't need more time or more discipline? Just fewer decisions!
2026/03/10
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
58. What are your top 3 priorities?
2026/02/26
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!
57. You don't have to do the New Year like everyone else
2026/01/08
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!
56. How to choose the right investments for your business
2025/11/25
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!
55. Breaking the burnout cycle
2025/11/11
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!
54. What If You Stopped Being So Afraid to Mess Up?
2025/10/28
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
53. What goes where? How to stop guessing and know where that content should go!
2025/10/21
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!)
52. Stop trying to give 150%! A better way to think about balance
2025/10/14
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
51. Unexpected things that get harder the longer you are in business
2025/10/07
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
50. Planning isn’t your problem, but sticking to it is!
2025/10/02
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
49. What Overthinkers need to know about AI (especially if you’re resistant to using it)
2025/09/23
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
48. How to get lucky in business (without relying on luck)
2025/09/16
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 youBeing operationally ready: simple systems for inquiries, orders, and follow up so a spike in interest does not make you panicBeing 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" 🦖💕
47. Are there patterns to your procrastination?
2025/09/09
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!
46. Content Myths That Keep You Stuck, and how to break free
2025/09/02
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” contentWhy you're spending too much time on your postsHow to stop chasing what “they” do and write like youFixed 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. 🦖💕
Podcast reviews
Read Overthinking Entrepreneur podcast reviews
Rebeccasarah14 2024/01/25
Great coach
Megan is an approachable but brilliant coach. She is super adept at connecting with people where they’re at. Her podcast shows just another way she is...
NaturallySarahBrown 2024/01/25
Fantastic coach and a fantastic podcast
Megan has taught me so much over the past few years about running my online business. She has helped me stop overthinking, start being relatable and n...
SimplyCindy 2024/01/24
Over-thinker- Giving myself grace
Listening to this I now realize what I’ve been doing all of these years. I used to call it Analyze to paralyze. However, I can now give myself grace a...
PZbyAmandaT 2024/01/24
Relatable on all levels!
I love how relatable Megan is! When I listened to this today, I wasn’t in the frame of mind to be thinking about my business. However, I found her tho...
M. Linch 2024/01/24
Megan does care about others!
If you would like to learn how to get out of your own way, do yourself a favor and listen to Megan.
I am living proof that stepping outside of your c...
teachbuildlearn 2024/01/24
So glad I found!!!
I have just come across Megan and her group a little over a month ago!! Her group is amazing and I’m so excited to have yet another place to her from ...
Jamidjc 2024/01/23
One of the best coaches on FB!!
I have been listening to Megan for several years now, and have watched her grow not only her business, but others who have followed her advice and coa...
aprilphipps 2024/01/23
Overthinkers Unite!!
Yes!!! I love the overthinking entrepreneurs podcast!! So many good nuggets, Megan is a great business coach. I’m excited there is now another way to ...
Tischann 2024/01/23
Simple, encouraging, action steps included
I like the way Megan tells it like it is, but has such a positive slant on why we overthink, where to use overthinking to our best advantage, and acti...
NuclearMama 2024/01/23
Informative and helpful
While I’m not typically an overthinker, I found this to be a helpful resource for my customers who ARE an overthinker to embrace it and find ways to u...
Podcast sponsorship advertising
Start advertising on Overthinking Entrepreneur relevant audience podcasts
You may also like to advertise on these Podcasts

4.9247831447
Unashamed with the Robertson Family
Tread Lively

4.853552000
Men In Blazers
Men In Blazers

4.7106622000
FantasyPros - Fantasy Football Podcast
iHeartPodcasts

4.930882000
The Quote of the Day Show | Daily Motivational Talks
Sean Croxton

4.8224781794
The Andrew Klavan Show
The Daily Wire

4.838342000
Entrepreneurs on Fire
John Lee Dumas of EOFire

4.922692003
First15 Devotional
First15

4.762582000
The Lawfare Podcast
The Lawfare Institute

4.6137781994
The Rubin Report
Dave Rubin

4.858201921
Sara Gonzales Unfiltered
Blaze Podcast Network