Episode #66: The Surprising Benefits of Having a Side Gig: Finding Joy and Financial Security with Jessica Winter
The Fearless Female Entrepreneur
Release Date: 10/05/2023
The Fearless Female Entrepreneur
Have you ever felt so stuck and stagnant in your life and business that you'd do almost anything to escape — even elect to have foot surgery just to get a month off work? 😅 Yeah. That was me. In this episode I'm getting really honest about the three times in my life I felt completely stuck and stagnant — and what finally helped me move forward each time. Because here's what I know for sure: being stuck isn't a sign you're broken, lazy, or not cut out for this. It's a sign that something in your life is ready to change. I'm also sharing 7 powerful questions that will help you get...
info_outlineThe Fearless Female Entrepreneur
Can we have an honest conversation about the coaching industry? Because after 11 years, I have some things to say — and I'm finally ready to say them. In this episode I'm getting real about what coaching actually is (hint: it's not what a lot of people are selling), how the "six figures in 90 days" crowd completely changed the game, and how I personally struggled to find my place in an industry that started to feel really icky. I'm also breaking down the red flags to watch for before you hire anyone, what real coaching actually looks like, and how to find the coach who will genuinely...
info_outlineThe Fearless Female Entrepreneur
In this episode, I’m getting brutally honest about all those sneaky energy leaks that have been draining me—and probably you too, especially if you’re a new or aspiring female entrepreneur! I talk about how I was totally burnt out from trying to juggle everything and chasing all the “best” apps and systems that everyone swears by. Spoiler: good old Google Sheets and a paper planner are now my best friends. If you’re tired of feeling scattered or like your business dreams are stuck on the back burner, you’ll definitely relate to this one. I’m sharing super down-to-earth tips on...
info_outlineThe Fearless Female Entrepreneur
Are you like me always asking yourself if we can just make things a little easier and a little less overwhelming? Life is hard enough! In this episode, I'm sharing how I actually plan my months and days as a business owner—without losing my sanity. I can't believe how much unnecessary pressure and hustle I used to put on myself. It took years to ditch that mindset for good (or at least some of the time). Today, I'm walking you through my own goal-setting process, how I take big dreamy ideas and turn them into simple, doable action steps, and why giving yourself permission to do less can...
info_outlineThe Fearless Female Entrepreneur
I just spent 30 minutes recording this episode only to realize I never actually pressed record—and honestly, that pretty much sums up how the first two weeks of January have felt! But here we are jumping into another episoide of The Fearless Female Entrepreneur Podcast. No matter what life throws at you, if you strategize to take into account the rough moments, you won't feel like you're failing. That is what we are talking about today -the Quarterly Plan. After years of throwing spaghetti at the wall, failing to stick to a plan, always feeling like life (and the entire world and...
info_outlineThe Fearless Female Entrepreneur
Hey lovelies! In this episode, I’m keeping it real about setting yearly goals that actually matter for us new and aspiring female entrepreneurs. I spill all the details about my own New Year’s rituals (solo hotel stays, skipping fireworks for sleep, and lots of dreamy journaling) and how I’m finally going after my big dream of launching printed journals and planners—even if it’s scary and the naysayers don’t get it. We’ll chat about how to set yearly goals that feel good (not forced), how to actually make progress without getting overwhelmed, and why mindset is just as important...
info_outlineThe Fearless Female Entrepreneur
I’m so glad you’re here for this special episode as we prepare to step into 2026 together . We’re currently in that cozy December season where it’s tempting to just pause and wait for January 1st to start fresh. It's more of a drink hot cocoa by the fire while watching Christmas movies type season. But, today, we are going to do something fun to get ready for what comes next. We aren't just dreaming about what we want to achieve; we are diving deep into the identity shift required to become the woman who already lives that dream. Exciting, right?! In this episode, I’m leading...
info_outlineThe Fearless Female Entrepreneur
Hello lovely! In this episode, I’m sharing my heartfelt reflections on 2025 and guiding us through a powerful process of wrapping up the year—whether it felt like a wild ride or a fresh start. I’m walking you through my favorite end-of-year journaling practice—the exact process I use to wrap up my year and get grounded before jumping into a new one. I’ll share my top reflection prompts (and a free workbook if you want to follow along!) so you can honor your journey, celebrate growth, and shake off those “I’m not where I want to be” vibes. We’ll dig into your wins—big...
info_outlineThe Fearless Female Entrepreneur
Hey beautiful, welcome back to The Fearless Female Entrepreneur Podcast! I’m so excited to share this special Thanksgiving episode with you, because today we’re talking all about gratitude—and trust me, this is an episode you don’t want to miss. I'm sharing my own vulnerable journey with gratitude, including how I resisted it for years and why it felt impossible to be thankful when nothing seemed to be going my way. But everything changed when I learned how to shift my mindset, one tiny step at a time. I share how starting with something as simple as being grateful for a hot cup of tea...
info_outlineThe Fearless Female Entrepreneur
Welcome to The Fearless Female Entrepreneur Podcast! In this episode, I revisit the all-too-common struggle of imposter syndrome. If you’ve ever felt like a fraud or doubted your right to pursue big dreams, you’re not alone (I struggle too)—and this episode is for you! We are diving into all aspects of imposter syndrome - what exactly it is, why it shows up (especially for female entrepreneurs), and practical, mindset-focused strategies to help you move through self-doubt. You'll learn how to reframe negative thoughts, celebrate progress over perfection, and step boldly into your goals....
info_outlineEver feel guilty about having a side job or staying in your full time job while building you business? Ever feel like a failure because your business isn’t fully supporting you yet or giving you the life you desire right now?
Well we’ve got a great conversation for you that will shift your mindset, fears, and the stigma around working multiple jobs, being multi-passionate, or even changing your mind in business.
This week on The Fearless Female Entrepreneur, I’m joined by my guest, Jessica Winter, where we delve into the realities of building a business while working a job on the side. We get real and raw and discuss the pressure to make entrepreneurship a full-time income and the impact it can have on our mental health. Jessica shares her experience of balancing her business and a side gig, why she likes doing both, how it fills the needs she has at the moment.
We really take you on a journey of breaking free from societal expectations, and giving you permission to fill your needs the way you need to in this moment of your life.
We take you beyond the highlight reel you see on social media, to the behind the scenes truth about what it takes and looks like to run a business.
So grab your headphones, your favorite hot beverage and let’s jump in!
----------------------------------------------------------------------------------------
If you are I’m READY to become the woman who has all she desires. If you’re tired of sitting on the sidelines watching everyone succeed, wondering when you’ll make you’re dreams happen, If you want to step into unwavering confidence and show up in your life and business with a renewed energy and unstoppable mindset, If you want to stop second guessing or letting doubts and fears stop you, If you are ready to feel purposeful, fulfilled, abundance and joy in all areas of your life…
Then BREAKTHROUGH is perfect for you. BREAKTHROUGH is my signature coaching program and we work together to guide you to release the SHOULDS and finally call the shots in your life and business.
This is where you make powerful, transformative shifts in your mindset, beliefs, perspectives and actions so that you are leading yourself to live life and create a business YOUR way.
This program is designed to help you find what’s holding you back, completely reframe your beliefs so you lead with empowering thoughts, deeply connect to what you desire and who you will be when you get there and have you leading your thoughts beliefs and actions every single day so they truly align to what you desire to be experiencing in your life.
If you’re interested in learning more, visit: https://start.katerinakormas.com/breakthroughinfo-2398-7792
---------------------------------------------------------------------------------------
Follow Jessica Winter
Instagram: @thejessicawinter
Youtube: https://youtube.com/@thejessicawinter?si=wKY0LYx7DaLKlTZb
Follow Katerina
Instagram: @Katerina.Kormas
Website: www.katerinakormas.com
Did you hear something you loved today? Leave a review, so others know what to expect from the show! And don’t forget to Subscribe so you receive the latest episodes right when they launch!