Pretty Philosophical with Denée Seaton isn’t really a podcast.
It’s her YouTube videos, in audio form; turned into sharp, voice-led reflections on the things most of us are silently working through: self-worth, ambition, identity, money, reinvention, femininity, and freelance life.
Sometimes it’s discipline, sometimes it’s relationships, sometimes it’s disappearing for six months and coming back as your highest self. But it always comes back to this:
How to live louder, freer, and more in alignment with the life that actually feels like yours.
Denée is a writer, marketer, and the founder of She Freelances™, (and a high-functioning romantic about becoming everything you know you’re meant to be).
If you’re obsessed with working on your mindset, your income, and your entire sense of self, I’m so glad you’re here.
I live rent-free in your ears now, no going backsies (;
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Pretty Philosophical with Denée Seaton isn’t really a podcast.
It’s her YouTube videos, in audio form; turned into sharp, voice-led reflections on the things most of us are silently working through: self-worth, ambition, identity, money, reinvention, femininity, and freelance life.
Sometimes it’s discipline, sometimes it’s relationships, sometimes it’s disappearing for six months and coming back as your highest self. But it always comes back to this:
How to live louder, freer, and more in alignment with the life that actually feels like yours.
Denée is a writer, marketer, and the founder of She Freelances™, (and a high-functioning romantic about becoming everything you know you’re meant to be).
If you’re obsessed with working on your mindset, your income, and your entire sense of self, I’m so glad you’re here.
I live rent-free in your ears now, no going backsies (;
Everyone discusses the concept of “lock-in season,” but what happens when life interrupts your motivation and crumbles your routines? You often find yourself reverting to the identity you aimed to leave behind.
This episode explores why your attempts to lock-in often fail: it's because you're trying to build a new life with your old self. Discover the transformative identity shift that raised the stakes for me, rejected comfort, and made success the only option, forcing a change my past self couldn’t endure.
If you've ever found yourself restarting every year, losing momentum, or struggling to remain consistent despite your desires, this episode will unravel the pattern and, most crucially, offer strategies to break it once and for all.
0:00: Intro2:08: Why people struggle to stay locked in6:22: On reshaping your identity9:41: How to engineer consequences11:50: The psychology of making quitting impossible14:33: Why optimism is a discipline17:48: The recipe behind people who “make it”
#identityshift #lock-inseason #motivation #consistency #successstrategies #reshapeidentity #overcomingobstacles
See show notes: https://inlet.fm/denee/episodes/6923ca3cde0f820d2f5f11ac
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This episode is a wake-up call for anyone feeling trapped in their current job, overwhelmed by systemic pressures, or anxious about the impact of AI and the evolving economy. The discussion highlights how the traditional employment landscape has shifted, why so-called 'stable' jobs may not be secure, and what true security will look like in the future.
Key points include:
Why the conventional career model is becoming obsolete
The difference between safety and predictability
The psychological trap of stability
The importance of owning your future
Freelancing as a means to gain control over your career and personal life
Steps to responsibly transition from your job
Building skills and income in the new economic environment
The growing trend of women leaving traditional jobs for autonomy
Designing a fulfilling life that aligns with your passions
If you're contemplating leaving your job, embarking on a freelance career, or redefining your identity outside the conventional system, this episode offers valuable insights.
In this episode:
00:00: How the script of work changed01:26: Safety vs predictability04:36: Why freelancing is exploding in 202507:07: Leverage over credentials12:13: Real stories of women leaving 9–513:43: How to leave your job responsibly14:36: The mindset + emotional shift16:53: The financial layer of quitting21:00: Becoming the main character of your life
#quittingyourjob2025 #freelancing #futureofwork #AIandjobs #escapingthe9-5 #careershift #autonomy #self-trust #designingyourlife
See show notes: https://inlet.fm/denee/episodes/691a8fbd06d4b22579b9f245
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Discover a comprehensive step-by-step guide on kickstarting your freelance journey in 2026! This in-depth course will teach you how to select profitable freelance skills and build a compelling portfolio, even if you're starting from scratch. Dive into strategies for finding freelance clients through inbound, warm, and cold outreach. Learn to price your services confidently, set up efficient workflows, negotiate effectively, and secure a steady income stream. This guide is perfect for those aiming to transition into full-time freelancing or establish a successful side hustle.
If you're eager to learn how to freelance, start without experience, or enhance your client acquisition strategies, this guide is your essential resource.
00:00:00: Intro00:01:02: What to expect00:01:21: Get your free notion board00:01:49: Who I am00:02:08: Part 1: Foundation00:04:40: Getting close to the money00:05:20: What skill to freelance00:13:32: Part 2: How to find clients00:13:58: Inbound clients00:17:44: Cold outbound00:19:37: Good cold outreach examples00:23:11: Warm outbound00:27:55: Working with clients globally00:33:38: Creating your portfolio00:38:58: Part 3: Pricing00:40:39: Retainer offers00:42:36: One-off projects00:47:22: Calculating your rate00:51:00: Retainer offer tiers00:52:50: Freelance pricing examples00:55:20: How to raise your rates00:58:00: How to negotiate with clients00:59:40: Doing test projects01:00:03: How to conduct a client call01:06:43: Following up after a client call01:07:22: When you’re asked to work “full-time”01:10:50: Creating a qualifying questionnaire for inbounds01:12:11: Preparing for a call with a cold client01:13:20: How long a client call should be01:14:08: Part 4: Workflow01:15:55: Freelance contracts01:22:30: Where and how to do client work01:26:19: Thinking in systems01:28:00: How to work faster as a freelancer01:31:55: Sending work to clients01:34:30: Collecting payment from clients01:36:16: Part 5: Longevity01:37:32: Keeping multiple clients01:38:56: Diversifying your freelance income01:41:20: Being easy to work with01:45:48: SEO + AEO for inbound leads01:48:41: Travelling while freelancing01:50:57: Closing thoughts
#freelancing #freelanceskills #clientacquisition #pricingstrategies #portfoliobuilding #workflow #incomestability #full-timefreelancer #sidehustle #freelancing2026 #freelancecourse
See show notes: https://inlet.fm/denee/episodes/691549baf92e0f343846f61d
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Most people believe that overthinking is a protective measure, but in reality, it only leads to stagnation. In this episode, we explore the liberating power of making "dumb" decisions. Discover the journey from being the "smart girl" with a plan to embracing decisions that truly impact life. If you find yourself stuck in analysis paralysis, whether it's due to fears of leaving a 9-5 job, expanding a freelance business, or embarking on a new venture you've delayed for too long, this discussion will provide the push you need.
Learn how to minimize overthinking, take swift action, and overcome the fear of making mistakes—because action is what breeds confidence, clarity, and momentum.
00:00: Intro01:33: Why I clung to the 'smart girl' identity03:34: My first 'dumb' decision that changed everything05:45: Why being dumb is an ego death06:19: Step one: Think less07:36: Step two: Reframe discomfort09:55: Step three: Track what actually matters10:36: Step four: Detach from the Ls12:33: Step five: You are what you do13:41: The cost of not acting dumb
#overthinking #analysisparalysis #dumbdecisions #confidence #momentum #freelance #ego
See show notes: https://inlet.fm/denee/episodes/6910d79bbf74dfd5cf78f880
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Are you feeling stuck, living the same year over and over? This episode offers a fresh perspective to break free from routine and embrace radical ownership of your life. We explore simple yet effective systems focusing on energy, output, and reflection, along with practical strategies to avoid pitfalls that can derail your journey. Near the end, discover actionable steps you can implement immediately to transform your year—no vision board needed.
00:00: Intro02:19: Why you feel numb05:51: You can't be the passenger princess07:11: Radical ownership10:42: Main character energy in practice17:50: Avoiding the pickles21:39: Final pep talk
#radicalownership #maincharacterenergy #lifetransformation #practicalsteps #breakfreefromroutine
See show notes: https://inlet.fm/denee/episodes/69079e27eb875a3350714b73
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Jealousy isn’t always negative. Discover how envy and comparison can become powerful tools for transformation. In this episode, learn how to turn jealousy into discipline and self-awareness to build a successful freelance career. Understand how to harness these emotions to achieve your own professional dreams, whether you're in a 9-5 job or freelancing.
This discussion includes:
How to reframe envy as useful data.
Building self-awareness about your desires.
Channeling negative energy into focus and consistency.
This episode provides practical steps to ignite your motivation and guide you towards a rewarding freelance lifestyle.
00:00:00: Intro00:01:28: My angsty teenage years00:03:23: Turning jealousy into fuel00:04:39: Using negative emotions as data00:07:23: Step 1: Getting clear00:10:06: Step 2: Earn your stripes00:12:06: Step 3: Accept the sacrifice00:15:39: Practical steps to making this work
#jealousy #freelance #envy #self-awareness #discipline #freelancecareer #motivation #professionalgrowth
See show notes: https://inlet.fm/denee/episodes/68fe62686d98d3715f6bd06f
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Many people believe being introverted is a limitation, but I found it to be my greatest strength. I discuss my journey from feeling awkward in social settings to embracing my introversion, which transformed my life and career. Learn how solitude, self-awareness, and focus helped me achieve freedom, creativity, and peace. If you've ever felt misunderstood or drained by social interactions, this episode is for you.
Explore how to turn your personality into your biggest asset.
My no-BS, how-to-start-freelancing crash course will change your perspective on work forever.Listen on Spotify and Apple.She Freelances InstagramPersonal InstagramLinkedInTikTok
00:00:00: Intro00:01:02: Defining the 'freak aura'00:03:05: Why big groups drain me00:04:05: Introversion as an advantage00:05:40: Socializing enjoyably00:08:40: Creativity through solitude00:10:06: Mindset shift to freelancing00:11:26: Using introversion as power00:13:27: Message for the misunderstood
#introversion #self-awareness #solitude #creativity #freelancing #socialsettings #personalitypower
See show notes: https://inlet.fm/denee/episodes/68f527f31bc349f8d6ebe8c0
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Discover how quitting traditional employment and embracing freelancing can transform your mental health. Learn how financial independence can reduce stress and anxiety, particularly in relation to ADHD, and explore practical steps for replacing a 9-to-5 income with freelancing.
Understand the concept of 'financial freedom' and its impact on well-being. Whether you're already freelancing or contemplating a career change, this episode provides insights into achieving calm, focus, and independence.
01:01: Disclaimer02:03: Money and anxiety04:02: Money and ADHD05:34: 'Easy mode,' explained07:49: Why self-employment09:16: How I make money09:47: What I get paid10:10: Why I freelance
#freelancing #mentalhealth #financialindependence #anxiety #ADHD #financialfreedom #self-employment
See show notes: https://inlet.fm/denee/episodes/68ebee50aa0f3410b9d46a48
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I used to live in so much shame that I was afraid to admit my struggles out loud—not to friends, not even to God.
In this episode, I discuss why and how I faced my challenges and what it takes to fight back. Discover how I began to break free, the role of shame in keeping you stuck in cycles, and how to start rebuilding your self-respect.
Understand why willpower alone isn’t enough, how your environment impacts you, and the routines that anchored me. Learn about using micro-commitments to rebuild self-trust and the importance of accountability by sharing with others and God.
00:00:00: Intro00:02:09: Disclaimer00:02:41: Rethinking what self-harm is00:04:00: The day I finally confessed00:06:05: Why willpower alone isn’t enough00:07:30: Your environment can make or break you00:10:12: The routines that anchored me00:11:00: Using micro-commitments to rebuild self-trust00:12:28: Accountability: telling people and telling God00:14:06: Final thoughts & reflections
#shame #self-respect #micro-commitments #accountability #self-harm #environment #willpower
See show notes: https://inlet.fm/denee/episodes/68e2b2ef94a319dd5fd8a8a0
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I don't simply 'overcome' imposter syndrome—I tackle it head-on. Instead of letting it overshadow me, I refuse to label it in a way that makes it seem insurmountable. This episode is for those who are tired of self-diagnosing instead of taking action. Discover why most people don't actually have imposter syndrome, how self-labeling can hold you back, and the reframing techniques I used to transform zero experience into earning $30K per month at 25.
Free crash course
Listen on Spotify: Pretty PhilosophicalListen on Apple: Pretty Philosophical
Connect with me on social media:She Freelances InstagramPersonal InstagramLinkedInTikTok
0:00: Intro1:00: What imposter syndrome actually means4:12: How to compare yourself to others6:33: How perfectionism feeds the cycle8:33: On creating better narratives12:59: Have the audacity of a man17:00: Recap
#impostersyndrome #reframingtechniques #$30Kmonthly #self-diagnosing #actionablesteps #self-labeling #narrativecreation #perfectionism
See show notes: https://inlet.fm/denee/episodes/68d97874d14bfeb08f7b4c26
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Most "glow up" advice focuses on surface-level changes like makeup and hair, but this episode dives into the deeper, inner work needed for genuine transformation. Learn how to break free from repetitive loops, tackle difficult conversations, eliminate unnecessary burdens, and make decisive choices independently. Discover how a temporary obsession with inner change can align your exterior with your true self.
Key moments from the episode include:
[0:00] Introduction
[1:33] Why Your Caloric Deficit Isn't Working
[2:42] Closing Unfinished Loops
[5:34] Letting Go of Clutter
[8:03] Dealing with Micro Decisions and Fatigue
[10:02] The Importance of a Nightly Debrief
[11:39] Embracing Obsession
[12:50] Battling Inner Demons
0:00: Introduction1:33: Why Your Caloric Deficit Isn't Working2:42: Closing Unfinished Loops5:34: Letting Go of Clutter8:03: Dealing with Micro Decisions and Fatigue10:02: The Importance of a Nightly Debrief11:39: Embracing Obsession12:50: Battling Inner Demons
#innerwork #transformation #self-improvement #decisionmaking #obsession #glowup #innerdemons
See show notes: https://inlet.fm/denee/episodes/68ceec6a40a7c65027595b6f
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Social media often portrays a lifestyle that's appealing but fragile beneath the surface. The 'soft life,' curated jobs, and consumerism can lead to dependence mistaken for freedom. In this episode, we explore the traps being sold to women, the risks of depending solely on a man or a paycheck, and why developing your own skills and income is the true insurance plan.
00:00:00: Intro00:01:53: The 'reality' of the soft life00:05:01: Consumerism & identity as a product00:08:49: The danger of relying on one job00:13:03: The real insurance plan: betting on yourself
#softlife #financialindependence #consumerism #incomesecurity #self-reliance
See show notes: https://inlet.fm/denee/episodes/68c5b1f4cb90fde9c2325346
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Most people follow a path they didn't choose, often indoctrinated into “safe” careers and borrowed definitions of a “good life.” In our rapidly changing world, safety is often just a narrative. This episode explores how breaking away from the curated path and taking specific risks transformed my life: not applying for traditional jobs, moving across the world, and investing in mentorship, along with the sacrifice and discipline these choices entailed.
0:00: Intro1:18: Risk #1: Choosing Uncertainty5:30: Risk #2: Mentorship and the ROI9:39: Risk #3: Proximity12:37: Zooming Out
#risk-taking #mentorship #lifetransformation #careerchange #investinginoneself
See show notes: https://inlet.fm/denee/episodes/68bc776edaab9f50782c3353
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Explore the concept of real security by visiting this link.
If you lost your job tomorrow, what would your plan be? Many people might rush to update their resume and hope for interviews. However, in this episode, I share an alternative path: building a multi-six-figure freelance business.
This isn't about quitting your job to earn $10k/month online. It's a detailed guide on creating income security on your own terms. I'll discuss the first skill I marketed, how I attracted clients, and the simplicity of freelancing as a way to maintain income in a dynamic labor market.
0:00: What would your plan be if you got laid off?1:07: How freelancing changed everything for me2:01: Free work, cringe networking, and strategic positioning5:15: The importance of solving real problems6:54: The 3 steps that built my freelance business13:04: Why this is true security in the new economy
#freelancing #incomesecurity #freelancebusiness #realsecurity #dynamiclabormarket
See show notes: https://inlet.fm/denee/episodes/688baff3ed27aafa94d7d1b8
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In this episode, we explore why saying 'I'm confident' or 'I'm enough' every morning doesn't truly change your self-perception. Find out why affirmations alone can't solve low self-esteem issues. Confidence isn't derived from mantras but from self-trust. If you consistently break promises to yourself, no number of sticky notes on the mirror will help.
We discuss:
— Why affirmations fail if you're not honest with yourself— How confidence is built through evidence, not pretense— The small daily promises that can either erode or build self-trust— Why you still struggle with self-acceptance despite countless 'I am enoughs'
0:00: Intro0:55: Why fake it till you make it always cracks2:50: Confidence is just a track record4:23: Keeping promises to yourself6:53: Why you still don’t feel confident
#affirmations #self-esteem #confidence #self-trust #self-acceptance #personalgrowth
See show notes: https://inlet.fm/denee/episodes/68a75f7afb236390d1db348c
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Learn how to build a $10k/month freelance business with actionable steps. Explore why overthinking is a trap and taking action is the key to change. This episode uncovers how to break free from paralysis and why momentum outweighs clarity. If you've been stuck in a cycle of just contemplating rather than doing—be it freelancing, fitness, or any other endeavor—consider this your wake-up call to start taking action.
Check out the freelance crash course for more insights.
0:00: Introduction0:48: Why you feel stuck2:54: The only way to break paralysis3:43: Motion vs inertia5:03: Easy choices = hard life7:15: Change your life in the next 10 min
#freelancebusiness #overthinking #action #momentum #paralysis #change
See show notes: https://inlet.fm/denee/episodes/68aca572aa89d2a2cc055a38
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This episode marks the first Q&A dilemma session where I address your questions on ambition, discipline, identity, relationships, freelancing, and more.
Topics covered include:
Why balance is a myth and obsession is essential
Knowing when to cut people off and detach
Living for your parents versus building your own life
The difference between wanting a life and wanting its aesthetic
Why self-respect might mean disappointing the right people
Creating loops to make discipline sustainable
Freelancing as an ideal business model when you start with nothing
Surviving the transition to self-employment
Check out She Freelances, a female-only community and program, starting with a free course: She Freelances
Want me to cover your dilemma next time? Submit here: Submission Form
00:00:00: Intro00:01:05: Cutting people off & detachment00:06:08: Balance, FOMO & perfectionism00:11:50: Making new friends00:17:59: Living for your parents vs. building your own life00:22:27: Surviving the pivot into entrepreneurship00:25:37: Why freelancing is the best business model when you have nothing
#ambition #discipline #identity #relationships #freelancing #balance #self-respect #entrepreneurship
See show notes: https://inlet.fm/denee/episodes/68b33cf82cc5fa2730288f21
Learn more about your ad choices. Visit podcastchoices.com/adchoices
Pretty Philosophical with Denée Seaton isn’t really a podcast.
It’s her YouTube videos, in audio form; turned into sharp, voice-led reflections on the things most of us are silently working through: self-worth, ambition, identity, money, reinvention, femininity, and freelance life.
Sometimes it’s discipline, sometimes it’s relationships, sometimes it’s disappearing for six months and coming back as your highest self. But it always comes back to this:
How to live louder, freer, and more in alignment with the life that actually feels like yours.
Denée is a writer, marketer, and the founder of She Freelances™, (and a high-functioning romantic about becoming everything you know you’re meant to be).
If you’re obsessed with working on your mindset, your income, and your entire sense of self, I’m so glad you’re here.
I live rent-free in your ears now, no going backsies (;