PODCAST · business
Freelance AF
by Sean Kelly & Michelle Elliott
Freelance AF is a cheeky peek behind the curtain into the world of being your own boss! Join freelancing friends Sean Kelly (owner and founder of Barrel to Basket, a wine and cider tasting event company) and Michelle Elliott (professional brand photographer, and owner and founder of MEE Photography) as they dive into the nitty gritty of owning a small business. These intrepid hosts cover a range of topics - like crucial steps to starting your own business, the importance of developing your brand, and how to stay organized - all while laughing and drinking, and never taking themselves too seriously. From the corporate world to becoming entrepreneurs, Sean and Michelle share their successes and struggles to help you find your own path to freelance freedom. Whether you're an established business owner, or just starting on your journey, their hope is to impart some semblance of wisdom on you - or at the very least show you what NOT to do! Episodes release weekly and occasionally featu
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Episode 10: Viral Isn't The Flex You Think It Is
Hey Freelancers! Remember when going viral was the dream?Yeah...we need to talk about that.Because as a small business owner, a viral post doesn’t automatically mean your inbox is blowing up with dream clients. Awkward, right?This week, Sean and Michelle are diving back into the socials to break down the difference between content that gets views and content that actually converts, and why posting for the algorithm is not the same as posting for your people.Unless your job title is “Influencer,” chasing virality with every post might be doing more harm than good.Trendy content can absolutely get eyes on your page, but if what people find when they land there doesn’t speak to who you are and what you offer? Those views are doing a quick little bounce.So put down the TikTok, grab a pen, and let’s get into why Viral Isn’t The Flex You Think It Is.
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Episode 9: Confidently Competent
Pop quiz, Freelancers: what actually makes you more successful, confidence or competence?Trick question! You need both.This week, Sean and Michelle are breaking down why being good at what you do isn’t enough if no one knows about it, and why confidence without the skills to back it up will only get you so far.Because let’s be honest: at some point in your business, you’ve probably been heavy on one and lacking in the other. Maybe you’ve been quietly excellent but afraid to sell it, or boldly selling and hoping your skills catch up. Either way, we’ve all been there.Confidence gets you in the room. It helps you pitch, post, and put yourself out there. But competence? That’s what keeps clients coming back, referring their friends, and trusting you with their money.So whether you need to hype yourself up or sharpen your skills, this episode is your reminder: the goal isn’t one or the other…it’s both.It’s time to get you Confidently Competent.
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Episode 8: Stop Taking It Personally
Call us a broken record, because yep, we’re talking about social media again.That’s right, Freelancers; following up on our last episode, we’re diving into how to separate your marketing from your actual identity. Because when you are the boss, the marketing team, and the social media manager all rolled into one chaotic human, that line gets REAL blurry.One minute you’re posting content, the next minute you’re spiralling because it got 12 likes and your brain goes, “Cool, so we’re irrelevant now.” (Love that for us.)But here’s the truth: likes don’t pay your bills, and they sure as hell don’t define the quality of your work. A post flopping doesn’t mean you flopped; it just means you gathered data, babe.Social media is a tool, not a personality trait. And if you can learn to reframe how you show up on it, you’ll not only use it better, you’ll feel a whole lot less unhinged while doing it.So if you’ve ever taken a low-engagement post as a personal attack, don’t worry, we’ve been there. Today, we’re helping you to finally Stop Taking It Personally.
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Episode 7: Sharing Ain't Always Caring
Ever written a text or email in the heat of the moment and then thought, “Erm…maybe I shouldn’t send that…”? Yeah. This episode is for you.Social media’s been around for decades, and somehow we’re still figuring out how not to absolutely spiral on it. Sure, it’s a powerful tool for marketing and self-promotion, and yes, people want the real, relatable version of you. But there’s a fine line between authentic and “please log off for a bit.”So how do you know when you’ve crossed it?Sean and Michelle are diving into how you shouldn’t post while emotional, oversharing, and why your first draft probably shouldn’t see the light of day. From putting space between feeling and posting to showing up online without going full rant mode, we’re giving you the tools to keep it real and keep it professional. Because not every thought needs a timestamp.So sit down, log off of Instagram, and let’s talk about how Sharing Ain’t Always Caring.
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Episode 6: Everywhere All at Once
Freelancers, you should take this advice to heart…Yeah, Sean cringed a little, but that doesn’t make it any less true. The pressure to show up on every social media platform is real. And so is the guilt when you don’t. But trying to be everything, everywhere, all at once is a fast track to burnout. Trust us, we’ve been there.Here’s the good news: you don’t have to do it all. This business world is your oyster, baby!Figure out where your people actually are, show up there, and give yourself full permission to ignore the rest. And hey, if you do want to juggle multiple platforms, go for it; but do it smart. Batch your content. Schedule it out. Reuse what works. Focus on quality over quantity.So go ahead, delete the FOMO, unclench your algorithm anxiety, and strap in. We’re officially letting go of the pressure to be Everywhere All at Once.
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Episode 5: Success Era
Strap in, Freelancers; we’re about to get a little introspective.Think back to your baby adult era. We know, terrifying. But go with us. What did success look like back then? All cash and flash? Or did it already have a little more depth?Now fast forward to today. Where do your priorities actually sit? Is it still about chasing the bag, or has your version of success evolved into something with a few more layers, like a perfectly constructed Drag Race look?Because here’s the thing: as we grow, so does our definition of success. And just because someone else measures theirs one way doesn’t mean it has to fit for you.When you understand what your success actually looks like, you can set goals that make sense, and actually achieve them.And success? That’s what we’re all about, baby.So dust off that pookah shell necklace (don’t lie, you still have it) and get ready to step into your Success Era.
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Episode 4: Build It or Bill It
To DIY, or not to DIY…yeah, that’s the question.Because Freelancers, this one? It actually matters.Sure, doing it yourself can save you money, and when your margins are looking a little *ahem* humble, that’s a big deal. But on the flip side, hiring someone who actually knows what they’re doing can save you from expensive mistakes, mental breakdowns, and a few “why did I think I could do this?” moments.The real power move? Knowing when to roll up your sleeves, and when to pull out your credit card.So grab a drink, maybe a notebook, and get ready, because we’re breaking down exactly when to Build It or Bill It.
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Episode 3: What it Costs to be the Boss
Buckle up, Freelancers, because today’s episode is all about cost.Don’t worry, you won’t need a calculator. We’re talking about what you give up to be a small business owner: things like winding down after hours, free weekends, and having a predictable social life.Of course, it’s not just about what you lose; it’s also about what you gain when you’re the one calling the shots. Think creative freedom, being the ultimate decision-maker, and the pride that comes with building something that’s truly yours.Everything in life is a give and take, and running a business is no different. But if you play your cards right, what you gain in return can make every sacrifice worth it!So settle in with your coffee and hold all calls, because it’s time to talk about What it Costs to Be the Boss.
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Episode 2: From Hot Mess to Progress
Plot twist, Freelancers: we learned something!You know how people say hindsight is 20/20? This week, Sean and Michelle are strolling down Memory Lane, making a quick detour onto Reflection Avenue, and unpacking the biggest lessons from Season 1.Because here’s the thing: reflecting on what worked (and what absolutely did not) is one of the best ways to grow. Not just as a business owner, but as an actual human person with feelings and boundaries. Wild concept, we know!From hard-earned lessons to those “oh…that’s what that was supposed to teach me” moments, we’re talking about what we’ve learned, how we’ve applied it, and why growth sometimes comes in multiple attempts.Take it from our anxious selves: reflection can feel intimidating. But it’s also how you realize just how far you’ve come.So grab a cozy spot and join us as we take things from Hot Mess to Progress!
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Episode 1: Sassy B*tches Say What?
Freelancers…we’re back!Season 2 of Freelance AF is officially in session and we’re coming in hotter, sharper, and slightly more self-aware. Double the strategy. Double the sass. Double the tangents.And we’re kicking things off with a spicy little word that most business owners are allergic to: no. Because saying yes to everything is cute, but it’s also how you end up exhausted, underpaid, and resentful AF.This episode is about capacity. Knowing your limits. Auditing what’s draining you. And having the guts to scrap what doesn’t serve you anymore, even if it used to.So grab your coffee, mute those notifications, and open up your Notes app. Because Sassy B*tches Say What? “No!”
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Episode 40: That's All Folks (For Now...)
Holy moly, this week marks the Season 1 finale of the Freelance AF Podcast! Sean and Michelle are strutting down memory lane, spilling tea, and cackling their way through the highs, lows, and utterly unhinged tangents that made their very first season what it was. We’re reliving our favourite moments, discussing behind-the-scenes chaos, and handing out a few delightfully fake awards nobody asked for (but we’re giving out anyway).This show simply wouldn’t exist without the love and support from our family, friends, and every single listener who tuned in – whether you’ve been here since episode one or just popped by for a little freelance wisdom (or nonsense). From the bottom of our hearts, thank you. Creating this season with you has been pure magic.We’ll be taking a short break (because even your favourite freelancers need a nap) but don’t worry. Season 2 is already brewing and will be hitting your ears in the first quarter of 2026.Until then, keep freelancing, keep dreaming, and remember: you’ve got this, you’re the boss, and if we can pull this off so can you. Or, as the ever-iconic Porky Pig said best: “That’s all, folks!”
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Episode 39: Motivation Makeover
Feeling tired, run-down, or like your motivation packed its bags and ghosted you? Good news; this week we’re serving up a full-on Motivation Makeover!Motivation might be our ride-or-die, but wow does it love to play hard to get. It’s not magic; it’s a muscle. And we’re talking how to grow it, flex it, and keep it from tapping out when life gets a little “nope.”Sean and Michelle are diving into what motivation actually is, how to build it from scratch, and how to keep that fire lit so you can keep showing up like the boss you are.Because let’s be real: down days happen. What matters is how fast you can bounce back, dust off, and strut right on through.Buckle up, because it’s time to get Motivated AF.
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Episode 38: Flag on the Play!
This week on the Freelance AF Podcast, your favourite duo is lacing up their metaphorical cleats and diving headfirst into the world of red and green flags – and calling in a surprise new colour off the bench!From dream clients who make you wanna pop champagne to collaborators who make you wanna fake bad Wi-Fi, every interaction in business comes with its own set of signals. But here’s the kicker: sometimes you’re the one waving the flag.Sean and Michelle are calling the plays and breaking down the cues that scream “let’s do this forever” versus the ones that yell “run for the hills”. That way hopefully you can spot the signs and chart the appropriate course before it’s too late.So…are you the ultimate teammate or the walking red flag your group chat warns people about?
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Episode 37: Advocacy in Bloom with Jodie Buttigieg
Class is officially in session this week on the Freelance AF Podcast. And our teacher? The brilliant Jodie Buttigieg!Jodie’s the director and lead educator at Neubloom London, a neuro-affirming school shaking up the “one-size-fits-all” education system and proving that learning should actually fit the learner.She’s spilling the tea on what it really takes to build a school from scratch, the highs and lows of bucking tradition, and what advocating for holistic education truly looks like in action.And of course, it wouldn’t be a Freelance AF episode without a little chaos: tech fails (thanks, Sean), caffeine-fueled energy (looking at you, Michelle), and the unforgettable phrase “skin babies” (we’ll let Jodie explain that one).So grab your favourite notebook (or your emotional support coffee) because we’re about to get educational AF.
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Episode 36: Spooktacular AF
It’s that time of year when the veil is thin…and so are our boundaries when it comes to oversharing! We’re getting Spooktacular AF this week and digging up the skeletons in our freelance closets – the tricks we’ve learned, the treats we’ve earned, and the fears we’ve had to face in the dark corners of small biz life. Along with the usual unhinged rhetoric, Sean and Michelle are serving up chills, giggles, and maybe a little witchy wisdom, too. (But only if you dare listen.) Grab your costume, your courage, and a king-size chocolate bar; it’s gonna be a boo-tifully chaotic ride.
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Episode 35: Ghostbusters!
This week on the Freelance AF podcast your favourite hosts are slipping on their proton packs and gearing up to battle every entrepreneur’s nightmare: ghosting.Ghosting is all-too common, with over half of Canadians saying they’ve been ghosted at least once in the past year. And for small businesses? Depending on the industry you’re in that could be even higher (think 60-70%).Whether you blame app and phone-based culture or our ever-increasingly apathetic populace, it’s clear us small biz owners need to toughen up. After all, it’s business not personal! Sean and Michelle dive into it, talking about the how, what, why and when of those eerily ephemeral clients and what you can do to ease the toll on yourself. And maybe, just maybe, even reduce the chances of it happening to you.So ask Janine to hold all calls and say it with us now: I ain’t afraid of no ghost!Who you gonna call?
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Episode 34: Dream Big or Go Home with Candice Neufeld
This week on the Freelance AF Podcast, we’re kicking back with our girl Candice Neufeld; entrepreneur, coach, and literal ray of human sunshine. She showed up with good vibes, big dreams, and energy so contagious we’re honestly still rockin’ the high!Candice gets real about what it’s like to peace out of your biz’s physical space, and how sometimes walking away is actually the most badass move you can make. Spoiler: it’s giving freedom, flow, and full-on trust in your purpose.We’re talking big plans, bigger goals, and how a solid dose of positivity can make all the difference between burning out and blowing up. Because success isn’t one-size-fits-all; it’s whatever the hell you say it is.So grab your coffee, your manifestation journal, or maybe just a mimosa, and get ready to Dream Big or Go Home!
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Episode 33: Lost in Translation
This week on the Freelance AF Podcast, your favourite freelancers are diving headfirst into the wild world of professional communication for the bold and scrappy small biz owner.Here’s the thing: the way you communicate says everything about how you do business. And let’s be real; some people (not Sean, nope, never Sean, absolutely not Sean…) get majorly turned off if your vibe isn’t hitting right.From tailoring your tone to your audience, to picking a style that actually matches your brand, to keeping things consistent and clear, we’re serving up all the juicy tips to help you say what you mean and actually get heard.Struggle with this? Same! (Have you met our podcast?) But hey, stick with us and you’ll be communicating like the boss you were always meant to be.And remember: do as we say, not as we do.This week's pour is Dutch Crumble Hard Apple Cider from London, Ontario's hometown hero, Heeman's Cellar!
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Episode 32: Talking to Ourselves...Again
Do you hear that? Oh, it’s just us…Talking to Ourselves. Again.Yep, we’ve said this before, but some advice is too good not to put on repeat. These are the nuggets we wish we could whisper to our past selves when we were just getting started, whether that was 9 years ago or, let’s be real, 18 months back.This episode is jam-packed with the pep talk every entrepreneur needs: be patient, trust your gut, stand your ground, say no when you need to, build that hype squad, and jump at the right opportunities. Freelancing takes thick skin and quick reflexes, but don’t forget; you also need to pause, breathe, and hype yourself up.So grab a sticky note, a vision board, or heck, a megaphone, because these reminders are worth keeping front and center. You got this, babe!
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Episode 31: Talk Giftii To Me with Katie Brooks
Ooooh baby, your favourite Freelancers are back with another juicy interview, and this one’s a total Giftii!We’re sitting down with the powerhouse herself, Katie Brooks, founder of Giftii Canada, gifter extraordinaire, and queen of turning “just because” into jaw-dropping wow. With her hubby by her side, Katie has built a biz that’s all about heart, thoughtfulness, and making people feel like the main character with every box.From championing Canadian makers before it was trendy, to weaving family, tradition, and pure magic into every curated gift, Katie’s not just sending boxes; she’s building connections. Trust us, you’re gonna want in on this magical conversation!
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Episode 30: Too Hot To Handle (The Burnout Episode)
Sizzle, fizzle, poof – burnout strikes again!This week on the Freelance AF Podcast, Sean and Michelle are diving headfirst into the not-so-glam side of hustle life: burnout. You know it, you’ve felt it, and let’s be real; half of Canada is feeling it right now (stats don’t lie, honey).But don’t panic; your favourite freelancers have your back! From spotting the warning signs to building your burnout bounce-back toolkit (think sleep, support, and a whole whack of self-care), we’re serving up tips with our usual side of sass to get you feeling right as rain.Grab your headphones, sideline the fretting, and tune in. Burnout might be inevitable, but staying there? That’s optional AF.This week's pour is Brunch's delicious Rosé Cider from Niagara, Ontario!
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Episode 29: Chaos Catch-up!
Oh my god, we’re back again!Your favourite Freelancers have returned from their not-a-break break with stories, chaos, and just a little too much caffeine.Sean and Michelle are spilling on what they’ve actually been up to. Surprise: it wasn’t relaxing! Think big projects, family chaos, drinks, road trips, planning apple picking trips, mental health curveballs, and even a few hair updates (some greys gone, some hair REALLY gone).It’s a slightly updated format, the same ol’ sass, and a whole lot of catching up. Missed the craziness? We know you did. Welcome to the Chaos Catch-up, baby!This week we’re drinking something from one of the oldest Canadian cider-makers, Growers’ Honeycrisp Apple cider!
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Episode 28: Haggle Free Zone Mini Episode
Your favourite Freelancers are here with the grand finale of our mini episode series, and this one’s all about a lesson we should’ve mastered in elementary school: no means no.When a client asks if you can “do it cheaper,” it’s easy to panic. From our lips to your ears, here’s the truth: your prices aren’t up for debate. You set them for a reason, and standing behind them is part of owning your worth.In this episode, we’re breaking down how to say no without being defensive (or a doormat). From offering alternatives to holding the line with confidence, we’ll show you how to handle discount requests like the boss that you are.So take a load off, hit play, and get ready to flex those boundary-setting muscles. Remember: saying yes to discounts means saying no to yourself.
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Episode 27: The Emergency Post Kit Mini Episode
Blank brain, empty feed, and zero inspo? We got you. This week’s mini is The Emergency Post Kit, aka your lifeline when the content well runs dry.You’re not the only one staring at your grid like it owes you money (trust us, Sean’s a permanent resident here). But lucky for you, the FAF duo is serving up quick-hit content ideas that’ll snap you out of scroll-staring paralysis.Think bloopers from behind the scenes, a juicy throwback, or the universally adored “here’s my coffee” flex, all easy AF posts you can spin up in minutes and still look like the boss babe you are.So take a breath, push past the panic, and let’s give that feed the glow-up it’s been begging for!
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Episode 26: Season Proofing Mini Episode
Your fave Freelancers are back with another snack-sized episode, and this one’s all about Season Proofing! Yeah, yeah, we hear you. The sun’s still shining and we’re already talking about the snowy stuff. But like Michelle says: if you’re not planning ahead, you’re planning to panic.That means pulling out your old numbers, locking down supplier timelines, and actually getting your marketing together before the rush hits. Take it from us; do it now and future-you will be sipping that pumpkin spice in peace while your business runs smoother than fresh apple cider.Basically: prep smart, sell hard, and let’s leave the scrambling to the turkeys.
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Episode 25: Automation Nation Mini Episode
This week, your favourite Freelancers are dropping the first of four snack-sized episodes…because sometimes you just need a quick hit of business wisdom (bizdom?) without the full meal deal.Today’s topic? Automation, AKA: “Let the robots do it so you can stop losing your mind.” Free up your time and energy for the important stuff, like chasing that next big payday or spiraling about why Netflix keeps cancelling your comfort shows.Small biz owners are the ultimate jugglers – CEO, IT, customer service, coffee runner – all before lunch! These automation tips won’t solve everything, but they’ll make that hat collection a little lighter. Take a beat, figure out where automation fits in your workflow, and watch your business (and stress levels) thank you.
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Episode 24: Vacation Mode
Your favourite freelancers are back, but only just. Why? Because they’ve been living that out of office life, baby! But now they have thoughts. (Can’t you smell the smoke?)Sean and Michelle have both returned from vacation, and let’s just say the vibes were immaculate…until reality hit. Where did the time go? Why can’t vacation be a full-time job? And who, exactly, is better at unplugging from work? (Surprise, it’s not Sean.)From packing up the laptop (or not) to resisting the urge to “just check in,” they’re dishing on how small biz owners can take time off without everything falling apart. Whether you’re flying solo or juggling a team, they have some tips to help you actually enjoy your time away, and a few tricks to help set yourself up for a smoother re-entry upon your return.Let’s be real: you deserve a break, and you CAN step away. Your business (and your brain) will thank you.This week’s pour is Reinhart’s Strong Apple Cider, a tasty back-to-basics offering from Stayner, Ontario!
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Episode 23: Podfluenced
That’s Sean. That’s Michelle. And honey, this week we’re flipping the script.Your favourite freelance duo is pressing pause on the biz talk and chatting about their ultimate podcast obsessions. Because guess what? Entrepreneurs don’t hustle all the time. Sometimes we binge like the rest of you.Michelle? She’s a podcast queen. Editing photos? Working in the studio? Folding laundry like a domestic goddess? You know she’s got a true crime podcast blasting in the background. (So maybe don’t get on her bad side.)Sean? He’s not quite as addicted (Spotify receipts say he listens to less than half as much as Michelle). But when he does tune in, he goes from murder mysteries to deep dives in history to completely unhinged nonsense. Basically, he’s Shrek; the boy got layers.So go ahead, mute that Zoom call, pretend you're “working,” and let us drop some podcast recs that’ll have you hooked faster than a Netflix docuseries with a wild twist. It’s time to get Podfluenced.This week’s pour is the delicious, thirst-quenching Apple & Cherry cider from Collective Arts, coming at you from Hamilton, Ontario!
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Episode 22: The Spicier Side of Life with Matt Hammond
Things are heating up in the Freelance AF studio this week, and not just because we’re talking to the founder of RimJobs and Meat Rub Co. (Yes, you read that right. And yes, we giggled too.)We’re joined by the spicy legend himself, Matt Hammond, who dishes on building a bold AF solo business from the ground up, one that’s just as flavour-packed as it is brand-forward. From cooking memories growing up to the convo that sparked a whole range of rimmers and rubs, Matt spills it all.We cover everything from how to (*ahem*) properly core a pepper (NSFW alert) to the solid support network for foodpreneurs in London. And the biggest takeaway? Going all-in on bold choices can often bring seriously spicy results.So grab yourself a Caesar, prepare for some snort-laughs, and remember: always lick the rim clean.This week’s pour is Apple Water, a non-alcoholic cider from Shale Ridge Estate Winery and Cidery in Thedford, Ontario!
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Episode 21: There's an Imposter!
Something’s feeling a little off in the Freelance AF studio this week…and spoiler alert, it’s Imposter Syndrome, that shady little voice in your head telling you you’re not good enough (rude!).This week, Sean and Michelle are dragging that sneaky gremlin into the spotlight and calling it out for the lying little liar it is. From everyday self-doubt to full-blown fraud feelings, your hosts get real AF about how Imposter Syndrome has crept into their own lives, and why it needs to STFU.They’re dishing on where this mess comes from, how it shows up in all its annoying forms, and how to kick it to the curb when it’s killing your vibe.And don’t worry, we’re still bringing the chaos you know and love, including a surprisingly passionate tangent about Allen’s Apple Juice (yes, in the can, obviously), plus sound effects that honestly deserve their own award.You’ll laugh, you’ll relate, you’ll maybe side-eye your inner critic; it’s Freelance AF, baby.This week’s pour is Twin Pines Orchard’s award-winning Hammer Bent Red Cider, from Thedford, Ontario!
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Episode 20: Bakes for the Memories with Karna Brennan
Hope you're hungry, because this episode is baked to perfection!This week, your fave podcast duo is serving up something extra sweet with Karna Brennan of the oh-so-fabulous Brennan Baking Co. Karna’s spilling the (brown) sugar on baking the treats people actually crave, sharing family recipes, and finding that cozy, magical joy in homemade pies. We’re also getting into the juicy stuff, like hitting the sweet spot in business growth, the perks of being your own boss, and why there’s truly no place like home (especially if it smells like cookies).Oh, and did we mention? Karna brought the baked goods. And Sean, being the overachiever he is, paired them with cider. Four of ‘em, to be exact! As Michelle wisely puts it, the way to our hearts is through our stomachs...so basically, we’re in a committed relationship now.This special episode features the following totally drool-worthy Ontario ciders - Thornbury Craft's Wild Blueberry and Elderflower Cider, Heeman's Cellar's Strawberry Rhubarb Cider, Lost Craft's Apple Cider, and Shale Ridge Estate Winery and Cidery's Peach Apple Cider!
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Episode 19: Canada Day, Eh Eff
O Canadaaaa… you better believe we’re celebrating!It’s Canada Day, and your favourite Freelancers are raising a glass (not a double-double) to the Great White North with a proudly semi-accurate dive into some fun Canadian business facts! From oddly American-sounding company names to a shocking number of world-changing inventions, we’re spilling the maple tea on what makes our biz scene so iconic.Regardless of our factual accuracy, one thing’s crystal clear: Canadian entrepreneurs are tough, creative, and full of grit – and we’re so here for it.So a very happy Canada Day to all, and remember that the amazing people who live here are what’s truly great about our country.This week’s pour is Muskoka Lakes Farm and Winery’s super tart and delicious Cliff Jump Cranberry cider, made in Bala, Ontario!
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Episode 18: Proud AF (and Older, too)
It’s a glitter-soaked, confetti-filled kinda week on the podcast as your favourite Freelancers throw a double celebration: Pride Month and Sean’s birthday!That’s right, Sean’s another year older (but no wiser), and Michelle’s putting him in the hot seat with all the hard-hitting questions. Like which Fab Five member does he emulate? What really matters when you're celebrating your birthday? And how has being a gay man shaped his journey as a boss-level biz owner?Spoiler alert: it’s all about leading with love, embracing your sparkle, and never saying no to glitter, especially on your birthday.So pour yourself something strong (because hydration is cute, but cocktails are cuter), throw on that feather boa, and join us for laughs, honesty, and a whole lotta Proud AF energy.This week’s pour is Loch Mór Cider Co.’s Sour Cherry Cider, from Prince Edward County! This cider was a recent winner at the 2025 GLINTCAP Awards!
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Episode 17: Journal Like a Mother with Jessie Daypuck
Your favourite Freelancers are back with their second-ever interview episode, and this one’s a motherload of goodness.We’re sitting down with the incredible Jessie Daypuck, author of Me, Myself and Motherhood, a guided journal that’s basically a love letter to moms who are doing their best while trying to keep their sanity intact. Jessie took her own mental health journey and turned it into a jam-packed collection of tools and exercises to boost positivity, self-worth, gratitude, and tackle that never-ending mom guilt. If you know, you REALLY know.But let’s be real – this is Freelance AF, so things veer off the rails in the best possible way. Michelle’s out here researching the perfect murder (don’t worry, it’s hypothetical… we think). Sean’s spiritually Spice-Girling alongside Jessie to “Wannabe.” And somehow we end up learning that Michelle is a full-on “peeper” pleaser and Sean has a vendetta against Jos Louis'. We also talk about how passion projects, especially the ones close to your heart, don’t always come together overnight. But when they do, they’re worth every messy, glorious step.So grab a coffee, stake out your comfiest corner, and get ready to Journal like a Mother. Trust us – this one’s got heart, humour, and a hell of a lot of honesty.This week’s pour is Sober Carpenter’s Dealcoholized Craft Cider, courtesy of our friends at Designated Drinks!
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Episode 16: B.D.E. (Big Dad Energy)
Father’s Day is upon us, and your Freelance AF hosts are getting sentimental (but like, in our own unhinged way). This week, we’re raising a glass to the father figures who taught us everything from how to use power tools and our voices, to why showing up matters – and why farts are never, ever to be trusted. (Seriously; apparently, Michelle has stories.)We asked our listeners to spill the best life lessons they’ve picked up from their dads, stepdads, bonus dads, and dad-adjacents, and y’all delivered. From heartwarming gems to wildly inappropriate wisdom, we’re dishing it all out with our signature cocktail of chaos and charm.So whether you’re a dad, a daddy, or just someone who gives big “hold my flashlight while I fix this” energy, we’re toasting you today; fatherly AF and proud of it!This week’s pour is Spirit Tree Estate Cidery’s Draught Cider, a deliciously bubbly and smooth creation from Caledon, Ontario!
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Episode 15: Mind Your Boundaries, Betch
Your favourite Freelancers are back, baby, and this week they’re dishing up a delicious combo of chaos and clarity with a big ol’ side of boundary talk!Sean and Michelle kick things off with a very important PSA: cold bedrooms are superior. Don’t @ them. It’s science (probably). Naturally, the conversation drifts to their fur babies, because what’s more wholesome than your pet curled up with you in bed? Michelle reminisces about her pup who had a thing for snoozing in the toxic zone under the duvet by her feet. We’re not here to judge… just to gag a little.Somewhere between floofy cuddles and unsolicited BBQ RSVPs, the duo dives into the meat of the episode: boundaries, and why you absolutely need them in both your personal and professional life. From protecting your time, energy, and money, to keeping your work-life balance from going up in flames, boundaries aren’t just nice to have – they’re essential AF.So grab a cushion and settle in for laughs, relatable rants, and some solid boundary-setting wisdom that’ll help keep your freelance life fierce, focused, and fabulous AF!This week’s pour is Stock & Row’s Cold Tea, a delicious zero sugar cider from Ontario’s Prince Edward County!
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Episode 14: Would You Rather: AF Edition
This week your Freelance AF hosts are throwing it way back to their teenage years with a cheeky AF edition of Would You Rather?Spoiler alert: Sean’s a total newbie to this game (bless), while Michelle is alarmingly prepared and just a little too hyped for it. What starts as light-hearted fun takes a turn for the existential real quick. And Sean? Fully spiraling from question one. (Honestly, it doesn't take much.)Ever wondered if your fave hosts would rather hustle in the city or vibe out in the countryside? Curious whether Sean could actually survive without caffeine, or worse, wine and cider? And what about Michelle; does she prefer working with fresh-faced startups or big brand baddies? We’re spilling all the tea in this episode… and then some. Buckle up, babes, because as usual, it’s about to get wild AF!This week’s pour is Niagara Cider Company’s summery standout Peach and Chardonnay cider, from outside Beamsville, Ontario!
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Episode 13: Keepin' it Real(ty) with Alex Ward & Chauntelle Molfese
Buckle up, Freelancers, because we’re cranking up the volume with our FIRST ever interview episode!This week, Sean and Michelle are getting real (and a little ridiculous) with the lovely Alex Ward and Chauntelle Molfese from Village Realty Team! These powerhouse ladies are juggling more hats than a catwalk at Fashion Week – running a booming real estate biz, hosting the third season of their hit The EmpowerMoms Podcast, and throwing epic events with their Village Mom and Village Women’s Clubs. Oh, and did we mention they’re also basically fielding their own sports team of kiddos? Yeah, these two don’t mess around.Alex and Chauntelle spill the tea on bringing big heart and fierce compassion to their business, the importance of setting goals and delegating like a pro, and the wild ride of watching their dreams blossom. Plus, they share the hacks that keep them (somewhat) sane, like calendars that look like novels, the art of letting go, and why finding the right people to partner with is the secret to success.And just when you thought it couldn’t get any juicier, things go delightfully off the rails with a debate about which fictional character would make the best dinner date (where Sean gets way too hyped about Alex’s choice) in our first round of Unfiltered AF. So grab a drink, set your status to “Away” and don’t say we didn’t warn you!This week’s pour is Ironwood Cider House’s OG, a yummy and wonderfully-approachable cider from Niagara-on-the-Lake, Ontario!
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Episode 12: Batch, Please!
Your Freelance AF hosts are getting down and dirty with content batching this week, and trust us, it’s a total game changer.Before they dive into the nitty-gritty, Sean and Michelle take a little detour down memory lane, reminiscing about their console gaming glory days and the N64 classic, Goldeneye (and no, Michelle definitely did not skip classes for it, wink wink). But once the nostalgia trip ends, it’s time to talk batching, the secret sauce for creating content like a boss.It’s all about locking in your direction, making a killer plan, and executing it with precision – or at least with enough buffer to fix the inevitable slip-ups. For their podcast, batching is the MVP of production, hands down. Michelle’s got it down to a science; Sean…well, let’s just say there’s room for improvement, babes.These freelancers know that efficiency is everything, and blocking out time to batch your content now means less stress and more slay later. Plus, it’s the trick to making your stuff look polished and hella consistent while giving you that oh-so-precious breathing room to step away when you need it.So, batch it up, buttercup. Work smarter, not harder, and keep that content flowing like a boss.This week’s pour is Spy Cider House’s tart and tangy Goldeneye cider, a delicious offering from Ontario’s Blue Mountains!
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Episode 11: Moms are Special AF
Oh hey there, mama!That’s right, it’s a Mother’s Day extravaganza on this week’s extra-fabulous episode of the Freelance AF Podcast, where Sean and Michelle raise their glasses (of MOMosa, obv) to their fierce, fabulous moms.But first, they tackle hard-hitting questions, like why do their dark-coloured fur babies insist on roasting in the blazing sun? And is that cider can black or navy? (The debate is real.)Then it’s time to get sentimental as Sean talks about his mom’s farm-girl roots, her stint as a record store boss babe in her twenties, and that classic entrepreneur mantra, “How hard can it be?” Meanwhile, Michelle dishes on being raised by a powerhouse posse of strong women, her mom's climb from the bottom rung to CEO realness, and why commitment isn’t just a ten letter word in Scrabble.Expect detours into topics like showing compassion for everyone, the “good” kind of psychological warfare, and how meditation in the '80s looked suspiciously like cracking a beer and lighting a cig.To all the moms out there grinding, glowing, and getting it done – we see you, we love you, and we’re raising a glass of MOMosa in your honour!This week’s pour is Pommies’ Mimosa Cider, a delicious cider and orange juice concoction from Ontario, perfect for celebrating Mother’s Day!
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Episode 10: Who's Down With GPT?
You down with GPT? Yeah, you know me!This week, Sean and Michelle are all about the AI. Whether you’re out here using it to make ridiculous memes, fully married to it in your daily grind, or giving it major side-eye, everyone has questions. Like, super serious ones; if ChatGPT were a Transformer, would it be an Autobot or a Decepticon? Michelle’s got thoughts, trust.Your favourite freelance duo gets real on how they’ve been using ChatGPT to boss up their small biz game, and where it’s crashed and burned in spectacular fashion (“Paging Nurse Michelle for a full AI meltdown!”). They’re breaking down the highs and the lows, and even discussing the environmental impacts of these Large Language Models (yes Sean, that’s what they’re called; write it down, babes). Love it, hate it, scream into the void about it, you’re not escaping AI. So once again we ask: Who’s down with GPT?This week’s pour is another delicious London, Ontario offering: Generation Cider Co.’s 1910 Original!
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Episode 9: A Day in the Life
Guess who's back to spill the entrepreneurial tea? Sean and Michelle are pulling back the curtain and letting you sneak a peek at what really goes down in the wild world of boss life. Spoiler: it's way more than just vibes and vision boards. Think freelancing is just chillin’ in your PJs, sippin’ mimosas while the money magically appears? We wish! Our hosts kick off their days with caffeine, obviously! Then Michelle’s breaking a sweat while Sean’s off channeling his inner spa day. After that, it's go-time: emails, social media deep dives, and big-brain biz ideas. Sprinkle in some serious skill-stacking - Sean’s all about that "liquid learning" while Michelle’s earning her degree from YouTube U. Throw in photoshoots, tasting events, admin days and voilà! they’ve officially outworked your average 9-5. Freelance AF? More like Fierce And Full-time.This week's cider pour is Porter's Perfection from our homegrown hero, Heeman's Cellar, right here in good ol' London, Ontario!
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Episode 8: Mythbusters
Throw on that lab coat, grab your safety goggles and get ready to bust some myths, freelancer style! This week, your fabulous neighbourhood hustlers are channeling their inner MythBusters – sorry, no Bigfoot or aliens here (though we’re not ruling out intergalactic side gigs). That means diving into the wild, wacky world of entrepreneurial myths. You know, the kind people love to whisper about behind their lattes, and, even more dangerously, the ones entrepreneurs believe about themselves.Think you have to be rolling in dough, grinding 24/7, or under 30 with a ring light to make it? Think again. Sean and Michelle are calling BS on those tired clichés. They’re breaking it all down, from the “I must do everything myself” delusion to the “success should be instant” fantasy. And don’t even get them started on the obsession with social media followers.Believing a myth now and then? Totally human. Letting it steer your business? Major red flag. Stay sharp, freelancers – these streets are no joke, but with the right mindset (and a handful of sass), you’ve got this!This week’s pour is Reif Estate Winery’s Drea’s Dornfelder, a deliciously smooth and fruity red wine from Ontario’s Niagara wine region!
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Episode 7: Community Totally Slays Competition
Oh, it's that time again! Your favourite freelancer squad is back at it, sipping cider and throwing down the real talk about community vs. competition.After Sean gives Michelle a lesson in "equidistant" (yep, it’s a word), and Michelle takes a victory lap for being the only one who did the homework, the hosts dive into the juicy stuff – why building a solid community of fellow entrepreneurs is EVERYTHING. We’re talking real, no-strings-attached connections, endless support, and finding those ride-or-dies who vibe with your values. Plus, they get real on how even a simple social media interaction or client referral can make a world of difference for a small biz, and how sticking together is the secret sauce to leveling up. Strength in numbers, baby!So grab a zesty drink, kick back, and let’s get into how Community Totally Slays Competition!
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Episode 6: Resourceful AF: A Very Brief Overview
Oh lawd, they comin’!Sean and Michelle are back, bringing the laughs and a dash of wisdom as they chat about their favourite resources!Did you know Michelle might actually work at a library in some parallel universe? Neither did Sean! Between deciding if Michelle’s dream café could survive the current economy (spoiler: it’s touch-and-go) and Sean emphatically declaring that he’s definitely not a vegetarian, they dive into the good stuff. They’re talking the three F’s (nope, not THOSE F’s), small business centres and libraries, and why Canva is their go-to for social media magic. They also share why continuing education is a must, why reaching out to a pro is always worth it, and how having a squad of small biz pals can save you from Thelma and Louise-ing your business off a cliff!Hey, just because they’re Freelance AF doesn’t mean they don’t know how to be Resourceful AF.This week’s pour is Thornbury Craft Co.’s Blood Orange cider, a spectacular cidery-exclusive from Thornbury, Ontario!
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Episode 5: Getting the Brand Together
This week, get ready to roll with our hosts as they work on Getting the Brand Together!Michelle’s in the hot seat, schooling everyone on the importance of branding. She’s quick to remind you that she's all self-taught, but Sean is here to drop the mic by saying that as a branding photographer, Michelle really knows her stuff—like, way more than most.After they totally veer off track discussing the ridiculous winter weather at the time of recording (and whether Sean should be wearing hats that are strictly décor), our Freelance AF duo finally gets into the branding basics module that Michelle created from scratch. We're talking everything from uncovering your brand values (like, don’t be a d***), to figuring out your ideal customer, and how choosing the right colours, fonts, and being consistent can craft a visual story that’s unforgettable, recognizable, and oh-so-authentic to your biz. Of course, it all makes way more sense when you hear it for yourself, so go ahead, give it a listen and discover the real secrets behind branding!This week’s pour is West Avenue Cider House’s Firecracker fire cider, a deliciously rich and robust specialty cider from Ontario’s Golden Horsehoe!
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Episode 4: Bossin' it from the Start
Oh, it’s on! This week our Freelance AF hosts are about to drop some tips on how to kickstart your own business.Let’s face it – turning your entrepreneurial dreams into a reality can feel pretty daunting, especially if you’re a newbie. But hey, every business owner has been there, and getting started with a solid foundation is key to cruising through the chaos.Big surprise, Sean and Michelle were total opposites in how they started out – one went with the flow, the other plotted every move. This episode they’re chatting about why you should build your network, when to ask for advice (professionally or not), and the importance of always doing your homework. While it’s not an exhaustive guide, these two are pointing fresh freelancers in the right direction – no matter your hustle – so you can be bossin’ it from the start!This week's pour is Ardiel Cider House's Apple Dry Cider! Hailing from Beaver Valley in Ontario's Blue Mountains, this classic dry cider features rich apple flavours and balanced acidity, with a crisp, clean finish.
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Episode 3: Corporate Escapees - Part 2
Our hosts are back at it, ready to sip some cider and uncover the juicy details of Michelle's career in the conclusion of this two part series! Spoiler alert: she's all about commitment!Even though her career aspirations changed faster than she switched outfits (classic Libra move), she was in it for the long haul with her employers. Michelle spills the tea on enjoying her time in the corporate grind and what it was like working for an employer that valued her hard work. Of course, it wasn't all sunshine and rainbows - Michelle gets real about craving flexibility to be there for her family, not being a morning person, and working like a boss until the job was finally done!Other hot topics? How to pivot your business when the world throws a curveball (looking at you, COVID), staying true to your vibe on socials, and the never-ending learning that comes with being Freelance AF!(This episode and the last ran a little longer than anticipated, but rest assured our episodes will return to their 20-30 minute target next week.)
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Episode 2: Corporate Escapees - Part 1
Your favourite corporate escapees are back in the first of a two part series to tell the tale of how they broke free of their corporate overlords' chains and struck out on their own to become freelance AF.Michelle and Sean start by fulfilling a promise from the first episode - to have a drink! This episode's pour is Duntroon Cyder House's Empire Extra Dry cyder, a deliciously dry offering that is similar to a traditional English cyder.From there, Michelle delves into a thought-provoking series of questions, tracing Sean's career journey from his childhood aspirations to the corporate role he held before launching his own business. They discuss the peaks and valleys of working in both large corporations and small enterprises, highlighting the invaluable insights diverse work experiences offer budding entrepreneurs. Sean opens up about his mental health journey, reflecting on how he discovered the right mindset and strategies to realize his career ambitions. He concludes the interview with three pieces of advice he would give to his pre-entrepreneurial self.
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Episode 1: Episode 1 - Allow Us to Introduce Ourselves
The journey begins!Join Sean and Michelle as they introduce themselves and the podcast, setting expectations for what's to come. Topics include their "meet cute," why they decided to do a podcast and a not-so-serious explanation of why they believe they're qualified to speak about being entrepreneurs! Laughter, compliments and tangents abound!
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ABOUT THIS SHOW
Freelance AF is a cheeky peek behind the curtain into the world of being your own boss! Join freelancing friends Sean Kelly (owner and founder of Barrel to Basket, a wine and cider tasting event company) and Michelle Elliott (professional brand photographer, and owner and founder of MEE Photography) as they dive into the nitty gritty of owning a small business. These intrepid hosts cover a range of topics - like crucial steps to starting your own business, the importance of developing your brand, and how to stay organized - all while laughing and drinking, and never taking themselves too seriously. From the corporate world to becoming entrepreneurs, Sean and Michelle share their successes and struggles to help you find your own path to freelance freedom. Whether you're an established business owner, or just starting on your journey, their hope is to impart some semblance of wisdom on you - or at the very least show you what NOT to do! Episodes release weekly and occasionally featu
HOSTED BY
Sean Kelly & Michelle Elliott
CATEGORIES
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