Freelance AF Podcast By Sean Kelly & Michelle Elliott cover art

Freelance AF

Freelance AF

By: Sean Kelly & Michelle Elliott
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About this listen

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 feature guest interviews with friends and fellow business owners.

So hand in that key card and hit 'send' on your sassy resignation letter, and prepare to be Freelance AF!

Copyright 2025 Sean Kelly & Michelle Elliott
Economics Leadership Management & Leadership
Episodes
  • Episode 17: Journal Like a Mother with Jessie Daypuck
    Jun 17 2025

    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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    54 mins
  • Episode 16: B.D.E. (Big Dad Energy)
    Jun 10 2025

    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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    36 mins
  • Episode 15: Mind Your Boundaries, Betch
    Jun 3 2025

    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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    36 mins
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