Freelance AF Podcast By Sean Kelly & Michelle Elliott cover art

Freelance AF

Freelance AF

By: Sean Kelly & Michelle Elliott
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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 2026 Sean Kelly & Michelle Elliott
Economics Leadership Management & Leadership
Episodes
  • Episode 3: What it Costs to be the Boss
    Mar 17 2026

    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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    29 mins
  • Episode 2: From Hot Mess to Progress
    Mar 10 2026

    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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    20 mins
  • Episode 1: Sassy B*tches Say What?
    Mar 3 2026

    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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    24 mins
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