Business Your Way

Caryn Gillen
  • 5.0 (115)
  • Business
  • Updated Weekly

Business Your Way is a podcast for those of us who have always done things in our own way. This show offers quick perspective shifts from Caryn, ideas that crack something open for you from a guest, and live coaching. It’s the relevant, interesting, permission-giving stuff you want to hear about because it will create more space for you to do business YOUR way! ⇒ Follow Business Your Way on your favorite podcast platform, then leave us a rating and review. Thanks for listening!

  1. 3d ago

    224: 475 "Ordinary" Business Owners Tell the Truth with Jessica Freeman

    In this episode of Business Your Way, host Caryn Gillen sits down with Jessica Freeman – the founder of Jess Creatives and The Ordinary Business Network – to break down the results of her third annual State of Online Business Survey, based on responses from 475 service providers. They get into: - The crucial difference between revenue and profit - The surprising gap between people's public success stories and what the data actually shows - What remains people's number one lead source, three years running - The thing that actually generates clients - What nearly every respondent is walking away from and prioritizing this year can use it to build your business around what's actually working in 2026. Or, do as Jess does, and use the data to support your own marketing and sales pages! View the State of Online Business Survey 2026 results here: https://theordinarybusiness.com/state-of-online-business-survey-2026/ Book your Checkpoint Session here: https://caryngillen.com/checkpoint ----- ** If you enjoyed this episode, make sure to hit that subscribe button, share it with a friend, like and/or leave a comment. I appreciate each one! ** ----- Jess Freeman is the founder of Jess Creatives and The Ordinary Business Network. While she designs for health and fitness experts, The Ordinary Business Network is for all types of service providers who want to focus on becoming better, not bigger. Learn more about and connect with Jess at: theordinarybusiness.com jesscreatives.com ----- To learn more about and connect with host Caryn Gillen, visit: https://caryngillen.com/ Caryn is a Master Leadership and Business Coach who asks really great questions to help people clarify their next move, holding space for them as they do it. ----- Tags: online business survey, online business owner statistics, state of online business, business strategy, business coaching podcast

  2. Aug 12

    223: The Operating System Behind Every Successful Coaching Business

    What if running your business came down to just 5 repeatable steps? In this episode of Business Your Way, I pull back the curtain on the exact operating system I use when coaching entrepreneurs, life coaches, and small business owners. I break down my signature 5-step framework: See, Decide, Move, Learn, and Adjust, and describe how to apply it to the 5 core areas of any coaching business: lead generation, nurturing, sales, client delivery, and resell/upsell.  This episode may just change how you look at and interact with your business – and it's only 11 minutes long. Such a win! Learn more about The Advisor Circle at caryngillen.com/advisors-circle In this episode: The 5-step business operating system: See, Decide, Move, Learn, AdjustThe 5 core areas of every coaching businessHow to assess your business data without self-judgmentWhy "the next best step" beats a perfect long-term planA real client story: from consistent posting to a qualified leadWhy quitting what doesn't work is a superpower, not a failure tags: business operating system, coaching business framework, life coach business tips, small business strategy, entrepreneur mindset

  3. Aug 5

    222: Your Voice Builds Trust – The Human Advantage Roundtable

    Your written content can only take a relationship so far. When someone hears you think or speak out loud, on a podcast or from a stage, they get a sense of you that no blog post or social caption alone can replicate. That's the moment a stranger starts to trust you before you've ever spoken one-on-one. In this roundtable, host Steph Walker of Clarity Web Design Studio sits down with Kimberly Lyall (a keynote speaker and leadership facilitator) and me, Caryn Gillen (thought partner/coach and podcast host). Together, we dig into: - Why your spoken voice changes the way people relate to you - How to start when doing so feels like a huge leap - What actually turns a one-time appearance into a real relationship instead of just exposure Plus: - Why you don't need the whole marketing engine before testing whether an idea connects - Why a real conversation beats a polished PDF - Why your website has to match the person people just heard speak Takeaway quotes: "Relax and BE YOU. It sounds simple, but it's so hard!" "Say what makes you nervous (but you know is true and matters)." This conversation was originally part of The Human Advantage roundtable series. Tags: building trust with your voice, personal brand visibility, business roundtable podcast, turning listeners into clients

  4. Jul 26

    Feeling Stuck on a Big Decision?

    When you've done the internal work, but need someone else in the room. You know that feeling, when you've been sitting with a big decision for weeks, maybe months. You've done the internal processing. You know something needs to change. But you haven't said it out loud to anyone yet, because the people closest to you have a stake in what you decide. That's exactly what Checkpoints are for. In this episode of Business Your Way, Caryn introduces a brand new private coaching offer: a 90-minute one-on-one session designed for high achievers, coaches, entrepreneurs, and leaders who are at a pivot point and need a thought partner with no agenda. Think of it like a pit crew for a high-performance race car. The more you're performing at a high level, the more often you need fine-tuning to keep going at your best. Whether you're stepping into a new season of life or leadership, weighing a consequential move, or just need someone to think it through with you from angles you haven't considered — this is that space. No homework. No pressure. Just 90 minutes with Caryn's full attention, intuition, and curiosity on your biggest thing. The session also includes a week of follow-up via audio and text, so when the "ahas" hit after the call, you've got somewhere to put them. Founding price is $199 (goes up to $300 after July 29th). Book at caryngillen.com/checkpoint. This episode covers: What a Checkpoint Session is and who it's forWhy high achievers often can't think through big moves with the people closest to themHow the pit crew model applies to business and life decisionsWhat to expect from 90 minutes of private coaching with CarynWhy this is also a low-risk way to experience coaching with Caryn if you've been curious 🎯 Ready for your checkpoint? Book at caryngillen.com/checkpoint before July 29th to lock in the founding price. tags: private coaching session, high-performance coaching, business decision making, thought partner, business clarity session

  5. Jul 22

    221: The Saboteur Voice in Your Business and How to Stop Listening to It

    This episode is a clip from one of Caryn's small group coaching calls. The conversation was too good NOT to share! If you've ever looked at your coaching business and thought "I should be further along by now" or "maybe I'm just not cut out for this" — this episode will stop you in your tracks in the best way. These thoughts are among the most universal in entrepreneurship. And they're so relatable! Who here hasn't wondered if anyone else struggles with imposter syndrome, or feels like they're bad at business sometimes? The good news: You're not bad at this; you're probably just new at it, or being too hard on yourself. This conversation digs into why coaches and small business owners tend to be far harsher on themselves in business than they ever were as employees, how to redefine what success actually looks like when you're the one setting the bar, and why internal growth and progress are often reason enough to keep going — even before the external results show up. If your saboteur voice has been loud lately, this one's for you. Send it to a friend who needs to hear it, too! Topics covered: Why imposter syndrome hits differently when you run your own businessReframing the "I should know this by now" storyTying success to internal growth, not just external resultsHow to be the best boss and best employee you've ever had — to yourselfChanging your relationship with what it means to be a business ownerUsing internal listening as a measure of success 👥 Want a thought partner and mindset/business coach to be in it with you, or to join this incredible small group, The Advisors Circle? Book a sales call with Caryn here. [⁠https://clients.caryngillen.com/public/appointment-scheduler/6560fa439474035a892b07c7/schedule⁠] Tags: imposter syndrome coaches, coaching business mindset, life coach business tips, group coaching, coaching business podcast

  6. Jul 15

    220: The Invisible Line Between Working For Yourself and Owning It with Melisa Liberman

    In this episode, Caryn talks with business coach for independent consultants Melissa Liberman about the identity shift that changes everything — the moment you stop operating like an employee (or an extra pair of hands) and start actually owning your business. Melissa shares her own journey from an unplanned side gig to a thriving business, the exact moment she stopped dropping everything at a client's whim, and why she believes mindset, not strategy, is 80% of what makes a business succeed. Caryn and Melissa dig into: imposter syndromethe courage it takes to make big decisionssetting audacious goals instead of "safe" oneshow to stop fighting for your limitations and start fighting for what's possible ----- ** If you enjoyed this episode, make sure to hit that subscribe button, share it with a friend, like and/or leave a comment. I appreciate each one! ** ----- To learn more about and connect with Melisa, visit: https://www.melisaliberman.com/ Her podcast, Grow Your Independent Consulting Business, is on all major platforms. ----- To learn more about and connect with host Caryn Gillen, visit: https://caryngillen.com/ Caryn is a Master Leadership and Business Coach who asks really great questions to help people clarify their next move, holding space for them as they do it. ----- Tags: business owner mindset, identity shift in business, independent consultants, stop working like an employee, business coaching podcast

  7. Jul 8

    219: Stop Doing What No Longer Serves You: A Coach's Guide to Quitting

    Is it time to quit something? In this episode of Business Your Way, host Caryn Gillen challenges coaches and small business owners to audit their weekly habits and ask one simple, but powerful question: "Would I choose this again?" Does what you're doing now get you to where you're going? Caryn breaks down why we cling to habits, routines, and commitments long after they stop serving us, not because they're working, but because we've always done them. She shares her favorite "house-clearing" tip for deciding what to keep and what to release and walks through how to spot the difference between things that drain your energy vs. things that grow you (and your business). ----- Need clarity on what to quit or accountability in actually doing it? Book a call with Caryn here. [⁠https://clients.caryngillen.com/public/appointment-scheduler/6560fa439474035a892b07c7/schedule⁠] You can also connect with her on Instagram or LinkedIn: @caryngillen ----- ** If you enjoyed this episode, make sure to hit that subscribe button, share it with a friend, like and/or leave a comment. We appreciate each one! ** ----- Tags: business coaching podcast, energy management, quitting habits, growth mindset, productivity for solopreneurs

  8. Jul 1

    218: You Can't Coach From Empty – The Elite Athlete Mindset for Business Owners

    In this episode of Business Your Way, host Caryn Gillen explores what life coaches and small business owners can gain by treating themselves like elite athletes. She breaks down what high performance really requires: honest self-awareness about your energy limits (like knowing you're a "one-experience-a-day" introvert), rejecting depletion as a badge of honor, and building personal systems (so you stop relearning the same lessons about what works for you). Can anyone relate?! 🫠 In this episode, we get into: Why "what are you training for?" is the most important business question you're not askingHow to identify your personal energy rules (social limits, screen time, rest needs)Reframing self-care as performance fuel, not indulgenceBuilding systems so you stop hitting the same walls over and overHow to show up for your clients and your business without burning out----- 👥 Need clarity, a "training plan," or accountability? Book a call with Caryn here. [⁠https://clients.caryngillen.com/public/appointment-scheduler/6560fa439474035a892b07c7/schedule⁠] ----- ** If you enjoyed this episode, make sure to hit that subscribe button, share it with a friend, like and/or leave a comment. I appreciate each one! ** ----- Tags: self-care for business owners, entrepreneur burnout, how to sustain energy in business, coaching business growth strategies

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5
out of 5
115 Ratings

About

Business Your Way is a podcast for those of us who have always done things in our own way. This show offers quick perspective shifts from Caryn, ideas that crack something open for you from a guest, and live coaching. It’s the relevant, interesting, permission-giving stuff you want to hear about because it will create more space for you to do business YOUR way! ⇒ Follow Business Your Way on your favorite podcast platform, then leave us a rating and review. Thanks for listening!

Information

  • Creator
    Caryn Gillen
  • Years Active
    2021 - 2026
  • Episodes
    231
  • Rating
    Clean
  • Copyright
    © Caryn Gillen
  • Show Website
    Business Your Way

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