Our Entrepreneurial Lives | The Struggle and Strategy of Building a Business

Our Entrepreneurial Lives | The Struggle and Strategy of Building a Business

By Jen Howat and Erica BollingerBusinessEntrepreneurshipMarketing
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Our Entrepreneurial Lives | The Struggle and Strategy of Building a Business episodes

  • What Should You Charge for Your Course or Membership?

    Have you ever found yourself staring at your course or membership wondering… What in the world should I charge for this?

    You're not alone. Pricing can feel confusing, emotional, and even paralyzing—but it doesn't have to be.

    In this episode, I'm breaking down the three essential questions to ask when setting the price for your offer. Whether you're just getting started or you're refining an existing program, these questions will give you a solid foundation to work from:

    • Where does this offer fit in your business? Is it your signature program or a stepping stone in a larger ecosystem?
    • How much of you do they get? Remember: the more of you they get, the higher the price should be.
    • What's the value of the transformation? It's not about how much content you include—it's about what's at stake for your audience.

    If pricing has been a stumbling block and had you second guessing yourself—this episode is for you!

    Connect With Jen

    Let's connect on Instagram or LinkedIn.

    Are you wondering if you should build an online course or membership? Schedule your free discovery call with me and get clarity on what to do next.

    15 min
  • When Overwhelm Hits: How to Realign Before You Burn Out

    Do you ever feel like you're doing all the things—but still feel like you're barely keeping up?

    In this week's episode of My Entrepreneurial Life, I'm talking about a feeling most of us know too well: overwhelm.

    You'll learn:

    • The difference between busy and overwhelmed (and why it matters).

    • Why overwhelm is actually a helpful signal.

    • A few powerful questions to help you realign your business and life.

    Your business should help you be more of the person you were created to be, not less. So come and join me in this candid conversation. It might just spark the change you desperately need.

    Connect With Jen

    Let's connect on Instagram or LinkedIn.

    Are you wondering if you should build an online course or membership? Schedule your free discovery call with me and get clarity on what to do next.

    15 min
  • What to Look for When Choosing a Platform for Your Course or Membership

    If you're thinking about getting your course or membership out into the world—but feel stuck trying to choose the "right" platform—this one's for you.

    In this episode, I break down the 6 essential features your platform must have to give your audience a great experience and keep your business running smoothly. We're talking about what really matters—things like:

    A flexible course builder Multimedia support Built-in marketing tools Smart automations …and more.

    This is a strategic conversation to help you move forward with clarity instead of staying stuck in decision mode.

    You've got what it takes to build something great—and the right platform can make all the difference.

    Connect With Jen

    Let's connect on Instagram or LinkedIn.

    If you want to try Kajabi for yourself, I'm a Kajabi partner which means I am able to offer a 30-day free trial and small commission from Kajabi. To make sure you know how to get started, I also offer a free 60-minute strategy session with me. This way you can explore the platform, ask your questions, and see if it's the right fit for your business.

    Start your free trial here: jenhowat.com/kajabi

    15 min
  • What I Wish You Knew: Lessons to Create Your Course or Membership With Confidence

    If you've been thinking about builidng an online course or membership but feel stuck, this episode is for you. So many business owners hesitate because they want everything to be just right before taking action. But waiting for perfection only keeps you from helping the people who need you most.

    In this episode, I'm sharing six key lessons I've learned from helping business owners successfully create and launch their programs—lessons that will help you move forward with clarity and confidence. We'll talk about:

    • Why you don't need to have everything figured out before you start
    • How keeping it simple creates a better experience for your audience
    • The reason marketing is just as important as your program itself
    • What do to when you might feel like quitting
    • The power of staying focused on your why
    • How trusting the process helps you create a program that truly serves your people

    If you're tired of second-guessing and overthinking, this episode will give you the clarity and encouragement you need to take the next step.

    Connect With Jen

    Let's connect on Instagram or LinkedIn.

    Are you wondering if you should build an online course or membership? Schedule your free discovery call with me and get clarity on what to do next.

    26 min
  • But What If No One Buys? How to Overcome Fear and Take the Leap

    Have you ever had a great idea for an online program, workshop, or offer—only to stop yourself before you even start because of that nagging thought: What if no one buys?

    If that question has been swirling in your mind, you're not alone. But here's the truth: it's not really about sales. It's about something deeper—the fear of failure.

    In this episode of My Entrepreneurial Life, we talk about:

    • Why What if no one buys? is actually a fear of failure in disguise

    • How to move past the doubt that keeps you stuck

    • Why fear isn't a sign you're not ready

    • How to reframe failure as the key to growth

    If launching your online program feels overwhelming, or if fear has been holding you back, this episode is for you.

    Connect With Jen

    If you know an online program is your next step but fear has been holding you back—I'd love to help. Schedule your free discovery call with me and let's talk through it. I promise, you'll walk away with clarity and direction.

    20 min
  • How to Choose a Lead Magnet That Converts

    If you've ever wondered how to create a lead magnet that actually leads somewhere—like straight into your online program—this episode is for you.

    In the final episode of our Build It Better series, we're talking about one of the most powerful tools in your business: the right lead magnet. Not just any freebie, but a resource that helps your audience make progress and naturally leads them to say yes to your course or membership.

    Here's what you'll learn:

    • Why the best lead magnets aren't about format—they're about results
    • The #1 mistake entrepreneurs make when designing a lead magnet (and how to avoid it)
    • Why you should stop worrying about "giving away too much" and start focusing on real value
    • The simple questions you can ask your audience right now to create a lead magnet that truly works

    If you're serious about growing your online program with a strategy that actually converts, this is an episode you don't want to miss! 🎧

    Leave a Review

    I'd love to hear your thoughts about the podcast. If you are finding value, please take a moment to leave a review so others can find it and join our community!

    Connect With Jen

    Let's connect on Instagram or LinkedIn.

    Are you wondering if you should build an online course or membership? Schedule your free discovery call with me and get clarity on what to do next.

    14 min
  • Transform Your Online Program with a Winning Launch Plan

    Have you ever wondered what truly sets a standout online program apart from the rest?

    In my latest podcast episode, "Transform Your Online Program with a Winning Launch Plan," I dive into the essential strategies that will not only help you launch your course or membership with confidence but also position you well ahead of the competition.

    In this episode, you'll learn how to:

    • Harness the Power of Planning: Discover why a well-thought-out launch plan is your secret weapon, reducing overwhelm and ensuring every piece of your program gets the attention it deserves.
    • Strategically Engage Your Audience: Learn how planning 2-3 months ahead primes your audience with valuable content and small wins—so when the launch window opens, they're ready to join you.
    • Boost Your Conversion Rates: Understand how a focused, intentional content strategy can lead to higher conversion rates, helping you achieve both your personal and professional goals.
    • Implement Actionable Steps: From creating transformational stories to crafting a compelling pre-launch content strategy, get practical tips that make your launch both effective and efficient.

    Whether you're creating a self-paced course or a membership program, this episode is packed with insights to help you navigate what to do after you've created your program, so you can truly make an impact.

    Connect With Jen

    Let's connect on Instagram or LinkedIn.

    Are you wondering if you should build an online course or membership? Schedule your free discovery call with me and get clarity on what to do next.

    13 min
  • Build it Better: How Flexibility Can Make or Break Your Online Course or Membership

    Have you ever felt stuck trying to create the perfect online course or membership? You tweak, refine, and delay—only to feel like you're never quite ready to launch? If so, you're not alone.

    The truth is, perfection is a moving target—and the most successful course creators and membership site owners don't get it right the first time. Instead, they build with flexibility.

    Flexibility means launching with a strong foundation but staying open to learning, listening, and refining. It allows you to:

    • Adapt to real feedback and make improvements
    • Keep your course or membership relevant in a changing market
    • Increase engagement and retention by serving your people better

    In this episode we're going to talk about how to let go of the need for perfection and embrace flexibility. Your people will notice—and they'll thank you for it!

    Connect With Jen

    Let's connect on Instagram or LinkedIn.

    Are you wondering if you should build an online course or membership? Schedule your free discovery call with me and get clarity on what to do next.

    20 min
  • Build it Better: Use Imagination to Create Must-Join Program

    It's one thing to say you have an online program—it's another to have one that people actually join. With so many courses and memberships out there, how do you stand out? How do you create something that rises above the noise and becomes the go-to choice for your audience—just like your favorite coffee shop, gym, or brand that you can't live without?

    In this episode, we're kicking off the Build It Better series, where we'll explore what it takes to craft an online program that truly connects and converts. Today, we're starting with the power of imagination—because the best programs aren't just built; they're designed to capture attention and create impact.

    Let's Connect

    Come join the conversation on Instagram or LinkedIn

    Are you wondering if you should build an online course or membership? Schedule your free discovery call with me and get clarity on what to do next.

    13 min
  • Build it Better: Start With the End in Mind

    When creating your online course or membership, it's tempting to focus on the features—templates, video lessons, group calls, and bonuses. But here's the truth: your audience doesn't buy features; they buy results.

    In this episode, we dive into why the key to a high-impact, profitable online program isn't just about what's inside—it's about the transformation you promise. You'll learn:

    • Why every lesson, worksheet, and resource is just a vehicle to get your people where they want to go
    • The two essential questions you must answer before building your course or membership
    • How starting with the end in mind saves you time, energy, and frustration while creating a program people rave about

    If you're ready to stop spinning your wheels and start building an offer your audience can't refuse, this episode is for you. Let's create with intention and turn your knowledge into something truly transformational.

    Connect With Jen

    Let's connect on Instagram or LinkedIn.

    Are you wondering if you should build an online course or membership? Schedule your free discovery call with me and get clarity on what to do next.

    13 min

About Our Entrepreneurial Lives | The Struggle and Strategy of Building a Business

From the publisher's feed

Go behind the scenes with agency owners and friends Jen Howat and Erica Bollinger as they have candid conversations about the struggle and strategy behind building and growing a business and life you love.