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

  • Feeling Stuck? How to Restart Your Momentum

    If you've been feeling frustrated in your business—stuck, spinning, or wondering why things aren't moving the way you hoped—you're not alone. In this episode, I'm sharing a very real behind-the-scenes look at my own journey this year… including the moment when all my momentum stalled and what I decided to do about it.

    I'll also share with you how to create your own list of small, doable steps so you can commit to taking action every day this month. You don't have to control the outcome—you only have to control what you do next.

    And if one of the actions you want to take is building your online course or membership in 2026, I invite you to join me inside the Build It Better Accelerator. It's a 90-day hybrid program where I walk alongside you as you build, refine, and launch your online program using the same proven process I use for my private clients. Exclusive pricing is available through December 12th. I'd love for you to join me!

    16 min
  • More Than Strategy: How Community Fuels Real Progress

    If you're feeling tired, stuck, or strangely disconnected in your business right now, you're not alone. Many entrepreneurs are realizing something deeper is happening beneath the surface — it's not a strategy problem, it's a community problem.

    In this episode, we explore the real power of community in our personal lives and businesses — why it's essential, what it looks like, and how to begin reconnecting when you've been in your own bubble for too long. You'll also receive several simple next steps you can take this week to create more meaningful connection in your life.

    If you've been craving support, connection, or just don't want to do this alone anymore… 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.

    24 min
  • 5 Simple Habits to Reduce Overwhelm in Business

    If you've an entrepreneur or business owner who has been feeling stretched thin or constantly reacting to everything around you, you're not alone. In this episode, I share five simple habits that have helped me reduce overwhelm and stay focused even when life and business feel chaotic.

    These habits are not about adding more to your plate or following complicated systems. They are small, practical changes that help you protect your time, quiet the noise, and make space to breathe.

    If you've been juggling client work, strategy, and content creation, or just trying to keep up, this episode will help you take charge of your work instead of letting your work take charge of you.

    Connect With Jen

    Let's connect on Instagram or LinkedIn.

    24 min
  • The Heart of Selling: What You Actually Sell

    Most entrepreneurs think they're selling their product or service—but that's not what your audience is really buying. In this episode, we dive into the second key shift that brings clarity and confidence to every offer you make. You'll learn how to identify the true results and transformation your clients want, so your messaging connects and your sales conversations feel effortless. Once you understand what you truly sell, every piece of your marketing will make more sense.

    Master Your Messaging

    Do you need clarity and confidence around your message? My Messaging Matrix helps you uncover what your audience truly needs to hear and how to say it in a way that resonates.

    BOOK YOUR STRATEGY CALL NOW

    17 min
  • The Heart of Selling: Rethinking What Selling Really Is

    If the word "sales" makes you cringe, you're not alone. In this episode, I unpack the first fundamental shift that will change the way you think about selling forever. You'll learn how to separate the idea of sales from manipulation, redefine it as an exchange of value, and see how this shift can restore your confidence and integrity as a business owner. This conversation will help you see that selling isn't in opposition to serving—it's actually an extension of it.

    Master Your Messaging

    Do you need clarity and confidence around your message? My Messaging Matrix helps you uncover what your audience truly needs to hear and how to say it in a way that resonates.

    BOOK YOUR STRATEGY CALL NOW

    14 min
  • How to Stop Undermining the Business You're Building

    Have you ever realized you're the one standing in your own way? In this episode, I talk about how we unintentionally undermine the very business we're trying to build. I share a moment when I almost sold out on the vision I had for my future and what it taught me about self-sabotage, alignment, and growth.

    If you've ever lowered your prices, said yes to something that no longer fits, or clung to what's familiar instead of stepping into what's next, this conversation is for you. We'll unpack what self-sabotage can look like for entrepreneurs, how to recognize the tension when it shows up, and what to do about 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.

    15 min
  • The Truth No One Tells You About 10K Months

    Can you really make $10,000 a month with an online course or membership? Is that goal realistic—or just clever marketing? Why do we see those headlines everywhere, and what do they leave out of the story?

    In this episode, I pull back the curtain on the "10K month" promise and share some truths that don't always make the highlight reel. If you've ever compared yourself to those big claims and wondered what's real, this conversation is for you.

    Want to learn how to build an online program that gets people results? Join me for my free Build it Better virtual workshop.

    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.

    25 min
  • What Three Years in Business Taught Me About Growth, Grit, and Trusting Myself

    I'm celebrating a milestone—three years of building this business—and in today's episode, I'm reflecting on the journey. It's been filled with unexpected turns, slow seasons, and hard-won clarity. Along the way, I've learned some powerful lessons that have shaped how I show up as an entrepreneur and how I help others build programs that actually work.

    In this episode, I talk about:

    • The power of taking action before you feel ready

    • Why you are the best expert for your audience (not the voices online)

    • And how giving something 90 days of consistent effort can lead to real clarity

    Whether you're just starting out or a few years in, I hope these lessons encourage you to keep going—and to trust yourself more in the process.

    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.

    17 min
  • The Secret Ingredient to Getting Your Projects Done: Deadlines!

    Can you imagine a world without deadlines? At first, it might sound freeing—no more pressure, no last-minute scrambles—but without them, our lives and businesses would look very different. Deadlines guide our actions, help us prioritize, and ensure we actually cross the finish line on the projects that matter most.

    In this episode we explore:

    • 3 key reasons why we resist
    • how deadlines liberate rather than limit

    and so much more!

    If creating a new lead magnet or launching an online program has been something you've been working on for the last year or two but still haven't brought it across the finish line, let's connect.

    You have something important that your people need, let's talk about how we can actually make that happen, both for your benefit and for theirs. Schedule your free discovery call with me and let's get this done!

    17 min
  • Should You Hire Someone to Build Your Course or Membership?

    So you're ready to get your course or membership out into the world…but should you hire someone to help you do it?

    In this episode, I walk you through the honest questions to ask yourself before deciding whether to DIY or get professional help. We talk about what it really takes to build and launch a course or membership—beyond just recording some videos and uploading them to a platform.

    If you've ever thought:

    • Can I do this on my own?

    • Do I need strategy or tech support—or both?

    • Is it worth the investment to hire someone?

    …this conversation is for you.

    We'll explore the pros and cons of each path, what to expect from a "done for you" service (spoiler alert: it's actually a "done with you" partnership), and how to make the right decision based on your time, energy, desire, and goals.

    Need strategic guidance without the full build? Book a 90-minute strategy session with me.

    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.