Friend, have you ever found yourself stuck in that "waiting place"?
You know the one. Waiting for the right timing. Second-guessing yourself. Paralyzed by fear. Stuck between knowing what you want and actually doing something about it.
My guest today, Jeanne Olmor, knows that place intimately. And she's going to show you how to break free.
Jeanne's story will blow your mind:
At 54, she was a single mom, a coach for 8 years, drowning in debt. All the old strategies—networking, speaking, endless hustle—weren't creating the income she needed.
Then one morning, a voice in her head asked: "If not now, when?"
She couldn't answer it. Next year? Two years? Six years when she'd be 60 and still broke?
So she got out of bed and decided: NOW.
What happened next? She got online, learned organic social media marketing, and hit $1 million in 17 months at 92% profit—with no ads, no funnels, barely any branding.
But here's what makes Jeanne's story so powerful: It wasn't luck. It wasn't magic. It was a mindset shift.
In this episode, Jeanne reveals:
The universal disease keeping entrepreneurs stuck: Over-fear. We're all afraid, but when fear paralyzes you from taking action, you're living in anxiety and torture.
The two types of people: Those who SAY they want success but won't do what it takes (illegal, immoral, or unethical aside). And those who will do whatever it takes. Which one are you?
Why "I'm waiting until..." is a trap: Waiting for more clarity, more money, the right time, perfect conditions—these are excuses dressed up as wisdom.
The commitment test: On a scale of 1-10, how committed are you to getting what you want? If you're at a 5, you're neutral. You don't actually want it enough.
Her "make lemonade" philosophy: When she paid $10K for a program that didn't deliver, she didn't complain. She asked, "How do I make this work?" That attitude changed everything.
The clarity exercise anyone can do: Get a piece of paper. Write two columns: What I DON'T want and What I DO want. Then ask yourself: Do I want this enough to invest? To take action? If not, scratch it off.
The WHO, not HOW principle: Stop trying to figure everything out yourself. Time is the one thing you can't get more of. Find the person who knows what you need and collapse time.
Why "it's all within you" is nonsense: If everything were within us, we wouldn't need law school or medical school. You need guidance, mentorship, and expertise you don't have.
The dating analogy for hiring help: One bad accountant doesn't mean you give up. You keep interviewing until you find the right one. Same with coaches, service providers, everything.
Jeanne's non-negotiables as a single mom: She never lowered her standards. No TV babysitting her kids. No skimping on their activities and education. No settling for mediocrity. That mindset translated to her business.
The power of "even when I lose, I win": When things go wrong, suspend judgment. Look for the arc of the story. Often what seems like failure is actually redirection.
The harsh truth about wanting success: If you're not willing to invest time, money, or energy... if you love talking about your dreams more than executing them... you need to be honest with yourself. Maybe you'd rather just have a job. And that's okay. Just stop torturing yourself with the in-between.
My favorite moment:
Jeanne said, "The worst place to be is unclear in any part of your life. You've got one foot in, one foot out. That's purgatory."
She's right. And if you're living in that purgatory right now—saying you want to build a business but not taking action—this episode is your wake-up call.
The question you need to answer today:
If not now, when?
Really answer it. Not next year. Not when conditions are perfect. Not when you feel ready.
When?
Because if you can't answer that question with anything other than "now," you're lying to yourself about how badly you want this.
Listen to this episode. Let Jeanne's story shake you out of complacency.
Then decide: Are you going to stay stuck in the waiting place? Or are you going to move?
ABOUT JEANNE OLMOR:
Jeanne Olmor is a business coach specializing in helping coaches, consultants, and service providers build profitable online businesses. After 8 years of traditional coaching that left her deep in debt as a single mother, Jeanne learned organic social media marketing at age 54 and scaled to $1 million in revenue in just 17 months—at 92% profit margins—without ads, funnels, or fancy branding.
Now she helps hundreds of clients replicate her success using simple, organic strategies that actually work. Jeanne is known for her no-nonsense approach, her "make lemonade from lemons" philosophy, and her ability to simplify complex business strategies into actionable steps.
She's also a fierce advocate for maintaining high standards in both business and life, proving that you don't have to sacrifice what matters most (like being present for your kids) to build a thriving business.
Connect with Jeanne:
Lindsay Sutherland is a business consultant, speaker, and entrepreneur dedicated to helping business owners build companies that run with freedom, purpose, and profit. With over 20 years of leadership and sales experience in the automotive industry, Lindsay understands the challenges of growing a business that feels more like a burden than a blessing. After leaving corporate life, she co-founded Biz in a Box Solutions, a CRM and automation company that empowers small service-based businesses to streamline their operations and reclaim their time.
Her signature consulting program, The Clockwork Method, guides overwhelmed business owners through the process of systemizing, scaling, and stepping back into the true role of visionary leader. Lindsay’s approach blends practical business systems with faith-led alignment, helping entrepreneurs not only make more money but also create a business that supports their life — not the other way around.
As the host of The Freedom Entrepreneur Podcast, Lindsay shares strategies, stories, and mindset shifts that challenge conventional thinking and inspire business owners to grow without burning out. She also co-owned Off Grid Unlimited Installations, an electrical and renewable energy company in Idaho, where she lives with her husband and four children on their family farm.
Passionate about redefining success beyond hustle culture, Lindsay helps leaders build businesses rooted in clarity, sustainability, and freedom. Whether she’s speaking on stage, consulting with executives, or mentoring faith-led entrepreneurs, her mission is the same: to help people transform their business into a vehicle for purpose, profit, and lasting impact.
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Biz in a Box CRM is the ultimate all-in-one solution designed to simplify and scale your business. Imagine managing every aspect of your operations — from smart contact segmentation and automated follow-ups to call and text functionality, calendar booking, funnels, websites, and even social media scheduling — all from one intuitive platform. No more juggling multiple tools or paying for endless subscriptions. With built-in AI employee support, Biz in a Box CRM doesn’t just organize your business, it actively helps you run it. It’s like having a full-time team behind the scenes, so you can focus on growth, impact, and freedom.
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