Keeping it Real with Gina Keeping: Mindset and Business Coaching for Female Entrepreneurs

What does winning my first football championship in my 40s, after playing for 20 years, have to do with building a successful business?

Turns out... a LOT. 😂

After two decades of playing football, I finally made it to my first championship game and we freaking won.

But this isn't an episode about simply “never giving up” or blindly doing the same thing until it eventually works.

Because here's what I realized:

Staying in the game matters. But staying in the game doesn't mean staying the same.

If I had continued doing exactly what I had been doing, I probably still wouldn't have a championship.

I had to make a hard decision. I changed teams. I changed my environment. I put myself around people who approached the game differently. And then I still had to get on the field and do the work.

Sound familiar?

Because the same thing happens in business.

Sometimes we think consistency means doing the same thing over and over again. We put in more reps, create more content, work more hours and tell ourselves to just keep going.

But not all action is created equal.

Sometimes business growth requires you to stop, look at the evidence and ask whether the strategy you're so committed to is actually taking you where you want to go.

In this episode, I'm sharing what 20 years of football taught me about playing the long game in business, knowing when to pivot, taking radical responsibility for your results, choosing the right environment, and taking intentional action toward the things you say you want.

We're also talking about why your environment matters more than you might realize. Because just like spending all day at a fish market or a perfume shop...

the scent of your environment follows you.

And maybe one of the most important questions you can ask yourself as a business owner is:

What has become normal in the rooms I'm spending my time in?

In this episode, you'll hear:

• Why playing the long game in business doesn't mean doing the same thing forever

• The difference between consistency and effective action

• Why not all action is created equal when you're trying to grow your business

• How to know when it might be time to change your strategy instead of changing your goal

• Why I made the hard decision to change football teams after years of playing

• How your environment can influence your business mindset, standards and actions

• Why putting yourself in the right room is only part of the equation

• What taking radical responsibility in business actually looks like

• Why sometimes you have to stop waiting for the perfect opportunity and go get the freaking ball

• What winning my first championship in my 40s reminded me about success, ambition and feeling like you're “late”

• Why you can want MORE without missing the life and business you're living right now

If you've been wondering whether you should keep going, pivot your business strategy, change something that isn't working, or simply give yourself more time, this episode is for you.

You don't necessarily need to give up on the goal.

You might just need to change the way you're going after it.

Stay in the game. But don't stay the same.

And for goodness sake...

enjoy the freaking game while you're playing it.

Because most of your life happens between championships.

How do you slow down and enjoy your life when you're still an ambitious person who wants more?

Recently, I was at an event when a woman said something to me that caught me off guard:

“You find joy in everything.”

And I remember thinking...

Yeah. I kind of do.

But I worked really hard for that.

Because I wasn't always this way.

There was a version of me who was constantly moving, achieving and chasing the next goal. And after getting sick, I made a decision that completely changed the way I wanted to experience my life.

In this episode, we're talking about how to practice gratitude, romanticize your life, slow down, be more present and actually enjoy the life you're building without giving up your ambition or desire for more.

I’m sharing some of the very real shifts I’ve made in my life, business and relationship with money that have helped me stop constantly rushing toward the next thing and start noticing what's already right in front of me.

We get into:

• Why slowing down and practicing gratitude didn't come naturally to me

• Romanticizing your life beyond the Instagram version of it

• Money, success and what it actually means to live a rich life

• Staying present while still having big goals for your life and business

• Why ambitious women can struggle to enjoy where they are while they're working toward what's next

If you're always thinking about the next goal, the next level or the next version of yourself, this episode is for you.

Because maybe you don't have to choose between being grateful for where you are and wanting more for where you're going.

And maybe, while you're busy trying to get there...

this is the good part too.

What happens when the life and business you’ve built is GOOD… but there’s still a little voice inside you asking:

What if there’s more?

In this episode of Keeping It Real, I’m sitting down with my longtime client, Business Circle member and friend Amanda Dawe, owner of The Natural Emporium.

And friends, this conversation is about SO much more than business.

After eight years of building The Natural Emporium and an incredible community in Newfoundland, Amanda made a massive decision: close the chapter she knew and loved, pack up her life, and take her business to Toronto’s Distillery District.

A dream she had once written down in a journal and quietly tucked away as a “maybe someday.”

But getting the dream didn’t mean everything suddenly became easy.

We talk about the part of growth that doesn’t get talked about enough.

The grief.

The fear.

The moments you wonder if you’ve made a gigantic mistake.

The temptation to stay where things are comfortable because you should be grateful for what you already have.

And the courage it takes to trust yourself when you have absolutely no evidence that the thing you’re stepping into is going to work.

Amanda shares what it looked like to go from being so exhausted she was considering walking away from entrepreneurship altogether… to reconnecting with what she actually wanted and making one of the biggest moves of her life.

We also get into:

✨ The difference between running AWAY from something and moving TOWARD something

✨ Why you can be wildly grateful for what you have and still want more

✨ The very real grief that can come with growth

✨ Making big decisions from your power instead of exhaustion or desperation

✨ The small daily rituals Amanda uses to ground herself and regulate her nervous system

✨ Why comparison can pull you away from the very thing that makes your business special

✨ Learning to trust your intuition when there’s no proof your next move will work

✨ Being willing to not be for everyone

✨ Why celebrating the tiny moments matters just as much as celebrating the giant milestones

✨ And what Amanda has learned about going after a dream at 50

One of my favourite moments in this conversation is when Amanda says:

“Not doing it is a bigger cost than doing it.”

OOF.

Because sometimes the question isn’t:

“What if I do this and it doesn’t work?”

Sometimes the better question is:

“What will it cost me if I never find out?”

This is a conversation about business, yes.

But it’s also about trusting yourself enough to follow the thing that keeps tugging at you.

About realizing you don’t need permission.

About understanding that fear and grief don’t automatically mean you’re on the wrong path.

And about becoming the version of you who is willing to find out what’s possible.

If you’re standing at the edge of a decision, a pivot, a dream or a next chapter that feels exciting AND terrifying…

this episode is for you.

CONNECT WITH AMANDA:

Follow Amanda and The Natural Emporium on Instagram: @EmporiumontheSquare

You can also find The Natural Emporium on Facebook and visit Amanda at her new location in Toronto’s Distillery District.

And make sure you get yourself on Amanda’s newsletter to follow along with this next chapter and everything she has coming.

Feeling overwhelmed, stuck, scattered or like your brain just isn’t braining?

You know those days.

You’ve been staring at the same task for 20 minutes. Your inbox feels personally offensive. Your to-do list is screaming at you. And somehow your solution is to sit there, get increasingly frustrated and tell yourself to JUST FREAKING FOCUS.

Yeah. That usually works really well. 😂

If you’re feeling overwhelmed at work or in your business, your instinct might be to push harder, work longer or force yourself to focus.

But sometimes the most productive thing you can do is actually stop.

In this episode of Keeping It Real, I’m sharing the simple reset I use when I catch myself spinning, overthinking, procrastinating or staring at my computer wondering where the hell my ability to think went.

It takes 10 minutes or less and comes down to three simple things:

MOVE → SHIFT → ANCHOR

We’re talking about why you can’t always think your way out of an emotion, how overwhelm can trick you into feeling productive when you’re actually just spinning, and why taking a few minutes to reset can help you come back calmer, clearer and ready to actually move forward.

Because one crappy moment does not need to turn into a crappy day.

In this episode, we’re talking about:

• What to do when you feel overwhelmed and can’t focus

• Why pushing through stress and overwhelm can actually make you less productive

• How overthinking can keep you stuck in a cycle of indecision

• Why changing your physical state can help you reset your mind

• My simple Move → Shift → Anchor method

• How to reset your day in 10 minutes or less

• Why stepping away from your work isn't necessarily wasting time

• How to stop one frustrating moment from derailing your entire day

• Why managing your energy can be just as important as managing your time

If you’ve been feeling overwhelmed, mentally stuck or frustrated because you know what you need to do but cannot seem to make yourself freaking do it, this episode is for you.

Before you write off the whole day, try the reset.

Move your body.Shift your mind.Anchor back into what matters next.

You might be surprised by what 10 minutes can change. ❤️

🔥 COURSE CREATOR BOOTCAMP DOORS OPEN THIS MONTH!

If you’ve been thinking about turning what you know into a digital offer, Course Creator Bootcamp doors are opening THIS MONTH!

I’m only taking 20 new students, and if you’re on the waitlist, you’ll save $500 AND get first dibs on one of those limited spots.

👉 Hop on the Course Creator Bootcamp waitlist here.

What if the secret to building a successful, scalable business… was making it a little more boring? 😂

Hear me out.

So many entrepreneurs build businesses that rely on constant launching, creating new offers, chasing clients, posting like maniacs, and basically running on adrenaline.

It might feel exciting for a while.

But it’s also a really freaking good recipe for inconsistent income, feast-or-famine cycles, and eventually… burnout.

In this episode of the Keeping It Real Podcast, I’m breaking down why I believe a simple, predictable, repeatable business model is one of the smartest things you can build if you want more consistent revenue AND more freedom.

We’re talking about how to stop reinventing your business every month, why having an anchor offer can simplify your marketing and sales, and how digital assets can help you scale your income without continuing to trade more of your time for money.

But we’re also going a little deeper.

Because your business was never meant to be your entire freaking life.

It doesn’t need to provide all of your creativity, purpose, identity, joy AND income.

Sometimes the goal is to let your business be steady so YOU have more space to actually live.

In this episode, we’re chatting about:

• Why constantly chasing new ideas can keep your business stuck

• The difference between a business that runs on adrenaline and one built on systems

• How an anchor offer can create more predictable revenue

• Why digital assets can help you build a more scalable business

• The sneaky entrepreneur trap of confusing excitement with progress

• Why your business doesn’t need to fill every bucket in your life

• How simplifying your business can create more time, energy, creativity, and freedom

If your business currently feels like a roller coaster of create → sell → deliver → panic → repeat, this episode is for you.

Because building a sustainable business doesn’t mean building a boring LIFE.

Quite the opposite.

Build stability in your business so you can have excitement in your life.

And if you’re listening to this thinking, “Okay Gina, I KNOW I need a digital asset in my business…” 👀

The Course Creator Bootcamp waitlist is open and this is where I’ll help you take what you know and turn it into a digital offer you can actually sell on repeat.

🔥 Join the Course Creator Bootcamp waitlist here:

Because the goal isn’t to keep adding more work to your plate.

It’s to build something that can make money without requiring more and more of your time.

🎧 Hit play and let’s talk about what it really takes to build a business that supports the life you actually want.

The Side of Growth Nobody Talks About: When Choosing Yourself Hurts

What if setting the boundary was the right thing to do… but it still feels absolutely awful?

We talk a LOT about growth, healing, setting boundaries and choosing yourself.

But we don’t talk nearly enough about what happens after you start doing it.

The guilt.

The second-guessing.

The relationships that start to change.

The people who don’t understand the new version of you.

And the grief that can come with realizing that not everyone is meant to come with you.

In this episode of the Burn the Rule Book Summer Series, we’re talking about the side of personal growth that doesn’t usually make the highlight reel.

Because sometimes growth doesn’t feel like a breakthrough.

Sometimes it feels like a breakup.

You’re breaking up with the version of you who kept the peace.

The people pleaser.

The fixer.

The one who over-gave, over-explained and said yes when she really wanted to say no.

And when you stop playing the role everyone is used to you playing, not everyone is going to celebrate it.

That doesn’t automatically mean you’re doing something wrong.

In this episode, I’m talking about what really happens when you start setting boundaries, choosing yourself and raising the standards for your life, including:

• Why healthy boundaries can still feel painful, uncomfortable and even heartbreaking

• The guilt and second-guessing that can happen after you finally say no

• Why personal growth can change your friendships, family dynamics and other relationships

• The very real grief that comes with outgrowing people you love

• What happens when you stop being the fixer, people pleaser or peacekeeper

• Why becoming the “black sheep” might actually mean you’re the pattern breaker

• How to stop taking responsibility for other people’s reactions to your boundaries

• A simple journaling exercise to separate what’s yours from what’s theirs

• How to hold space for both grief AND growth as you become the person you want to be

If you’re in a season where you know you’re changing, but some of that change feels lonely, heavy or confusing, this episode is for you.

You can love someone and still need a boundary.

You can miss someone and still move forward.

You can grieve what was and still know you’re making the right decision for what comes next.

And you can choose yourself without apologizing for the person you’re becoming.

Your response is your responsibility. Their response is not.

🎧 Grab your headphones and listen to this one when you need the reminder that becoming more of yourself doesn’t require you to keep shrinking so everyone else can stay comfortable.

I can hold space for both grief and growth.I trust that what’s meant for me will never require me to shrink.

Ready to Finally Create That Course?

And speaking of choosing yourself and going after the thing you really want…

If creating a course has been sitting on your business wish list for months (or, ahem, years 👀), Course Creator Bootcamp is coming back this September.

This is for the business owner who has knowledge, experience and an idea she KNOWS could help people, but hasn’t quite turned it into an actual course yet.

Inside Course Creator Bootcamp, I’ll help you take that idea out of your head and turn it into a course you can actually launch and sell.

Because you don’t need another year of thinking about it, tweaking the idea or waiting until you feel 100% ready.

At some point, you have to back yourself and build the dang thing. 😂

👉 Join the Course Creator Bootcamp waitlist here.

And remember:

I can hold space for both grief and growth.I trust that what’s meant for me will never require me to shrink.

You can have the strategy.

You can have the offer.

You can have the plan.

But if you’re still standing with one foot in your business and one foot out, waiting for proof that it’s going to work before you fully commit… THAT might be the thing keeping you stuck.

For this week’s summer replay, I’m bringing back an episode that I think every business owner needs to hear, especially when things aren’t moving as quickly as you hoped.

Because building a successful business takes more than the right business strategy. It takes the mindset to keep showing up before the results arrive.

In this episode, we’re talking about the three things I believe every entrepreneur needs to build a business that lasts: commitment, certainty, and courage.

We’re diving into what it actually means to go all in on your business without hustling yourself into the ground, why waiting for external validation can keep you stuck, and how to build the self-trust to keep moving when your business feels quiet, messy, or uncertain.

Because you cannot build a long-term business with short-term energy.

In this episode, you’ll learn:

• Why being half in, half out can stall your business growth

• The difference between commitment and working more hours

• Why certainty doesn’t come from results and how it actually helps create them

• How self-trust changes the way you show up in your business

• Why courage is essential when you’re building something that matters to you

• How perfectionism and waiting until you feel “ready” can keep you stuck

• The gut check to ask yourself if you’re wondering why your business isn’t gaining momentum

You do not need another shiny strategy every time things get hard.

Sometimes the next level of your business comes from deciding you’re going to back yourself, keep putting in the reps, and stay in the room long enough to figure it out.

Commitment. Certainty. Courage.

Let’s go.

READY TO TURN WHAT YOU KNOW INTO A COURSE THAT SELLS?

If you’ve been sitting on an idea for a course, wondering how to turn all that knowledge in your head into something people actually want to buy, this is exactly what we do inside Course Creator Bootcamp.

I’ll walk you step by step through creating, positioning, launching, and selling your course without making the whole dang thing more complicated than it needs to be.

Because you don’t need to keep thinking about the course you could create.

It might be time to actually build the thing.

👉 Join the Course Creator Bootcamp waitlist here: WAITLIST

What if the business you've built... isn't the business you actually want?

We've been taught that success looks like a fully booked calendar, more clients, and working longer hours.

But what happens when you finally get there... and realize you're exhausted?

In this episode, I'm sharing the story of how I realized I had built myself another job after leaving teaching. From the outside, everything looked successful. My calendar was full, my clients were getting incredible results, and my business was growing.

But behind the scenes?

I had no space.No capacity.And no real plan for how I was going to keep growing without burning myself out.

This episode is an invitation to challenge everything you've been told about what a "successful" business should look like and to start asking better questions about the business you actually want to build.

Because freedom doesn't happen by accident.It's designed.

In This Episode, We Talk About:

• Why a fully booked calendar isn't always the goal.

• The moment I realized I had recreated another full-time job for myself.

• How I shifted from trading time for money to building a business that could grow without requiring more of me.

• The mindset shifts that helped me stop chasing hustle and start creating space.

• Five powerful questions to help you determine whether your current business model can actually support the life you want.

Questions to Reflect On

Grab a notebook and spend a few minutes with these:

• How many hours are you actually working each week?

• How many clients can you realistically support without burning out?

• Can your current business model actually create the income you want?

• If 10 new clients signed up tomorrow, would you feel excited... or overwhelmed?

• Does your current business model support the freedom you want, or just the pressure you've normalized?

Sometimes awareness is the first step toward building something better.

Ready to Build a Business That Gives You More Freedom?

If this episode has you thinking there's got to be a better way, I'd love to invite you to join the Course Creator Bootcamp Waitlist.

Inside Course Creator Bootcamp, I'll help you turn your expertise into a scalable digital course that creates more freedom, impact, and income without simply adding more hours to your week.

👉 Join the waitlist here: HERE

Let's Connect

I'd love to hear what came up for you while listening to this episode.

Come say hi on Instagram and let me know:

Which reflection question hit you the hardest?

If you enjoyed this episode, I'd be so grateful if you'd subscribe, leave a review, or share it with another business owner who needs the reminder that there is more than one way to build a successful business.

Remember...

Burn the rule book.

Build your business your way. 🤍

If You Stop Working... Does Your Income Stop Too?

What would happen if you took a week off?

Would your business keep running...

...or would everything come to a halt?

In this episode of Keeping It Real, we're diving into one of the biggest shifts I made in my own business—and the one that ultimately gave me the freedom I'd been chasing all along.

For years, I believed working harder was the answer. More clients. More hours. More hustle.

Until I realized I had simply built myself another job.

If you're a coach, consultant, creative, service provider, or even a brick-and-mortar business owner, this episode will challenge the way you think about growth, income, and what's actually possible.

Because building a scalable business doesn't mean working more.

It means building smarter.

In this episode, you'll learn:

• Why trading time for money eventually creates a ceiling

• The hidden problem with being fully booked

• Why scalability isn't just for online businesses

• How digital offers, workshops, memberships, and hybrid models create more freedom

• The three questions every business owner should ask before trying to grow

• Why leverage—not hustle—is the key to long-term success

• How creating repeatable systems benefits both you and your clients

This isn't about abandoning the business you've built.

It's about creating one that gives back to you.

Ready to Build a Business That Supports Your Life?

If you've been thinking about creating a course, workshop, membership, or digital offer, Course Creator Bootcamp was designed to help you do exactly that.

I'll walk you through turning your expertise into a clear, repeatable framework that creates more impact without requiring more hours.

Join the waitlist HERE

If today's episode encouraged you, I'd love for you to share it on Instagram and tag me @gina_keeping.

Feeling like you're doing all the things in your business... but still not getting the results you want?

You're not alone.

As business owners, it's easy to believe that more effort equals more success. More content. More offers. More platforms. More hustle.

But what if the answer wasn't doing more...

What if it was doing less... better?

In this episode, we cover:

In this episode of Keeping It Real, I'm sharing why trying to wear every hat in your business is actually slowing you down, how focusing on one strategic priority creates momentum, and the simple framework I use with my clients to help them stop spinning their wheels and start building businesses that actually support the life they want.

If you've been feeling overwhelmed, scattered, or wondering where to focus next, this episode is your permission slip to simplify.

• Why doing everything is keeping your business stuck

• The biggest mistake I see entrepreneurs make every quarter

• How to identify the true "needle mover" in your business

• Why focus creates more freedom than hustle ever will

• The three-step framework I use to help clients create momentum

• A simple mindset shift that can completely change the way you approach your business

• Why building a successful business is a lot like refinishing a piece of furniture

Remember:

One thing done with intention beats ten things done halfway. Every. Single. Time.

If you've been sitting on an idea for a course, membership, workshop, coaching program, or digital product...

...maybe that's your one thing.

Ready to Build Something Bigger?

Course Creator Bootcamp opens soon, and I'll walk you through turning what's already in your head into a clear, organized, sellable digital asset—without making it more complicated than it needs to be.

Join the waitlist here: JOIN THE WAITLIST

If this episode encouraged you, I'd love for you to share it on Instagram and tag me @gina_keeping. I absolutely love seeing what you're working on and hearing what your "one thing" is.