Stuck in Comfort, Starving for Courage: A Love Letter to the Struggling Entrepreneur

This blog is written by Jen Josey, a public speaker, coach, podcast host, and entrepreneur known for her real, unfiltered, and slightly sassy style. She writes the way she talks, so put your red pen away. Jen is highly opinionated but reserves the right to change her mind whenever she wants, because that’s how she grows. She also finds it weird to write in the third person. Enjoy!

My Dear Struggling Entrepreneur,

You didn’t start your business to feel this small.

You didn’t sign up for late nights, tight bank accounts, and a brain full of “What if I’m not cut out for this?” just so you could tiptoe through your days, terrified to make your next move.

Yet here you are.

You’re making some money. Enough to prove this isn’t a hobby, but not enough to feel like the badass you know you could be. You’re busy, but not fulfilled. You’re working, but not really growing. You’re moving, but not moving forward.

And deep down, you know the truth:

You’re stuck in comfort.

And you are absolutely starving for courage.

How Comfort Quietly Took Over

Comfort doesn’t show up waving a red flag.

It doesn’t announce, “Hey, I’m here to keep you small forever!”

Comfort is sneaky. It slides in wearing the mask of “responsible,” “practical,” and “realistic.”

You don’t get stuck in comfort because you’re lazy.

You get stuck in comfort because you’re tired, responsible, and trying to survive.

At the beginning of your business, everything was new. You were fired up. You took messy action. You said yes to opportunities that scared you. You were willing to look like a beginner because your vision was bigger than your fear.

But over time, you found routines that felt safe:

• You worked with the same type of clients.

• You offered the same services at the same prices.

• You posted the same kind of content when you felt like it.

• You stayed in the same circles, had the same conversations, and got the same results.

Little by little, bold moves were replaced by comfortable habits.

Risk was replaced by routine.

Courage was replaced by “maybe later.”

You didn’t fail.

You just got comfortable.

The Wild Part: You’re Already Where Others Want to Be

Here’s what blows my mind about you...

You are standing in a place most aspiring entrepreneurs dream of reaching.

You started. You launched. You got clients or customers.

You built something real from absolutely nothing.

There are people out there still stuck in “someday,” wishing they had the courage you had on the day you said, “I’m doing this.”

You didn’t wait for “ready.” You moved.

But you’ve forgotten that version of you.

Fear got louder. Bills got real. Comparison got brutal. Algorithms changed. That coach on Instagram made one hundred thousand dollars in ten minutes, and suddenly your progress felt embarrassingly small.

Somewhere along the way, your original spark got buried under a pile of “shoulds,” “what-ifs,” and “who do I think I am?”

So let’s go back to the beginning for a second.

Remember Why You Started

Before fear moved in and made itself at home, there was a reason you said yes to this.

You didn’t start your business just to make money.

You started it because something inside you refused to stay quiet.

Maybe you were tired of watching mediocre work get celebrated while you knew you could do better.

Maybe you were done with someone else deciding when you could take a day off.

Maybe you wanted to be present with your kids and still build something that was yours.

Maybe you were just sick of living on autopilot and needed to know you could create your own life.

Take a deep breath. Really. Right now.

Then ask yourself:

• Who did I want to help when I first started this business?

• What problem was I obsessed with solving?

• What kind of freedom was I chasing? Time, money, creativity, impact, or all of the above?

• Who was I hoping to become in the process?

If you feel a lump in your throat or a sting behind your eyes as you answer, good.

That’s your spark talking.

There was a version of you who was willing to trade comfort for possibility. Who was willing to be seen trying. Who was willing to risk being misunderstood in order to be fully expressed.

That version of you is not gone. They’re just buried under fear and fatigue.

Your job now isn’t to become someone new.

Your job is to remember who you were before you started doubting yourself.

Comfort vs. Courage: The Mindset Shift to Fearless Growth

Let’s be clear. Fearless growth does not mean you’ll never feel fear.

Fearless growth means you stop letting fear be the decision-maker.

Fear can ride in the car. It just doesn’t get to drive.

Here’s the difference:

Comfort mindset: “I’ll take action when I feel ready.”

Courage mindset: “I’ll take action, and readiness will catch up.”

Comfort mindset: “I’ll keep my prices where they are so I don’t scare anyone off.”

Courage mindset: “I’ll charge what my work is worth and trust I can rise to that level.”

Comfort mindset: “I’ll wait until it’s perfect.”

Courage mindset: “I’ll launch it imperfectly and improve as I go.”

Comfort will always argue for staying where you are. It will use very convincing language:

“Be realistic.”

“Don’t rock the boat.”

“What if this doesn’t work?”

“What will people think?”

Experience is useful. Strategy is helpful. Systems are smart.

But without courage, they just keep you circling the same level.

Courage is what creates new experiences.

Courage is what unlocks fearless growth.

Courage is the moment you raise your hand for the opportunity you feel underqualified for.

It’s the email you send that makes your palms sweat.

It’s the boundary you set with a client who’s been walking all over you.

You don’t need to become fearless to grow.

You just need to become unwilling to let fear be the boss.

The Moment I Got Pushed Out of My Comfort Zone

About a year after my husband and I started our real estate business, we were asked to present one of our flip projects to a group of forty to fifty real estate investors.

My immediate thoughts when we were asked to present?

“Who would find value in what we have to say?”

“We’re still newbies ourselves.”

Imposter syndrome pulled up a chair real quick.

But someone believed in us enough to invite us. Someone saw value in what we had done and basically shoved us out of our comfort zone.

So we said yes.

And the second I got on that stage, something wild happened.

That tiny teacher spark inside me, the one I thought I had burned out years ago, reignited into a full flame. I slipped right back into teacher mode. I loved breaking things down, explaining the process, answering questions, and watching the lightbulb moments in the room.

I walked off that stage knowing two things:

• I needed more of that.

• People needed my badassery. I just had to figure out the best way to deliver it.

Then, because the universe has a sense of humor, a random email landed in my inbox about a new Tony Robbins program on becoming a “Knowledge Business Broker.”

Hmmm, I thought. Let me check this out.

I signed up for the free webinar, and the course turned out to be about starting a mastermind.

This was it. I couldn’t enter my credit card number fast enough.

That was the beginning of REIGN: the Real Estate Investor Growth Network.

By creating that mastermind, I did not just create a program. I created a new level for myself and for everyone who joined. I was surrounded by other investors who were thinking bigger, taking bolder action, and challenging me to rise with them.

I got to put my teacher hat back on without going back to the classroom. I got to connect with other like-minded entrepreneurs. I got to be the connector, not the know-it-all.

Because the smartest person in the room is never as smart as all the people in the room.

I was pushed out of my comfort zone and, in the process, I created a safe space not only for myself, but for others to grow.

That is what courage does.

It does not just change your life. It creates room for other people to rise, too.

A Small Exercise to Reignite Your Spark

I’m not here just to hype you up.

I’m here to hand you a match.

Grab a notebook or open a blank document. Do this with me, not “someday,” but today. Right now.

1. Rewrite Your Why, For Real This Time

Finish this sentence, in your own words:

“I started this business because…”

Don’t write what sounds good on a website. Don’t write what you think your audience wants to hear. And for the love of all things holy, stop saying you want to create a legacy. This is your dream, not your kids. If they want you to pass it down to them, that is a bonus.

Write what’s true in your gut.

This is your anchor. When comfort starts whispering again, this is what you come back to.

2. Call Out One Way You’ve Been Hiding in Comfort

Be brutally honest with yourself. Where have you been choosing comfort over courage?

• Undercharging because you’re scared to hear “no”?

• Avoiding visibility, no lives, no speaking, no pitching, because you’re afraid of being judged?

• Saying yes to clients who drain you because you’re scared of the space a “no” might create?

• Hiding behind “research” and “planning” instead of making offers?

Badassery starts with telling yourself the truth.

You can’t shift what you won’t name. So name it.

“I’ve been hiding by ________.”

No shame. No self-beating. Just clarity.

3. Choose One Courageous Action Aligned with Your Why

Now, pick one action that:

• Feels a little scary, and

• Has the potential to move the needle on your growth, whether that is revenue, visibility, or impact.

Not ten actions. Not a ninety day plan. One.

Examples:

• Raise your price for the next client you sign.

• Pitch yourself to one podcast, one local stage, or one event.

• Reach out to five past clients with a new, more aligned offer.

• Go live and share the real story behind why you started.

• Send the email you’ve been avoiding because you’re afraid of the response.

If your brain starts screaming, “That’s too much,” you’re probably in the right neighborhood.

Courage isn’t comfortable. That’s the point.

4. Set a Courage Deadline

Give yourself seventy two hours.

Write it down:

“Within the next seventy two hours, I will __________________.”

Fear thrives in delay.

Courage thrives in deadlines.

You don’t need a full rebrand, a new website, or a twelve week course to get unstuck.

You need one honest moment and one courageous move.

You’re Closer Than You Think

You are not behind.

You are not a failure.

You are not too late, too old, or too inexperienced.

You are an entrepreneur who got stuck in comfort, and that is fixable.

You are already standing in a place that proves you’re capable of more.

You’ve already done brave things. You already have evidence that you can do hard, scary, uncomfortable stuff. You’ve already survived things you once thought would break you.

This isn’t about becoming someone else.

It’s about deciding you’re done letting comfort run the show.

Fearless growth doesn’t start with a perfect plan. It starts with one honest moment and one courageous decision.

This is your reminder:

You didn’t start this journey to play small.

You started it to change your life, and maybe even someone else’s.

The world does not need a watered down, overthinking, comfort obsessed version of you.

The world needs the badass who said yes to this dream in the first place.

With love and a spark of badassery,

Jen, The Bestower of Badassery™️

PS: Now go out there and make it a great day! Whoop Whoop!