Overcoming Business Roadblocks: How to Thrive in the Messy Middle
The quiet courage of holding a dream through its awkward middle
There’s a moment in every entrepreneur’s journey—usually several—when the dream you’re holding doesn’t look anything like the one you pictured.
You thought you’d be further by now.
You thought it would feel different.
You thought the support would be louder, the path clearer, the wins more frequent.
Instead, you’re staring at something half-formed and uncooperative… a business that isn’t what you imagined—at least, not yet.
That gap between expectation and reality can ache like disappointment, or shame, or confusion.
It can make you wonder if you misread the signs.
If you’re cut out for this.
If your dream was too bold or too naïve.
Every dream has an awkward middle
Every business has a chapter where it looks like nothing is working—right before everything starts to make sense.
We don’t often talk about this chapter because it’s messy.
It’s the part where confidence wavers, where the plan feels flimsy, where you’re tempted to settle, quit, or shrink your dream to something safer.
But this is also the part where something remarkable happens—
a quiet recalibration,
a deepening,
a stripping away of what was never yours to hold in the first place.
This is when you are forced to look deeper within than ever before.
This is when you meet the core of what built you.
This is when you remember that you didn’t come this far to only come this far.
It’s the reminder not to believe everything you see, but to remember that what you feel will shape your next chapter.
When your business isn’t failing—it’s revealing
When your business doesn’t match your expectations, it isn’t failing.
It’s revealing.
It’s showing you what it actually needs from you—
where it wants to grow,
what it wants to become.
My own awkward middle
I know this space well. When I first started the Flying Upstream Podcast, it felt like an adventure that would challenge me to grow alongside it. I wanted it to be an extension of my own journey—one rooted in growth, curiosity, and depth.
I dreamed of uncovering the wisdom of the unconventional, of sharing the timeless art of storytelling that connects us to our truth. I pictured myself in a beautiful studio—soundproofed, perfectly lit, with a professional teleprompter to help me craft heartfelt conversations about loss, healing, and the emotions that shape us.
But expectations are sketches.
Reality is the sculpture we discover as we carve.
And sometimes the sculpture is more beautiful—more honest and uniquely yours—because you’re forced to be scrappy. You record in your imperfect front-room office. You make do with a plain white background. You embrace your lack of aesthetic and, in doing so, lay the strong, humble foundations that will one day hold the legacy you’re building.
There is wisdom in this season
So if you find yourself in that in-between space—between the business you envisioned and the one that’s taking shape—don’t rush it.
Don’t walk away from it.
Look closer.
There is wisdom in this season.
Patience in this season.
Possibility in this season.
You are not behind.
You are not failing.
You are simply in the middle of becoming.
The moment that shapes you
One day, not too far from now, you’ll look back and realize this was the moment that shaped you into the entrepreneur you were meant to be.
Not when everything was working, but when nothing quite matched—and you chose to keep going.
When you decided that “good enough” wasn’t enough and began shaping your dream brick by brick into reality.
When you stopped waiting for others to deliver on their promises and started mining the gems within yourself.
That was the moment the lioness in you lit up your path—blinding at first, but guiding you forward toward the future you’ve been building all along.
Your story deserves to be heard
If you’ve been waiting for a sign to start or grow your podcast, this is it.
Join the Flying Upstream Podcasting Club today and connect with a community of creators turning passion into practice—one episode, one story, one bold step at a time.
