Navigating the Messy Middle of Entrepreneurship, Purpose, and Life Transitions
Entrepreneurship is not for the weak, the faint of heart, or those easily discouraged.
Striking out on your own with little or no safety net is no small undertaking. It’s a beast.
A behemoth that consumes your energy, demands your time, and stretches your mind in every direction—just to keep the train on the tracks, even when it’s not moving.
It takes grit, guts, faith, resilience, fortitude, a deep internal belief in self and purpose, and an undeniable resolve that this is your path.
Because on some days, belief is all you’ve got.
When progress is invisible and momentum feels like a myth, the only thing keeping you going is the whisper that says: keep building anyway.
I used to hear this from others—friends, mentors, colleagues.
“Buckle up. It’s going to be a bumpy ride.”
Now I know they weren’t exaggerating. They were giving me the softest warning they could.
While I’m relatively new to the journey, I’m sure I have many more “failures” ahead of me as I continue down this path.
But I also know those failures don’t define me. They refine me.
Because even with the bumps, the quiet days, and the long nights…
I know this is the path.
I didn’t stumble onto it—I chose it. Or maybe it chose me.
That doesn’t make it easier.
Cash flow? Not flowing.
Expenses? Eating into every bit of the savings I set aside.
Leads? Coming in.
Sales? Not yet. And sales are what I desperately need. Seven months in, I’ve done the work—but the return hasn’t arrived. Not like I hoped. Not like I prayed for.
And the question that keeps coming up—whispering in the background, sometimes screaming in the silence—is this:
Why aren’t we there yet?
The Illusion of Arrival
Somewhere in the back of my mind, I expected to feel a shift by now.
Like there would be a moment—some milestone—where I’d exhale, look around, and say, “Okay, we made it.” A moment when the pressure lets up, the path gets clearer, and things finally start to click. When the sales roll in, the clients come knocking, and the doubt fades into the background.
But if there’s anything entrepreneurship is teaching me, it’s this:
There is no “there.”
At least not in the way we’ve been conditioned to believe.
Psychologists call this the “arrival fallacy”—the belief that happiness lies just beyond the next goalpost. Dr. Tal Ben-Shahar, who taught one of Harvard’s most popular courses on positive psychology, explains that this fallacy tricks us into chasing success as a destination. We expect lasting fulfillment when we finally “arrive,” but often we feel a sense of emptiness or disappointment instead.
The science backs it up: research in the Journal of Personality and Social Psychology shows that we derive more joy from progress toward a goal than the actual achievement itself. The brain releases dopamine—the feel-good chemical—when we’re anticipating success, not when we’ve already gotten it.
In other words: it’s the movement, not the milestone, that matters.
That’s not just true in business. That’s true in life.
We think once we get the job, buy the house, find the relationship, or reach the goal weight—then we’ll feel whole. But over and over again, we arrive only to realize… there’s another stretch of road ahead. Another version of success to chase. Another part of ourselves that still feels unfinished.
That’s the danger of tying your peace to performance.
If your peace is always waiting on outcomes, it’ll always feel just out of reach.
But if your peace is rooted in alignment—if your definition of “success” is tied to values, growth, and purpose—then you’re free to show up fully, even when results are slow.
That’s the shift I’m trying to make right now.
I’m learning to let go of the myth that arrival equals relief.
Because the truth? There is no final destination in this work—only the next right step.
And sometimes, that step looks like trusting the process when there’s no applause.
Sometimes, it’s reminding yourself that peace isn’t found in perfection—it’s found in purpose.
The Messy Middle
Nobody talks enough about the middle.
We glamorize the leap—quitting the job, launching the thing, chasing the dream. And we love the success story—the viral moment, the six-figure breakthrough, the inbox full of client requests.
But the middle?
The part where you’re in motion but not yet in momentum?
Where you’re showing up, doing the work, and still unsure if it’s working?
That part is quiet. Lonely. Stretching.
And most of the time, it’s where we quit.
Because the middle messes with your mind. It tempts you to question your gift. To doubt the calling that once felt so clear. To compare your slow, faithful steps to someone else’s highlight reel.
And it doesn’t just touch your business.
It spills into everything—your confidence, your focus, your energy, your relationships.
It becomes harder to be present with people you love when your mind is racing with how to make ends meet. It’s tough to rest when you feel like you haven’t “earned it.” It’s exhausting to keep believing when the external validation is still MIA.
Psychologists in Gestalt therapy refer to this space as the “fertile void”—a season of stillness where old identities are dissolving, but new ones haven’t yet formed. It’s uncomfortable, yes, but also profoundly necessary. In mindfulness theory, this fertile void is the space where insight and creativity emerge—not through control, but through presence and relaxed awareness. (Brown, Ryan, & Creswell, 2007).
In both entrepreneurship and life, this is where transformation actually happens.
You’re shedding expectations. Rebuilding beliefs.
Learning to measure progress by what’s internal—your resilience, your boundaries, your clarity—not just what shows up on a spreadsheet.
In life, the messy middle looks like:
💔 That season between heartbreak and healing.
👨🏽💻 The job you’ve outgrown, but haven’t left yet.
📉 The quiet progress that no one claps for, but takes everything you’ve got.
Psychologist Scott Barry Kaufman notes that while we often admire vulnerability in others, we tend to fear it in ourselves. Yet it’s precisely this willingness to stay present in uncertainty that unlocks deeper growth and transformation.
And in his book Transcend: The New Science of Self-Actualization, Kaufman reminds us that personal evolution isn’t about perfection—it’s about becoming more fully yourself, especially when life gets messy.
“Self-actualization is not a destination,” he writes, “but a process of becoming—of living a life of authenticity, meaning, and growth, despite the chaos.”
Science supports this too: studies from Stanford and the University of Chicago show that people who persist through ambiguity—who tolerate the tension of not knowing—are more likely to reach long-term success. Not because they’re more talented. But because they stay in it.
This is the zone where character is formed.
Where identity gets refined.
Where success stops being about results and starts becoming about resilience.
I’m learning—day by day—to sit in the middle without rushing to escape it.
To feel the discomfort without letting it define me.
To name what’s hard—but also to name what’s still true:
I am still called. I am still capable. And I am still becoming.
Recalibrating the GPS
When you’re stuck in the messy middle, it’s easy to feel lost.
You start second-guessing the path. Wondering if you missed a turn somewhere. Wishing for a sign—any sign—that you’re still on the right track. But the truth is, there are moments on this journey where the destination disappears from view, and all you’ve got is your next best step.
That’s when it’s time to recalibrate your GPS.
Not the external one—the one tracking revenue, social metrics, or validation from others.
I’m talking about your internal navigation system: the voice that remembers why you started, the clarity you had when you said yes to this vision, the values that make you feel aligned even when the results are slow.
I’ll be honest: patience has never been my strong suit.
I tend to anticipate outcomes on unrealistic timelines, and when things don’t move as fast as I think they should, I get anxious. Frustrated. Sometimes, that impatience has stalled my progress more than any failure ever could.
Right now, I’m feeling that pull hard—because my severance is running out.
I haven’t been actively looking for work, because I’ve been all-in on building this thing.
But life circumstances are shifting, and I can feel the pressure mounting.
It’s not just the money. It’s the timeline. The invisible deadline that whispers, “You’re running out of time. This needs to work—now.”
And that pressure? It’s messing with my peace.
It’s making me question whether to keep going, whether I should pivot, whether I need to abandon the path just to feel secure again. It’s that familiar tension between faith and fear. Purpose and panic.
But here’s what I’ve learned: when urgency starts shouting, I have to get quiet.
Because if I don’t pause and reconnect to my inner compass, I’ll start steering from survival—not vision.
In both life and business, we’re taught to measure success by outcomes:
💰 How much did you make?
👥 How many people signed up?
📈 How fast did it grow?
But sometimes progress looks like:
🚫 Saying no to something that drains you.
🔒 Staying committed to a path even when it’s not easy.
⚠️ Creating boundaries that honor your peace.
😴 Choosing rest without guilt.
🚨Letting go of urgency so you can move with clarity.
Recalibrating means shifting your focus from how far you’ve gone to how well you’re aligned.
From chasing productivity to pursuing purpose.
From looking for external permission to trusting your internal direction.
In psychology, this is called self-concordance—when your goals are aligned with your personal values and sense of identity. Research shows that people who pursue goals that are self-concordant experience greater well-being, more sustained motivation, and less burnout—even when the outcomes are unpredictable.
In other words, clarity is a more powerful fuel than hustle.
That’s what I’m leaning into now. Not grinding just to get ahead, but pausing long enough to ask:
Is this still true to who I am?
Because alignment is the only way forward that doesn’t cost you yourself.
It’s not easy. But it’s necessary.
And when you start steering by that kind of clarity, you stop asking, “Are we there yet?”
You start asking, “Am I still becoming who I’m called to be?”
What Keeps You Moving
There are days when the numbers don’t make sense.
When the return doesn’t match the effort.
When you’re giving your all and still not sure if it’s working.
So what keeps you going?
For me, it’s faith.
Faith in the calling.
Faith in the vision I was given.
And faith that God didn’t bring me this far to leave me stuck in uncertainty.
It’s also a commitment to something deeper than metrics—something unshakable even when the outcomes are delayed. A deep sense of purpose that reminds me: This is not just about building a business. This is about becoming. About honoring the assignment—even when it costs me comfort. About trusting that I was called to this for a reason, even when the results are on hold.
We talk a lot about grit like it’s just effort or hustle. But grit is more than working hard—it’s stewardship. It’s holding onto what was placed in your hands and choosing to show up for it. To protect it. To grow it with intention, even in uncertainty.
That kind of grit doesn’t scream.
It doesn’t always look productive.
🙏🏽 Sometimes it looks like praying through tears.
🥱 Sometimes it looks like showing up when you’re tired of believing.
⛔️ Sometimes it’s just deciding not to quit today.
And when the metrics don’t validate you—what does?
For me, it’s the stillness I feel when I know I’m in alignment.
It’s the peace that follows obedience.
It’s the clarity that returns when I stop chasing and start listening again.
It’s remembering that success isn’t just about what you accomplish—it’s about what you carry.
And here’s the thing: entrepreneurship doesn’t live in a vacuum.
It touches everything—your mindset, your energy, your health, your relationships.
The boundary between business and life isn’t a line. It’s a bleed.
And if you don’t manage your life while you build your business, your life will end up managing you.
That’s why resilience matters. Not just so you can push harder—but so you can live wiser. So you can create with your values intact. So you don’t sacrifice your peace for your platform.
From Entrepreneur to Life Designer
At some point, the question shifts from “Are we there yet?” to “What kind of life am I designing while I wait?”
Because success—real success—isn’t just about what you build. It’s about how you live.
It’s about alignment. Intentionality. Integrity with yourself.
You don’t need more hustle.
You need more clarity.
You don’t need to push harder.
You need to lead yourself better.
That’s the shift I’ve been making.
That’s the shift I guide my clients through.
And that’s the heart of my coaching method.
Here are five mindset shifts and action steps rooted in the LIFE Method that can help you keep moving forward—not just as an entrepreneur, but as a life designer:
Leverage What You Know
Stop focusing on what you lack and start using what you already have.
Too often, we overlook our experience, relationships, and even pain. But everything you’ve lived through has given you tools. Instead of striving for something new, ask: What do I already have that I can repurpose, reposition, or relaunch?
➡ Action: Make an inventory of assets—skills, networks, past wins, and lessons—and identify one you can activate this week.
Integrate the Personal and the Professional
Stop separating your business life from your real life—your peace depends on wholeness.
When you compartmentalize, you drain energy from both sides. Your business should reflect your values. Your values should inform your schedule, your offers, your boundaries.
➡ Action: Identify one area where your life and work feel out of sync—then make one small change to bring them into better alignment (ex: clearer client boundaries, protecting your mornings, shifting your messaging).
Focus Your Energy Where It Counts
Everything urgent isn’t important—and everything important isn’t urgent.Clarity beats complexity every time. When you’re overwhelmed or discouraged, simplify. Narrow your focus. Focus on the needle-moving activities that connect directly to your mission.
➡ Action: Choose one core priority for the next 7 days and let the rest be background noise. Commit to one daily task that honors that focus.
Execute with Intention, Not Perfection
Progress isn’t about flawless execution—it’s about consistent alignment.
The fear of not doing it “right” can paralyze you. But perfection is the enemy of progress. Action doesn’t have to be loud to be effective. Just make the next right move.
➡ Action: Choose one small action you’ve been avoiding. Break it into micro-steps. Then take the first imperfect one today.
Expand Your Definition of Success
What if being “on track” isn’t about where you are—but about how fully you’re showing up?
Success is more than sales. It’s emotional capacity. It’s self-leadership. It’s faith in motion. Redefining success frees you to thrive in the process, not just after the breakthrough.
➡ Action: Journal your new success metrics: What does success look like emotionally? Spiritually? Relationally? What does a “win” feel like on a random Tuesday?
This isn’t just a coaching model.
It’s a way of being. A way of building. A way of becoming.
One step at a time.
You may not be “there” yet. But you’re becoming.
And that counts for more than the world gives credit for.
So take a breath. Realign your focus.
You’re not behind. You’re in process.
You’re not lost. You’re in the making.
And the life you’re building?
It’s still worth it.
Final Thought
I started this post asking, “Are we there yet?”—exhausted from the grind, anxious about the timeline, wondering if the vision I committed to was still worth the cost.
And now, a few thousand words later, I still don’t have all the answers.
But what I do have is something stronger: clarity.
Clarity that the destination was never the point.
Clarity that peace doesn’t come from outcomes—it comes from alignment.
Clarity that even when the numbers aren’t moving, I am.
I’m learning that the middle isn’t a detour—it’s the actual path.
And progress isn’t just about what’s measurable—it’s about what’s meaningful.
So no, I may not be “there” yet.
But I’m still standing. Still building. Still becoming.
And that, in itself, is a win.
If you’re somewhere in the middle too—don’t quit.
Pause if you need to. Recalibrate.
But don’t let this stretch of the journey convince you that your calling was a mistake.
You’re not lost. You’re becoming.
And the life you’re designing? It’s still unfolding.
On purpose.
With purpose.
Right on time.
💭 Be honest…
Are you in that space where you’re doing the work but the results still aren’t showing up?
Where you’re questioning if it’s worth it?
Drop a comment if you’re in the messy middle. I want to hear your story—because this journey gets easier when we stop pretending we’re not struggling.
Take the Journey With Me
If any part of this hit home—if you’re in your own messy middle, questioning your pace or your path—I want you to know you’re not alone.
I’m still in it too. Still building. Still navigating. Still learning to lead myself through uncertainty with clarity and faith.
But here’s the good news: you don’t have to do this alone either.
Let’s walk this road together.
Whether you’re building a business, rebuilding a life, or trying to figure out what’s next—this journey is easier when you have space to reflect, reset, and realign.
If you’re ready to stop spinning and start moving forward with intention, I invite you to reach out. Let’s talk. Let’s map the road ahead.
Let’s design a life that reflects who you are, what you value, and where you’re called to go.
Because you may not be “there” yet.
But forward is still a direction.
And clarity makes the road feel lighter.
0 Comments