3 A.M. Thoughts of an Entrepreneur (And Why No One Talks About the Real Stuff)
Ever wake up in the middle of the night, heart racing, brain on fire with thoughts like:
“How am I going to pay next month’s bills?”
“Can I actually make this work with almost no budget, or is that just some fairytale entrepreneurs tell themselves?”
“Do only the loud, extroverted ones make it because they know how to work a room?”
“How long do I keep pushing before I admit this might not be working?”
Yeah, me too.
These are the unfiltered, middle-of-the-night questions that so many entrepreneurs wrestle with but rarely say out loud. And yet, just like the seasons, business has its cycles—times of growth, times of waiting, times of renewal. When we align with these rhythms instead of resisting them, we can find clarity in uncertainty. We hear the pep talks—“Just keep going!” “Success is around the corner!”—but what happens when you’ve been ‘just keeping going’ and that corner still feels miles away?
At our recent Spring Planting Retreat, we explored the intersection of seasonal living and heart-centered goal setting. Some of the women who are entrepreneurs voiced these exact fears. And I realized—we need to talk about them. Openly. Honestly. Without the polished Instagram captions or business-coach soundbites.
So let’s explore them together. Not with easy answers, but with real contemplation and possibility.
Can You Make It Without a Second Job?
Bootstrapping. That word alone can make you feel like a warrior—proof that you’re tough, resourceful, and serious about your dream. And yeah, technically, you can build a business on grit and a WiFi connection. But let’s be real—bootstrapping takes more than money. It takes energy, time, and often, sacrifice.
If you’re pouring everything into your business without a financial cushion, something else is paying the price—your self-care, your relationships, your sense of stability.
So is bootstrapping actually the best move? Or is taking on a part-time job a smarter way to ease the pressure?
While you can’t ride two horses with one butt, as the saying goes, you can split your time as part of your business strategy. I recommend choosing a part time job that is not highly stressful or requires you to learn an entirely new skill and optimizes the time for money exchange. Once your work in the world begins to bear fruit, cut back on the part time job so that you can focus your attention on your intention so that it can grow.
Let me be clear that this should be a short term strategy! That’s why knowing what you need every month is so important.
If you don’t know exactly what you need to survive—both financially and emotionally—you might start making fear-based choices just to keep your head above water. And that’s where exhaustion creeps in. When you know your numbers, you can make intentional decisions, and give yourself permission to grow at a pace that doesn’t break you. Slow and steady isn’t failure—it’s sustainability. Every thriving ecosystem has a rhythm—rest in winter, renewal in spring, growth in summer, and harvest in fall. Your business is no different.
We need to set realistic expectations for our businesses to become economically stable and profitable. Studies show that, on average, it takes two to three years for a business to become self-sustaining, and even longer—often five years or more—to turn a consistent profit. Despite what social media hype might suggest, six-figure incomes in the first year are the exception, not the norm. Sustainable success is built over time, not overnight.
Do Extroverts Have the Advantage?
I used to think the loudest voices got the most success—the ones who thrive in networking rooms, sell without hesitation, and seem to always be “on.”
But the reality? Sales is equal parts numbers game and connection.
Introverts often build deep, meaningful relationships. But if you connect deeply with five people, and none of them need what you offer right now, your impact stops there. Meanwhile, an extrovert with 5,000 connections only needs five of them to say yes, and boom—momentum.
It’s not about who connects better, but about who connects at a scale that leads to results—while also nurturing the depth of relationships that make those connections meaningful. While introverts may not connect at scale, they often build deeper loyalty. A well-nurtured, smaller audience can become a stronger foundation than a disengaged large one.
And that’s where it gets hard. Because deep connections take time, and if this process stretches too long without a broader audience to pull from, we start to lose hope. We lose momentum. We lose faith in our ability to make this work.
And that? That’s what drains our energy and pulls us out of alignment. Not lack of passion. Not lack of skill. Lack of sustainable hope—the kind that keeps your energy high and your vision clear. Hope isn’t just a feeling—it’s a practice. Just like we tend to our gardens, we must tend to our entrepreneurial spirit. Regular reflection, support systems, and seasonal goal-setting can keep you aligned even in the waiting periods.
So if you’re an introvert, the goal isn’t to “network more.” It’s to expand your reach in a way that feels natural and sustainable for you.
How Do You Do That Without Burning Out?
- Leverage content. Writing, video, and podcasting allow you to connect deeply without constantly showing up in real-time. Let your content work for you while you sleep.
- Build strategic partnerships. You don’t need thousands of people—just the right few who can introduce you to your ideal clients.
- Automate and streamline. Use thoughtful email sequences, social media, and follow-ups to nurture relationships in a way that feels right for you.
- Trust in your way of selling. You don’t have to be loud to be effective. You just have to be clear, consistent, and magnetic in your energy.
How Long Do You Hang On Before Calling It Quits?
Ohhh, the million-dollar question.
Every entrepreneur has wondered, “How much longer do I give this?” Business coaches will tell you, “Keep going! You’re just one step away!” But sometimes, you’re not. Sometimes, you’re pouring money, time, and energy into something that feels like watering a tree that refuses to grow—no matter how much effort you put in, it stays stagnant because it’s planted in the wrong spot. Sometimes, it’s not about abandoning your vision—it’s about repositioning it. Moving the tree to a sunnier spot doesn’t mean the seed was wrong—it means the conditions weren’t right. The bravest thing you can do is move it to a sunnier place where it has the chance to thrive.
So here are some gut-check questions:
- Have I exhausted every possible pivot?
- Is my market actually willing (and able) to pay for this?
- Do I still feel lit up by this, or am I holding on because I don’t want to “fail”?
Because letting go isn’t failure. It’s clearing space for what does want to grow.
So… Should You Keep Going?
If you’re waking up at 3 a.m. with these questions swirling in your head, take it as a sign. Not necessarily a sign to quit. But a sign to pause. To breathe. To reassess with honesty.
Are you still excited about what you’re building?
Are you seeing growth, even if it’s slow?
Are you willing to keep learning and evolving?
If the answer is yes—then keep going. Trust the rhythm of your own pace. The seasons don’t rush their cycles, and neither should you.
But if you’re holding on because you think you have to, because you don’t want to “fail,” or because some coach told you success is just around the corner… maybe it’s time for a deeper conversation with yourself.
Because entrepreneurship isn’t about pushing endlessly. It’s about knowing when to shift gears, when to rest, and when to plant new seeds.
And trust me—no matter what choice you make, you’re not alone in those 3 a.m. thoughts.