When Nischa Shah left her banking job to pursue her side business full-time, she had this rosy image in her head. She thought she’d be her own boss, make her own hours, and build something meaningful while working from cute cafes. But starting your own business is nothing like the fantasy — reality hit hard just a few weeks in. After reflecting on her journey as a qualified accountant and former investment banker who made the same leap, Nischa realized her experience wasn’t unique. Starting your own business follows a predictable pattern, with specific challenges emerging at each revenue milestone.
The Survival Phase: Getting to $50K
The first stage of starting your own business is all about survival – figuring out if the idea works, if anyone will pay, and if this path is actually doable. This is where most people quit, and for good reason.
You must climb the “cringe mountain” – in public. When you’re starting your own business and friends and family can see your work, you’re climbing this mountain while everyone watches. At the bottom, it’s embarrassing. Your work isn’t great because you’re learning in public. You can feel the silent judgment and criticism.
To overcome this, Nischa recommends creating a small support circle of people who understand what you’re doing. Focus on serving one person well rather than trying to please everyone. Save screenshots of kind comments you receive and revisit them regularly to remember why you started.
Next comes the income roller coaster. After years of predictable salary payments, business income fluctuates wildly. One month might bring in three times the old banking salary, and the next just 20% of it. This isn’t just financially stressful – it messes with your head.
During quiet periods, panic sets in. You wonder if this is the new normal and if you should update your resume. What makes this especially challenging early on is that each downturn feels permanent because there’s no long-term data to show it’s just a natural cycle.
To manage this, Nischa Shah suggests:
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Creating a financial buffer specifically for the business (separate from a personal emergency fund)
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Developing something that brings in recurring revenue, even if small
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Having a specific “slow period plan” ready to activate
When starting your own business, motivation will flatline repeatedly. The myth that passion equals constant motivation is nonsense. Even when you love what you do, there will be days or weeks where showing up feels pointless. When you’re alone, there’s no boss or team counting on you to push through the low periods.
The Scaling Phase: Breaking $100K
Once you’ve survived and hit $50K in annual revenue, new challenges emerge. Analysis paralysis becomes real. In a regular job, you’re responsible for your specific role. As a solo entrepreneur, you’re suddenly the CEO, CFO, CMO, COO, and customer service rep all at once.
The sheer number of decisions you make daily becomes exhausting. “Have I priced this right? Should I use Stripe or PayPal? What about my logo? How can I improve my website?” Your brain only has capacity for so many complex decisions each day.
To combat this, Nischa Shah recommends creating systems for decisions that repeat. Use the “good enough for now” rule — get things 80% right and move on. Find one entrepreneur you respect and initially copy their tools and systems.
When starting your own business, resource constraints become a daily reality. You’re limited by time, skills, connections, and energy — not just money. Early on, Nischa compared her starting point to others who were five years into their journey and felt discouraged.
What she now realizes is that those constraints can actually be a huge advantage. When you’re just starting, you have permission to be scrappy. You can implement ideas quickly, test concepts without bureaucracy, and pivot instantly when something isn’t working.
Impostor syndrome never leaves. Nischa once believed that reaching certain milestones would make her feel confident and legitimate — but that doesn’t happen. With no boss, promotion, or formal structure to validate your success, it’s easy to wonder if it’s all just luck.
What helps, she says, is keeping an “evidence log” of wins, testimonials, and successful outcomes. Reframe “I don’t know what I’m doing” to “I’m learning as I go, just like everyone else.” The most successful business owners take action despite their doubts.
The Sustainability Phase: Beyond $100K
Breaking through to $100K and beyond isn’t about doing more of what got you to $50K. It requires reinventing how you operate.
The systems that got you here will fail you. When Nischa Shah hit $100K, she thought she had made it. But just six months later, everything began breaking down — her inbox overflowed, deliverables slipped through the cracks, and she was working more than ever just to fix mistakes.
This is the scaling paradox: the very systems that help you succeed eventually become your biggest bottlenecks. What once felt scrappy and efficient becomes chaotic and limiting.
To prepare, Nischa advises investing in proper automation and tools before you desperately need them. Document everything so it can be handed off when the time comes. Build with 5x growth in mind, not just 2x.
When starting your own business, success eventually brings unwanted complexity. At $50K, Nischa’s business was simple — one core offer, a focused audience, and straightforward marketing. At $150K, she was juggling partnership opportunities, speaking engagements, multiple revenue streams, tax complexities, and legal considerations.
The more options that come in, the harder it becomes to stay focused. You begin to question your original mission and wonder whether to launch a membership, start a podcast, or create another course.
To stay grounded, Nischa regularly revisits and recommits to her core mission. She emphasizes learning to say no to good opportunities so you can say yes to great ones. A decision-making framework helps her evaluate what truly aligns with long-term goals.
Despite all the challenges, Nischa Shah wouldn’t trade being a solo entrepreneur for anything. The freedom to create something meaningful on her own terms outweighs the struggles. When you push through the isolation, build a supportive community, make confident decisions, and establish sustainable systems, entrepreneurship becomes what you imagined — not easy, but deeply rewarding.
Frequently Asked Questions
Q: How long does it typically take to reach the first $50K in revenue as a solo entrepreneur?
This varies widely depending on your industry, pricing model, and marketing strategy. Many solo entrepreneurs reach $50K within 12-18 months, but some achieve it faster with high-ticket offerings or by leveraging existing networks. The key is consistency and serving your target audience well rather than focusing on a specific timeline.
Q: What’s the best way to handle the financial uncertainty during the early stages?
Create three separate financial buffers: a personal emergency fund covering 3-6 months of expenses, a business operating fund for slow periods, and a tax savings account. Consider maintaining a part-time job or freelance work during the initial phase to provide some stable income while you build. Setting up recurring revenue streams, even small ones, can also help smooth out the income roller coaster.
Q: How do you know when it’s time to hire help versus continuing to do everything yourself?
Look for these signals: you’re consistently turning down opportunities due to lack of time, you’re spending significant hours on tasks outside your expertise, your revenue has plateaued despite market demand, or you’re experiencing burnout. Start with contractors for specific projects before committing to employees. The right time to hire is often earlier than most entrepreneurs think – when you’re at about 70-80% capacity, not when you’re already overwhelmed.
Q: What are the most common reasons solo businesses fail after reaching initial success?
Many solo entrepreneurs fail after initial success because they don’t adapt their systems for scale, they say yes to too many opportunities and lose focus, they fail to delegate effectively, they don’t raise prices as their expertise grows, or they neglect self-care and burn out. Success requires different skills than startup – shifting from doing everything yourself to strategic thinking and leadership.
Q: Is it necessary to use social media to grow a solo business?
While social media can be powerful for building awareness, it’s not mandatory for every business model. Many successful solo entrepreneurs focus on email marketing, SEO, networking, partnerships, or word-of-mouth referrals instead. The key is choosing marketing channels that align with your strengths and where your ideal clients spend time. If social media drains your energy or doesn’t connect with your audience, explore alternatives rather than forcing yourself to use platforms that don’t serve your business goals.