Growing pains: 7 challenges new entrepreneurs should expect in the first two years of business

Have you ever felt that spark of excitement and terror all at once?

That’s how I felt when I launched my first major venture, fully aware that the path ahead would be both thrilling and uncertain.

The early stages of entrepreneurship can be a crash course in personal growth—pushing you to face your limitations, question your assumptions, and discover strengths you didn’t know you had.

Still, I’ve met many aspiring founders who assume the hardest part is having a solid idea. But an idea is just the beginning.

It’s the day-to-day hustle, the doubts, the tiny wins, and the setbacks that truly define your entrepreneurial journey.

And while every business path is different, there are universal challenges you can expect to meet in the first couple of years.

Below are seven common hurdles and how I’ve learned to navigate them—sometimes the hard way.

1. Navigating the emotional rollercoaster

Starting a business isn’t just a financial leap—it’s an emotional one. 

One day you’re convinced you’re building the next big thing. The next day, you’re wondering if you made a colossal mistake.

In my experience, the emotional highs can be almost addictive. Yet the lows can make you question your core beliefs.

Psychologists like Brene Brown often talk about the vulnerability that comes with taking risks.

Entrepreneurship amplifies that vulnerability because you’re pouring your heart (and possibly your life savings) into something with no guarantee of success.

So how do you keep your sanity intact? 

Allow yourself some mental space. Meditate if that’s your thing. Take regular walks. Journal your thoughts every morning. 

In other words, treat your emotional well-being like an actual business asset. Because it is.

2. Dealing with financial instability

No steady paycheck.

Unpredictable cash flow.

Spending more than you earn during the early months.

Sound familiar?

It was a rude awakening for me when I first realized that a single invoice delay could ripple through my entire month.

I learned that managing money isn’t just about accounting—it’s about staying calm when your bank balance fluctuates like a rollercoaster.

One practical tip is to keep personal and business finances separate. Make a clear line between your company’s cash flow and your personal expenses.

If possible, set aside an emergency fund before you dive full-time into your startup, even if it’s modest.

Think of it as a cushion that can absorb a few tough bumps. It won’t fix every problem, but it’ll help you sleep better at night.

3. Overcoming fear of failure and self-doubt

Most of us claim to accept failure as part of the process—until we’re faced with the possibility ourselves.

I still remember the night I stayed up, replaying every misstep in my head, convinced I’d never recover if my project went belly-up.

Fear of failure can become a self-fulfilling prophecy if we let it fester. 

According to Adam Grant, re-framing familiar stories can create more compelling narratives. In this case, reframing setbacks as data points rather than personal flaws can keep us moving forward. 

When a product launch flopped for me, I treated it like a grand experiment. I asked, “What can I learn?” rather than “Why do I suck?”

Easier said than done, right?

But a shift in perspective can be a lifesaver. When you see failure as feedback, you transform fear into curiosity.

It’s no longer about your worth as a person—it’s about fine-tuning your approach.

4. Feeling isolated (and facing the dark side)

Entrepreneurship can be lonely. You often trade the structure of a 9-to-5 for long nights alone with your laptop, especially in those formative months.

I used to work in coffee shops just to feel the buzz of people around me, because constant solitude can be draining.

This is also where the “dark side” of the hustle can show up: burnout, existential angst, and a nagging question of whether all the stress is actually worth it.

If that resonates, you might want to check out a video I made on my YouTube channel about the dark side of entrepreneurship. In it, I dive deeper into the emotional and psychological toll this path can take.

But isolation doesn’t have to be your destiny. Seek out like-minded founders at meetups or online communities. Find a mentor or even just a friend who “gets it.”

Sometimes, hearing someone else’s war stories can help you realize you’re not the only one juggling uncertainty and ambition.

5. Building a team (or learning to delegate)

When you’re starting out, you often wear all the hats. Marketing, accounting, product design—it’s all on you.

At first, I thought I could handle it, but I quickly discovered that my days felt stretched and my nights were filled with undone tasks.

Hiring that first employee or freelancer is a big psychological leap.

It means trusting someone else with your “baby” and paying them from a budget that might already feel tight.

But in my view, it’s not just about offloading tasks—it’s about creating a dynamic where your vision is expanded by other people’s expertise.

If you’re not ready for a full hire, consider virtual assistants or short-term contractors. They can handle repetitive or specialized tasks, freeing you up to focus on strategy or innovation.

Think about the tasks that drain you the most or the ones you’re not particularly skilled at. Hand those off first and watch how it elevates your game.

6. Standing out in a crowded market

Ever felt like you’re shouting into a void where everyone else is shouting, too? That’s often how new entrepreneurs feel. 

Competition is fierce, and the internet has made it both easier and harder to get noticed.

I often say that uniqueness is your true currency. Even if your product idea isn’t radically new, your perspective or personal story can be what sets you apart.

Early in my journey, I tried to mimic what I saw successful entrepreneurs doing. 

But I realized that by copying someone else’s approach, I was just blending in with the crowd.

According to Forbes, authenticity is a key driver of genuine connection, even in business contexts.  

So share your backstory, show your passion, and communicate in a style that feels like you.

You might lose the people who want cookie-cutter offerings, but you’ll gain those who resonate with your particular brand of realness.

7. Confronting growth demands and scaling headaches

Finally, let’s talk about growth. It’s the milestone every entrepreneur strives for, yet it can introduce a fresh set of complexities. 

In the early stage, it’s about finding your first paying clients or your first thousand users.

Once you start growing, you face new pressures like expanding your team, refining your processes, and maybe even seeking outside investment.

I learned this the hard way when I underestimated how much support I’d need after a sudden surge in demand. 

My inbox was flooded, my systems weren’t ready for the scale, and I was putting out fires left and right.

The irony? Getting what I wanted—growth—came with a new level of chaos I wasn’t ready to handle.

At this phase, long-term vision and systems become crucial. You might need better project management tools, clearer roles within the team, and a stronger support network.

It’s also a good time to revisit your mission: Are you building something that still aligns with your core values? Scaling up can blur your original intentions if you’re not careful.

Conclusion

The first two years of a new business can be a wild ride—full of exhilaration, setbacks, and, hopefully, transformation.

Whether you’re wrestling with self-doubt, feeling alone, or struggling to stand out, these challenges are part of the deal.

And each hurdle is also a lesson, nudging you to refine your vision and grow as both an entrepreneur and a human being.

If you found these insights useful and want to dive deeper into real-world, no-fluff discussions on personal growth and entrepreneurship, I invite you to join me on my YouTube channel, Wake-Up Call.

I explore these topics from a philosophical and practical standpoint, sharing what I’ve learned and the mistakes I’ve made along the way.

Remember: these growing pains might be tough, but they’re also the catalyst for genuine progress. 

Embrace them, keep questioning everything, and stay true to the vision that led you here in the first place.