The Hardest Parts of Running a Company (and How I Deal With Them)

But until you get to that moment, here’s the truth no one tells you: the hardest part of being a CEO isn’t the late nights or the client meetings. It’s carrying 10 challenges at once, knowing one wrong move could cost your team, your clients, and your company’s future.

I’ve lived it, and instead of talking about the good parts that everyone knows, I want to share the real problems I face running a company, and the solutions that keep me (and my team) moving forward.

Let’s go through the key issues almost every CEO faces and explain the approaches that worked for me.

1. Cash Flow and Financial Pressure

Cash flow issues are a significant concern for many businesses. According to recent studies:

• 82% of small businesses fail due to poor cash flow management or a lack of understanding of cash flow
• 60% of business owners report cash flow as a major challenge, with 89% stating these problems have negatively impacted their business
• 45% of U.S. small business owners have sacrificed their own paychecks due to cash flow shortages

These statistics highlight the critical nature of cash flow management.

Running a company is rarely just about ideas and strategy. There’s a constant tension that keeps you awake at night: “Do we have enough money to cover salaries? What if a client delays payment? How will we pay rent, tools, and overhead next month?”

You might be growing, bringing in new clients, and landing exciting projects, but if cash isn’t flowing, even a successful company can be on unstable ground. This is not just numbers on a spreadsheet; it’s real stress that weighs on your decisions every day.

How do I deal with this?

Over time, I learned that staying reactive only adds stress. So I built systems to take control:

Plan ahead: I use Notion to plan and track all income and expenses for the next 3-6 months. It shows me where money might run short and lets me plan before it becomes a crisis.

Save a buffer: I always keep extra money aside, enough to cover about three months of salaries and essentials. That safety net makes it easier to breathe.

Milestone payments: For clients, I ask for part of the payment upfront and link the rest to completed milestones. This way, a late payment doesn’t disrupt everything.

Monthly check-ins: I review finances with the team regularly. It keeps us all on the same page and helps spot problems early.

These steps don’t make cash flow effortless, but they make it manageable. And when you know your money is under control, you can focus on what really matters: growing your company, supporting your team, and making decisions with confidence.

2. Finding the Right Team

Hiring is one of the hardest parts of running a company, especially when you’re small and don’t have a dedicated HR team. Every new hire feels like a big gamble.

You’ve probably experienced this feeling:

• Do I trust this person to take ownership?
• Will they fit the team culture?
• Can they handle the workload when things get tough?

One wrong hire can slow down projects, create tension, and cost you both money and energy. According to studies, a single bad hire can cost a company up to 30% of that person’s first-year earnings, not to mention lost productivity and team energy.

When your company is small, every decision matters even more. Unlike large organizations, you don’t have layers of management to catch mistakes; one mismatch can spread across every project.

How do I deal with this?

I truly believe that “one bad apple can spoil the whole bunch.” No matter how thorough and detailed you are during hiring, people are unpredictable. I’ve experienced this firsthand: a person seemed like a perfect fit at first, but over time, the team’s energy was weak, communication slowed, and motivation dropped.

That’s why I pay close attention not just to skills, but to how someone affects the team’s spirit and dynamics.

Here’s how I approach it without needing a full HR department:

I hire people, my co-founder hires code: I focus on bringing in the right human fit, someone curious, accountable, and adaptable, while my co-founder handles technical skills and capabilities. This lets us focus on what we do best and keeps the hiring process balanced.

Use small test projects: Instead of committing immediately, I start with a small assignment or freelance task. It shows how they work, communicate, and solve problems in real conditions.

Focus on culture fit first: Skills can be taught; mindset can’t. I look for people who align with our values and work style.

Document everything: I keep candidate notes, interview questions, and feedback in Notion. This makes hiring repeatable and ensures I don’t lose insights when evaluating multiple candidates.

Pay attention to team dynamics: As I mentioned above, no matter how detailed you are during hiring, people are unpredictable. I monitor how new hires affect the team, use small test projects, and keep regular check-ins to catch issues early.

Talk openly about expectations: Transparency from day one prevents misunderstandings. Everyone knows their role, responsibilities, and goals.

This approach doesn’t remove the stress entirely; hiring is always a mix of strategy and instinct, but it reduces risk and helps me build a team that grows with the company, not against it.

3. Leading and Staying Motivated as a CEO

Every decision, big or small, lands on your shoulders:

• How do we keep clients happy without burning out the team?
• Are we growing fast enough, or are we missing opportunities?

This constant pressure isn’t just mentally exhausting; it can start to drain your motivation and creativity. Even when things are going well, the feeling of “never enough time” can slip in. And unlike other roles, the CEO can’t just ignore it because the business always needs you in some capacity.

How do I deal with this?

Daily practices to stay grounded and motivated!

Over the years, I’ve learned that motivation doesn’t just happen; it has to be maintained intentionally. My formula for success is simple: work out, eat healthy, take cold showers in the morning, and read books. That sense of control, like you’re hacking your own system, helps me get through the day and make decisions.

Besides planning in business, I do the same in my personal life. I truly believe the habits you build have a huge impact on your mindset. There comes a moment in life when you realize how much that foundation actually helps. For me, that moment came during a tough phase at work. Just like in any business, there are ups and downs. But the fact that I didn’t let go of my habits, just adjusted them to the situation, helped me stay clear-headed and make smart decisions.

Here are other ways I stay grounded:

Delegate and trust: I can’t (and shouldn’t) do everything. By leaning on my co-founder and team, I free mental space for strategic thinking instead of micromanaging.

Check in with yourself: Small habits like morning walks, journaling, or short breaks, reset energy and maintain clarity.

Surround yourself with success stories: Listen to podcasts, read books, and follow people who’ve built something great, because what you consume shapes how you think. If you're always focused on failure, your mind will keep looking for reasons to quit. But if you focus on people who overcame challenges, you’ll start seeing solutions instead of barriers.

Don’t ignore numbers: You need to stay grounded in data: track your finances, your time, and your progress. Numbers give you clarity and help you make smarter decisions and adjust when things aren’t working.

Zoom out regularly: I step back from day-to-day tasks to see the bigger picture. I track long-term goals, key metrics, and strategic priorities so I don’t get lost in the small stuff.

Celebrate micro-wins: Every small progress, a client’s positive feedback, a feature deployed, or a team milestone deserves recognition. These moments remind you why you do what you do.

If you’re already in the process of starting your business and need help scaling it quickly, my team and I are always here to support you. Don’t hesitate to contact us and let’s talk more about your idea!

4. Scaling and Growth Challenges

Scaling a company sounds exciting, but it often comes with unexpected headaches. What worked for a small team suddenly doesn’t work for 20+ people. Processes that were fine for a few clients become bottlenecks.

For many founders, growth can feel like trying to manage more clients, a growing team, and better systems at the same time, without losing quality. According to statistics, over 50% of small businesses fail within the first five years, often due to growing too quickly without proper systems in place.

Emotionally, this is exhausting. You want to expand, take on new opportunities, and be ambitious, but the fear of losing control or overextending resources can be paralyzing. You worry about hiring too fast, missing deadlines, or not having enough time for your core customers.

How do I deal with this?

Growth doesn’t have to be chaotic, it just needs a plan. One of the most important things is knowing from the start what you want your company to become. Ask yourself: do you want to scale into a large corporation someday, or do you want to keep it small and agile? Your strategy, hiring, and processes should align with that vision.

Other practices that help:

Document processes early: Even small routines like client onboarding, project tracking, and internal communication should be written down. This keeps everyone aligned and makes scaling smoother.

Hire gradually, test fit: Bring new team members on with small projects first, making sure they fit culturally and can handle the workload before fully integrating them.

Track KPIs: Metrics aren’t just numbers; they tell the story of where you need to adjust. Track project timelines, client satisfaction, team workload, and financial metrics to avoid surprises.

Prioritize: Not every opportunity is worth chasing. Evaluate each potential project, client, or feature against your long-term strategy before committing resources.

Keep communication open: As the team grows, transparency becomes critical. Regular check-ins and clear expectations prevent misalignment and burnout.

Scaling isn’t just about hiring more people or winning more clients, it’s about building a system that can handle growth sustainably. With a clear vision, intentional processes, careful hires, and disciplined tracking, growth can be exciting instead of overwhelming.

Conclusion

Scaling a company is never easy, and it’s normal to feel stretched in multiple directions. But here’s the thing: it doesn’t have to feel like you’re spinning out of control.

There were days I felt like I was just putting out fires and barely keeping everything together.

What helped me most was having a clear vision for the company from the start. Knowing whether I wanted to stay small and agile, or build a bigger organization, guided every decision I made, from who I hired to which clients I took on. Pair that with simple but intentional systems, careful hires, and tracking key metrics, and suddenly, growth feels manageable.

I also learned that it’s okay to reach out for advice, share concerns, and ask for support. Leading a company doesn’t mean you have to do everything alone. Having a co-founder has made all the difference. It’s not just about splitting the workload, but about having someone who sees the same vision, challenges your decisions, and celebrates the wins with you. I’ll share more about why this matters in some of the future posts.

If any of this resonates with you, or you’re facing similar challenges in your business, I’d love to connect and hear your story. Let’s chat on LinkedIn, sometimes just talking it through is enough to see the way forward.