Entrepreneurs
5 Frustrating Hurdles Every Entrepreneur Will Face
If you’d like to learn how to push past the struggles of entrepreneurship so you can have a successful business, sign up for the free 90-Day Master Class hosted by the founder of Addicted2Success.com, Joel Brown.
Becoming an entrepreneur isn’t as glamorous as it seems. Some motivated entrepreneurs are blinded by the clout that comes with the title of “business owner.” Their ambition is so great that they overlook potential frustrations and hurdles. Although being a successful entrepreneur comes with plenty of rewards and financial freedom, it takes plenty of work to get there. And success doesn’t come without some frustrating hurdles along the way.
Let’s take a look at a few of the most frustrating things you’ll face as an entrepreneur just starting out and how to overcome them:
1. Who’s the boss?
As a business owner and entrepreneur, you get to be your own boss, right? Not quite. This is one myth that many new entrepreneurs face. Being a business owner is risky. The lines between employee and owner are sometimes blurred. There are no clear boundaries for when your day starts and ends.
Entrepreneurship isn’t a 9-5 job where you punch a clock and leave without another thought. You’re the one in charge! And while this is attractive to some people, most ambitious business owners don’t realize the level of stress and responsibility that comes along with owning your own business.
Your livelihood depends on the success of your product or service. Your customers are your primary source of income. There are no guarantees and that means no protected income. Not only are you dealing with the stress of paying the bills both at work and at home, but you’re now responsible for dealing with all the tedious tasks that help your business run day-to-day.
As an entrepreneur, you’re still held accountable but instead of answering to the boss (you), you have to answer to employees and customers. One way to handle this hurdle is to surround yourself with responsible employees that can help take on some of this stress and handle customers when your patience wears thin.
“Be so good they can’t ignore you.” – Steve Martin
2. Financial Uncertainty
It’s no secret that you need money to get your business started. Planning ahead can help you get there. Obtaining financial backing and putting aside an “emergency fund” before you launch your business is a good start.
Once things get off the ground, you’ll rely on revenue and payments from customers and clients to cover overhead costs. This includes things like inventory, payroll, and rent or a mortgage. But what happens when your customers can’t pay on time?
Late payments can kill your business. This is a common hurdle for small businesses dealing with big-name clients. These big businesses don’t think a few late payments are a big deal. They know they’ll pay you eventually.
The problem is, many small businesses rely on these payments for day-to-day survival. A few late payments could mean the difference between paying your rent and getting evicted.
To avoid these headaches, create a detailed payment schedule and hold customers accountable for paying on time. If you can, collect payments before providing your service or product. Some businesses choose to set-up an automated payment schedule to guarantee they receive payments when you need them most.
3. Invest more than just your money
When you’re the boss you don’t have to do much more than signing the checks and count your stacks of money, right? Wrong! Successful business owners get their hands dirty by working alongside their employees.
Most businesses start out small, which means a lot of the responsibility will fall on your shoulders to start. You’ll be involved in a little bit of everything from sales and advertising to customer service and finances. While this might be frustrating at first, it’s a good way to learn and build your business from the bottom up.
Be prepared because these tasks are usually tedious and labor-intensive. As your business grows and you start making money and building your team, you can hire more reliable employees to do these jobs for you.
As frustrating as this is for many new entrepreneurs, there are some benefits. You’re in control of everything from the color of your advertisement to how inventory is arranged on the shelves. While these might seem like insignificant details, they go a long way in attracting customers and bringing in revenue.
You’re also creating the foundation for the processes and systems you want to use in the future. You’ll gain insight into all aspects of the business. Once things stabilize, you can move into a more administrative position, but never forget where you came from.
“Don’t worry about failure; you only have to be right once.” – Drew Houston
4. The customer is always right
As infuriating as the old saying is, “The customer IS always right.” Eating humble pie is one of the less-glamorous parts of being an entrepreneur. Bad reviews and customer complaints can do major damage to your business including your reputation and your income.
While no one likes dealing with a displeased client, big businesses can handle it without much trouble. Small and new businesses, on the other hand, can get hit hard by just a few unhappy customers. Customer complaints can cause big problems and require emergency damage control.
Unhappy customer comments can also be hard to swallow as an entrepreneur. They feel like a direct, personal attack. You may start doubting yourself and your potential for success. Can I come back from this? Is my business good enough? Am I good enough?
Don’t let a few unpleasant customers get you down! Do your best to make things right and recover. Don’t get lost in feeling sorry for yourself or the damage could be much worse and last much longer.
Negative online reviews are especially hard to deal with. With so many people on the internet, you can’t hide from a bad review. But it’s important to remember that how you react to a bad review is just as important as what the review says.
It’s also important to respond fast. Don’t let bad reviews linger on the internet for too long. This increases the chances that a prospective client will see them and make a decision based on them. The longer a negative review sits online without a response, the greater the risk that you lose potential new customers.
5. The buck stops with you
Most entrepreneurs consider their business their baby. You live and breathe your work. While this is admirable, don’t be surprised that your employees aren’t quite as impassioned as you. At the end of the workday, they leave work behind. You take it with you everywhere you go.
Regardless of how loyal your employees are, your business just doesn’t mean that much to them — but don’t take it personally.
But employees aren’t the only ones who might leave you high and dry. Vendors and third-party dealers probably don’t share your same sense of urgency when it comes to stocking shelves and meeting deadlines.
One way to deal with this hurdle is to have a plan B. Be honest about the things you can’t change. Getting upset or overly stressed will cause panic and stress throughout your business and won’t do anyone any good. Don’t take three delays personally.
Check your emotions at the door and focus on the task at hand. Take one day at a time and you’ll be surprised at how successful you’ll become.
What do you think is the most challenging part about starting your own business? Share your thoughts with us below!
Business
The Entrepreneur’s Reading List That Transforms Ideas Into Empires
These must-read titles and writing insights reveal how entrepreneurs turn bold ideas into empire-level success.
Entrepreneurship is powered by stories—of accomplishment, failure, and decision moments that define businesses. Books are maps, providing insight from individuals who’ve traversed the road ahead. (more…)
Entrepreneurs
The Leadership Shift Every Company Needs in 2025
Struggling to keep your team engaged? Here’s how leaders can turn frustrated employees into loyal advocates.
In workplaces around the world, there’s a growing gap between employers and employees and between superiors and their teams. It’s a common refrain: “People don’t leave companies, they leave bad bosses.”
While there are, of course, cases where management could do better, this isn’t just a “bad boss” problem. The relationship between leaders and employees is complex. Instead of assigning blame, we should explore practical solutions to build stronger, healthier workplaces where everyone thrives.
Why This Gap Exists
Every workplace needs someone to guide, supervise, and provide feedback. That’s essential for productivity and performance. But because there are usually far more employees than managers, dissatisfaction, fair or not, spreads quickly.
What if, instead of focusing on blame, we focused on building trust, empathy, and communication? This is where modern leadership and human-centered management can make a difference.
Tools and Techniques to Bridge the Gap
Here are proven strategies leaders and employees can use to foster stronger relationships and create a workplace where people actually want to stay.
1. Practice Mutual Empathy
Both managers and employees need to recognize they are ultimately on the same team. Leaders have to balance people and performance, and often face intense pressure to hit targets. Employees who understand this reality are more likely to cooperate and problem-solve collaboratively.
2. Maintain Professional Boundaries
Superiors should separate personal issues from professional decision-making. Consistency, fairness, and integrity build trust, and trust is the foundation of a motivated team.
3. Follow the Golden Rule
Treat people how you would like to be treated. This simple principle encourages compassion and respect, two qualities every effective leader must demonstrate.
4. Avoid Micromanagement
Micromanaging stifles creativity and damages morale. Great leaders see themselves as partners, not just bosses, and treat their teams as collaborators working toward a shared goal.
5. Empower Employees to Grow
Empowerment means giving employees responsibility that matches their capacity, and then trusting them to deliver. Encourage them to take calculated risks, learn from mistakes, and problem-solve independently. If something goes wrong, turn it into a learning opportunity, not a reprimand.
6. Communicate in All Directions
Communication shouldn’t just be top-down. Invite feedback, create open channels for suggestions, and genuinely listen to what your people have to say. Healthy upward communication closes gaps before they become conflicts.
7. Overcome Insecurities
Many leaders secretly fear being outshone by younger, more tech-savvy employees. Instead of resisting, embrace the chance to learn from them. Humility earns respect and helps the team innovate faster.
8. Invest in Coaching and Mentorship
True leaders grow other leaders. Provide mentorship, career guidance, and stretch opportunities so employees can develop new skills. Leadership is learned through experience, but guided experience is even more powerful.
9. Eliminate Favoritism
Avoid cliques and office politics. Decisions should be based on facts and fairness, not gossip. Objective, transparent decision-making builds credibility.
10. Recognize Efforts Promptly
Recognition often matters more than rewards. Publicly appreciate employees’ contributions and do so consistently and fairly. A timely “thank you” can be more motivating than a quarterly bonus.
11. Conduct Thoughtful Exit Interviews
When employees leave, treat it as an opportunity to learn. Keep interviews confidential and use the insights to improve management practices and culture.
12. Provide Leadership Development
Train managers to lead, not just supervise. Leadership development programs help shift mindsets from “command and control” to “coach and empower.” This transformation has a direct impact on morale and retention.
13. Adopt Soft Leadership Principles
Today’s workforce, largely millennials and Gen Z, value collaboration over hierarchy. Soft leadership focuses on partnership, mutual respect, and shared purpose, rather than rigid top-down control.
The Bigger Picture: HR’s Role
Mercer’s global research highlights five key priorities for organizations:
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Build diverse talent pipelines
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Embrace flexible work models
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Design compelling career paths
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Simplify HR processes
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Redefine the value HR brings
The challenge? Employers and employees often view these priorities differently. Bridging that perception gap is just as important as bridging the relational gap between leaders and staff.
Treat Employees Like Associates, Not Just Staff
When you treat employees like partners, they bring their best selves to work. HR leaders must develop strategies to keep talent engaged, empowered, and prepared for the future.
Organizational success starts with people, always. Build the relationship with your team first, and the results will follow.
Entrepreneurs
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Learn essential lessons, success strategies, and mindset shifts every aspiring entrepreneur needs to overcome challenges and build a thriving business.
Back in July 2017, I attended a business seminar on entrepreneurship in India. With my appetite for learning and meeting new people, I wanted to explore the latest developments in the entrepreneurial world. (more…)
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