What Are the Challenges of Entrepreneurship?

From firing a bad hire to creating a solid routine, here are 15 answers to the question, “What are your biggest challenges as an entrepreneur?”

• Saying Goodbye to a Bad Hire Right Away
• Hiring Qualified Candidates
• Learning to Let Go 
• Trading Time for Money
• Staying Organized and Delegating
• Curbing Impatience With Scaling
• Discovering Your Audience’s Market 
• Remaining Competitive
• Staying Creative
• Avoiding Burnout
• Getting Your First Client
• Keeping Up With the Latest Trends
• Taking Calculated Risks
• Finding a Good Work-Life Balance
• Establishing a Cadence for Marketing My Services

Saying Goodbye to a Bad Hire Right Away

As a techpreneur of 11 years, I used to have difficulty saying goodbye to a bad hire right away. Back in the day, I would keep an underperforming employee to the bitter end just because they seemed to have a great personality.

Unsurprisingly, this noble endeavor turned into an uphill battle in 99 out of 100 cases. An incompetent employee would delay others in getting their work done, negatively impact the bottom line, and become a burden on project managers. 

Performance targets, incentives, and personal guidance did not help. In the end, I’d have to terminate the relationship anyway—but at a greater cost. So, “hire slow, fire quickly” is definitely one of those ingrained business principles that you shouldn’t question. Today, I’m lucky to have the team of my dreams, where every employee perfectly fits into their roles.

Tatsiana Kerimova, CEO, Orangesoft

Hiring Qualified Candidates

As an entrepreneur, trying to find suitably qualified candidates can be incredibly draining. The hiring process often takes several days of my time, during which I’m placing ads, reviewing resumes, and interviewing. 

When I find a dream candidate, it can be a struggle to offer them a sufficiently attractive package to get them on board. One thing that has helped is to be ultra-specific about what I’m looking for and upfront about what the job entails. Pre-qualifying candidates in this way helps me to quickly sift out the ones who are unlikely to be a good fit.

Shawn Plummer, CEO, The Annuity Expert

Learning to Let Go 

As an entrepreneur, I’ve spent years building businesses from the ground up. Many of my fellow business owners will agree that some of our best ideas and sparks of motivation come during our solitude in the middle of the night. 

We’re subconsciously trained to rely on ourselves to accomplish our goals. While I support living independently, I can’t deny the detriments that come with tackling every major task on my own. It doesn’t take long for burnout to take over. When that happens, your productivity drops as you’re forced to take a step back to recover. 

Perhaps the biggest lesson that I’m still learning from entrepreneurship is that delegation isn’t a sign of weakness; rather, it is a strategy for sustainable, long-term success—the kind that doesn’t require you to be on the hamster wheel 24/7 to see returns.

Stephan Baldwin, Founder, Assisted Living Center

Trading Time for Money

My biggest challenge as an entrepreneur is figuring out how to trade less time for more money. Among other things, I provide digital marketing and project management services to several clients. 

Periodically, I try to optimize my model where I bring in more help as needed. I also adjust my product offering, particularly for new clients. What I’ve learned is that clients just want to see value, and that doesn’t always have a one-to-one relationship with time worked. 

Figure out how to maximize value while minimizing work and overhead, and you’ve got a scalable business. Sometimes it even means making hard decisions and dropping clients who just aren’t as profitable, while you replace them with clients that are more aligned with your current goals and business model.

Dennis Consorte, Digital Marketing and Leadership Consultant for Startups, Snackable Solutions

Staying Organized and Delegating

As an entrepreneur, my biggest challenge is not having enough time. Balancing all the different tasks and responsibilities that come with running a business can be overwhelming and stressful, and it’s difficult to prioritize and focus on the most important ones. 

I try to stay organized and efficient by using tools such as to-do lists and calendars to overcome this challenge. When possible, I assign tasks to others. I know that time management is critical for success as an entrepreneur, and I’m committed to improving my productivity and using my time as effectively as possible.

James Credland, Founder and Editor, Jimmy’s Handbook

Curbing Impatience With Scaling

The biggest challenge I’ve experienced as an entrepreneur is curbing my impatience with business expansion. 

Like any entrepreneur, I want to scale my business quickly. Scaling means I’d be able to serve more clients and help them pursue opportunities in investing and business. While passion and drive help me stay committed, I know that letting these emotions take over could cause hasty, impetuous decisions. 

Working toward your long-term goals is one thing, but prematurely expanding operations is another. From my experience, you can curb impatience by making realistic, grounded business expansion plans. Set milestones that show your venture is growing. Instead of making big decisions based on subjective factors, you can use objective, quantified growth metrics.

Mark Damsgaard, Partner and Head of Client Advisory, Global Residence Index

Discovering Your Audience’s Market 

I have an excellent product that my market just “gets” when they see it. So there is almost no need to explain what it does—it’s all in the name. But getting in front of enough people is the challenge. 

My market is horse people, and they are quite pragmatic and down-to-earth. They are also tightly knit as far as markets go. It took me a while to find where they were to talk about my product. 

In the end, Facebook and Instagram turned out to be good markets to advertise. Google Adwords didn’t work at all. I also find trade shows to be quite successful in getting new customers. My suggestion to entrepreneurs in the same position is to try a bunch of markets until you find the one your customer demographic is present in and responds to!

Andy Ide, Founder and Director, HorseRecords

Remaining Competitive

One of the biggest challenges I’ve encountered as an entrepreneur is maintaining a competitive edge. The couponing industry is extremely competitive, and it’s a constant battle to create new ideas and develop innovative ways to save money for our customers. 

With so many people looking for ways to be frugal with their finances, we must stay ahead of the curve and come up with new ideas and concepts before anyone else does. We also have to keep our eye on emerging trends in the couponing world—such as digital marketing, social media campaigns, and even mobile apps—to ensure that we stay relevant in an ever-changing market. It’s a lot to keep up with, but it’s worthwhile in the long run.

Gary Gray, CFO, CouponChief

Staying Creative

A recent Accenture study showed that 62% of large companies have invested in innovative technologies to grow their business. This shows that innovation is an essential part of every business. 

With the business landscape getting more unpredictable every day, encouraging creativity is one of the important ingredients of innovation. This has become a challenge for me because I cannot predict when a product will lose its popularity. The industry is saturated with a sea of competitors and a unique product today might be a thing of the past tomorrow.

Staying innovative is a ticket to gaining long-term traction in the industry. There is no other option but to go big or go home.

Becky Moore, Founder, Global Grasshopper

Avoiding Burnout

As a serial entrepreneur, I always knew that my biggest challenge was avoiding and preventing burnout. I have 24/7 access to my business, and in business, there is always something that needs to be done or can be done. 

However, it is important for entrepreneurs to strike the right balance and prevent burnout so that they can make clear, smart decisions for the long-term benefit of their business and themselves.

Michael Maximoff, Co-Founder and Managing Partner, Belkins

Getting Your First Client

I think the biggest challenge as a founder of a startup was getting that first client. We can do all sorts of magic on our websites and create sales decks that sing, but when the rubber meets the road (or gets close to the road) and the client wants to talk to your past clients—and you don’t have past clients—sometimes you’re just hosed. 

My organization provides DEI consulting services, which is a bit of a departure from my “first” career. Fortunately, we landed our first client sans referrals (none were requested), so we got lucky. 

But I think the best sage advice I can share with those running organizations still in the infancy stages would be to keep driving forward, keep pitching, keep selling, and if you’re passionate and determined enough, eventually you’ll get your first too.

Rhonda Moret, Founder and CEO, Elevated Diversity

Keeping Up With the Latest Trends

My biggest challenge as an entrepreneur in real estate agent coaching is staying ahead of the curve in an ever-changing industry. Real estate agents need to keep up to date with the latest market trends, regulations, and technologies, and I need to ensure that my coaching methods and strategies are up to date with these changes. 

Additionally, I ensure that my coaching methods are effective in helping real estate agents reach their goals. It’s difficult to stay positive and motivated amidst the highs and lows of being an entrepreneur, so I’m all about encouraging my students to stay positive.

Jasen Edwards, The Chair of the Agent Editorial Board, Agent Advice

Taking Calculated Risks

As an entrepreneur, my biggest challenge is finding the right balance between risk and reward. I have to take calculated risks in order to grow my business, but I also have to be aware of the potential pitfalls that come with taking that risk.

It’s a tricky balance to maintain, but it’s one that can be the difference between success and failure. I have to trust my instincts and make sure that the decisions I make are well-researched and thought-out. After all, I’m the one responsible for the success or failure of my business.

Ray Schultz, VP, Marketing, Liquid Rubber

Finding a Good Work-Life Balance

As an entrepreneur, my biggest challenge is finding the perfect balance between managing my business and managing my personal life. 

It’s difficult to find time for both, and I often stretch myself too thin. For example, I recently launched my clothing line and had to put in a lot of extra hours to get it off the ground. Unfortunately, this took away time from my family and personal hobbies, and I had to make some sacrifices. 

Although it’s been a challenge, I’m learning how to better manage my time and prioritize what matters most.

Abdullah Prem, Digital Marketer, Bloggersneed

Establishing a Cadence for Marketing My Services

My biggest challenge has been keeping up a regular cadence of marketing efforts for my services. 

Meeting project deadlines for my clients is no problem for me, but somehow, setting and meeting my own deadlines to market myself is more challenging. I tend to go through cycles of heavily marketing myself and then dropping my marketing efforts too quickly when I get busy with client projects.

Rachel Heston-Davis, Freelance Content Marketing Writer

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