12 Pain Points Entrepreneurs Should Expect and Embrace

Pain points entrepreneurs face

To prepare you for what’s to come as an entrepreneur, here are 12 pain points many entrepreneurs experience when starting and running a business.

1. Finding the first users

The first users of your product or service are key because they can tell others about what you offer. However, convincing someone to be the first user can be painful because the most work goes into influencing the decision. That’s why many companies desperately try anything to get those first users, including giving away their product or service or offering a free trial period. It can seem like an impossible task, but it’s worth the considerable effort it will take to locate and win over those first users.

These first users will come faster if you take the time to get to know your prospects and find out what they are really seeking. Then, go back and make sure what you’re offering fills that void for them. Return to those prospects and show them what you’ve done, to see if it’s something they want. If they say yes, then you have the first users.

2. Being rejected by investors

It hurts your confidence and wallet when investors don’t want to fund your startup. Hearing no over and over again stings. If no one else believes in your idea, then it can’t be that good, right? That’s not necessarily true, and the pain is a sign to find out why there is a lack of interest from investors. It could be that you’ve been targeting the wrong types of investors for your business or that you need to provide more evidence of current and future success to secure funding. [Related article: How to Find and Attract Business Investors]

3. Getting and keeping talent

In sports, the winning teams are usually those that have the most money to get the talent they need. However, when you’re creating a startup, there are typically insufficient funds to hire the best and brightest. It may seem that without access to a skilled team, you won’t be able to develop your product or service or that you may not be able to market and launch it. But not every talented individual is looking for the highest bidder. Many want to get in on the ground floor and grow with a company because their goals are to be a part of something that will become big someday.

You can leverage this desire while taking advantage of the incredible number of talented freelancers willing to work from anywhere in the world for startup rates. While you may not be able to keep everyone you come across, some will stay if they see career and growth potential. It takes effort, and not every individual you select will ultimately be right for the company. But online marketplaces and networking sites put you in front of many talented individuals looking for work.

4. Realizing it’s the wrong direction

Nothing cuts deeper than the realization that you’ve been heading in the wrong direction with your business after you’ve dedicated your time and money to it. You can kick yourself for thinking you’ve wasted resources, but what you really need to do is be glad you realized sooner rather than later that you need to pivot and alter your course to better meet your market and target customers’ needs. Take what you learned, and keep going.

5. Lacking support

It hurts when it feels like you’re all alone on your mission. Stephen King was rejected more than 30 times with his first book, “Carrie,” to the point where he gave up and threw it away. However, his wife removed it from the trash and encouraged him to try again, and from then on, he was a success. Everyone needs that cheerleader on their side who believes in them and provides the emotional support necessary to work through the rejection, self-doubt and frustration. 

Look to offline and online networking groups for a mentor or coach who can lend their support and advice to help you avoid the pain of working alone. Plus, you may even learn from your support network.

6. Doing it all — and trying to do it well

Like a lack of support, doing everything yourself and trying to be good at it can leave you physically, mentally and emotionally drained. If you overwork those muscles, you’ll not only experience pain, but you could also be doing more damage than good. While working hard feels satisfying, it’s important to strike a balance, ask for help and recognize when a particular area is not your strong suit. This doesn’t mean you are a weak person; instead, it says you’re smart and savvy in your understanding of where your skills and knowledge can be best utilized. Beyond relying on those around them, many entrepreneurs also look to tech tools that can boost productivity.

7. Not understanding cash flow

Many budding entrepreneurs face cash flow challenges if they don’t fully understand their revenue sources and where their money is going. However, proper cash flow management is crucial to maintaining a healthy cash reserve, which allows businesses to prepare for big expenditures, take advantage of investment opportunities or handle unexpected costs. It also enables businesses to forecast their financial positions, thereby driving budgeting decisions. 

Managing cash flow helps businesses avoid financial shortfalls where they can’t pay off outstanding debts. While no business can be fully in control of its cash flow, it can help to understand the cash flow cycle — knowing what money should be coming in, where it will be spent and what will be left over. 

To ensure steady cash flow, set clear payment terms with clients for timely payments and reduce your spending when possible. Consider external resources, too: According to data from OnDeck, one of the most prevalent methods businesses use to manage their cash flow is a line of credit, with 56.2 percent of companies adopting this approach. 

8. Keeping up with rapidly changing technology

While technological advancements help businesses improve their workflows and daily processes, many small businesses struggle to keep up with these constant changes. In fact, data from an Infosys report shows that 71 percent of businesses are concerned that the rate of technological change is outpacing their organization’s ability to adapt and integrate it into their operations.

Entrepreneurs should expect a learning curve when adopting new technologies into their business. Employees need time to learn how to use new tools, and businesses shouldn’t rush to implement them until they understand their benefits in long-term strategies. For example, artificial intelligence (AI) has led to the emergence of many tools, and many existing technologies have been upgraded to include AI features. However, this means that employees who are accustomed to older versions have to relearn or adapt to changes in the tools they use every day. 

To make the adjustment easier for employees, offer continued training and workshops. These educational efforts will ensure that all employees are proficient in the latest technologies, thereby streamlining workflows and leveling the playing field.

9. Maintaining legal compliance

Every year can bring changes in laws, regulations and frameworks, which affect security, employee classification, wages, taxes and more. If your business is found to be noncompliant, you could face costly repercussions, such as fines, operational interruptions or even criminal charges, all of which can tarnish your reputation. In fact, 87 percent of organizations suffered negative consequences from either low compliance maturity or reactive compliance strategies, according to a report from Drata.

It’s your responsibility as a business owner to understand what these changes are and how they affect your business. Start by conducting an internal audit to assess your compliance status. Then, ensure continued compliance by implementing and enforcing clear policies across the workplace and developing a system that consistently monitors for relevant changes. 

If your business can pay the upfront costs, consider working with a compliance expert. This is an effective strategy that can help save your business from costly issues down the road. 

10. Managing inventory

Inventory management is among the common pain points for small businesses. Despite its importance, over 50 percent of companies lack full visibility into their supply chain, according to a report from The Association for Supply Chain Management. This leaves many entrepreneurs in the dark about the intricate processes behind their operations. This lack of insight complicates planning and increases a business’s vulnerability to supply chain disruptions such as cyberattacks and unexpected IT outages. 

Addressing supply chain visibility is crucial for improving your inventory management. Start by consistently monitoring your inventory. You can use inventory management software to audit stock and ensure you’re purchasing only what you need. Then, explore strategies to reduce your supply chain expenses; cutting costs from even 9 percent to 4 percent could affect your profits. 

If you manage your own stock, optimize your storage space and develop a production plan based on accurate forecasting. This ensures that you maintain the right inventory levels to meet customer demands while avoiding excess stock of unwanted items.

11. Overlooking cybersecurity risks

Too often, entrepreneurs overlook their cybersecurity until it’s too late. Working under the assumption that small businesses aren’t as vulnerable to attacks as large corporations are, many choose to hold off on implementing cybersecurity measures, whether due to the cost, a lack of expertise or another reason. 

However, small businesses face many cyber risks, including data loss threats and asset damage. Cyber attacks on small businesses are at a record high, affecting 73 percent of small businesses in 2023, according to a report by the Identity Theft Resource Center. The causes of the attacks vary, with the most common reasons being outside attackers and internal bad actors.

While it’s not always possible to fully prevent an attack, you can take measures to reduce the risk. Start by educating your employees on best practices and signs employees should look out for, such as phishing schemes or other exploits. Protect your business’s inbound and outbound data by encrypting it and setting complex passwords with multifactor authentication. Keep backups of your data, and if possible, establish a kill switch to disable server and website access during a breach.

12. Failing and shutting down the business

No one wants to have that moment when it’s time to acknowledge that your business is just not going to work. You feel as though you’ve let yourself down, as well as your investors, staff, family and friends. If it happens, you can’t let that failure consume you and stop you from trying something new. Some of the most successful and admired people have failed numerous times, and they will say they are glad they did. 

Thomas Edison is often quoted as saying, “I have not failed. I’ve just found 10,000 ways that won’t work.” Henry Ford famously said, “Failure is simply the opportunity to begin again, this time more intelligently.” And a quote attributed to author Napoleon Hill asserts, “Most great people have attained their greatest success just one step beyond their greatest failure.” Accept that this particular venture did not work out, learn from it and focus on making your next startup a success.

Tips for dealing with business pain points

While entrepreneurs can’t completely avoid pain points, these four tips can make bumps in the road less painful.

Practice work-life balance.

Work-life balance can feel elusive to entrepreneurs, but finding a comfortable equilibrium between work responsibilities and your personal life will eliminate a mountain of stress. While the perfect work-life balance does not exist, establishing realistic expectations for yourself and sharing them with your team and loved ones is vital to finding as much balance as possible.

Demands will ebb and flow, and a 50/50 split of your time isn’t always feasible or sustainable. Still, taking care of your health, working on something you’re passionate about, communicating transparently with employees and loved ones, and having hobbies that bring you joy can help establish a proper work-life balance. 

Become more flexible and adaptable.

Adaptability in business remains a nonnegotiable skill for entrepreneurs. Learning to embrace the unexpected while planning for all conceivable scenarios sets you and your business up for success. Becoming more adaptable and flexible doesn’t mean becoming careless or reckless. Instead, it requires you to think simultaneously about the small and big picture while maintaining your ambitions.

Entrepreneurial adaptability manifests in multiple ways. Keep your internal monologue positive and encouraging, and always remember to be your own biggest cheerleader. Invest in becoming more creative and open-minded to find innovative solutions to problems. Take care of yourself physically, mentally and emotionally so you can bring your fully energized self to work each day, ready to tackle complex problems.

Build and utilize your network.

The business world thrives on networking; it fosters new ideas, increases audience reach and opens doors to new opportunities. Building your network takes effort. Always be prepared with an elevator pitch for your business, and keep business cards handy. Attend events at your local chamber of commerce, professional associations and even virtual conferences to meet other industry leaders. Volunteer in your community to meet potential customers and connect with other local businesses.

Once you’ve built a network of peers, make sure to maintain those relationships. Learn how to engage with followers on LinkedIn, ask for coaching, become a mentor and ensure you foster symbiotic give-and-take relationships rather than merely using others for your own gain. [Find out how to create a business profile on LinkedIn.]

Delegate some of your responsibilities.

Often, startups and growing businesses demand that the founders do everything, including research, HR, marketing and accounting. While having your hand in every aspect of your business may feel natural and even necessary, learning to delegate responsibilities can reduce stress and propel your company forward. Delegation is how you work smarter, not harder, as an entrepreneur.

Successfully delegating responsibilities to employees strikes a balance between micromanaging and doing it all yourself. To set up your business for success, delegate any tasks that others have more expertise in, that drain your energy, or that don’t lead to growth. When you award responsibility and hold staffers accountable, team members will feel empowered because you trust them. 

If being an entrepreneur were easy, success wouldn’t feel so satisfying. Pain doesn’t last forever, especially if you’re prepared with these tips. Failing in business — but growing in character, experience and wisdom — is beneficial for personal and professional growth. With each startup, certain pain points may lessen while new ones appear. When they do, embrace and work through them on the path to success.

Peter Daisyme contributed to this article.