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7 Pain Points Entrepreneurs Should Expect and Embrace

Sean Peek
Sean Peek
business.com Contributing Writer
Updated Sep 20, 2022

As an entrepreneur, you need to roll with the punches. Here are a few necessary evils of the business world.


The famous saying “no pain, no gain” rings especially true for entrepreneurs. When starting out, there are bound to be some bumps and bruises as you stumble through new situations and experiences. Even as your company develops and begins to take flight, there will be growing pains. The good news is, there are practical steps that can make dealing with business pain points much easier.

Pain points entrepreneurs face

To prepare you for what’s to come as an entrepreneur, here are seven pain points that 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 one 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, pride and wallet when investors don’t want to fund your startup. Hearing no over and over again will sting. 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 just 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, typically when creating a startup, there are no 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 you may not be able to market and launch it. But not every talented individual out there 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 one day will become big.

You can leverage this desire while also taking advantage of the incredible number of freelancers willing to work from anywhere in the world for startup rates. While you may not be able to keep all the talent you come across, there are those who 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 fish in the workforce sea.

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, especially after dedicating 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 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.

TipTip: While realizing you’re going in the wrong direction feels painful at first, see the experience as an opportunity to grow and be grateful for what you’ve learned. It’s better to try and fail than never to try at all.

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 those supporting you.

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. Overwork those muscles, and 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. Not even superheroes can do everything well. That’s why they often work in pairs or as a team. Beyond relying on those around them, many entrepreneurs also look to tech tools that assist with productivity.

7. 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 moving forward to try 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 the fact that this particular venture did not work out, learn from it and focus on making your next startup a success.

Bottom LineBottom Line: Entrepreneurs endure pain in pursuit of their dreams and business success. The pain won’t last forever, and you can find supportive and skilled people to lean on to make the process more bearable.

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 a realistic expectation of yourself and sharing it with your team and loved ones are 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. 

FYI: Honest self-reflection keeps you accountable to yourself and helps pinpoint the roots of your stress, which will help you maintain a healthy work-life balance.

Become more flexible and adaptable.

Adaptability in business remains a nonnegotiable skill for entrepreneurs. Learning to embrace the unexpected while also planning for all conceivable scenarios sets up you and your business for success. Becoming more adaptable and flexible doesn’t mean becoming careless or reckless. Instead, it’s the conscious practice of simultaneously small- and big-picture thinking coupled with mindfulness and ambition.

Entrepreneurial adaptability manifests in multiple ways. Keep your internal monologue positive and encouraging, always remembering 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.]

Did you know? Consumers have pain points too. It’s your job as an entrepreneur to try to address them.

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. Assigning tedious tasks that don’t impact growth, ones that drain you of energy and passion and those that others have more skill or expertise in sets up your business for success. Avoid the pain of things falling through the cracks and your team members feeling that you don’t trust them by awarding responsibility and holding staffers accountable for their assignments. 

If being an entrepreneur was easy, it wouldn’t feel as satisfying as it does when success finally comes. Pain doesn’t last forever, especially if you’re prepared with these “first aid” 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 the writing and reporting in this article.

Image Credit:

Rawpixel / Getty Images

Sean Peek
Sean Peek
business.com Contributing Writer
Sean Peek has written more than 100 B2B-focused articles on various subjects including business technology, marketing and business finance. In addition to researching trends, reviewing products and writing articles that help small business owners, Sean runs a content marketing agency that creates high-quality editorial content for both B2B and B2C businesses.