7 Pain Points Entrepreneurs Should Expect and Embrace

Pain points entrepreneurs face

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

1. Finding the first users

Your first users are critical because they can validate your idea and help spread the word about your product or service. But convincing someone to be that first customer can be challenging; it’s often where the most effort and uncertainty collide.

In an often-cited CB Insights analysis that examined why startups fail, about 42 percent of founders said lack of market need was the primary reason their business didn’t succeed. That’s why so many early-stage companies try everything to attract their first users and avoid a bad product launch, from offering free trials to giving their product away entirely.

These users will come faster if you take the time to truly understand what your potential customers want. Try conducting customer discovery interviews to gather feedback and identify and validate end users’ pain points before you build. Schedule 15 to 30 short conversations with prospects to test your assumptions about their needs. Then, refine your offering to ensure it genuinely solves their problem. Once those same people tell you, “Yes, that’s what I’ve been looking for,” you’ve found your first users.

2. Being rejected by investors

It hurts your confidence and your wallet when investors don’t want to fund your startup. Hearing “no” again and again can sting. If no one else believes in your idea, it’s easy to assume it isn’t good enough, but that’s not necessarily true. Instead, treat the rejection as feedback and look for the reason behind the lack of interest.

According to the Federal Reserve’s 2025 Small Business Credit Survey, only 2 percent of employer firms received any equity investment last year, and of those, 19 percent said the money came from venture capital. That means fewer than half a percent of small businesses overall secured VC funding, showing just how selective the process really is.

It could be that you’re taking the wrong approach to finding and attracting investors or that you need stronger evidence of current and future success to earn their confidence. Rethink your approach and focus on building relationships with investors who align with your goals. 

3. Getting and keeping talent

In sports, the winning teams are usually those with the budget to secure top talent. But when you’re building a startup, there are typically insufficient funds in the hiring process to secure all the best and brightest. Keeping them is also a challenge. The U.S. Bureau of Labor Statistics reports that the private-sector quits rate averaged 2.3 percent in 2024, with monthly readings falling to around 1.9 percent by year-end. This is evidence that while turnover is easing, hiring and retention remain challenging across industries.

It may feel like without access to a skilled team, you can’t develop, market or launch your product successfully. But not every talented professional is chasing the highest bidder. Many want to join something new, help shape it and grow alongside it.

You can tap into that motivation while leveraging the global pool of talented freelancers and contractors eager to work with startups. Freelancer websites make it easier than ever to match with the right professional. If money’s tight, think about offering small equity shares or future profit-sharing instead of trying to outbid competitors on salary. What really draws people in (and keeps them around) is often your mission and sense of direction, not just the paycheck. 

You won’t win over everyone, and that’s fine. The right people will stay if they see real opportunity ahead. 

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 months or even years of your time, hard work and money. According to the same CB Insights report cited above, about 35 percent of startups fail because they misread market demand. That’s why knowing when and how to pivot isn’t just helpful — it’s essential.

It’s easy to dwell on the time or money you’ve spent, but spotting a problem early can be a turning point. It gives you the chance to regroup, test new ideas and move toward what your customers actually want. Take what you’ve learned, make the shift and keep building.

5. Lacking support

It’s tough when it feels like you’re carrying your business dreams alone. Stephen King was rejected more than 30 times when trying to publish Carrie, and he even threw the manuscript away. His wife famously pulled it out of the trash and pushed him to try again. Everyone needs that kind of person in their corner: someone who believes in them and helps them push through rejection, self-doubt and frustration.

Look to both offline and online entrepreneurial communities for encouragement and mentorship. For example, SCORE, an SBA partner, offers free mentoring services and has helped over 17 million entrepreneurs since 1964. Plus, the more you engage with your support network, the more you’ll learn from the experiences of others who’ve been where you are.

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

Trying to do everything yourself (and do it perfectly) can leave you physically, mentally and emotionally drained. According to Adobe’s 2025 report on entrepreneurs, one in five small business owners works more than 50 hours a week, and a full 82 percent say they lose sleep over work-related concerns. But having your business in your head 24/7 isn’t just a badge of honor: It’s a warning sign.

Working hard matters, but smart work matters more. Know where your time and energy are best used, and give yourself permission to delegate or automate the rest. For example, tech tools, especially automation and AI, are helping many entrepreneurs reclaim time and boost productivity. The report says folks are saving about six hours a week through smarter workflows. 

7. Managing cash flow effectively

Many new entrepreneurs run into cash flow challenges when they don’t fully track where their revenue comes from or how it’s spent. According to the Federal Reserve’s 2025 Small Business Credit Survey, more than half of small employer firms listed uneven cash flow (51 percent) and paying operational costs (56 percent) as their top financial challenges.

Strong cash flow management is essential to building a healthy reserve, one that prepares your business for big purchases, new opportunities or surprise costs. It also helps you forecast your financial position and guide better budget planning.

Keeping tabs on cash flow prevents shortfalls that can make it hard to pay vendors or cover day-to-day expenses. While no business can control cash flow completely, understanding your cycle — what’s coming in, what’s going out and what’s left — can make a huge difference.

To keep things steady, set clear payment terms with clients to encourage timely payments and trim unnecessary spending where possible. Consider offering early-payment discounts of 2 to 3 percent on net-15 or net-30 terms, and keep three to six months of operating expenses in reserve, as recommended by the SBA.

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 for entrepreneurs, but finding even a workable rhythm between your business and personal life can ease a mountain of stress. According to the American Psychological Association’s 2024 Work in America report, 61 percent of workers in low-support environments said they feel tense or stressed during a typical workday, compared with only 27 percent of those who feel psychologically safe. The same study found that a quarter of employees experience emotional exhaustion and a third struggle to maintain work-life balance — clear reminders of how much constant pressure affects performance and well-being.

While the perfect balance doesn’t exist, setting realistic expectations for yourself and communicating them with your team and loved ones is key to finding a rhythm that works. Demands will always ebb and flow, and a 50/50 split of your time isn’t always feasible. Still, taking care of your health and finding work that genuinely energizes you, while staying open with your team and making time for things you enjoy, can go a long way toward keeping your life in balance.

Become more flexible and adaptable

Adaptability in business isn’t optional; it’s a core survival skill for entrepreneurs. The ability to shift gears quickly and stay composed when plans change often separates thriving startups from those that stall. According to Deloitte’s 2025 Global Human Capital Trends report, 85 percent of executives say their organizations need to become more agile to respond to market shifts, yet only 39 percent are taking meaningful steps toward it, and just 6 percent are making real progress.

Learning to embrace the unexpected while still planning for what’s ahead sets you and your business up for long-term success. Being adaptable doesn’t mean acting impulsively; it’s about balancing boldness with foresight and staying grounded while you pivot.

Entrepreneurial adaptability shows up in many forms. Keep your self-talk constructive, and be your own best advocate. Build your scenario-planning skills with “what if” exercises for key decisions. Practice mindfulness to stay centered during stressful pivots. And keep yourself physically and mentally strong so you can meet each challenge with energy and creativity.

Build and utilize your network

The business world runs on relationships. Networking sparks new ideas, expands your reach, and opens doors you might not find on your own. According to ResumeNow’s 2025 Networking in the New Job Market survey, 70 percent of professionals say “who you know” matters more than what’s on your résumé — a reminder that genuine connections can be just as powerful as credentials.

Building a network takes time and a little courage. While networking on LinkedIn is valuable, in-person meetups are essential. Always have a short, memorable and genuine elevator pitch ready to describe your business. Share your contact info in whatever way feels natural, whether that’s a business card, LinkedIn message or even a quick text after meeting someone. Go where the conversations are, such as your local chamber events, industry meetups or virtual conferences, and talk with people who are doing work that excites you. Even volunteering can spark unexpected connections and put your business on more local radar.

Once you start meeting people, focus on keeping the relationships alive and cordial. Easy ways to keep in touch include commenting on their posts, sending an occasional check-in or offering help when you can. These are all small, consistent gestures that show you care. 

Remember that the best networks grow from authenticity and reciprocity, not transactions. When everyone’s getting something meaningful out of the connection, that’s when it really starts to work.

Delegate some of your responsibilities

Startups and growing businesses often expect founders to do everything, from research and HR to marketing, sales and accounting. According to Simply Business’s 2025 Solopreneur Report, more than 60 percent of business owners said they underestimated how many hats they’d have to wear, and 61 percent admitted managing every part of the business alone was harder than expected. That’s a clear reminder that no one can do it all indefinitely, and trying to only adds stress and slows growth.

Learning to delegate effectively is how you work smarter, not harder, as an entrepreneur. Delegation helps you focus on what you do best while building trust and confidence in your team. To get started, list your daily tasks for a week, then sort them using a productivity method like the Eisenhower Matrix (urgent/important, not urgent/important, urgent/not important, not urgent/not important) to spot which jobs someone else could handle. Hand off the tasks that drain your energy or fall outside your expertise, and hold your team accountable once you’ve assigned them. That’s what builds ownership and momentum.

Building resilience from pain

If entrepreneurship were easy, success wouldn’t feel so satisfying. These seven pain points — from finding your first users to learning how to delegate — are the challenges that build resilience. The struggles won’t last forever, especially when you face them with a plan. Every failure brings experience, clarity and wisdom that make the next phase easier. When new challenges appear, meet them with flexibility and confidence, as they’re proof that you’re still growing.

Peter Daisyme contributed to this article.