Navigating the Early Challenges of Entrepreneurship & How to Overcome Them

I know this isn’t a mind-blowing or revolutionary thing to say, but being an entrepreneur isn’t easy. It takes a lot of guts, persistence, business acumen, and strategic thinking — and even having those qualities in spades isn’t always enough for a business owner to stay afloat.

The challenges of entrepreneurship can exist well beyond any entrepreneur’s control — but those troubling roadblocks aren’t insurmountable. Here, I’ve spoken to entrepreneurs to get their takes on the most common challenges of entrepreneurship and their advice for overcoming them.

Let’s jump in.

Challenges Entrepreneurs Will Face This Year

1. Work-life balance

In the State of Entrepreneurship survey I ran in early June 2024, I asked respondents about their biggest pain points as entrepreneurs and business owners. The top response was work-life balance.

The definition of a good work-life balance is different for everyone, but to me, the main idea is that one doesn’t have to sacrifice work or personal life to accommodate the other.

Evan McCarthy, President and CEO of SportingSmiles, told me he faced this challenge when he started entrepreneurship. He said, “I launched my company 15 years ago, and as a business owner, there’s always a mountain of tasks to tackle. The main challenge I faced was finding a balance between my work and personal life.”

When he started his business, he was single, which he says made things easier, but he worked nonstop for two months straight without taking days off. He said, “I was completely dedicated to making my business succeed, without any backup plan if things didn’t work out.”

He adds, “Looking back, I realize I should have paid more attention to my personal life. Taking better care of myself would have reduced stress and probably helped me focus more on growing the business.”

How to Overcome This Challenge

One of the biggest benefits of entrepreneurship is being your own boss. It gives you the freedom to set your hours and develop the work-life balance that works best for you, but things like hustle culture can make it seem like it’s important to always be on and ready to work.

My recommendations for maintaining a work-life balance include:

Setting boundaries: This can be as simple as setting work hours that you stick to whenever possible. Busier days happen, but you have a primary schedule.
Take clear breaks: I’m a strong proponent of taking breaks. It helps me clear my head and come back with fresh eyes.
Set realistic expectations: Overcommitting can make you feel like you have to keep working until everything on your list is complete, so aim to be honest about what you can accomplish every day.

Have fun when you’re not working: I’m sure this is a no-brainer, but it’s worth saying anyway. When you’re not working, do the activities that bring you joy, whether being with loved ones, setting aside time for a hobby, or even sitting around and doing nothing.

2. Accessing capital and funding.

Accessing capital and funding is the #2 challenge our survey respondents face.

This makes sense to me — starting a business without funding is impossible. In fact, the average small business owner spends around $40,000 in their first year of business.

A majority of entrepreneurs told us that most of their funding comes from personal funds, which can be an added stress factor as personal funds are for personal needs.

How to Overcome This Challenge

The best way to avoid cash flow issues is to create a budget. You’ll know how much you need and are supposed to have and can seek additional funding sources if expenses outweigh revenue. Some tried and true ways to get funding for your business include:

Crowdfunding: Websites like GoFundMe and Kickstarter give you financial backing from online campaigns.
Small Business Loans: Local small business organizations and development centers often offer loans for early-stage businesses to apply for.
Bank Loans: Bank loans are a common funding source. I recommend reviewing interest rates and repayment terms to make sure they align with your ability to repay.
Angel Investors: Angel investors are accredited professionals who offer funding. You typically have to pitch to these investors or apply for their funding offers.
Friends and Family: Some people have friends, family, and loved ones willing to pitch in and support. If this is the case for you, it’s a worthwhile source to take advantage of.

3. Finding Customers

72% of respondents to a study by the Kauffman Group said they struggled to find customers.

Finding customers is one of the (if not the) most fundamental tasks to address if they want their business to take off, especially since you can’t always bank on customers simply finding their way to you.

How to Overcome This Challenge

As an entrepreneur, it’s on you to get the word out about your brand — self-promotion is how you get the ball rolling.

The first step to finding customers is knowing who your ideal customer is. Doing buyer persona research will help you learn about your target audience, their interests, pain points, and the best way to attract them. You’ll also be able to determine your brand positioning, which helps you create targeted marketing efforts to get in front of customers.

I assume you’re proud of your business, so I recommend boasting about it every opportunity. If you serve a local customer base, ask if you can leave a business card or flier at local establishments.

Go to industry events and trade expos and really put your business on display. Keep an active presence on social media, and ask your friends, family, and anyone in your support network to get the word out. Create a referral program for your existing customers.

It comes down to visibility, so, one way or another, make your presence known. Customers won’t find you if you stay isolated.

4. Finding Mentorship

Entrepreneurial endeavors can be challenging to navigate alone — particularly for younger or first-time founders.

Access to advice, insight, and direction from more seasoned business owners can help keep things on an even keel, but pinning down that direction is easier said than done. In fact, 60% of aspiring entrepreneurs said finding a mentor who can provide guidance is challenging.

How to Overcome This Challenge

Networking events, industry-specific expos, and social media platforms are all opportunities to connect with like-minded and experienced businesspeople. You can also:

Talk to business people you admire. If you’ve developed a relationship, you can take it a step further and propose a mentoring situation.

Make it known that you’re looking for a mentor. People you might not have known yet might approach you first and present an opportunity.

Apply to mentorship programs designed to help you find qualified mentors in your industry. If you’re based in the U.S., contacting small business development centers is a great way to get started.

Connecting with your community, whether your local community or on platforms like LinkedIn, can help you find people with your shared interests. Hearing people’s stories can be as helpful as connecting with someone with seniority.

The key to finding a mentor is being willing to put yourself out there. There’s no guarantee that someone can offer guidance, but plenty of people are willing and excited to share their insights.

My Recommended Reading

5. Staying motivated.

Justin Silverman, Founder and CEO of Merchynt, told me, “The biggest challenge for me was staying motivated during the early days when revenue was nonexistent and growth was slow.”

Motivation can be a struggle for everyone, no matter what stage of business. It can become even harder to maintain if you’re experiencing burnout or a lack of work-life balance.

Motivation is, thankfully, something you can build back.

How to Overcome This Challenge

Here’s what Silverman did to regain motivation: “I took inspiration from The Messy Middle and set a mix of small and large achievement goals. I put them on a board in front of my desk and checked them off as I went. This approach helped me see that little wins add up to big achievements over time. It kept me going when I had previously given up on other ventures.”

He said this approach taught him the importance of celebrating small victories to maintain momentum and motivation.

Breaking down your goals can make responsibilities feel more manageable, help you feel less overwhelmed, and help you prioritize the most important tasks. It’s a win every time you meet one of your smaller goals, and hopefully, it will leave you feeling accomplished, excited, and motivated.

6. Being adaptable.

Scott Williamson, VP of Sales and Engineering at R. Williamson & Associates, said, “My biggest challenge as an entrepreneur was learning how to pivot and adapt quickly.”

Markets are always changing, so it’s an understandable challenge. Unexpected hurdles (cough cough, pandemic) can arise and, even with contingency planning, pivoting can still be a challenge.

Williamson adds, “When I first started my company, I had a vision for what I thought the business would become. But as we launched and started gaining real customers, the reality of the market and the competitive landscape became clear. Things weren’t evolving exactly as I had imagined.”

He said he had to learn to listen to customers and make quick adjustments to better align with their needs. Even though it was difficult to accept that his original vision wasn’t perfectly accurate, customer insight helped build a product that gained real traction.

How to Overcome This Challenge

Williamson’s tip is to recognize that entrepreneurship is not about rigidly sticking to a plan: “It’s [entrepreneurship] about having a vision, testing it in the real world, listening to feedback, and being willing and able to adapt. The market is always changing, so entrepreneurs have to change with it.”

I recommend also staying up to date with industry news and trends and monitoring consumer trends. You’ll get a sense of the state of your industry and whether any changes are coming down the line.

7. Inclusion and Opportunity-Related Barriers

I run Breaking the Blueprint, a HubSpot blog column dedicated to the unique challenges of underrepresented entrepreneurs. Many of the difficulties said groups face are because of historical practices that excluded them from equal opportunities.

As a result, minority-owned businesses still sometimes struggle to achieve the same level of success as their white counterparts. Here are some stats that outline the unique entrepreneurial landscape for minority entrepreneurs:

Almost half of women-owned small businesses responding to a QuickBooks survey said that having more funding or financial help would have the greatest impact on their business.
Nearly 8 in 10 Black small business owners say they’ve experienced racism from a customer.
LGBTQ+ founders created 36% more jobs, 114% more patents, and 44% more exists, but raised 16% less funding than the average founder.
Latino businesses received less than 1% of the $487 billion invested in the top 500 largest venture capital and private equity deals in 2020.

These discrepancies are unfortunate because minority entrepreneurs contribute nearly $2 trillion annually to the U.S. economy.

How to Overcome This Challenge

Many of the challenges underrepresented entrepreneurs face require action on behalf of institutions that have historically been unsupportive.

Thankfully, though, individuals can take action to better their circumstances. For example, you can:

Seek out resources specifically for underrepresented entrepreneurs. (Another shameless plug for Breaking the Blueprint, where I publish this kind of content)
Network and build relationships with people who have similar experiences. You can share advice, discuss challenges, and uplift each other through your entrepreneurial journeys.
Seek out business mentors who are willing to share their experience and expertise.
Apply for grants, loans, and funding opportunities for minority entrepreneurs, like minority business loans.

8. Asking for help.

Being comfortable asking for help is a learned skill. People like to be autonomous and can view asking for help as a sign of weakness.

I think asking for help means the opposite — it shows a willingness to learn, and it can leave us better off in the long run because we’re getting support, and the opinions of others can push us to consider new ideas.

Jody Swain, Founder of Hire & Fire Your Kids, struggled with asking for help when she started her journey. She told me, “By far, my biggest challenge as a first-time entrepreneur was trying to do it all by myself and not asking for help.”

Swain adds, “I didn’t want to bother people, take up their time, be judged, or be rejected, so instead, I did what I thought entrepreneurs were supposed to do. I hustled. Working too many hours in a day, for weeks that turned into months, triggered my family to host a full-blown intervention with me.”

She says the intervention caused her to slow down and start seeking help. She discovered various resources available for entrepreneurs, such as grants, small business hubs, and accelerator programs.

“What took me way too long to learn was that there were actual people out there who wanted to help. The answer will always be no if you don’t ask. Once I realized that all I had to do was be brave and just ask, the doors of support opened, and I haven’t looked back,” Swain says.

How to Overcome This Challenge

The best way to overcome feeling challenged by asking for help is to reframe it as a strength rather than a weakness. It shows that you’re self-aware, willing to receive feedback, and eager to grow.

9. Self-Doubt and Fear

Self-doubt and fear are common among entrepreneurs. You might feel like you’re risking your reputation, that you might fail, or that you’re not cut out for the job — 50% of entrepreneurs say these feelings are a major challenge.

Impostor syndrome is a common manifestation of self-doubt, and research shows that 82% of people have experienced it.

The business world is always in flux, so there’s no easy answer for remedying this issue, but there are ways to mitigate it.

How to Overcome This Challenge

This seems like something someone would write on a mocking SpongeBob meme, but I stand by my tip: patience and persistence are great ways to combat self-doubt.

You don’t know how things will turn out if you don’t give things a chance to happen. For example, if your self-doubt says you won’t be able to turn a profit, how can you confirm that to be true if you haven’t given yourself the time to bring in revenue?

Be kind to yourself when feelings of self-doubt arise because how you respond can impact how long it lasts. Positive self-talk and affirmations can help you avoid stress and anxiety.

Even if you have to fake it ‘till you make it, you’re building a positive habit that will benefit you in the long run.

10. Building and empowering a team.

If your entrepreneurship journey started as a one-person show, building and empowering a team is an entirely new playing field. Instead of doing everything yourself, you’ll have to become comfortable delegating and trusting others to do their assigned tasks.

Gauri Manglik, CEO and Co-founder of Instrumentl, told me that she struggled with this. She says, “As an entrepreneur, the biggest challenge I’ve faced has been finding the right balance between leading my team while also allowing them the autonomy to thrive. Early on, I tended to micromanage every detail out of fear that things wouldn’t get done properly.”

She adds, “I quickly learned that this level of control stifled creativity and hindered performance. The real key was hiring the right people, clearly communicating the vision and expectations, then getting out of their way. I had to recognize that innovation comes from empowered teams, not overbearing founders.”

How to Overcome This Challenge

Manglik dealt with this challenge by shifting her role. She learned to provide support through coaching and mentoring while trusting her staff to complete their tasks successfully. Embracing this approach brought greater engagement, output, employee job satisfaction, and better business results.

She says, “The experience taught me that leadership isn’t about control but enabling others to do their best work.”

Other effective strategies include:

Communicating expectations and giving clear instructions
Encourage your team to take ownership of their tasks and their achievements
Highlight team wins to boost morale and strengthen team bonds

11. Keeping Pace With Changing Laws

Note: This does not constitute legal advice for your company to use or as a recommendation of any particular legal understanding.

Business owners can struggle with keeping track of legal requirements. According to a list from Funding Circle, in 2020 alone, many companies had to account for overtime rule changes, shifts in health insurance requirements, minimum wage increases, and the introduction of internet privacy regulations like the California Consumer Privacy Act (CCPA) — among several other new and amended laws.

Luckily, most newly passed laws feature some runway before compliance becomes mandatory — giving you the flexibility to account and brace for new requirements.

Still, you need to remain mindful of any laws that might immediately affect your company, whether they are local, statewide, federal, or industry-specific.

How to Overcome This Challenge

The best ways to stay on top of legal, regulatory, and compliance matters are to monitor industry news, talk to peers, leverage reputable resources, or even have an attorney you can contact to guide you through this aspect of your business.

If you need specific certifications, routinely check for changes or important renewal times. Some of the legal requirements you want to be aware of are:

Applying for necessary licenses (seller’s permits, business licenses, etc.)
Understanding small business tax requirements (the IRS website has the most comprehensive info)
Monitoring global compliance and privacy requirements (like GDPR)

My Recommended Further Reading

Over to You

The roadblocks that entrepreneurs face can be imposing.

I mentioned it earlier, but the best policy for anyone facing these challenges is to remain patient and persistent. Overcoming these issues can take time, but doing everything you can to cross the hurdles gives you the best shot.