Overcoming Common Challenges Faced by New Entrepreneurs

The path to success is riddled with obstacles.

For new entrepreneurs, the thrill of pursuing their passion and realizing their dreams is often accompanied by a host of challenges, from financial constraints to uncertainty about market reception.

However, with sage advice from seasoned entrepreneurs, we consulted with for this article, aspiring business owners can emerge victorious.

Knowing Your “Why”

The biggest challenge for new entrepreneurs is knowing WHY they went into business. To build a long-term sustainable business, they must be deeply connected to their WHY. I recommend using the Five Whys technique developed by Toyota, which allows individuals to dig deep into their entrepreneurial desire. This exercise helps new entrepreneurs stay laser-focused and lessens the emotional rollercoaster of building a long-term legacy business.

Sailynn Doyle, your FUN business coach & creator of the legacy business system

Mastering Cashflow and Budgeting

When entrepreneurs are embarking on their initial journey, one of the make-or-break components is cash flow and budgeting.

It may seem obvious to some, but it isn’t uncommon for enthusiastic founders to mismanage their finances and make it harder to create a successful business.

It should be a priority to allocate time to budgeting analysis, and it is advisable to set out the key criteria beforehand.

Here are some tips for entrepreneurs starting a new business: Set a timeframe.

Decide whether you want to assess monthly or quarterly.

The speed of cash flow will determine the best timeframe – if money moves in and out quickly, then monthly will be acceptable, but if invoices take a while to be paid, etc., then it is worth analysing on a quarterly basis.

Decide on your strategy.

There are many different strategies you can choose from, such as standard subtracting budgeting, planning budgeting, zero-based budgeting, and priority budgeting… if you aren’t familiar with budgeting strategies, it’s worth speaking to an advisor to find out the most suitable for your business.

Itemise and track.

To assess a budget, you will need to keep a record of everything. Many programs and apps can help you record income and expenses, enabling you to view all your future transactions.

Assess results.

Analyse spending and income and see if there needs to be an adjustment.

If more money is going out than is coming in, look at options to reduce costs and explore different marketing avenues to create more sales.

Ian Wright, managing director of businessfinancing.co.uk

Leveraging Mentorship to Avoid Costly Mistakes

One of the common challenges I see new entrepreneurs face is a lack of clarity on what not to do and the common pitfalls to avoid. When you’re new to building something, it’s quite obvious not to know everything, but that leads to entrepreneurs making mistakes they’d not otherwise make.

This is something that can be overcome by getting an experienced mentor who has already built a business or is currently working in the niche you’re in. A mentor can save you countless hours and thousands of dollars you’d otherwise waste if you make even one wrong decision as a newbie.

Ram Shengale, founder & CEO of WANotifier

Establishing Work-Life Balance

Especially for entrepreneurs working completely alone, it can be difficult to balance doing the work required for a startup with making sure you’re giving yourself enough rest and downtime to avoid burnout. Burnout in the early stages of a startup is one of the most common problems entrepreneurs face (it’s something I faced), so it’s important to learn this type of balance early on. A strategy that’s worked for me is allotting one hour per day to something outside of work and other responsibilities. During this hour, I will take a walk, read a book, or engage in some other hobby. Even for entrepreneurs who can’t yet afford a full day off, having this time designated to rest and leisure can be a huge contributor to long-term success.

Andre Kazimierski, CEO of Improovy Painters of North Shore

Becoming Resilient

The biggest challenge new entrepreneurs face is resilience. There needs to be a certain kind of mindset to be an entrepreneur. It takes more than having a good business idea because if you don’t have the internal passion to follow your mission, not much will come of it. There will be good days and bad days. Being an entrepreneur requires persevering through those bad days and picking up the next day like it’s going to be a good one.

Dustin Lemick, CEO of BriteCo Jewelry Insurance

Navigating Legacy, Resources, and Uncertainty

As a new entrepreneur myself, I understand the unique obstacles we face. One of the biggest challenges was stepping into a business with a longstanding legacy, like CH Ellis, which was 125 years old when my wife and I took over. The pressure to revitalize and uphold the firm’s reputation was immense. Cultivating the right mindset was important, and we approached it as a chance to learn and build on the firm’s history while infusing our contemporary touch.

Resource management was another hurdle. Owning a business in the custom case industry demands balancing between meeting consumer needs efficiently and navigating raw material costs and supply chains — a balancing act most new entrepreneurs struggle with. My engineering background provided a significant advantage here, enabling me to identify cost-effective solutions, maintain quality, and deliver value to our customers. For example, we often purchase raw materials directly from the manufacturer to cut costs. 

However, the biggest lesson from my journey was learning to embrace fear and uncertainty. For instance, when we took over CH Ellis, the COVID pandemic was in full swing, adding more pressure. However, we used it as a catalyst to drive innovation, such as developing new case solutions to meet changing customer needs during the pandemic. My advice is: Never shy away from taking calculated risks and always be ready to adapt and learn. Stay true to your vision, even if the journey seems challenging, as these hurdles drive growth and innovation.

Brian Hipp, president of CH Ellis

Protecting Intellectual Property

When I first started as an entrepreneur, a big challenge I faced was determining when and how to protect my intellectual property. You don’t want to jump the gun too soon and spend money unnecessarily when funds are tight, but you also don’t want to risk leaving your business idea vulnerable before it’s had a chance to grow. I found the best route was to learn everything I could about IP protection and use a legal expert to guide my next moves. When your entire business is at stake, you can’t really afford to get it wrong.

Hardy Desai, founder of Supple

Embracing Entrepreneurial Autonomy

Reflecting on my early entrepreneurial days when I first started Tumble, here’s one challenge that I feel is universal to all entrepreneurs but also happens to be one that they won’t really see coming — changing work structure

We’re all basically trained to take on traditional jobs — and the problem is that most jobs expect us to respond to things — to-dos, emails, reports, meetings, etc., and this has given us a level of predictability and reliable structure to how we go about our days and make sure we’re productive.

Entrepreneurship demands us to decide how we will spend our time to accomplish all the tasks on our plate — all of which are needed to help build and grow the business. It can be hard to prioritize these, or worse, you could be spending a lot of time on things that cost money and don’t really matter–and that’s all on you. 

Early on at Tumble, this was a significant hurdle, and as an entrepreneur, you have to make a conscious effort to shift your approach to work. Instead of seeing yourself as someone who responds to the environment, you have to start seeing yourself as the one creating it. You have to adopt a mindset of a decision-maker, not a follower. For me, this meant starting each day by asking myself, “What decisions can I make today that will have the greatest impact on my goals?” This forced me to focus on strategic thinking and long-term vision rather than getting bogged down in day-to-day operational tasks.

Zach Dannett, co-founder of Tumble

Finding Your Niche and Embracing Technological Advancements

I think one of the hardest challenges faced by new entrepreneurs is the difficulty of finding their niche in the market.

You need to find a market with high demand, which often comes with an already high supply.

So, new entrepreneurs face the challenge of getting a company off the ground while also striving to be unique and fill a gap in the market.

And this challenge coexists with the rapidly advancing state of technological integration.

New entrepreneurs must juggle running a business, finding their niche, adapting to new technology, and trying to outpace their more established competitors.

To do this, I encourage new entrepreneurs to start small.

Find a specific service or product, refine it, and build a sustainable, scalable workflow.

Having this under control makes it easier to juggle the other demands of entrepreneurship.

Then when it comes to allocating time and resources, spending time each week conducting research into the market, competitors, and technological advances helps you keep on top of the need to constantly improve and develop.

Liam Wilson, editor-in-chief of Lottery ‘n Go

Staying Ahead of Industry Shifts

A major challenge for 2024 and the upcoming decades is the sheer size and growth of almost all entrepreneurial sectors.

In one regard, it’s great. Entrepreneurs have never had more access to global customers than they do today. Your options are virtually endless as long as you know how to identify opportunities. 

On the other hand, competition for funding, customers, and online relevance is at an all-time high. Trends and consumer demands are changing at unprecedented speed and so are tech and marketing. Being a successful entrepreneur today requires more than it did 20 years ago. It’s a real struggle when you’re a newbie. 

If there’s one way to overcome it, it’s to keep your finger on the industry pulse. Immerse yourself fully in your industry through networking, social media, newsletters, exhibitions, etc. You’ll understand consumers better and get a feel for industry shifts before or as they’re happening.

Brooke Paulin, owner of Biohacker Supply

Navigating the Uncertainty of AI Adoption

One of the newest challenges new entrepreneurs face is AI. It’s not a matter of implementing it, and even though figuring out how to do it is tough sometimes, it’s hard for new entrepreneurs to know if it’s for them. There are still those skeptics out there saying that AI is going to go away in a couple of years, but then there are those who live by it. Figuring out whether it’s worth investing in or not is a whole new obstacle for entrepreneurs.

Dan Bailey, president of WikiLawn Tampa Lawn Care

Conquering Self-Doubt

Based on my personal experiences, self-doubt is a significant challenge for new entrepreneurs. I can tell you personally that this has held me back from numerous opportunities over the years. Imposter syndrome is real! Sometimes, I look around a room and wonder whether I belong.

Overcoming self-doubt requires building confidence through small, achievable steps towards a goal. I have found that having my BIG goal and then breaking it down into things I can check off a list allows me to avoid the BIG challenge of looking at ahead.

Additionally, surrounding oneself with a supportive network of individuals who provide honest feedback and encouragement is crucial.

Entrepreneurship is not just about business but mental resilience and personal growth. As an entrepreneur, I’ve faced and conquered (some days) self-doubt, and I believe that sharing personal stories and valuable advice is essential to inspire and guide new entrepreneurs.

Sarah Narcus, owner of Olio & founder of Without A Hitch

Learning How to Delegate

I’d probably identify the single biggest challenge for most new entrepreneurs as an inability to delegate and, therefore, doing things that they aren’t equipped to do. By nature, an entrepreneur is a learner and a doer, so we look at things like website building, SEO, and social media and say to ourselves that we can learn these things, do them, and save money by not hiring an expert. It’s a fundamental flaw in logic, though, because you can’t learn it in a day, and it always takes longer than expected. For the price of a solid designer, you would’ve gotten much further and been more focused on things you can control. It’s not just a penny-wise pound fooling evaluation of money spent; it’s the opportunity cost of time invested on something that would’ve been better used in the core business.

Marc Snyderman, managing director of Next Point Ventures

Building an Emotional Safety Net

The hardest part of entrepreneurship is the loneliness, which can hit you like a ton of bricks in the early days. Most leaders tend to be extroverted, and in our previous roles, we had teammates and leaders to rely on for support. When you start your own business, you must build an emotional safety net and support system because you don’t have one built in — especially if you won’t make any hires for a while.

The loneliness of entrepreneurism can be quelled, but it takes mindful effort. You must build your network, find mentors, and deepen friendships with other entrepreneurs. Even when we go it alone, we’re all in this world together.

David Ciccarelli, CEO of Lake

Balancing Culture Fit with Skill Acquisition

It’s difficult to make those first few hires when so much rides on choosing the “right” people. You need to find people with personalities and personal values that align with the culture you want to set, but you also need them to possess the skills that maximize your ability to grow revenue and business value. 

The easiest way to hire is to take stock of the tasks that are getting in the way of your ability to grow your business. Hire someone to take over those duties so you can focus on contributing your expertise. Remember that your fledgling business is still vulnerable, so use non-compete and NDA contracts as necessary to protect it.

Robert Kaskel, chief people officer at Checkr

Dispelling the Myth of Easy Success

There’s somewhat of a misconception surrounding entrepreneurship. Countless “entrepreneurs” online are trying to convince you it’s easy to start a business and that you can succeed in only a few weeks. These people all have one thing in common — they’re trying to sell you a system that will purportedly make you wealthy in a matter of weeks. Their success is built off your naivety. 

Building a business that’s successful and can last for years to come is not easy. You’re going to work harder than you’ve ever worked at a job working for someone else. You’re going to have long days and long nights. You’ll lose time with friends and family because you have work. There’s little balance, especially in the first few years of starting a business. You do it because you’re passionate about your product or service. If you’re looking for a quick way to make some extra cash, entrepreneurship might not be your best option. It’s not going to be easy, and it’s not going to be quick. But it will be worth it for those that stick it out and keep going. 

Daivat Dholakia, VP of operations at Essenvia

Navigating the CVE Certification Process

I’m a former army ranger who served in Operation Desert Shield and Desert Storm. As a service-disabled veteran business owner, I know firsthand how difficult it can be for new veteran-owned companies to get verified by the Center for Verification and Evaluation (CVE). I had to take my firm through the CVE certification process, which took more than five years. That’s why I decided to prioritize representing veterans in this unnecessarily complex process in my legal practice. 

Veteran-owned small businesses (VOSB) and service-disabled veteran-owned small Businesses (SDVOSB) should seek advice from an experienced government procurement attorney in the early stages of forming the business. Taking this step will ensure your VOSB or SDVOSB correctly navigates federal agencies and complies with specific regulations that will make it eligible for government contracts that can substantially increase profits. An attorney in this field can help you understand the government’s contracting determinations and explain exactly what you need to do to win lucrative contracting opportunities.

Joe Whitcomb, attorney & founder of Whitcomb Selinsky, PC

Avoiding Common Pitfalls

I am not only a CPA but also a business owner and entrepreneur. I have made some rookie mistakes and avoided some because other experts forewarned me. It is true what they say: “Experience is the best teacher (and I add, someone else’s experience is an even better teacher!)”. Use these tidbits of knowledge so you do not repeat these mistakes in your business. Mistakes cost time, money, and momentum, none of which you can get back!

Mistake #1: Perfection. Perfection is the death of progress. Don’t wait until all aspects of your business are perfect (perfect marketing, perfect processes, perfect pitch, perfect … you fill in the blank). Your business needs to generate revenue to survive and thrive so that you can provide value to others with your business. If your business cannot generate revenue, it is halted and becomes useless. Make sure to balance obtaining clients and creating that unique gift bag that will blow everyone’s socks off. In the meantime, use a gift bag that “works.” Don’t let the pursuit of perfection halt your progress.

Mistake #2: My business is unique! I hear this a lot. This line gets many business owners and entrepreneurs stuck in a cycle where they continue to recreate the wheel. You may have a unique perspective, gift, or process/product/idea, but at the end of the day, business is business. Business generates revenue, pays expenses, and yearns to be profitable, so, in turn, the business can add more value or solve a problem for the consumer. Period. I see this with our tax, accounting, and tax strategy clients. Yes, you have a unique perspective in a specific industry, but it must still operate as a business. Reach out to your trusted advisors so they can provide you with guidance and shorten your desired path to success. Use their experience and knowledge to your benefit, and instead of recreating the wheel, focus on reaching more clients.

Mistake #3: Overpaying your taxes corresponds with mistake #2. Reach out to your trusted tax professional and strategist and have them assist you in designing a plan or strategy to reduce your taxes, increase business profits, and keep more money in your pocket! More than 90% of business owners overpay their taxes for far too long because they are scared to reach out for help. The benefits and tax savings far outweigh the costs of overpaying your taxes and being unable to utilize those tax savings for things important to you!

Marta Harich, CPA, wealth & profitability strategist & owner of Prestige Business Enterprises

Building Teams and Processes for Entrepreneurial Freedom

One thing that really stumped me as a new entrepreneur was learning how to build a team and a company that could operate without me. Everything would run smoothly while I was available, and the second I wasn’t, it seemed like all training and processes fell apart. I would say this is easier to accomplish when it’s your priority from the beginning. You should be hiring competent staff you trust and who align with your overall goals and values for your business from the start. You should be working with them to develop processes that don’t require your oversight or guidance. This is the best way I have found to allow myself to step away from time to time, either for a mental health reset or to focus on bigger-picture pursuits for my company.

Carter Seuthe, CEO of Credit Summit Consolidation

Navigating Uncertainty

It’s easy for the average Joe to slap on a “billionaire = exploiting others” and call it a day. In reality, even if you’re a descendant of a billionaire, it takes a lot of skill not to lose the money. Let alone becoming a billionaire in the first place (not that I am one).

The biggest difference between being a CEO and a worker is not the amount of work that has to be done. Being a startup CEO is much more draining than working a regular 9–5. The difference is that as a CEO, you don’t even know what to work on.

Working on the wrong thing = failure.

Working on the right thing but taking too long to figure out the right thing = failure.

Quickly and consistently identifying the right action and working hard to execute it = possible success.

Growing a business is not magic. It is mundane and repetitive, from reaching out to a website for backlinks to cold-calling to addressing user feedback.

There is no rubric or instructions. If you are doing something wrong, you can’t realize that until you fail unless you create a rubric to judge actions. But then, how do you know if your rubric is wrong?

Hard work, stress, time management, etc., are all challenges of starting a business, but uncertainty is the biggest one because, ultimately, having that manager might be annoying, but it’s a steady income.

Darren Oliver, founder of PLI Writers

Strategic Planning & Networking

New entrepreneurs usually struggle to get through the rocky beginnings and find clients and associates.

My first tip is: don’t start without a proper plan; I mean a very well-outlined, detailed plan. I spent about seven years in preparation for starting my business, and even then, I had to deal with many unforeseen circumstances and curveballs. You can never be fully prepared, so take your time to bootstrap your new venture as much as possible.

For instance, I understood there was a considerable initial investment, and I probably wouldn’t turn a profit immediately. That’s why I had savings for the first six months to a year. It took me that long until I had a few solid team members, and we started generating a sustainable income to keep us moving forward.

Additionally, I can’t emphasize enough how important it is to build a strong network. Don’t burn any bridges with previous associates or employers. If you maintain good relationships with past colleagues, they’re most likely to become your first business partners. That’s what I did, and now, one of my biggest clients is a former employer.

Surround yourself with mentors, advisors, and fellow entrepreneurs who can help you through the motions. Try participating in as many networking events and communities as possible to connect with like-minded individuals.

Nikola Baldikov, founder of InBoundBlogging

Prioritizing Authentic Connections Over Expensive Solutions

New entrepreneurs face many challenges, but the first one that comes to mind is being overwhelmed. Many experts give conflicting advice about what you need to do to grow your new business, and if their messaging is good, you’re probably going to fall for a lot of it. When I started my first business, I didn’t have any idea where to start, so I hired an expensive business coach. I joined an expensive mastermind. I hired an SEO expert and bought a class about making the best Instagram reels. In retrospect, I didn’t need any of that, and none of it made me money.

The one thing that DID bring me clients and making money was going out, meeting people, telling them what I do, and creating REAL relationships. I’m not talking about the salesy weirdos that show up at networking events, hand their business cards out to everyone and then leave. I’m talking about showing up authentically, getting to know people, and finding ways to provide value to them without expecting anything in return. Not only was this way less expensive than everything else I tried, but it was also a lot more fun, and the ROI was much greater.
Melissa Snow, founder & CEO of Powerful Women Rising