We asked industry experts to share one unexpected challenge they faced as a new entrepreneur and what advice they’d give to someone just starting out to help them overcome it. Here are their tips for overcoming common challenges so you can transform obstacles into growth opportunities.
- Get Comfortable With Selling
- Network In Person
- Ask for Help and Take Action
- Build Systems Before Scaling
- Stay Lean and Prioritize
- Hire Specialized Experts
- Delegate Effectively and Trust Your Team
- Trust Your Judgment and Take Action
- Prioritize Legal and Compliance Basics
- Seek Relevant Mentorship
- Establish Clear Payment Terms
- Focus on Intentional Time Management
- Master the Art of Follow-Up
- Embrace Delegation Early
- Embrace Flexibility and Resilience
- Be Selective With Opportunities
- Implement Task Management Systems
- Believe in Yourself and Your Product
How to Overcome Unexpected Challenges
Get Comfortable With Selling
One of the biggest surprises for me as a new entrepreneur was realizing that being great at what I do wasn’t enough—I also had to become great at sales. I left corporate with a decade of experience managing brands, overseeing finances, and leading teams, so I thought running my own business would be a natural transition. But suddenly, I wasn’t just doing the work; I had to sell it. And that was a whole different skill set.
If you’re just starting out, don’t assume your work will speak for itself. You need to get comfortable with selling—not in a pushy way, but in a way that communicates the real value you bring. Instead of feeling like you’re convincing people to buy, shift your mindset to showing them how your solution makes their life easier. Also, don’t be afraid to talk about money confidently. The sooner you get past any discomfort around pricing and sales conversations, the sooner you’ll start closing deals.
Inbar Madar
Founder and Principal Consultant, M.I. Business Consulting
Network In Person
Consistently work at being seen and known. When I started I thought I could just put up a website, create some social media accounts, and that clients would come pouring in. Not the case at all. Yes, it’s a digital world, but in person networking will stand the test of time when it comes to getting client leads and referrals for your business. We are humans not robots, and humans are built to thrive through true connection, which can only be done in person. It builds a rapport with other individuals that are complementary to your business, and they’ll want to join forces with you because they were able to connect personally with you. So, don’t hide behind the computer—go out to as many in-person networking events, summits, conferences, etc. and that’s when you’ll see the clients pour in!
Charlene Lazewski
Founder, Charlene and Co. Media
Ask for Help and Take Action
One unexpected challenge I faced as a new entrepreneur was putting myself out there. As an introvert, I struggled with reaching out to people, asking for advice, and learning from others. I was afraid of being judged or that people might think my ideas were weird.
But one of the most valuable lessons I learned is that people are more willing to help than you might expect. If you have questions or need guidance, just send that email—many people are happy to share their insights and experiences. You’d be surprised at how much you can learn just by asking.
Another key piece of advice: If you’re struggling to gain traction or figure out where to start, read. There are so many great books that can help. One book that really helped me was “How to Get Traction for Startups.” Learning from other founders and proven strategies can give you a clearer direction and help you avoid common pitfalls.
Most importantly, take action. It’s easy to get stuck in the planning phase, overthinking every detail and feeling overwhelmed by uncertainty. The best way to push through is to set clear, achievable goals. Break things down into small, actionable steps—like setting a goal to accomplish the basics by the end of the week.
You’ve probably heard this before, but think of it like building a house. Before you can start adding the walls and roof, you need to lay a solid foundation. That foundation includes understanding your mission, knowing your audience, and taking small but meaningful steps toward your goal.
Starting is the hardest part, but once you push past the fear, you’ll realize that progress comes from learning, adapting, and just doing. One step at a time, brick by brick—you’ll get there.
Divya Murakonda
Co-Founder & CEO, TEEZR
Build Systems Before Scaling
One unexpected challenge I faced as a new entrepreneur was navigating the complexities of scaling my business while maintaining the quality of service. When I developed the “DIY Insurance Billing for Private Practice” course, I had to balance between my therapy practice and managing an influx of nearly 950 clinicians eager to learn from me. The demands were overwhelming, and scaling required efficient delegation and process automation.
My advice is to focus on building a solid, replicable system before scaling. This involves documenting every step of your process and gradually delegating tasks to a virtual assistant or trusted team member. When launching my course, I ensured all resources and communications were standardized and automated where possible, allowing me to manage growth without sacrificing service quality or my sanity.
Another tip is to engage with your community actively. I built the “Bill Like A Boss” community to support therapists in insurance billing, and it turned into a platform for direct feedback and improvement. Leverage such communities to gain insights, adjust your offerings, and create an engaged customer base that supports your business’s growth.
Kym Tolson
Therapist Coach, The Traveling Therapist
Stay Lean and Prioritize
One of the biggest unexpected challenges I faced as a bootstrapped entrepreneur was learning how to do everything without completely burning out. When we launched, we made the decision to self-fund instead of taking outside investment early on. That meant we weren’t just building a product, but we were also running marketing, handling operations, and figuring out growth—all while making sure we could actually afford to keep going.
The hardest part? Prioritization. With limited resources, every decision mattered. What features should we build first? How do we attract users without a massive ad budget? How do we keep momentum without exhausting ourselves? Bootstrapping forced us to be brutally efficient, focusing only on what moved the needle and finding creative ways to generate traction.
My advice? Stay lean, test early, and use your network. Get an MVP out fast and make sure real people actually want it before spending too much time or money. Automate or outsource where you can, but also embrace the DIY hustle. It’s part of the journey. And don’t underestimate the power of relationships. Partnerships, organic marketing, and word of mouth can be just as valuable as paid strategies.
Bootstrapping isn’t easy, but it teaches you resilience. When you’re forced to be scrappy, you learn what really matters—and that’s what builds a business that lasts.
Kara Peterson
Co-Founder, Descrybe.ai
Hire Specialized Experts
One unexpected challenge I faced was finding and retaining skilled consultants who could deliver at the same high standard I set for myself. In the early days, I struggled with delegating specialized work because I was concerned about consistency and maintaining the trust of our clients. Hiring the right people was difficult—not just in terms of expertise, but also in finding consultants who aligned with our consultative, data-driven approach. I quickly realized that relying on generalist consultants diluted our value, while overloading a small in-house team led to burnout.
To overcome this, I shifted my hiring strategy to focus on highly specialized experts in key areas, but with a flexible model. Instead of immediately committing to full-time hires, I built a network of vetted industry specialists and fractional consultants. This allowed us to scale expertise on-demand, ensuring that each client engagement was handled by someone with deep domain knowledge. We also implemented structured onboarding and quality control processes, so every consultant understood our methodology and client expectations before taking on work.
For those just starting out, my advice is to prioritize quality over speed when hiring—don’t rush to fill roles, but instead build a reliable expert network. Also, invest in knowledge-sharing systems (such as standardized frameworks and documented best practices) to ensure consistency across different consultants. Finally, establish strong relationships with your contractors and consultants, treating them as strategic partners rather than just temporary resources. This approach has allowed us to scale efficiently while maintaining the high-quality insights and strategic impact our clients expect.
Habib Rkha
Founder, QCADVISOR
Delegate Effectively and Trust Your Team
One of the biggest unexpected challenges I faced as a new entrepreneur was learning to delegate effectively. In the early days, I felt like I had to be involved in everything-sales, development, project management, even minor operational decisions. It wasn’t just about control; I genuinely believed no one else would care about the company’s success as much as I did. But that mindset quickly became a bottleneck. As the business grew, I had to shift from doing everything to leading—trusting my team, setting clear expectations, and letting experts take ownership of their roles.
My advice to new entrepreneurs? Focus on building systems that allow your business to scale, not just solving immediate problems. Document your processes, hire people who align with your vision, and create a culture where your team feels ownership over their work. The sooner you empower others, the sooner your business can operate beyond just you. Once I embraced this shift, Pumex became more agile, our execution improved, and I had the freedom to focus on strategic growth rather than getting lost in the weeds.
Antony Marceles
Founder, Pumex Computing
Trust Your Judgment and Take Action
Learning to trust my judgment was one unforeseen obstacle I encountered as a new business owner, particularly when the “safe” option conflicted with my intuition.
I wasted time in the beginning by doubting everything, looking for constant approval, and waiting when I ought to have taken action. The truth is that nobody knows everything. Experience is the only way to make the best judgments, and experience can only be gained by making decisions, whether they are good or wrong.
My recommendation is to make a choice, take action, grow, and adapt. Although no choice is final, a poor choice will cost you more than inaction. Be in the company of intelligent people, heed their advice, but ultimately, believe in yourself. What distinguishes those who succeed from those who stall out is the capacity to proceed in the face of uncertainty.
Gil Dodson
Owner, Corridor Recycling
Prioritize Legal and Compliance Basics
One unexpected challenge I faced as a new entrepreneur was underestimating the importance of legal and compliance basics. In my excitement to build the business, I focused on growth, marketing, and delivering services, assuming I could handle the legal details later. I thought contracts, trademarks, and proper agreements were things only bigger businesses needed to worry about. That assumption cost me. I learned the hard way when a client refused to pay, and because we had no formal agreement in place, I had no legal ground to stand on. What could have been a straightforward resolution turned into a stressful, costly situation that drained my time and energy.
I quickly realized that fixing legal mistakes after they happen is far more expensive than preventing them from the start. From contracts and service agreements to business registration and intellectual property protection, these are not just formalities, they are your business’s safety net. I had to backtrack, hire legal support, and put proper agreements in place, which was time-consuming and costly, but necessary.
My advice to anyone starting out? Don’t skip the legal foundation, no matter how small you think your business is. Start with the basics: get contracts in writing, register your business properly, and protect your brand with trademarks or copyrights if applicable. Also, take time to understand local business laws, tax requirements, and necessary permits. It may feel like a chore or an unnecessary expense early on, but it will protect you from major headaches and losses down the line.
More importantly, review and update your agreements regularly. As your business grows, your legal needs will evolve. Having the right legal structure from day one not only protects your business but also gives you the confidence to operate without fear of costly disputes. Trust me, prevention is always cheaper and less stressful than correction.
Randy Kunik
CEO, Kunik Orthodontics
Seek Relevant Mentorship
One unexpected challenge I faced as a new entrepreneur was dealing with conflicting advice from mentors. I had multiple mentors, and they often gave me completely opposite recommendations. At first, I tried to follow both sets of advice, thinking that doing so would help me cover all bases. However, I later realized that this approach was counterproductive. It wasn’t until I reflected on my past year, analyzing what had worked and what hadn’t, that I saw the problem clearly.
My biggest lesson from this experience was that not all advice is equally relevant. Instead of listening to mentors who were far more steps ahead in their journey, I found that the most valuable guidance came from those who were just one or two steps ahead of me. They had recently faced the challenges I was dealing with and could provide practical, immediately applicable insights.
So, my advice to new entrepreneurs is this: Seek mentorship, but be selective. Follow those who are slightly ahead of you, as their experiences will be more relevant to your current stage. And most importantly, always filter advice through the lens of your unique business needs rather than blindly applying everything you hear.
Mira Eszter Kőmíves
CEO, Multilingual Virtual Miracles
Establish Clear Payment Terms
One unexpected challenge I faced as a new entrepreneur was navigating late payments from clients, which disrupted our cash flow in the early days. Even well-intentioned clients occasionally delayed settlements, making it hard to forecast operating costs or invest in new projects. To address this, we established clearer payment terms and introduced an automated invoicing platform. This system included follow-up reminders and small incentives for early payers, which improved our cash collection rate by nearly 30 percent.
If I were to give advice to someone just starting out, I would suggest building a stable financial cushion from the beginning. Have at least three months of operating costs in reserve so delayed payments do not undermine the business. Also, monitor each client’s payment patterns by reviewing historical data, if possible, to spot potential issues before they escalate. This blend of proper planning and structured follow-up helps reduce stress, supports growth, and keeps relationships professional.
Aleksei Gaidov
Director, Uniwide Formations
Focus on Intentional Time Management
When I started my journey, I was still working full-time in my corporate executive job while building my business on the side. Just as my business began to take off, I found out I was pregnant with my daughter, which was the most amazing surprise! However, I also felt a lot of fear and comparison about how quickly I could grow my business, especially since it seemed like I had only tiny windows of time to work with. I constantly felt like something was holding me back from achieving the level of success I wanted.
To overcome this, I distilled the business growth process into actionable tasks that I could complete in 15, 10, or even 5 minutes. I started carrying a little index card with me everywhere, so whenever I had just a couple of minutes, I could take meaningful steps toward growth. Eventually, my business began to soar rapidly, despite my limited time. I transformed from feeling overwhelmed and fearful about meeting my goals to proving to myself that I could succeed by focusing not on how much time I had, but on how intent and purposeful I could be with that time.
Kelly Roach
Founder & CEO of Kelly Roach International, Kelly Roach International
Master the Art of Follow-Up
When I launched my consulting firm, I understood that entrepreneurship would demand resilience, strategy, and grit. What caught me off guard was discovering that mastering the art of the follow-up would become crucial to my success but would be surprisingly uncomfortable.
In those early days, my finger would hover uncertainly over the “send” button for that third, fourth, or fifth follow-up email. The fear of appearing pushy or desperate loomed large. Yet experience taught me a valuable lesson: persistence isn’t pestering; it’s positioning. As I embraced the discomfort of consistent follow-up, I watched my calendar fill with clients and heard “yes” more frequently.
For entrepreneurs just starting their journey, I offer this insight: transform follow-up into your superpower. When sending that initial email, immediately schedule your next follow-up for the following week. After the second email, do it again. Develop a systematic approach and commit to it. Most importantly, reframe your mindset. Following up isn’t requesting a favor but offering an opportunity. Each contact serves as a reminder of your value proposition and demonstrates your commitment to serving potential clients.
I’ve discovered that the magic often materializes in the follow-up. It’s where deals reach completion, relationships deepen, and your reputation as a reliable professional solidifies. So summon your courage. Send that email. Make that call. The rewards consistently prove worth the momentary discomfort.
Dr. Erin Wilson
CEO & Principal Consultant, Design Ideal Consulting
Embrace Delegation Early
As a new entrepreneur, I quickly discovered that passion for my clients wasn’t enough. I had envisioned spending my days immersed in their cases, providing expert guidance and support. The reality, however, was far more complex. Running a business—finances, marketing, operations—demanded as much attention as the cases themselves, often pulling me away from the work I loved. I found myself spending hours each week on tasks I had little experience in, like creating marketing materials, managing invoices, and trying to understand the intricacies of small business accounting. Balancing these two roles felt overwhelming at times. There simply weren’t enough hours in the day to give both my clients and my business the attention they deserved. I was constantly playing catch-up, feeling like I was never quite doing enough in either area.
My advice to someone just starting out is to embrace delegation early. You can’t do everything alone. Hire professionals for areas outside your expertise, such as accounting, marketing, or case management, so you can stay focused on what you do best. Also, invest time in building efficient systems and processes from day one. This not only saves time but also allows your business to grow without sacrificing the quality of your work. Most importantly, trust your instincts but stay open to advice from mentors who have been through it before. Their guidance can help you avoid costly mistakes and navigate challenges with confidence.
Rick Hovde
Founding Partner, Hovde Dassow + Deets
Embrace Flexibility and Resilience
As a new entrepreneur, one of the biggest surprises for me was the emotional challenge that uncertainty presents. I anticipated financial and operational challenges, but had no idea what I’d face in terms of self-doubt, stress, and unpredictability that come with running a business. There were times when everything felt wrong; sales were slow, decisions were paralyzing, and I doubted whether I was headed in the right direction.
My advice for all of you, is to embrace flexibility and resilience. Everything could go wrong, and things certainly might not go according to plan, but that doesn’t mean you’ve failed. Have mentors, peers, and a support system around you to help you get perspective. Acknowledge the progress, not perfection, and reward the small wins. These things are not only common theory but also practice: entrepreneurship is a learning process, and being able to adapt may be more valuable than the best business plan. Be gracious in the process; you were built for this moment, and realize you learn more from wins and losses alike.
Nathan Barz
Financial Advisor, Management Expert, Founder and CEO, DocVA
Be Selective With Opportunities
In the beginning, I said yes to everything, every opportunity, every partnership, every request. I thought saying yes meant growth, that the more I took on, the faster I would succeed. In reality, it meant spreading myself too thin and putting energy into things that didn’t align with my vision. I quickly found myself overwhelmed, juggling too many projects, and losing sight of what actually mattered. Some of these commitments drained my time and focus, leaving little room for the work that truly moved my business forward.
I learned the hard way that not every opportunity is the right opportunity. Just because something seems beneficial on the surface doesn’t mean it’s aligned with your long-term goals. The hardest part wasn’t just declining offers, it was overcoming the fear that saying no meant missing out. But the truth is, every “yes” to something unimportant is a “no” to something that truly matters. The more I prioritized intentionality, the more I saw real progress.
My advice? Be ruthless with your time. Learn to evaluate opportunities based on whether they align with your mission and whether they contribute to meaningful growth. If they don’t, politely decline and move forward without guilt. It’s easy to fall into the trap of overcommitting, especially when you’re new and hungry for success. But true success comes not from doing everything, but from doing the right things well. Learning to say no is just as important as knowing when to say yes. Protect your time, stay focused, and trust that discipline in decision-making leads to sustainable growth.
Darryl Stevens
CEO, Digitech Web Design
Implement Task Management Systems
The biggest shock after resigning from my corporate job to start my own business was the lack of a structured work schedule. For the first time in years, I could do whatever I wanted, which ironically made it incredibly difficult to stay focused and actually get to work. When you’re accustomed to having your tasks managed and being told what to do, it’s hard to shift gears and motivate yourself.
It requires a lot of dedication and a plan to stay focused. For me, implementing a task management system and setting goals with deadlines helped immensely. It made it easier to prioritize tasks and get things done. Finding a co-founder for my SaaS was another game-changer. I no longer had to search for productivity tips once I had a team that held me accountable; things happened naturally because I felt a greater sense of responsibility.
Agnese Jaunosane
Founder and Chief Operating Officer, SIA AJELIX
Believe in Yourself and Your Product
One of the biggest and most unexpected challenges new entrepreneurs face isn’t competition, funding, or even marketing—it’s self-doubt. The hardest part of starting a business is simply taking that first step. Questions flood your mind: Is this the right time? Will people care about my product? What if I fail?
Success starts with confidence in what you’re offering. If you don’t believe in your product or service, why should anyone else? But belief alone isn’t enough—you need a solid business plan to back it up.
A business plan is crucial for direction, but it’s not set in stone. Markets shift, customers provide feedback, and you’ll need to adapt. Flexibility is key—be open to learning and refining your approach as you go.
Getting started is tough, but once you gain traction, momentum will carry you forward. Small wins add up, giving you confidence and pushing you through setbacks. Keep making progress, even if it’s just a small step each day.
Success isn’t a finish line. The moment you stop trying to improve is the moment you start falling behind. Stay hungry, seek new ways to refine your business, and never assume you’ve “made it.”
Starting a business is overwhelming, but don’t let overthinking paralyze you. Take action, adjust when needed, and keep pushing forward. The hardest part is getting the ball rolling—once it’s moving, momentum and persistence will take you the rest of the way.
Ryan Schimmel
Videographer, Ryan Schimmel
