15 Challenges Entrepreneurs Face When Starting a Bussiness


The majority of American businesses are sole proprietorships, according to the U.S. Small Business Administration. These “solopreneurs” have full control over the direction of their business and its operations.

There are plenty of advantages to working for yourself and by yourself–for instance, you never need another partner’s input or approval to make big business decisions. But there are plenty of challenges to being a sole proprietor, too.

1. Isolation

Most people start businesses out of sheer passion. They believe in who they are and what they want to accomplish. Unfortunately, there can be too much self wrapped up in that. Find a small group of entrepreneurs or even one to collaborate with. Share your ideas, collaborate and push each other. Know you are not alone so long as you choose to not be alone! – Ryan MillerRyan James Miller

2. Self-Doubt

Entrepreneurship is moxie and moxie is a willingness to fail more often than not. Failure causes self-doubt. After your next big win, create a list in thick red sharpie of all the feelings, words and previous wins that flood your mind while you bask in a recent win. Rewrite the list in sharpie on your mirror. Read the list daily until it’s embedded in your brain. I am a solopreneur. I do this and it works. – Elaine Rosenblum, J.D.ProForm U®MORE FOR YOU6 Things Women In Business Know That Men Don’tHow To Succeed In A Male-Dominated Industry From Savile Row’s First Female Tailor

3. Networking

Solopreneurs have limited capacity to take on large engagements. The value of having a strong network of competitors (who also are your collaborators) is critically important in order to respond to jobs that require more resources than you can muster alone. Such a network needs to be built and nurtured so that you can activate it in moments of need. – Antonia BowringABstrategies LLC

4. Business Development

It will take time to find your “people” in terms of where to target your business development so that it brings you any type of ROI from membership dues, event fees, etc. Be patience with it. While it means spending some time and money initially to try on some groups and see if they’re a fit, trust that it will be worth it eventually when it’s right. – Lisa DownsNew Aspect Coaching

5. Knowing When To Stop Working

Say goodbye to nights and weekends. Most solopreneurs work all the time and not always because they want to, but because they feel they have to. Unlike working for someone else, there’s literally no end to what you “should” do. To prevent getting stuck in this trap, start each day with the question, “What would a successful and balanced day look like?” Be clear and specific and stop when done. – Ashley GoodAshley Good Coaching & Consulting

6. Self-Actualization

If you are a solopreneur who is an extrovert, it can be hard to keep motivating yourself when you are working in isolation. The EQ skill of self-actualization is about the desire to become the best version of yourself you can possibly be. Connect to your passion by writing a narrative of where you want to be in five years and read it out loud daily in front of the mirror. – Roberta MooreThe EQ-i Coach

7. Never-Ending Task Lists

Solopreneurs are often working harder rather than smarter. What I’ve found to be incredibly helpful is to ruthlessly prioritize what needs to be done in my business while ensuring key tasks tie back to company goals. I create my “list of five” or my list of the five most important tasks each night before bed so I have a plan and strategy to hit the ground running in the morning by working on the most critical things. – Holly KnollHolly Knoll Coaching and Consulting

8. Finding Business Partners

Running your own business doesn’t mean you need to run it alone. Seek out other business owners, learn from their experiences, build a strong network and you’ll soon see that you’re not a solopreneur, but a strong business partner with others. Having a solid circle of business partners will help you activate your goals and accomplish great things. – Sheila CarmichaelTransitions D2D, LLC

9. Multiple Income Streams

Many solopreneurs fall into the practitioner category by offering a professional service. This can be limiting for an income stream, which is a challenge for every company, but even more so for this business group. Adding products to their mix is one way to expand your financial reach. Selling other people’s products is another. The key is having multiple streams of income you can leverage over time. – Kathi LaughmanThe Mackenzie Circle LLC

10. Loneliness

Women in business really thrive in a community. When we are running our business on our own, it can get lonely fast. This leads to a lack of motivation and productivity. Be sure to surround yourself with like-minded entrepreneurs for a hit of connections, collaboration, accountability and fun. This simple action can catapult your business and allow you to enjoy the journey that much more. – Elise MontgomeryCoach Elise Montgomery

11. Overworking

It’s important to be scrappy, creative and agile in the early phases. However, doing every single thing yourself is putting additional pressure to perform in areas where you could be doing more harm than good. When possible, outsource to the experts and leverage platforms where services can be obtained at reasonable price points. Focus on your genius as you create an impact in the marketplace. – Dorothy EnriquezThe Communication Strategist

12. Sales And Marketing

If you’re not comfortable doing business development and you don’t have clients knocking down your door, you may be in for an awakening. Many professionals who are technical experts in their discipline and decide to strike out on their own are shocked when they realize that half—or more—of their time is devoted to sales and marketing activities just to get business in the door. – Scott SingerInsider Career Strategies

13. Mindset

Solopreneur is just that: solo. And you’re it. This can be a daunting and overwhelming reality, but if you’re built for it, it can be the most exhilarating ride of your life. The reality is that when you work for yourself, you’re the one responsible for winning and losing. Most can’t bear that burden so they work for other people. The lesser-known truth is that everything starts with the mindset. – Adriana RosalesAdriana & Company™ LLC

14. Lack Of Support

Isolation is one of the biggest challenges to solopreneurs. It causes stuck mindsets, discouragement, distraction, and loneliness. Input from friends creates confusion. Coaches cost money. An accountability partner is a mutually supportive relationship. You brainstorming ideas, keep each other accountable and support each other emotionally. It’s fun, keeps you on track and builds confidence. – Mark SamuelIMPAQ Corporation

15. The Psychological Aspect

One of the overlooked aspects of running a business on your own is the psychological aspect. It’s a lonely journey and it can be a challenging ride. Every business owner must consider the mental aspect of doing business alone. The best advice I can offer the solopreneur is to surround yourself with influential people who are more successful than you are and are willing to mentor you. – Roger DoumanianThe Roger Doumanian CorporationCheck out my website