6 min read

What Do Solopreneurs Struggle With? A Comprehensive Guide

The rise of solopreneurship has given individuals the freedom and flexibility to pursue their passions and create their own career paths. But as someone who has been a solopreneur since 2005, it’s not all fun and games. Solopreneurs face a unique set of challenges and struggles that can make it difficult to succeed on their own. In this comprehensive guide, we'll explore the various obstacles that solopreneurs often face and provide actionable tips for overcoming them.

Understanding the Solopreneur Lifestyle

Before we dive into the specific struggles that solopreneurs face, it's important to first understand what solopreneurship is all about. At its core, solopreneurship involves running a business on your own, without any employees or partners. It doesn’t mean though that you do business by yourself. The top-earning solopreneurs embrace an expert community of peers to succeed as a one-person business, fractional executives, or business coaches to avoid common challenges and go faster.

While solopreneurship offers many benefits, including the ability to work from anywhere and the freedom to make your own decisions, it can also be challenging. Solopreneurs are responsible for everything from product development and marketing to customer service and finances. This level of responsibility can be overwhelming, especially for those who are just starting out.

Defining Solopreneurship

Solopreneurship is about more than just working alone. It involves taking full ownership of your business and taking on all of the risks and rewards that come with it. As a solopreneur, you have complete control over your business decisions and the direction of your career. But this also means that you bear the full weight of any mistakes or setbacks.

One of the biggest benefits of being a solopreneur is the ability to create a business that aligns with your values and vision. You have the freedom to make decisions that reflect your personal beliefs and goals. Additionally, you have complete autonomy over your work, allowing you to choose who to work with, what projects to take on, and how to structure your workday.

The Benefits and Challenges of Being a Solopreneur

While being a solopreneur offers many benefits, it also comes with its fair share of challenges. I’ve seen these firsthand and also in leading and coaching solopreneurs one-on-one and in my solopreneur community. One of the biggest struggles that solopreneurs face when not embracing one of these is isolation. Without coworkers or colleagues to bounce ideas off of or collaborate with, solopreneurs can feel lonely and disconnected from the broader business community. That’s why finding a solopreneur community or solopreneur coach is so key.

Another challenge that solopreneurs face is the need to wear many hats. As the sole employee of your business, you are responsible for marketing, sales, operations, and more. This can be overwhelming and time-consuming, especially if you are not experienced in all of these areas.

Finally, solopreneurs may struggle with work-life balance. When you are the only person running your business, it can be difficult to switch off and take time for yourself. This can lead to burnout and decreased productivity over time, which is why you need a tech stack specifically built for solopreneurs.

Time Management Struggles

Time management is one of the biggest struggles that solopreneurs face. Without a boss to hold you accountable, it can be easy to become distracted or feel overwhelmed by the sheer volume of tasks on your to-do list. Here are three common time management struggles that solopreneurs face - and how to overcome them.

Balancing Work and Personal Life

One of the biggest challenges that solopreneurs face is finding balance between work and personal life. When you work for yourself, the lines between work and personal time can blur, making it difficult to switch off from work mode. To overcome this challenge, it's important to create clear boundaries between work and personal time. A great way to address that is through a Day Theme vs. time blocking, which includes specific days where you don’t do meetings. Creating a dedicated work space or even finding a local co-working space can also offer this separation.

Prioritizing Tasks and Projects

As a solopreneur, you will have a ton on your plate. From business development and sales to managing existing clients, there's always something that needs your attention. To ensure that you're making the most of your time, it's important to prioritize your tasks and projects. I recommend apps like Akiflow to integrate your to-do and calendar as well as project management apps like Trello with clients to stay organized.

Akiflow is what I use personally for to-do and task management.

Overcoming Procrastination

Procrastination is a common challenge that solopreneurs face. When you're the boss, it can be tempting to put off work until later or choose easier “busy work” tasks over ones that will drive revenue. To overcome procrastination, it's important to understand why you're avoiding certain tasks. If you’re not oriented towards operations, for example, turn to your solopreneur community or hire contractors to assist. If you’re great at marketing but having a problem closing deals, get a solopreneur coach who has experience there. For example, I’ve closed more than $50M as solopreneur or solo agency founder.

Financial Challenges

Another common struggle that solopreneurs face is financial stability. When you don’t have a scalable service offer, your income is often irregular - meaning that some months you may have plenty of clients, while other months may be lean. Here are a few financial challenges that solopreneurs often face, and how to deal with them.

Managing Irregular Income

Managing your cash flow is critical to your success as a solopreneur. One month, you may be swimming in projects, while the next you may be struggling to find work if you don’t have your marketing systems in place. To manage irregular income, it's important to create a budget and stick to it. This includes setting aside money for expenses such as taxes, software tools, and fractional help, as well as any unexpected expenses that may arise.

Budgeting and Saving for the Future

As a solopreneur, you're responsible for funding your own retirement and future financial goals. This means that it's important to budget and save for the future. Consider setting up a retirement account such as a 401(k) or IRA, or creating a separate savings account for emergencies or long-term financial goals.

Tax season can be especially daunting for solopreneurs, who are responsible for filing their own taxes and managing their finances. To navigate this challenge, have an accountant or tax professional regularly available to help you stay on top of your finances and avoid any surprises come tax time.

Marketing and Branding Difficulties

Marketing and branding are essential components to any business, including solopreneurship. As a solopreneur, build a personal brand to help promote your business, including a strong brand identity. Here are some common challenges and solutions to consider.

Building a Strong Personal Brand

As a solopreneur, your personal brand is everything. It's how potential clients, customers, and collaborators perceive you. Building a strong personal brand takes time and effort. Start by clarifying your brand messaging and values, and use social media and other digital tools to build an online presence that reflects those values.

Effective Marketing Strategies for Solopreneurs

Marketing can be a challenge for solopreneurs, particularly those who are new to the game. It's important to understand your target audience, which I call your Lighthouse Clients in my framework to attract and convert premium clients as a solopreneur. Everything you do once your “Laser Targeting” is dialed in comes through content and marketing materials that speak to their specific needs and pain points. Consider collaborating with other businesses or solopreneurs to expand your reach and find new customers.

Networking and Collaboration Opportunities

Networking and collaboration opportunities can be harder to come by when you're a solopreneur unless you join an expert community of peers These activities are critical for building your brand and finding new clients or collaborators. Make an effort to go deeper than social networks, join a solopreneur community, and connect with other solopreneurs in your field to expand your network and create new opportunities.


Being a solopreneur is a rewarding experience when done right. By understanding the unique struggles and challenges that solopreneurs face, you can take proactive steps to overcome them and succeed in your business. Whether it's managing your time, finances, or marketing efforts, remember that as a solopreneur, you have the power to shape your career and create the life that you want. Embrace the tentpoles of a successful solopreneur: growth without hiring, an expert community of peers, modern tooling, systems, and automation. These will help keep pushing you forward towards your goals.

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About the Author

Hey, I'm Ken. I've been running online businesses since 2005. My work has been featured by Apple, WSJ, Levi's, and reached millions of people.

After scaling my remote agency to $5M, I'm now helping entrepreneurs grow without big payrolls with offers, sales, and proven systems.

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