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7 Challenges of Being a Solopreneur and How to Overcome Them

Independence is a beautiful thing. There is something to be said about the power one feels when being in total control. When it comes to business ventures, many entrepreneurs enter this voyage with the idea of being the “boss” and having that independence. They will be the one in charge. They will make the rules, create the company policies, and be the one who will have the final say when it comes to making decisions on a company’s future. They build a team that they can depend on and grow alongside during their entrepreneurial journey.

However, some individuals take the road of entrepreneurship completely on their own. This advantageous journey is known as solopreneurship. In a previous article, I had looked at the pros and cons of being a solopreneur. Going into business is always risky, but the choice to pursue it with a team, or by yourself, is also a move that is pivotal to the success of your company.

If you are solopreneur or have decided that is the route you want to take in creating your company, then you probably know of the struggles one can face. To help ease the worry of these potential hardships, I am going to share some insight on how to overcome the challenges you’ll face in order to become a successful solopreneur. The cons that one faces do not have to deter you away from this road to success, but only serve as a reminder that you can do this all on your own.

1. Building a Portfolio

As a solopreneur, one of the first challenges you may face is building a portfolio of your work. Having a portfolio, positive customer reviews, and other social proof is extremely beneficial but tough to do as a solopreneur. This is particularly important for solopreneurs who are freelancers. Freelance businesses such as graphic design, consulting, social media management, and others rely on a strong portfolio to show potential clients to showcase the quality of their work.

As a solopreneur, building a portfolio should be one of the first things you should do. You can begin by offering your services for free or at a discounted rate. The next step is to build a responsive website where you can display your work and your accomplishments. Your personal website should also have customer reviews.

If you are a freelancer using a site like Upwork or Fiverr, you will want to apply a similar strategy. Offer your service at a discount will attract more work. It is important, however, to deliver exceptional work as these first few jobs will set the tone. You want to avoid getting any negative reviews early on in your journey.

2. Building a Client Base

All good things take time. Over that time, you will build relationships and grow from the referrals of others in your business. The beautiful aspect of this world now is that social media helps get your name out there even faster. While you still have to spend time building up your brand, and what you offer, you can use social media tools to reach a broader audience at a faster rate.

Use your Facebook page to promote your work, show what you do, and answer questions from potential customers. Instagram is an awesome tool to share a powerful photo and talk about your business and why you love doing it. You can also use LinkedIn to make professional connections within your business industry.

While building your reputation and getting the word out about your company does take time, utilizing social media to help with your brand does not. Do not feel deterred by this venture, as once you get started in social media, it’s easy to make it a part of your everyday life (don’t we already?).

3. Keeping Yourself Motivated

Staying motivated as a solopreneur is a challenge we all will face. You are your own cheerleader, only you have the power to drive success, because there is no one else to depend on.

We all enjoy being complimented and told that we are doing a good job. This gives us the reassurance that what we are doing is okay, and that others believe in our dream as well. When you are a solopreneur, there is no one else around to compliment you, or to give you that extra reassurance. However, along with those compliments, can also come constant feedback and criticism.

Sometimes when we let others into our business, we can also set ourselves up to doubt our decisions. Being a solopreneur means you get to have a clear head and mind, without someone else dashing your goals or minimizing your dream. While your gut may say one thing, the people around you could be pushing you to do something else. Flying solo means there is no one to deter your intuition, and leave you regretting listening to anybody but yourself.

Be sure to surround yourself with positive forces too. Buy a calendar with inspirational leadership quotes or join a 411 group where you can connect with other business leaders. This is a nice way to get support from others, without feeling like you are losing your business identity to the opinions of others.

4. Doing Everything Yourself

A lot of time spent doing the little daunting (but important) tasks that could take away valuable time that would otherwise be spent working and making money.  While I say “daunting,”  for some people doing the little things may be a nice break from always focusing on the big picture. As a solopreneur, you may like taking the time to reconcile your credit card report, answering phone calls, responding to emails, or keeping up with your website and social media accounts.

Managing clients, multiple tasks and marketing as a solopreneur is challenging. Having a knowledge of all aspects of your business keeps you up-to-date and in touch with what’s going in all realms of your company. In return, you won’t get caught off guard by something, or blindsided, because you put the responsibility on someone else to manage. By being in total control, you can’t get hurt or disappointed in that a task wasn’t followed through due to someone’s ineptness. You only have yourself to depend on, and in that regard, it can be a great benefit to always staying in the loop of things.


5. Working Long Hours 

One of the unfortunate side effects of having to do most of the work yourself is it may lead to working long hours. A study by Gallup found that 39% of small business owners work an average of 60 hours per week. Another study found that just 57% of small business owners take vacations. However, even when they’re on vacation, 67% of small business owners will check in to work at least once a day.

Working long hours and not taking vacations can be a normal part of entrepreneurship. But solopreneurs often find it even more difficult. Working long hours as solopreneur can often lead to burnout. This is because, as a solopreneur, you have no co-founders or assistant managers that can cover for you when you take time off. To take time off for vacations, you will need to find a way to do so without impacting your business.

One way to do this is to hire and train a virtual assistant. Your VA will probably not be able to do your work while you are gone. However, a good VA will make it easier for you to step away from your business. They should be able to take care of common customer questions, operational tasks, and basic managing of your business. While this won’t guarantee you will never work long hours, it may help you minimize your long days and allow for some much-needed time off.


6. Employment Benefits (retirement, paid time-Off, and healthcare)

This can be more bothersome to solopreneurs whose country’s policies dictate something as important as healthcare. Many first world countries do provide national healthcare to their people, which makes it easier for some business leaders to pursue an entrepreneurial dream solo. However, the United States is not one of those countries. For many Americans, benefits are a huge factor in leaving or staying at a job. These sorts of enticements make it hard to leave a secure job to pursue something that may not work out or leave us (and our family) without our health insurance.

In this case, it may be hard to see the silver lining to this con, but there is always something positive to be found. Strides have been made to make health insurance more affordable for all Americans. While it is far from perfect, it is better than what we had before: nothing at all. Some solopreneurs may also be able to pursue their dream by having a spouse that provides the benefits and health insurance through their job. Having a partner that supports your dream is just as important as having benefits.

In this case, you may have to do a solopreneurial gig as a side job until you become more established. This is not a bad thing, and it will give you the peace of mind that you have coverage, while growing your solopreneurial empire. You can also set up a retirement account such as an IRA or an individual 401K plan. You can do this on your own or with the help of a financial planner. Having someone in the loop of your professional finances is proactive, and helps you prepare for a future in a more stable and reassuring way.


7. Dealing With Isolation

Feeling lonely as an entrepreneur is common. Solopreneurs can experience a sense of loneliness more often due to the very nature of their work. Solopreneurs do not have co-workers, bosses, or full-time employees. Working by yourself day-in and day-out can often make solopreneurs feel isolated and alone.

To combat this feeling, it is important that solopreneurs make a conscious effort to interact with others in the real world. This could be by going to networking meetings, setting up lunch meeting and communicating with friends and family more often.

As a solopreneur, you could also rent a dedicated desk or office at a co-working space in your city. Having a place that you can go and work outside of your home can help combat the sense of isolation.



Even though there are many benefits of being a solopreneur, there are also many challenges. When it comes to running YOUR business, you are the most qualified person to do it. You are the one that has the passion, ambition, and perseverance to make it happen. You may feel that others can bring different and unique insight into your business vision, but inevitably, it is your aspiration that inspires others to follow.

Do not let others tell you differently, as only you have the insight to know what’s best for your company and business. Find ways to stay motivated while working as a solopreneur. This was your dream after all, and in that regard, it should be yours to live out the way you want it to.



This article was originally published in April 2018 but has been updated and expanded.

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Summer Anderson
Staff Writer: Summer Anderson is a mother, wife, writer and long time lover of the game of golf. Her passion lies in writing from the heart, and on topics that are most important to the Millennial generation. She hopes to impact those through her writing and advice on marketing and social media communication. When she is not on the golf course, blogging or watching "Frozen" with her little ones, she can be found designing websites in her home state of Pennsylvania.

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Entrepreneurial Lifestyle · Find Your Way · Grow Your Business · Solopreneur · Your Mindset

Staff Writer: Summer Anderson is a mother, wife, writer and long time lover of the game of golf. Her passion lies in writing from the heart, and on topics that are most important to the Millennial generation. She hopes to impact those through her writing and advice on marketing and social media communication. When she is not on the golf course, blogging or watching "Frozen" with her little ones, she can be found designing websites in her home state of Pennsylvania.

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