There are certain things that solopreneurs struggle with that are quite specific to us who work on our own for ourselves. Obviously those issues are not related to employees, colleagues or management, because we are all of that in one.
At the same time the issues are centered around all of those things because we are all of it in one. It’s a bizarre way to exist, but as remote work becomes more and more popular, the amount of solopreneurs could also rise.
In case you already are working for yourself, or would like to do so in the near future, this article is for you. These are very specific issues that solopreneurs face in their everyday life, and that can unnecessarily make running a business much harder than it should be. Let’s dig in!
9 Unique Issues Solopreneurs Struggle With
A solopreneur refers to a person who starts a business by themselves and performs all the tasks required to run the business themselves. Once you employ people to help you with running the business, you’re no longer a solopreneur.
The Covid-19 pandemic was an extremely fruitful arena for solopreneurship to flourish. In fact, in the United States alone over 5,4 million new businesses were registered in 2021. And already in 2020 over 85% of all businesses were run by solopreneurs.
Today those numbers are estimated to be much higher, and the popularity of remote work only accelerates this development. But before you embark on this adventure, take into account these aspects of it that many solopreneurs struggle with.
And if you’re already in the solopreneur game, I’d love to know how many of these you can relate to?
1. Confusing your business with your self worth
Many solopreneurs struggle with the notion that if their business isn’t successful then they are not successful as people. We weave our self worth into the fabric of our business oh, so easily. But there are some major issues to this.
First of all, business is an entity that is outside of your person, and as such there are things you can’t control about it.
- Whatever happens in the markets and among market trends defines your business success to an extent, but none of it has anything to do with you.
- Even if your products and services aren’t super popular or receiving rave reviews, you are still loved, appreciated and respected by your peers, family and friends.
- If you feel like the only reason for you to release your creativity is for business and money-making purposes you limit your inner child to the point where you can cause harm to your own mental health.
Confusing two completely different and separate entities as one like that is certainly a learned mindset. The whole point of capitalism has been to make you feel like you owe it your life.
But as solopreneurs we have an opportunity to create completely new ways to make money and reframe our mindset to support that. Capitalism doesn’t benefit us so let’s create better systems to thrive and succeed! And remember; it is your business, but you are not the business.
2. You must be the jack of all trades
Who in this world was born to be good at absolutely everything? That’s right, nobody ever! But that’s sort of what is expected of you as a solopreneur. You should be
- an accountant
- the CEO
- marketing manager
- the face of the business
- IT specialist
- mentor
- cheerleader
- content creator
- salesperson
- HR
- lawyer, etc., etc., etc.
Now, who could do all of that on their own? Believe it or not, many solopreneurs do! Are they well on their way to pure burnout and depression? Absolutely they are. Thankfully most solopreneurs struggle to juggle all of the above, and thus we opt to outsource.
For example, I am number-dyslexic (undiagnosed) so having an accountant is something that I am extremely happy to spend money on! Also, while I do consider myself somewhat of a nerd, I’m not that gifted with solving IT issues.
Thus, I make sure I have a website host that takes care of all the technical stuff for me regardless of what time of day I need them. What is such a hosting service, you ask?
That would be Lyrical Host, I’m 4 years in and very happy to pay my bills for them in return for their excellent service.
3. Believing that making money should be hard
We’re raised to think that to make enough money to get by requires hard work throughout our lives. But one of the first things I learned as a solopreneur was that this is completely untrue!
While yes, it is a system we still exist in, many solopreneurs struggle to attract the sort of income they deserve because they are so stuck in these old and misleading thinking patterns. Especially us creatives – who are fortunate enough to make money doing what we actually enjoy – feel like we don’t deserve it.
Work should not be fun, right? WRONG! Quite the opposite! Why the hell did we ever agree to stay in jobs that weren’t fun at all? I’ve always been of the opinion that particuarly Gen Z is known for: meaningless work is not worth any time or bother.
- In most employment types you get a steady monthly salary, which is just enough to get by.
- But it doesn’t correspond with the amount of money you bring into the company per month.
- And it certainly doesn’t cover for the mental abuse many have to endure under incompetent management.
While many solopreneurs struggle to shake off these mouldy and outdated ideologies about earning money having to be bothersome, at least we have the opportunity to do so! We work on our own terms 100%, which means that we also make those terms.
4. Figuring out who to trust and invest in
There comes a time in a solopreneur’s life when they come face to face with the ugly fact that a lot of people in this world can’t be trusted. And this knowledge comes to us in a multitude of ways:
- Clients not paying their bills or doing their due diligence
- Falling for false marketing or downright scams online (courses that promise you 10K in a month, etc.)
- Lack of transparency: people selling services without anything to show for it (other than talk) and then disappoint to an epic extent.
As anyone would, solopreneurs struggle to find reliable people to work with. And it’s sometimes because they have nobody to rely on in their decision making other than themselves.
When a client lets you down or you can’t deliver to your client because you accidentally hired someone to do the job who wasn’t up to it, it can really damage one’s self esteem. Running a business alone is hard enough as it is, we really don’t need any outside “help” to make it even harder!
5. Managing to find a work-life balance
This seems to be a problem for most people regardless of their type of employment. But I’m not talking about the basic “I can’t switch off from work” or being flooded with inspiration and new service ideas when you’re supposed to fall asleep. Quiet quitting is a skill that both solopreneurs and employees should muster in the 2020’s.
Work-life balance is not easy for us who are solely responsible for our financial stability. Like we established earlier, having to be the jack of all trades in your business takes its toll on your personal life sometimes. The biggest challenge is to say “No!” when more and more work, aka money keeps coming in.
We know we’re overworked already, and if we take on more work, that means that family and friends will pay the toll. Which obviously costs us much morein the long run. This is an aspect that solopreneurs struggle with that I am personally very familiar with.
When you’re given an opportunity to make as much money as you possibly can by working as much as you please, even a lazy sod like me will sacrifice things that I normally wouldn’t. But is it worth it?
6. Thinking that clear vision and strategy is essential for success
Every big business owner will tell you there’s no success without a clear vision and strategy. And I’m here to tell you that that’s complete bullshit. Sure, some solopreneurs struggle with not having a clear business plan carved in stone.
But while it may give you peace of mind, having vision and strategy does not guarantee success either. You can be completely successful while just winging it. It depends on what you define as ‘success’.
- Are you successful when you overcome a challenging project?
- Is there a monetary limit that defines success for you?
- Are you successful when you have happy clients and earn enough, maybe more?
- Is success about finding the perfect balance between work and personal life?
- Does success require making an actual difference in the world?
Success is a brilliant thing because it doesn’t look the same for everyone. Which is why nobody has the divine right to tell you what success should look like to you! For one of us, getting out of bed in the morning is a success. For others hitting a 10K monthly income goal is success.
What does success look like to you?
7. Not knowing if next month is covered financially
I saw an interesting video recently: it said that the financial “zero level” is different for each of us. That’s the bottom amount of money in our account, after which we feel we’re out of money. We must always stay above that number. I knew immediately what they meant!
While for most people the zero level is literally an empty bank account, for some people it may be 2K or 50K. That’s the limit after which we consider ourselves in serious trouble financially. I have reached a point where I have set this limit to 10K, which says a lot about how insanely far I’ve come from living on benefits!
Fact is that solopreneurs struggle to know for certain where the next paycheck is going to come from. And that can be extremely stressful! Client contracts are usually shorter than 6 months, and these contracts are much easier to terminate than employment contracts (in Europe, obviously).
And THAT is the reason why many of us have this ‘raised’ zero level for our finances. We need to have a buffer to cover ourselves at least for some time if the worst should happen.
8. Comparisonitis
You’d think that only those solopreneurs who are just starting out suffer from this condition. But oh no, many solopreneurs who have been successful for years already still can’t help but compare themselves to other entrepreneurs.
And it doesn’t matter how well off they are themselves, solopreneurs struggle to recognize their own worth when they succumb to the symptoms of comparisonitis.
At the end of the day, the only way to get out of that destructive loop is to take full responsibility of oneself. Instead of complaining about everything that everybody else is doing that you’re not, set those goals for yourself and get to work!
If they managed to get there, so can you. YOU hold yourself back, nobody else.
9. Lack of support
Oh yes, most solopreneurs struggle with the fact that there is no safety net for us. We are solely responsible for our personal and business’s success, and it’s a completely personal and unique experience for each of us.
As much as our family and friends want to help us, a lot of the time they can’t. Heck, my family doesn’t even understand what I do to make money. They’re always happy to listen, but they have never in their life had to worry about the sorts of things that I wrestle with on a daily basis.
Whether it’s mental health issues, difficulties to set boundaries to achieve work-life balance or struggles with a client, people who are not in such a situation can’t relate. And let’s add to that the importance of brainstorming: you can’t do that on your own now, can you?
That’s why finding like minded people who are also solopreneurs is essential for people like us! Having a community is one of the biggest needs for human beings. And while you’re running a business on top of yourself, the importance of having like minded people around you is emphasised to a great extent.
Final Thoughts
It’s always a risk to leave behind the securities of employment (paid leave, sick leave, guaranteed salary, etc.) But it’s even more risky to do so completely on your own. To take responsibility for absolutely every facet of having a business is something that many solopreneurs struggle with. Yet still we thrive!
Our struggles can be quite unique but at the end of the day none of us are as alone as we may sometimes feel. Thanks to the online world, the trick is to find a community of like minded people that you can offload your solopreneur concerns, wins and ideas to. And brainstorm!
I found my community in the Point of Divergence, also known as POD community. A group of superstar women who all have very different businesses but who all aim to make this world a better place for all.
Are you self-employed, and if yes, did some of these points resonate particularly? Or even if you’re employed, did you relate to some of these points? Let’s chat below! ♥
Follow me on Instagram and use #styleoutlandish to showcase your style! I’m always on the lookout for outfit inspiration. Get to know me better by listening to my podcast, Random Rambles. If you wish to work with me, check out my services here!




