Dilemmas Faced by Every Solopreneur (+ How to Overcome Them)

Career & Business, Life Coach Library

How do successful solopreneurs and entrepreneurs get through the challenges that come with pursuing their passion?

At some point in our lives, we’ve all done the 9-5 daily grind.  You know the one,  feeling like a hamster in the cage.  Work, eat, sleep, rinse, repeat. Hundreds of hours wasted on the commute. We’ve met other’s expectations and spent 1/3 of our woken hours meeting their deadlines.   All while pushing our dreams aside. 

In the end, you feel no sense of ownership and suffer from disillusionment. However, it doesn’t have to be that way.  If you have any honed sense of drive and determination, you have probably already realized that the internet has opened a world of opportunity: This is an age of entrepreneurship.


Being a solopreneur is an exciting prospect. Who doesn’t dream of being their boss? To start with, you can come and go as you please and take vacations whenever you want.  And yet, while there’s work to be done, you’ll be sitting on a beautiful beach working from your laptop.  Right?

Maybe.  But, probably not.  At least, not for a long time.  The old saying goes, “ with great freedom comes great responsibility.”

Thank the internet that we have access to markets around the world. As a direct result, inventive minds have created products and services unthinkable just a few decades ago. For instance, eCommerce and online freelance consultancies have popped up everywhere.   Granted, there are still massive untapped markets, yet it is impossible to eliminate the challenges driven entrepreneurs and solopreneurs face.   

By that same token, the internet isn’t just an avenue to new markets: it’s also a repository of help. That’s where we come in. Just because you call yourself a solopreneur doesn’t mean you have to jump through these hoops alone.  Nor should you! 

What are the challenges Entrepreneurs and Solopreneurs often face?  

#1: Confidence: Taking the plunge

Indeed the key to being a successful solopreneur is transforming possibility into reality.

At first, the sheer volume of tasks and things to learn can be overwhelming. Therefore, it isn’t uncommon to experience anxiety and overwhelm.  What first seemed like a simple yet great idea now seems beyond daunting. In time, you might even lose sight of the end goal.

Or you might get stuck in a comfort zone, feeling like you’re just treading water.  For months or even years, you’ve hated your job. Nevertheless, it pays the bills, and you’re not comfortable taking the plunge and following your passion.  For instance, you’ve put up your website, and it’s been a hobby for a long, long time.  There aren’t enough hours in the day to give it more attention, and you wonder if you had the opportunity to give it everything you’ve got it you wouldn’t kick-ass!! 

You have to dive deep if you are looking for pearls. Treading water means you’re going nowhere. Eventually, you sink.

But that’s the art of solopreneurship: taking the plunge.


Overcoming the challenge

What’s crushing you is self-doubt.   You fear failure.   Self-limiting (damaging) beliefs have you convinced that if you fail, it’ll be catastrophic; that you’ll disappoint those you love if you don’t follow their dream for you; or that you’re just not good enough.  You can reprogram these old ideas that no longer serve your highest good.  Continuing to believe them is a choice that only you get to make. 

Similarly, there is a solution to diffusing overwhelm.  Solopreneurs start by setting SMART goals.  Consider what you’d like to accomplish in a year.   Next, think about what you have to do each month to get there.  From there, break it into weekly and then daily goals.  Next, prioritize a few tasks each day. From there, break tasks down to the smallest piece that you can accomplish in (about) an hour.

But ultimately, you need to take a chance.

‘…We only regret the chances we didn’t take, the relationships we were afraid to have, the decisions we waited too long to make.’ Lewis Carroll.

#2 The solopreneur knows it’s lonely at the top

Going it alone gets downright lonely! Conversely, at your miserable 9-5, someone else made the tough calls and took the heat.  Now, it’s all on you to make the hard decisions, and you’re wearing all the hats.  As a solopreneur, chances are you are the admin, marketer, manager, and service provider all at once.  Once upon a time, things were delegated to others, but today, it is a thing of the past. Even if you can afford to pay others, there’s that fear that they aren’t going to do it right.   

Successful business people develop their habitats and customs. Unfortunately, this only isolates them further, exacerbating the feeling of loneliness and the crushing weight of responsibility.   It’s challenging to admit it, but there is freedom in knowing that no one knows everything or can do it alone.  Everyone needs help.

Overcoming the Challenge

If you have the means, create a dream team of people you can trust and rely on. Do the tasks that you are passionate about and do best.   These will energize you and bring you joy.   Likewise, have a dream team of passionate and good people at the tasks you are not.   It will prevent you from feeling like the life is being sucked right out of you.

At the very least, build a professional network.   Seek out groups of kindred spirits who are living their passions.    Even if they are in a different industry, the challenges are similar, and you will exchange support and ideas.  You may also consider hiring a business consultant (more on this later). They can help you flourish.

Delegation should never be a dirty word. Find the best people you can, ensure they share your mindset.  At the same time, don’t be afraid of new ideas. Everyone thought Steve Jobs was crazy and look at how he changed the world. You might be surprised to find that your collaborators do things even better.

#3 Successful solopreneurs experience growing pains

Yes, this is a beautiful problem to have but a problem, just the same.  Eventually, being able to scale your business can be the make or break of it.

When you are ready to expand, you face the challenge of who to hire. If you thought the job interview was terrifying as a candidate, please know it’s no party as an interviewer.  It starts with sifting through dozens of resumes. Then you try to weed out the unqualified.  At the same time, keep your eyes open for the overqualified.    During the interview, you’ll find several candidates over-embellished their resume and wasted your time.   Ideally,  there’s one or two you might hire.   Hopefully, one of them wants the job.  

Here lies the challenge: finding someone right for your business and the right skills and the right attitude.

Overcoming the Challenge

Be specific. When you know what you want, you’ll know it when you see it. It will also help you target the search, by homing in on critical areas where prospective candidates can be found.  Finally, be clear on the skills and characteristics that are crucial and the ones that you can sacrifice if need be.

Don’t be afraid to ask specific questions (but make sure that you do not violate any legal parameters) Pay attention to how candidates answer, what they say, and what they don’t say.   Common yet insightful questions are: Will you stay long-term? “What value can you add?”How do you like to be managed?” and “What rewards would you want?”

The answers you receive will identify what kind of candidate they are and whether they are right.

#4 Managing time without letting it manage you.

With so much to do, you can struggle to know where to start. If you work from home, distractions are rife. But you can ill-afford to waste time: there are only so many hours in the day.

Rule of thumb: most things take longer than you think they will.  They typically cost more too.   Not always but often

With so many hats to wear, and tasks to learn, how do people manage?

Overcoming the Challenge

Excellent time management requires discipline, focus, and organization. If you waste time procrastinating on social media or playing games on your phone, not only will you get nothing done, you’ll beat yourself up about it later.  

Give yourself deadlines and set clear boundaries. This is when your list of daily goals (from #1) is crucial. Ultimately, deciding what needs to get done when and prioritizing which tasks are urgent and which can get done at a later date will save your mental and emotional health while bolstering efficiency.

Remember this essential question: Am I making the best use of my time?


Consider having a mentor.

Forbes Magazine,, and, all tout the benefits of working with professional coaches.   Some claim it is the single most profitable investment an entrepreneur or solopreneur can make.   Yes, it is an investment, but it can save you thousands of dollars and years of the learning curve

The Benefits of a Business Coach

Business coaches have years of experience and dozens, even hundreds, of prior clients.  Think of a business coach like a doctor. They can diagnose your problem and prescribe a solution.   They have seen it all and know what works and what doesn’t.   Experience has taught them which services are worth investing in (for example: hire an accountant or DIY with Quickbooks) and which ones aren’t.

Here are some key benefits to keep in mind:

  • Make better, smarter decisions.
  • Develop confidence
  • Gain a secondary perspective
  • Learn from other people’s mistakes and lessons.
  • Discover what you don’t know

Final thoughts

Being an entrepreneur or solopreneur can be one of the most rewarding experiences of your life.  It can also be one of the most distressing.   None of the challenges presented are insurmountable obstacles unless you give in to them.  The benefits will always be worth it. Remember: you get out of it what you put into it.  You have to do the work all by yourself, but you don’t have to do it alone! 

You might enjoy: Why are so people content with working 9-6? and What is the importance of passion in your life?

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