The Challenges of Freelancing

Freelancing isn’t easy.  Not everyone can do it.  When you decide to take the plunge into a freelance career, you will realize quickly how challenging it can be.


You will learn that…

  1. A lot of jobs you get don’t last long.
  2. A lot of bosses are not that nice (some pay late, some treat you like crap, etc etc.)
  3. Sometimes, it can even be challenging to find a new job

Freelancing is for those who can hustle to find the next opportunity and who are not afraid to fall.

There are a lot of businesses who will hire, not give you a contract, and then let you go or not give you anymore tasks for the next month.  But then maybe you will get lucky and get a job where you get a nice contract and you get tasks every month.

You basically live month-to-month depending who you work for.  Virtual Assistants and Executive Assistants or any job with “Assistant” in the name might last long but your are needed to do a variety of things.  SEO Speciaists and specific skill-based jobs may or may not last long due to whether or not your boss is impressed with you or is convinced they don’t need SEO anymore.

You may be thinking “why so cynical and pessimistic?”  This is the reality of it all.  Now….don’t get me wrong.  Not all freelancers have these experiences.  Some may be an SEO Specialist or a writer or some other skill-specific job for a business and work for several months to several years.  Some get lucky and find a great job with a great company.

Why pursue such a non-stable non-secure career?  As freelancers, we ask the secure corporate office world the question “why pursue a stable safe career that confines you between 4 walls and company rules?”  Freelancers are thrill-seekers meaning we sell ourselves purely based on our skills and we are always looking for the best opportunities.


But this post isn’t about why freelancers become freelancers, or the differences between the corporate office world and freelancing.  There are challenges in being a freelancer.  It is a challenging career and people should realize the kind of lifestyle (yes….lifestyle) they are getting themselves into.  Some people are born to do it.  Others grow into it.

As a freelancer, you will meet people who can connect you to a job and people who will just ignore you.  You will meet bosses who either care for you, demand weird things from you, or care a lot about you and treat you with dignity.  Your paycheck may also fluctuate month to month.

This is the life of a freelancer.

How do you overcome these challenges?

  1. Set expectations.  Let your boss or to-be boss what you expect from your work and compensation.
  2. Always leave room for additional jobs.  This may be a bit complicated since some jobs insist you work only for them so if you choose to have more than one job, you may want to be secretive about your other jobs.  Having more than one job can help you with having additional salary and saving you end up losing one job.
  3.  Reach out to different people.  Sometimes having the courage to network with people and asking for available opportunities is the key.
  4. Look long-term.  Look for jobs with potential for long-term work.  Is the company doing good?  Is the work good?
  5. Always be honest with what you looking for and who you work with.  Will save you time and energy


That’s it.  You will learn the challenges and how to overcome those challenges of a freelancer as time goes by.  Enjoy the ride!

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