Freelancing: The Pros and Cons and Perception vs. Reality

As I promised last week in my post Working in Thailand, I want to shed some light on the pros and cons of freelancing as well as the perceptions I had going into this type of work and whether those perceptions have turned out to be true.

In general, I am enjoying it very much for the simple most important factor of being in control of what I do with my time. It feels empowering doing something for yourself rather than working for someone else’s dream. Despite the overall positive experience, it’s far from perfect; here’s why:

Perception: I thought it would be much harder for me to find work in the beginning.
Reality: Finding work on oDesk has proven to be really easy.

Perception: I thought I would be writing fewer posts for a higher pay.
Reality: I have to write a lot of low paying posts per day to make enough money (so far). Keep in mind I’ve only been doing this for two months and I’m hopeful I’m gaining leverage with the pay I can demand. I’d love to get to the point of commanding $250 an hour.

Perception: I thought I would enjoy working from home more.
Reality: While I do enjoy the freedom of being able to work from wherever I want, I do get pretty bored sometimes. More so than I thought I would. I try to work from coffee shops as much as possible but sometimes I feel weird constantly going back to the same places over and over again, or I just don’t want to pay for lunch. I also miss coworkers more than I imagined I would.

Perception: I told myself I would be able to work any hours of the day I wanted and that would allow me to go out during the day and explore Thailand.
Reality: I end up working regular hours because I don’t want to be working when Alexis is home from work. For that same reason, I don’t want to go exploring during the day without her and not give her the opportunity to see and do the things I would be doing.

Keep in mind that the above were my preconceived perceptions, not necessarily anyone else’s. You might avoid these unexpected letdowns simple because you did not carry these notions into your freelance work. Hopefully this post helps on that front.

While there have been some unexpected, mostly negative, surprises, there are a lot of really important positives.


  • I don’t have to walk to work in the pouring rain or blazing heat.
  • I don’t have to wear pants and a tie every day like I would have had to as an English teacher.
  • I can work from anywhere with an internet connection.
  • I learn a lot. Researching all the topics I write about is fun and interesting and I’ve learned so many new things I didn’t know before.
  • I feel like I’m working towards something which is not a feeling I’ve had in any other job. I used to really like my old job in DC too. As an organization, we did really cool stuff and I was a big part of that, but it wasn’t my plans or my dreams. I’m working towards a future I’m creating for myself now.
  • Writing has unlocked creativity inside me. I was always confused by the simple comparison of creative types versus analytical types because I never thought I fell into either group. I’m not a perfectionist, I’m relatively free spirited and don’t like to get bogged down in the details, and while all of those qualities seem to point to the creative type, I never felt I had creativity. I don’t play any musical instrument, I can’t draw to save my life, arts and crafts and me end up in disaster… I just didn’t get it. I now realize writing is my creative passion. I love playing with words, with language, and being able to express ideas in funny or unique ways. I feel myself getting better at it every day too.

Those pros outweigh everything for me, but here are a few last cons to be aware of:


  • If I don’t work, I don’t get paid. I feel terrible slacking off or getting distracted for a few minutes now because I’m literally taking money from our pockets by doing that. If I’m sitting in front of my computer for eight hours a day but only do actual work for six of those, I only get paid for six hours. I appreciate the guaranteed salary aspect of my old job much more now.
  • I have basically zero human interaction most days.
  • Pay is low when you first start.
  • I get no built-in exercise. I used to walk a mile to and from every day which not only provided built-in exercise into my daily routine, but it also made me feel much more willing to do even more exercise. Sitting at home or a coffee shop all day makes me feel like a fat, disgusting slob.

So far, the positives have outweighed the negatives. I’m still extremely glad I turned down that teaching job and decided to start my freelance career. I firmly believe life is what you make it and that has never felt more true than now. Whether I succeed or fail is completely up to me. My skill, my dedication. While that’s terrifying, it’s also exciting and motivating in a very real way.

I hope this was helpful! If you have any questions or comments, please let me know below.


4 thoughts on “Freelancing: The Pros and Cons and Perception vs. Reality

  1. Freelance writing is a pretty interesting job. I’ve been doing this for two years now and got pretty much the same feeling as you (I’m not in need to gain that much money due to studying besides). I especially “hate” this “I have to do something or I won’t gain money”-feeling.

    Hope you will have more pros in the long run. The cons will be gone someday!


  2. Pingback: How to Spend Three Perfect Days in Bali | Roses on the Road

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