Career Choices: Freelance vs. Enterprise 🏢

Last year I gave it a shot to work at a huge Enterprise company. Before that, I dabbled with worked for my university, did freelance work and owned an e-commerce shop selling skateboards gear.

Now a year later I am getting back into the freelance world again. To celebrate the occasion I want to list my own pros and cons for each working types which may help paint a better picture of what either one is really like.

Regular 9-to-5

  • Predictable monthly paycheck.
  • Socialization benefits.
  • Potentially can get exposed to work with large impact.
  • Fairly straightforward path of progression.
  • Life has more structure compared to that of freelancers.
  • Generally, stress levels are low. No need to worry about work too much after 5PM. No need to find clients. No need to deal with paperwork, clients not paying, etc.
  • At least in the beginning of your career (maybe forever), you will be an insignificant cog in a huge wheel. This may feel dehumanizing.
  • Watercooler chit-chat can get bothersome.
  • Good work likely to get unnoticed or unrewarded.
  • If you finish tasks quickly, it will seem that they were easy tasks and thus you will get more of them. If you finish your tasks slowly (or quickly and then pretend to work), it will be just a normal practice of what I have seen a lot of people do.
  • Slow pay progression.
  • Little ability to have control over your time, must come and leave at agreed upon hours.
  • Hard to push new initiatives.


  • Choose your own hours.
  • Freedom to work from anywhere.
  • Earnings directly based on hours put in.
  • Ability to always find more clients and look for ways to increase rates, no need to wait for a yearly review.
  • Ability to ditch annoying clients, no single boss.
  • No watercooler chit-chat or having to pretend to work when there is nothing to do.
  • Instead of having little impact on a huge corporation, you have the potential to have a lot of impact to your clients.
  • Income is less stable.
  • Workload likely to not be stable where you have down periods of doing nothing
  • You need to find your own clients and work.
  • Additional paperwork in regards to invoicing, taxes and so on.
  • Lack of team leading to a lack of socialization in the workplace.
  • No office or equipment provided, you will need to create your own working conditions.
  • Work may be limited to less impactful of what you may get working at huge corporations.

Final Summary

Clearly freelancing is not for everyone. The stress of having to hunt for your own living may be a daunting prospect for some. However, if you are motivated and confident in your skill-set, you will quickly find clients and be fine. You will have direct control over your livelihood and it will not take long to feel consequences of your own decisions. This may turn out to be empowering or debilitating depending on your character.

Another thing to note about freelancing is that a significant portion of freelancing pros can turn into cons very quickly. For example, it takes extra discipline to work at consistent hours and not get into a state where you are never truly away from work. If working from home and being a freelancer is your dream, there has been studies that self-employment and working from home is actually bad for one's health, or at least have no positive impact. This is another study about freelancers mental health stating the same.

This article also "Why Freelancers Are So Depressed?" gives a well-rounded overview of challenges related to freelancing.

My Own Choice

Even when given that freelancing is not all that rosy as it is made out to be, I would not trade it for anything in the current moment. Freelancing makes it possible to earn a month's wage in just one week (at least in my home country) and spend the rest time as you wish.

Since my current goals are either to make a boatload of money, improve my skills as a developer, or just do something that I thoroughly enjoy as much as possible (please give me all 3 of those 😂), freelancing seems like the quickest gateway to all of those.

  1. When I'm freelancing, I have more free time to indulge in passions outside of work.

  2. Since I have more free time, I also have more time for fun but challenging side projects which greatly increase my speed of improvement. Also, it is possible to choose freelancing jobs that are outside your comfort zone (but still doable) which will also make you improve faster as a developer.

  3. At least in my country where the wages are low, it is easy to out-earn regular 9-to-5'ers as long as you can find foreign clients. Also, I see freelancing as a stepping stone to entrepreneurship which is good as long as you are interested in it.

Now if I am presented with an opportunity to join a company (big or small) where what I do has a significant impact, or I learn a lot; I can have at least some control over the direction that the company takes; and also output is measured in some way so that good work is rewarded, I will most likely join such a company. But for now, freelancing wins over enterprise! ✌️