What I learned from 2 years of freelancing 🤫💰

Tapajyoti Bose
5 min readApr 30, 2023

Ah freelancing, the dream of working from anywhere in the world, being your own boss, and making a ton of money. It’s a life numerous people dream of. I started freelancing in May 2021 & never looked back.

In one year, I became one of the top 3% of freelancers on the planet (as a Top Rated Plus Freelancer on Upwork) & I have already gone through the highest of highs & lowest of lows of freelancing.

Let’s discuss some of the pros & cons of freelancing I found out the hard way.


Let’s start off with the mindblowing pros that come with freelancing!

1. Money, money & some more money

If you DON’T reside in one of the developed countries, you are in for an incredible surprise my friend, as you can make a ton of money relatively easily by freelancing!

Of course, you need to have the skills to justify what you charge, but due to geographical arbitrage (a fancy term for earning in a strong currency & spending in a weak currency), you can make a lot of money.

Earning $60/hour might be classified as poor in New York, US, but in India, it’s mind-numbing money & can easily land you in the top 0.1% earners in the country.

2. Freedom to work from anywhere

There is unparallel freedom in working as a freelancer: you are not bound at any particular location while working. All you need is a laptop & an internet connection and you are golden.

As long as you can deliver quality work on time, nobody cares where you work.

So the next time you feel bored, you can pack your bags & head to Bali for thrills with minimal bills!

3. Freedom to work any time

As a cherry on top of the location freedom, you also have time freedom: you get to choose when you work & how long you work!

Most clients would allow you to work according to your schedule as long as you deliver.

Regardless of whether you are a part of the 5 AM club or the 5 PM club, there is always something for you!


Getting started with freelancing already? Hold your horses!

It is NOT all rainbows and sunshine. Let’s now explore the cons that come with freelancing!

1. With great money comes great responsibility

Financial Education

This is the most important life skill, which is taught in no school.

For example, since you don’t have a company to replace your work laptop when it’s damaged, you need to be prepared for such unforeseen expenses, as NOT replacing a malfunctioning laptop can potentially take you out of business.

Even though such expenses are expected to be rare, you never know when they would hit & can put a significant dent in your finances.


Rules of money change when you cross a specific threshold as a business owner. While the threshold varies from country to country, in India it is ₹20L (₹2M) & again at ₹50L (₹5M).

Assuming you are NOT working as a professional Chartered Accountant or Tax Attorney, you will need to hire one to help you out with your taxes.

The last thing you want is being slapped with a huge tax bill at the end of the year, just because you didn’t know how to do it correctly.

2. You trade one boss for a platoon of bosses

Being your own boss is a myth. It is true that as a freelancer, you DO NOT have one single boss, but you are answerable to each and every one of your clients.

When things go south, there is NO ONE holding your hand through the mess. Mostly, you are expected to figure it out & come up with a solution on your own, which can be a tad overwhelming at times.

3. Office life gives you FOMO

This might be my personal experience, but never having worked at an office, I feel like I am missing out on meeting people, making friends, and attending corporate events.

As a freelancer, you have to create your own opportunities to socialize, regardless of whether you work at a co-working place or talk to random strangers on the street (which is quite unwelcome in quite a few pockets of the world).

You might be thinking, I am an introvert & don’t care about socializing, but the 2020 pandemic must have shown you even if you identify yourself as one, you still need to interact with people to remain sane.

Even if you are offered multiple job opportunities, you can’t take them on as they do not make sense from a financial perspective.


So now we are down to the big question: should you freelance?

Well, even though my experience was mostly positive, I would encourage you to weigh the pros & cons and test out the freelancing waters.

One big caveat of freelancing is you absolutely must have a monetizable skill! Unless you can solve someone else’s woes, nobody is going to pay you.

With that said, I wish you the best of luck if you want to try freelancing!!!

Have you ever tried freelancing before? Or are you planning to get started? Let me know in the comments below!

Finding personal finance too intimidating? Checkout my Instagram to become a Dollar Ninja

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Tapajyoti Bose

Top Rated Freelancer || Blogger || Cross-Platform App Developer || Web Developer || Open Source Contributor || FIRE Enthusiast