freelance series II: what could go wrong?

Namaste! If you have read the part one, by now you must be thinking of starting your career as a freelance. Before you get into that I would suggest that you read this one. It's not there to deter you from doing it. I believe in making informed choices and not bets!

If you haven't seen my framework of thinking (youtube video for "How to manage your tech portfolio in 2020?, I request you to definitely watch this video. It talks about how you should decide which language/framework to learn. The ideas however, are so solid that you can take it to any situation where you feel like taking a bet and apply it there to convert into a safe and informed choice.

before we begin

First of all, thanks for signing up to the newsletter, and reading it. The best part however, was your replies and tweets telling how much you enjoyed the first part and that you are waiting for the part two.

There were questions on how to get started with freelancing. I am not an expert, but I will try and help with my own expertise. The answer to that part comes in the 4th part. This series was initially intended to share thoughts around freelancing, and not to get people started on it. However, the response was overwhelming, and thus, I am going to cover some Sales and Marketing tips in 5th part as well. Keep reading, most importantly though, keep the replies, linkedin posts and tweets coming.

the usual, personal thoughts warning
With all of that out of my system, let's dive into the bad parts of freelancing. Even though I say, these are "bad", it's just a naming convention, and thus depends on the choices of an individual. So, if you disagree, try to avoid picking a fight on me on the Internet, I am not going to entertain those negative thoughts.

it gets addictive

My biggest problem with freelancing is that it gets super addictive soon. As you start making money every hour, you start seeing everything with that lense. To give you an example, I like watching movies, but when I was freelancing, I used to think, "This movie!! hmmm!! It's not just Rs.500, It's 500 plus 3-4 hours of freelancing money, which makes it Rs.5000, hmmmmm..., is this movie worth watching for Rs. 5000?"

Now, you may or may not relate to this. With office work you know you have a fixed salary, you work your best 40 hours a week, sometimes 50 hours a week. But you never work 100 hours a week. With freelancing, the line between personal life and professional time is all blurred. And to me this was scary. In the previous post, when I said I made a lot of money, it meant a lot of personal hours. All of this eventually took a toll on my personal health. Good thing was that I was doing this with my girlfriend/wife and friends so it all seemed like fun, but if you don't have that and you keep working for long hours not only your physical but even your mental health will take a toll. So, beware of this.

craftsmanship gives life meaning

Human beings are hardwired to do good work. Impressive work. Work which would provide a challenge and then when you win over that challenge, you feel good about it. There are numerous studies done around this and how man derives meaning from craftsmanship and work.

The problem with freelancing is that in the first few projects, you learn a lot, and it makes you happy. But slowly this work becomes repetitive. The work which comes to you are all similar. If you think about it, Instagram is just Facebook but only for pictures and videos. And once you have created FB you won't be too interested in making Instagram. The work which you get as a freelance are small projects, so you don't get to go deep, don't get to scale, and thus, you get robbed of that fulfillment which you could have got.

I am not making this up. I know a few people who successfully started their own business, made it big, left Microsoft, got bored, and then came back to work for Microsoft while running the business on the side. Something to think about huh?

automation is coming

If you're doing low level web development, app development or similar things. Chances are that automation will eat your pie tomorrow. There will be a framework, a tool or something which will just make your work super easy and everyone will get on it making your price go down. No, I am not talking about AI, just old fashioned automation and better abstractions.

Webflow, Wordpress, Wix can already do things which web devs used to make money for 10 years back. No one is going to pay you (good money) to put together a website anymore. Shopify has made it super easy to create an e-commerce web store.

Note: BTW if you're into web/app dev and worried about the future after reading this. I suggest you listen to this piece and get some peace. :)

The reason I tell students not to do freelancing unless they really need the money is exactly this. Someone is paying them INR 10K to develop a website today, they reach out to more people and get 5 such projects. Problem? They have saturated their bandwidth on making 50K/month while in 2-3 years they could have gotten a job where they would be making 3-4X of that amount with all perks, as monthly salaries.

Takeaway: Smart students should avoid this trap and prepare for better placements. Keep your requirements low and hustle. Delayed gratification, always works!

lessons from corona crisis

There were people in the community who were doing great a few months back. Their freelancing gigs getting them money, they were hiring like crazy. However, come crisis and they were the first ones to let go. Subsequently, they had to downsize their own company. Twitter and LinkedIn is filled with people who are looking for jobs.
With freelancing, the cushion is less. As you're not the employee, you don't get any severance, hiring/firing you is the easiest thing to do for the budget. So, you're the first one to let go when there's any such financial crisis. It's sad for anyone, but read ahead and you'll understand why this matters even more in case of a freelance.

Takeway: Contractors go first in times of crisis.

there's a "tea" in team

Loneliness is a thing. The bitter truth about our society is that we form relationships in school, college and then work. It's the location which makes us grow fonder of other people's company. You go for team lunches, talk near the water cooler, evenings snacks and tea, do meetings and what not to form the bonds.

When working as a freelance, you miss out on the social aspect of work. Even if you're okay about this. Think about this, when you work with smart people, you learn from them. In the first part I talked about learning end to end development as a freelance. There's another side of this though, if you go wide, you don't get to go deep as well. When you work as a team, you'll be insightful in one domain, the other folks will be in another. And you'll learn from each other.

Takeaway: You can grow breadth, or you can grow depth, managing both becomes difficult.

the hunter mode

I didn't have to do this. But I said that this series will be inspired also by what I have seen. Folks who are freelance however, go to confs, go to meetups and they keep looking out for prospective clients. This gets tiring after sometime. In the upcoming parts we will talk about how to overcome this, it's not easy, however. A lot of my friends went into full time jobs after freelancing because of this, because they wanted to get into full time coding and get out of sourcing.

the boring parts

If you're an engineer, a programmer, a developer, no matter which term you use for yourself, you would love coding. The other parts of managing your own freelance business is Sales and Marketing. Which depending on your personality type you might like or detest. However, there are few things which no matter your personality you won't like: invoicing, paperwork, taxes, finance, accounting. You can ask for help, but if you're running the business you have to understand these things no matter what.

where do you go from here

As a freelance, you can get more clients, more projects. You can grow. But what's the scale of a freelance? You become a service company. You do development, but the product is never yours. Another problem is that when your company grows you become a people manager, a sales head, the marketing head. Basically, coding goes and operation comes in. Therefore, you start missing the thrill, the thing which got you started, you don't get to do it anymore. Almost all my friends and seniors, who started as programmers, grew their agency and now run the show.

Since, there's no product of your own, you never get an exit. You do get money, yes, but end up doing not so satisfying work for an extremely long period of time. You end up trying to get into the product space, sometimes you are successful but since you don't have a lot of experience building massively scaled products, it's hard to do. Mind that all of this is real for a job as well, just that in a job you have more options.

freelance as relevant experience

The worst thing which sometimes happens is that you want to quit freelance and get into a job. If you haven't made some really great projects, it will be tough to crack the interviews at your experience level. You have stayed out of the industry for too long and thus, industry doesn't know which level to interview. Sometimes you will get interviewed at a higher level and not qualify, while other times at lower level and your salary expectations won't match or you end up junior to a lot of people who started working after you.

This one especially is an extremely tricky situation to get into. Freelance in India is not mainstream, thus, HRs don't know how and where to place you in the corporate ladder.

before we go

I like writing this newsletter and the dialogue which we are having through emails. I wanted to send this earlier but this one got delayed as I fell sick. Managing a full time job and home with zero househelp (thanks to Corona) is tough as is. I wanted to give this one my best shot as well. So, somehow the delay is okay. The other parts won't take too long. Keep sending your replies and tweets to let me know your thoughts.


These are few issues when you start, and stay in the freelance industry for a long time. You will see influencers selling books and courses on freelance, selling you the independence dream, the travel the world while you work thing, or being your own boss. While all of that gets true only when you become successful, the parts I mentioned are also true. Now, when you have the 5 points product review, and the 1 point product review, you can make an informed decision.

In the next part, we will talk about how to do freelancing right. How to not fall for these gotchas, the one which we just discussed.

See you soon! :)