Experiences of a failed entrepreneur in the first year of freelancing

After I quit my own company - Moontara Technovations, in July 2013, I started looking for a stable job. I updated my CV & uploaded it to few job sites like Naukri, Hasjob and AngelList. The next three days, I got calls from 18 different companies expressing their interest. Interviews were scheduled back to back, somehow, I managed to crack few of them, finalized one and moved from Bangalore to Chennai to join the company.

Everything was going great until I was thrown out of the same company on April 27, 2015.

I will probably write another post detailing the lay-off process and the aftermath. If you are wondering, why do I even want to talk about my firing in public, do yourselves a favour and checkout Firing People post of Zach Holman from Github.

Having two marriages (one in Korea, one in India) scheduled just ahead, the firing took a bit of toll on both my personal and professional fronts.

I decided to explore freelancing, as it looked like a viable option. I thought I could get enough breathing space to travel, take care of pre and post marriage activities and at the same time, earn some money.

I updated my CV again, uploaded to all the job sites, but this time - as a remote contractor, and waited for my 18 calls. I waited a week. I got ghanta (zero) calls. I called up few recruiting agency heads whom I was close to. They said they cannot help me as they don’t operate in the freelancing space. That’s when I realized that I have to do things slightly differently.

Having started my own company, I always knew having a good mentor helps. So, I digged deep into my network and I could get in touch with Abhishek, the one and only full-time freelancer I had ever met in my life.

I travelled to Chennai to meet him. He gave lot of valuable information on the ups and downs of freelancing and how to cope up with them. Also, being well connected as he was, he referred me to one of his clients.

The client got in touch with me, there were a couple of interviews and boom!! I started working for them from July 6, 2015 for 75% of what I was earning as of 2013.

So, here am, celebrating my 1st year anniversary in the form of a blog post hoping to help people like my past-me gain more insights into the chaotic world of freelancing in the Indian software industry.

1. Upsides of freelancing

Nature of work

How many times in your full-time job career, you were shoved deep into your throat a shitty feature, which no one really cared about, may be except for your Product Manager?

Well, that is not the case in freelancing. When you and your client sign on an agreement, both the parties loosely agree on the nature of work involved in the association.

If the work defers too much from the original set of expectations, it is always possible to renegotiate the terms and in the worst case, walk away without ruining the relationship.

Work at your convenience

How many times you wanted to watch a English movie over the weekend but could not because of the insane holywood movie pricings in Bangalore?
How many times you wished you could travel to your home-town by booking a tatkal ticket of a weekday train but couldn’t because it spoils your work routine?
How many times you had to rush to your office with hangover just to attend a scrum ?


How many times you wanted to attended a Friday big-data meetup but couldn’t because it is Friday and not Saturday?

Although, you might think that work cultures in many corporates are flexible, things go awry, when a senior engineer or a manager himself indulge in these kind of activities. This is considered a inappropriate mainly for two reasons:

  1. The senior is setting a bad example to the team
  2. A senior is not an individual contributor. A day out of the senior might cost many of his junior’s man-days.

Again, this demarcation of live your life over the weekend and live company’s life over the weekday diminish in case of freelancing. Your client, based on your agreement with him, would really not care if you are working in the morning / evening or weekday / weekend, as long as you adhere to your promises.

Your slog accounted

There is this strange aura in software companies that it is okay to slog. Employees, in general work at least 8 hrs, and stretch it to 12–14hrs during releases. The saddest part is, many people do not even realize that there exists a problem. And to sum up, releases happen every other fortnight.

Many companies have work-life balance committees but the members of those committees are too busy in their own work to actually help out others.

All of this treacherous slog go unnoticed and unaccounted for. It is not even a topic of discussion during appraisals. Why? Because, everyone else in the company slogs including your manager, and you have been just meeting your expectations.

In freelancing, things are different. You hardly slog. And just in case, if you do, it will be a conscious call and more importantly, the slog gets accounted. You get paid extra for every extra hour that you spend.

Fun fact - Many of the experienced freelancers I talked to, consider working more than 6 hrs, as a slog. Do note that they earn similar, if not much more, compared to their full-time counterparts.


Unless you live very near-by to your office, there is a high chance that you spend more than 1 hr everyday — just in commute.

Let us say, you charge 20$ / hour in freelancing. The amount you currently invest in commuting is ~ 30K / month. And, I dint even consider the after-effects of driving so long, in a highly polluted city.

I completely cut this factor out in my life, once I started freelancing. I made it very clear to any client who approached me, that there was no way I would consider going to their office.

I lost few high-paying projects just because of this constraint, but things started panning out slowly.

Work remotely

How many of you fantasize of going to a chilly neighbouring place of Himalayas and work from there for sometime?


How many of you wanted to go to your parents place and work from there for a month or so - to handle few family situations.

Ideas like these, become increasingly difficult to get materialized as you progress in your career. Very few companies are okay with a lead roaming around the world, managing the in-house team.

In this regard, I’m quite happy with freelancing. In the last one year, I worked 60% from Suwon, 20% from Vijayawada, 10% from Bangalore and rest 10% roaming here and there. I visited my parent’s place every 3 months (from Korea) which I never did from Bangalore.

Heck, as a freelancer, you can even consider turning yourselves into a digital nomad.

2. Downsides of freelancing

Let us look at few of the downsides of freelancing.


It ain’t about the money, it ain’t about the recognition. It is the *king loneliness that is going to hit you hard.

When I first met Abhishek, he hinted me about the loneliness part of freelancing. Having always been a party animal, I never really cared about that statement. But, 6 months down the line, sitting alone in my house, in Korea, I realized that I underestimated his words.

Dec 2015 - Jan 2016 was probably the most depressing phase of my life. Although, I recovered pretty soon after that, it was nonetheless a nightmare.

My suggestion is, if you are serious about freelancing, make sure you have someone to co-work or co-live with you. If you are going to be alone in your house, try out co-working spaces like BHive.

Toll on Social life

It is often said that - You can’t choose your family but you can choose your friends. But, in many of the cases, it is rather - You can’t choose your family but you can choose your friends from a randomly chosen set.

Just as a small exercise, try to count the number of friends you have who are neither your (ex)colleagues, nor college / undergrad batch-mates, nor relatives. Sometimes, I feel that as software engineers, we don’t socialize much.

The point am trying to make here is, we always end up befriending people who are available nearby us. Be it college / office / whatever. Once you start freelancing, you are a lonely warrior. You should be conscious of this, otherwise freelancing can take a serious toll on your social life.

Scale of the product

This is more on the technical front.

As a freelancer from India, you mostly encounter clients who want you to build an MVP out of their idea. My personal suggestion is not to take up such projects as they are simple CRUD applications and not that challenging.

Few clients come up with interesting problems to be solved but almost none of the clients with Facebook / Netflix scale come to you to solve their problems. The reasons are obvious. They have their highly talented in-house team.

So, as a freelancer, your visibility to such highly scalable products is limited.

If I get any valuable information regarding this aspect, I will make a follow-up post.

Family & Friends

I was running my own company for almost 3 years, and my relationship with parents was going downhill during that time.

Can’t blame them. They are typical Indian parents who do not want their kid to get hurt. They used to nag alot on various aspects. Few of the complaints any typical Indian parent would have towards their entrepreneurial son are:

Look at unlce Rammurthy’s son. He is preparing for MS. He is going to US. What are you doing with your life selling dreams?
Look at your friends. They earn so much and they save so much every month. How much did you save in your whole career?
Your market rate (i.e.,dowry) is running all time low. You will not find a good girl. Get a freaking job already!

Although, they slowly faded once I joined a job in 2013. Many of them came back to life once I told them that I’m going to start freelancing. And yeah, I still have to listen to some every now & then. I got used to them. But you should be aware of these continuous nags, if you are serious about freelancing.

It doesn’t end with family. If you have friends working in elite companies like Flipkart, Amazon, Wallmart etc.. it is common to be referred to as jobless. Stop caring about that. They are just being funny ;-)

3. Gearing up for your first gig

Even after going through the pros and cons, if you still consider pursuing freelancing, read this section carefully. Just fyi, I personally am pathetic in executing some of the few suggestions that am going to give you below.

One point you should understand is, just like a full-time job, any high paying client would want to interview you and take in only after he is satisfied with your performance. As you know, interview process is a tedious one and is not scalable.

So, it is always advisable to have something a client can look at and shorten up the interview process. Below are few suggestions

Technical Blog Posts

A good technical blog post, can fetch you a highly-paid and a challenging project. You should market it and get it published in the famous newsletters.

Open-source contributions

Being a moderator / owner of a healthy repository gives you lot of credibility. Just in case, if you do not fall into that category, make sure you have few good contributions to the open source projects.

If you have never done a oss contribution, the whole notion of of Sharing is Caring might look a bit odd, but you will soon embrace the idea. Try it out :-)

If you really want to stand out, contribute to the popular frameworks like rails, phoenix etc.. Don’t get intimidated by the community built around the codebase. Most of the popular communities are friendly to work with.

Giving Talks at Confereneces & Meetups

Start attending your technology stack’s local meet-ups. Give presentations and talks about interesting ideas and executions whenever you can.

If you have a great topic that you want to talk about, submit your proposal to regional conferences. Once the conference videos are published to the external world, link those videos in your website.

Having a strong technical talk under your account gives you lot of credibility.

Marketing & Reaching out

Do not worry if you think you did not build enough reputation in the external world. If you want to anyway start freelancing, update your profile in Linkedin and AngelList.

If you have enough time and energy, give a shot at Toptal.

Just fyi, I couldn’t clear Toptal’s algorithms round. And, I detest interview processes which include invert a binary tree kind of algorithm questions. So, I never really bothered giving it another try.

Reach out to freelancers in your region. Meet them in person. Talk to them. Take their guidance.

Check out sites like WeWorkRemotely, remoteok and others.

A caveat though: Many jobs published here claim themselves as work from anywhere jobs, but they put a condition on your nationality or time-zone or something of that sort. They never really worked out for me.

Reach out to companies like Mavenhive, Codemancers, c42, Nilenso which are popular among freelancers.

fyi: My last two clients came to know about me through Linkedin & AngelList

It takes time to build traction as you just changed your career path. Be patient. Keep working on your external portfolio like blogs, talks etc. in parallel.

4. Before saying ‘yes’ to a client

Let us say, a client is really interested to hire you. Then carefully consider the below points, before you say yes

Background Check of the client

It is very easy for freelancers to get unpaid. At the least, do a sanity check on the client. Talk to people who worked with the company before. Talk to the local freelancer community. Talk to whoever you think could give a feedback. Search in google about their financial status.

Remote Support

I personally decline all offers which do not let me work from anywhere. Your mileage may vary but this is something to be discussed before signing up.

No of hours

I have been signing up for 40 hours / week. I will probably cut it down to 30 hrs / week in my next freelancing gig.

If you are planning to work with multiple clients, make sure you are not over promising them.

As conveyed earlier, many of the experienced freelancers work only 25–30 hrs / week.


Some US clients might demand you to work in the US timings. Be aware of health complications that might arise because of such commitments.

Notice Period

Make sure the notice period is atleast 2–4 weeks.

In my case, it was 1 month in my first project, and 3 weeks in my second one.

Contract term

This is my personal opinion

Unless you are really excited about the project that you are working on, do not stick to a project for more than 6 months.

Personally, I feel like I would get into the rat-race kind of mode, if I stay for too long in a single project. This also means, that you get a minimum of two breaks every year to think through what have you been doing and what you are going to do next.


If your client asks you to help them in maintaining the features you develop, even after the association, say NO.

You will never know what kind of situation you will be in (after the association) when the client actually needs some maintenance help.

5. Conclusion

Just FYI, I intentionally did not cover much on the income aspect of freelancing. I seriously believe that it shouldn’t be anyone’s main reason to choose this career.

But if you really are interested to know, you probably are going to earn more than what you can in your full-time job. It might take a bit of time though. Although, I made few compromises in the beginning, am doing good these days on the financial front.

It has been an year into freelancing. And, if you ask me how has been my experience: I would conclude it by saying

Freelancing gave me more control of my life. I got more time to spend with my family. At the end of every project, I got time to reflect upon what I had been doing and what I could’ve done better.
Moreover, it gave me enough time to scratch my resurfacing entrepreneurial itches.

If you are someone who wants to start freelancing and want to discuss in more detail, feel free to get in touch with me on twitter.

If you are an experienced freelancer and want to give your feedback, I’m all ears :-)

This post is a genuine effort from my side to help people like past-me who want to try out freelancing, but do not have much understanding of the pros and cons. If you found it useful, please spread it around ;-)