How to succeed as a contractor: 5 essential endeavors

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The sweet comfort zone

The majority of people like the fluffy comfort zone where you get a stable income, a decent place to work and a warm meal everyday. Add to this the benefits like paid holidays, private insurance scheme and you are a king/queen. It’s not difficult at all to be in such a zone: you just need to be in the office at 9am, take 1h lunch break, regular smoking breaks every hour and the last most delightful time of the day, rampaging through the door to go back home. Boy, what an envious life!

Although it might seem simple, going out of the comfort zone requires a lot of work from your side. You’ll need to be persistent, confident, pragmatic and accept that any situation is a complex sequence of events and facts you are responsible of.

So if you are really determined to take the challenge, why don’t you start to work as a contractor for different companies? It’s a rewarding journey that lets you taste a bit of entrepreneurship, legal issues, economics and many more. It really helps you spread your wings. In my case, it helped me by boosting my ASP.NET development expertise. I had the problem that the companies advertising permanent jobs on ASP.NET rejected me for not having enough experience. As a contractor, it’s easier to get a project because they don’t have to permanently hire you, they’ll do away with you if you’re not good. That’s why being a contractor is a tough experience.

So in this article I want to bring a light into the qualities I believe are important to get your way about being a contractor.

1. Competitivity

Remember that entering this market can be tough. You’ll need to stay ahead of the game and know your way about your favorite tech stack. Theoretically, the same goes for an employee, however as a contractor you can be fired very easily putting you back on the street and the project hunt starts again. This is where the competitivity kicks in: while job hunting, you aren’t always the only hunter. Guess who gets the game in this case? The best hunter.

Once, I lost an interview because of a tricky question I didn’t manage to respond. I was a candidate for an interesting project at a bank and got into the final battle with another candidate. The client didn’t know which one to pick so they decided to have a final round with the hardest questions they could ask. I answered them all right but I stuttered at the last question. I just didn’t have a clue what the answer was. Therefore, the client picked the other guy. Damn, I wanted to know who he is in order to congratulate him!

2. Resilience

No matter how competitive you are, even if your skills place you among the top shots in the market, you can still have a bad day making you lose an interview or get fired from a project. This can very easily put you down and you can start questioning and doubting yourself. It’s completely normal and natural to feel left out (just like after a breakup), however eliminating negative thoughts will put you back on track. Thoughts like “I’m not good enough for this job”, “They’ll never hire someone like me” shall never exist in your mind.

You must make efforts to eliminate negativity in your mind by taking a positive stance, involve in smaller projects, do some tutorials and try to analyze what the companies are looking for. This will help you during the bench period. Try to achieve something everyday. Try to always learn something new. This will ease your bench sitting period.

I’ve been on the bench quite a few times already and I focused on being positive and avail the opportunity to involve in my own small projects to keep my mind busy. I always try to get involved into something that because I suffer from hyperactivity; so in this way I can stay clear of bad thoughts. Moreover I share my quote here, I hope it serves as a good guidance:

Be always positive, but prepare yourself for the worst

Andrei-Flavius Ivan

To be more elaborate, interpret it like this: do your homework, be open to new things, embrace change, but remember that practically we cannot control everything and things are going for sure to be bad. This is what resilience is about.

3. Results oriented

Maybe you noticed in many job descriptions that they are looking for a results-oriented person. So why is it important for them?

First of all, they want to filter out the people who are sluggish, don’t push themselves harder or the nitpicky type. These characteristics can be more brutal if the person is a philosopher. Yes, that’s right, there are programmers out there who are philosophers, the opposite of results-oriented achievers. A philosopher can be dangerous for the company because they avoid doing that they are asked to by giving “smart” excuses, they focus on the bad parts instead of improving the software, they are approach a situation with grudge in general. I’ve met in my career so far 2-3 people like that and I assure you they had that position only because they were relatives with the boss or they were just secular within the company.

Lastly, a results-oriented person is a performer and a team player. He doesn’t focus on office gossips, he doesn’t kiss anyone’s ass, he doesn’t take advantage of other colleagues nor wastes time on coffee and cigarette breaks. A results-oriented person demonstrates professionalism, a can do attitude and delivers good value to the client, satisfying his requirements.

4. Money-saver policy

When working as a contractor, you’re kind of a small entrepreneur. Any entrepreneur has to keep his cashflow running. One leap of faith you have to do when you switch from employee to contractor is to save money as much as you can. Your income won’t be stable so you can’t really spend all your earnings just like that. Also, the burden of paying taxes rests on your shoulders now.

Don’t be tempted to spend your money fast. There’s a saying “You spend as much as you earn”; I advice against following it! I’m not saying you should go for a hunger strike either, just try to limit your expenses. Don’t spend it on flashy things, spend money on things that can bring value. Life as a contractor has ups and downs so don’t be illusioned by the great deal you’re doing today: tomorrow you may no longer have it.

One personal technique I use to limit my budget is to set daily limits for expenditure like food, drinking or transportation. If you consider only the general expenses (everything apart from rent, internet, electricity) you’ll see that you can limit those to a certain level. I personally set an allowance of 30 EUR per day which is more that enough for this. It’s very reasonable and I very rarely reach this limit. This will mean that on average you’ll need 900 EUR per month to live decently.

5. Enthusiasm

Back to the roots, I’ll ask you a question: why you wanted to pursue a career in IT industry? Is it because of the fame, money or pure love and passion? It can’t be for the hot girls, there aren’t many hot girls in this industry (and the ones that are, are already taken). Passion is the key motivator if you wish to succeed in this market. Nothing will happen if you lack passion, love and determination. It’s like in music: maybe many reach the top charts, but because of their lack of passion they don’t stay there for too long. Same in IT; if you are only for the money, you’re not going to get very far. As with any career, you need to start from somewhere low and grow from there.

That’s how it works! 😄


In this post, I explained a bit about 5 factors that will help you succeed as a contractor. It’s important to be versatile, hardworking but positive attitude matters as well and it’ll help you carry on.

Hope this post was helpful, thanks for reading and don’t forget to drop a comment or contact me if you need information or have thoughts to share!

Cheers! 😉

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Author: afivan

Enthusiast adventurer, software developer with a high sense of creativity, discipline and achievement. I like to travel, I like music and outdoor sports. Because I have a broken ligament, I prefer safer activities like running or biking. In a couple of years, my ambition is to become a good technical lead with entrepreneurial mindset. From a personal point of view, I’d like to establish my own family, so I’ll have lots of things to do, there’s never time to get bored 😂

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