In a professional life, there are often two main choices when it comes to deciding what someone wants to do: join a company or start one yourself. For those interested in the latter, that path is often fraught with complex decisions, including figuring out what the idea is, how to execute, and all the common questions one asks when doing a startup.

We wanted to know whether it was better to work for someone or start your own business so we spoke with Gregarious Narain about it. Turns out that he was quite happy being an entrepreneur first rather than a company employee.

As the co-founder of media-sharing and curation startup Chute, Narain says that he’s always had the entrepreneurial bug in him. Coming from immigrant parents, he’s been accustomed to creating his own ventures and over the past couple of decades, he’s been doing just that. Narain has been a consultant to companies and startups and was the first employee at influence measurement service Klout, where he helped to develop and shape the product.

Several years ago, Narain joined Klout and he readily admits that in his 15+ years of post-college experience, this was the first job he’s ever had. Why is it that he chose to go the entrepreneurial route instead of being like most of the rest of us and join an existing company? It’s because of two main reasons, which seems to resonate with most company founders:

  1. He doesn’t like to put a limit on the things that he can pursue. In other words, not having any boundaries frees him from “being institutionalized.” Narain references a scene from the movie “Shawshank Redemption” where the Morgan Freeman’s character speaks about how being in jail changes a man.
  2. He believes that deep in your core, you should love or believe in whatever it is that you want to do. If you join something, he says, you may love it, but it’s much different than if it was your own. It’s like if you had nieces and nephews: you love them very much, but that love is a bit different compared to if you had your own children.

Of course there are those who may feel that working in an established company or startup is better for them for different reasons, including at what phase in life they’re in. Paul Berry, the former Chief Technology Officer for the Huffington Post and now the CEO of content aggregator service RebelMouse, says that when he was going through graduate school full-time, he felt having a job at a company was good for him. The reason was that the work was not life or death for the company — he could contribute, be professional, but the company was going to be fine without him.

When Berry joined the Huffington Post, he thought of it as an excellent in-between. As the CTO running product, design an engineering, he says that he was an essential part of the management team, part of the board and operations meetings and worked with both the Chairman and the CEO. Working within a company helped give him an opportunity to understand very deeply from the inside how a company goes from a small valuation and audience to a large one. It also gave him exposure working with talented and experienced industry people.

In looking at Narain’s reasons, it can be said that there are some companies that offer employees the chance to be free and do whatever it is you want — look at what 3M and Google have done with their 20 percent time rule and how Facebook regularly holds hackathons to encourage innovation. He believed in the Klout product, but he said he left the company because he didn’t want to regret what might have been had he not continued his entrepreneurial endeavors.

For those still unsure about whether they want to leave their company to start one, Berry says that joining a startup is a happy compromise — being able to find a promising company where you can still contribute at the very core, but not quite be on your own is a “fantastic idea.” Narain agrees with this and tells us that when he joined Klout, it was just over a year old, but he felt he could still impart some of his DNA in the business model, team, and culture — something to help really make it his own.

But simply being an entrepreneur isn’t as simple as some might think. There are things that need to be thought of. Narain says that entrepreneurs typically have already done something to separate themselves as being one — whether it’s starting a small venture while in school or when they were younger — their minds have been made up. They’ve probably already proven it before.

When you do start your own company, both Narain and Berry suggest not going in on it alone — get a co-founder that can balance you out. Berry says that once a decision has been made to start a company, the easiest and “most dangerous thing” is to work in a bubble and decide that you’re finally “your own boss.” Find good people you can work with and can have a healthy discourse over the product, the direction of the company, etc.

In the end, being able to assess one’s risk is the most important thing in starting a company. Narain believes that entrepreneurs must figure out how far they can go while also realizing that money isn’t going to be exactly streaming in for the first few months or years. But if it doesn’t work out, step back and move on. Barry says that working on stuff you feel passionate about, but is largely new to you is much harder to pull off and success is far less frequent.

But that’s the life of an entrepreneur.

Photo credit: PATRICIA DE MELO MOREIRA/AFP/Getty Images

mag1 11 Issue v1.1: The entrepreneurial bug: How a founder decided running a company was better than joining one