Freelancer, Entrepreneur And Bootstrapper

Inspired by Seth Godin

These days being an entrepreneur is something you dream of. Because it seems like they are living the best lifestyle and all they do is make big decisions.

Or you want to become a freelancer and become your own boss so you don’t have for follow a particular schedule. Also being paid whatever it is your worth.

But if you jump in, chances are you will be disappointed. Not because you aren’t talented. But the road is uphill and you need to gear yourself for that.


A freelancer is a person who sells his services to clients for the money. And those clients can be one or many. And although you would think you can have the schedule, most of the times you are working around your clients requirements.

Being your own boss sounds amazing unless you realise it is difficult to do something unless someone tells you specifically what to do.

You need to learn all sorts of different things, learn to do taxes, find clients and understand pricing vs. value. And it will take a long time to match what you are earning from a 9 to 5 job.


Being an entrepreneur means you would be hiring a lot of other intelligent people. The main job of yours is to get job done by other people. You raise money, earn money while you sleep and make important decisions.

And doing these isn’t easy. Because you are making a company which is way bigger than yourself. There are staff to be paid, bills to be paid and one day you will be selling your company.

The first thing you need is to identify whether you are a freelancer or an entrepreneur and gear yourself for that. But what if you want a different route.


A bootstrapper is the one who is not quite the freelancer and not quite the entrepreneur. She is someone in between.

Like freelancer she is still involved. Her company won’t collapse if she is away for a week. But it won’t function without her presence for a long time.

She doesn’t earn money while she sleeps. She hasn’t raised money. But she has risked her money and time to make this venture a fruitful one.

When you have entrepreneurial desire and no one believes in you to invest their money or time, you bootstrap the company to do what your calling is. If it is profitable then you might become an entrepreneur or choose not to.

You Decide

There are many ways to go about it. You can become either of the three. But identifying yourself in correct way will help you for the challenges which is coming.

Another way is to test. Be a freelancer to feel what it is to work without a boss. Find clients, take stress and then make decisions which will impact your earnings.

Make your services packaged as a agency and bootstrap the company by hiring few other employees. And then work your way up to become the entrepreneur. Or not. You decide.

I hope this helps you to take on a journey which best suits you. Or at least help you in making a better decision.