How Do You Go From a 9-To-5 Job to Working for Yourself?

Working in this generation is vastly different than it used to be even 20 years ago. If you are tired of running the rat race, this article will provide you with all the strategies you need to start working for yourself.

We will cover everything from the basics and carry you through the thought process you need. While the perks of moving from a 9-to-5 job can be attractive, there are many questions you need to ask yourself.

This article aims to bridge the gap in knowledge and help you make an informed decision.

Without further ado, let’s get into it!

Know Your Interest

Before you start working for yourself, ask yourself this million-dollar question. What are your passions?

A simple method is to jot down what you believe you are interested in. Check to see if you’ve spent a vast majority of your time working on these interests. Passion and skills are not the same things. Unless you are good at your passion, there’s little chance you will succeed.

Or worse, after a few months of being at it, you’ll learn that this was not your true interest after all.

So, make sure that whatever it is you’re leaving your boring yet safe 9-To-5 job, is truly worth taking the risk.

Be Real About Your Skills

You are getting real serious about your own venture, good for you! It’s time to get working on your networking skills. Ask yourself, are you marketing your talents right? For example, do you have copywriting skills at others would pay you for?

You need to list down all your pros and cons based on the skills you have. Without it, you would be stepping into the unknown without any skill whatsoever. This would make working for yourself quite a challenging endeavour. 

Develop a Strategy to Leave Your Job

The next course of action is to test the waters. By that, we mean to come up with a plan to work at your current job and also work on your own venture at the same time. Sure, it can be tough to juggle both, but this is a very good way of minimizing risks.

This particular strategy will give you an idea of what you are getting yourself into. If you’re confident that your venture is doing well and has the potential to earn big, or just as much as your current job, you can the leap.

Following this, you would need to come up with a plan that works in the best interests of all parties involved. This should involve a transition plan that can help your successor carry out your duties without causing any hassle in your current workplace. Call it a moral obligation if you will.

Make Financial Preparations

As we’ve just mentioned in our previous point, you need to be financially prepared during the transition phase. By now, you should already have a project in the works that provides instant cash flow. Just in case it’s taking longer than you anticipated, keep a backup source of funds to assist you until you have achieved a good cash flow model.

While it’s true that nothing is set in stone, that doesn’t mean you can’t take some precautions! To avoid any unexpected hitches, try following through with proper order. For that, you’ll need at least a 3–4-month buffer. This time frame can also be altered by the industry you are in.

What happens when you don’t pre-plan your financial route? Well, there’s always a risk of you spiralling into debt, one that would be exceedingly difficult to recover from if not done correctly.

The whole situation may be drastic enough to put an end to the whole idea of working for yourself before it even begins.

Work Part-Time

One of the best ways to get cash flow positive is to pick up a part-time job in the sector you are interested in and see how it goes. Learn the ins and outs of the industry from within!

This also applies to those who don’t even have a particular passion or skill, and yet don’t want to work the 9-to-5 job. You’ll learn that there are many alternatives to working a 9-5. These jobs can also give you the freedom to be your own boss and choose your own working hours.

This is the most effective way to determine whether you are ready to start working for yourself. It will assist you in making the move to a self-employed profession as seamlessly as possible.

You may work as a consultant, a freelancer, or even an assistant. Whatever the work entails, be sure it meets the demands and specifications you’ve established for yourself.

Permanently Avoid 9-to-5

As the saying goes, it is easy to jump over the 9-to-5 wall but staying away from it is the hard part. This last point has to be made because the whole article is of no use if you do not understand this.

Your plan should include investments that stop you from hitting drywall if things go wrong. This would prevent you from joining a 9-to-5 again. Without investments or a positive income, it would be hard to not fall into the rat race again.


Don’t procrastinate. Easier said than done, but it’s often to just rip open a bandaid. And of course, don’t forget to make a solid strategy if you actually want to start working for yourself. If you follow the steps in this article, you will be safe even if things go wrong on the other side.

It’s also important not to be lazy when it comes to working for yourself. Do what has to be done and get started. Starting today. The longer you wait to make a strategy, the longer it will take you to break free from the confines of a 9-to-5 job. Time and tide wait for no man. So make every second count!

Photo by Clark Tibbs on Unsplash

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