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How to Transition into Freelancing from a 9-5 Job

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(Updated August 25, 2021)

The transition from working at a traditional job to becoming a freelancer is a pretty big shift.

Big changes in life are usually hard to make. This causes many people to not make many changes in their lives at all, even when it could really help them.

The difficulty in making the leap from a traditional 9-5 job to starting a freelancing business is especially pronounced if you’ve been working at that “regular” job for many years.

If you’re used to working 9-5 and have never worked for yourself, the best way to make the shift to freelancing is not by diving into it head first. Transition gradually into freelancing instead. You’ll find it’s a lot easier and probably less stressful too.

Here are four tips that will help you transition from your 9-5 job into freelancing.

4 Tips for Transitioning into

All-white home office with black monitor

1. Adjust Your Mindset

When you start freelancing, you’ll almost definitely be easing into it financially whether you want to or not. It will take a while to gain the experience and proficiency you’ll need to build up a clientele to the point that you’re making a full-time income.

But money is not everything. Mindset is another important part of this. 

If you start freelancing straight out of high school or college or somewhere else early in life, you’ll likely get right into the groove of being your own boss because you haven’t gotten used to any other way of working yet. 

If you begin freelancing after years or decades of working in a traditional job or career, though, it will probably be more difficult to make the shift.

When you’ve been working for someone else for years, you’re used to thinking like an employee. When you decide to start a freelancing business, you need to think like an entrepreneur and CEO. For some people this comes more easily than for others. 

My ebook, How to Shift Your Mindset from 9-5 to Freelancing, can help you get into the right frame of mind to be a freelancer. You can download this ebook for free right here.

2. Know the Pros and Cons of Freelancing

Freelancing isn’t for everyone.

Some people just aren’t interested. Some are very happy with their current work life. Some hold jobs they love for which there is no freelancing opportunity. Some people are interested in freelancing but, after learning more or trying it out for a while, decide it’s not for them.

If you are interested in freelancing and think it’s for you, you should still be aware of the pros and cons before you start. Knowing what you’re getting into before you get into it can be a big help. You can learn seven pros and cons about freelancing here.

3. Start a side gig before you quit your day job

You may not have much extra time in your daily life when you’re working full time. It’s a really good idea, though, to squeeze out a few extra hours every week for at least a few months and start freelancing as a side gig

Even one hour a night or a few hours on the weekend will give you an idea of what your chosen freelance work is really like. It will help you see whether you enjoy doing this type of work.

Working at a side gig will also help you become skilled at your new work. When you do begin doing it full time, you’ll already be good at it and able to work efficiently.

The hours you work at your side gig before you quit your day job will also help you see when you prefer working. When you then turn your side gig into a full-time freelance career, you’ll know exactly what hours and what days you can do your best work.

4. See what freelancers have to say about freelancing

The more you know about freelancing before you start, the better off you’ll be.

If there are any freelancers in your life, talk to them about what it’s like for them. Read up on the subject. If you’re on Twitter, check out hashtags like #freelancing,  #freelancers and #workforyourself to see what freelancers are saying. Feel free to ask questions too.

You’ll learn a lot from what other freelancers have to say. They can tell you personal experiences they’ve had, share lessons they’ve learned and give you advice about how to handle your personal journey to freelancing. So connect with other freelancers before you start.


Transitioning into freelancing rather than diving in head first will help you get off to a good start when you’re making the change from a 9-5 job. Be sure to download my free ebook about transitioning into freelancing, How to Shift Your Mindset from 9-5 to Freelancing, right here.

Image by Gabriel Beaudry

Sabina Lohr is a lifelong freelancer turned entrepreneur who created World of Freelancers to help others discover how to work for themselves online and live the freelance lifestyle. She’s always really enjoyed the freedom that freelancing brings, including several years on and off of working online while traveling and living abroad.

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