When Is The Right Time To Trade In Your “Steady” Job For Full-Time Freelancing

Note from Leah: My post on The Myth of Job Security and my question to you readers whether or not your steady paycheck is keeping you from making the jump to full-time freelancing, hit home with many of you. The overwhelming response in my inbox was “Yes! But how do I know when it’s the right time to quit”? I knew my friend Anna Long is an expert on the subject, having been through it herself, and now daily with her clients as a business coach. So today I’ve brought her into the Freelance To Freedom Project to give us her best advice!

When is the right time to make the jump?

It doesn’t matter if you run a “formal” business on the side or if you simply freelance here and there. Making the transition from steady JOB money to less steady freelance/business money can be frightening!

The list of common “job-quitting” worries are endless: 

What if I can’t pay my bills? 

What if the clients I have quit coming the minute I quit my job? 

What if I can’t “cut it” and I have to sheepishly return to my day job with my tail between my legs? 

How much money should I have saved? 

Will I have to live in the basement at great aunt Myrtle’s?

Etc, etc.

I like to speak on this topic because my personal story is a great case study.

I was born with two strange split-personalities. On the one hand I LOVE business (entrepreneur-addict ALL THE WAY). There is nothing like the thrill of taking an idea and creatively bringing it forth into reality. On the other hand I HATE not know who I will be working with each month and whether or not they will “show up”, believe in me, and willingly place their money into my piggy bank. Split personalities aside I also managed to stay in a steady job for about 4 years while I built my first business.

If you have questions about the “Right time” to leave a job, I have answers.

So let’s dig in! When shall you take the LEAP from your perceived secure job to doing your own thing?

Here are 3 key things to consider when debating the timing of your transition:


While you may not feel totally confident or “ready” to transition away from your job, you should at least have confidence in your skills and abilities to do “X” (‘x’ being that thing you are selling or freelancing about).

Most people don’t have clients growing from magical trees which means that they have to go out into the world (online and offline) and confidently express their talents that they hope to get paid for. If you don’t believe in your abilities…most buyers won’t either!

Overcome this by working with a number of clients and getting testimonials about your work. Not only will this add value to our website, it will also give you a boost of confidence. If you already have these and have been doing your trade for quite some time and still have confidence issues, hire a coach or specialist to help you get over this. Chances are they can help you get to the root of your semi-dysfunction much sooner than you going it alone.

You’re likely amazing at what you do and you deserve to bask in that glory!


If you are debating quitting your job and you have confidence and skills (but no clients) then hold off on quitting your job. This may seem obvious to people who have already started producing money from their side-gig or side-biz, but newbies tend to under-estimate how long getting clients can take. The hardest part of starting a biz or freelancing can be getting your first few paying clients (after this you begin to gain more traction).

So instead of spending those countless “bored” hours checking Facebook at work, I recommend you begin strategizing getting a handful of clients. These guys/gals will pay you AND give you more clout (see above about testimonials). These will also be referral sources. I STILL have referrals coming my way from my very first clients despite the fact that I wasn’t a polished business owner back then.


The number one thing that comes to most people’s mind when they are debating quitting their job is this…CASH! Do you have it and are you making it? An irresponsible trend I’ve noticed in the coaching and abundance world is the mumbo-jumbo thought propositioning that if you simply dream it, it will happen. All the dreams and “good vibes” in the world won’t necessarily help you generate income via freelancing or starting your business.

However what WILL help you generate income (so that you can leave your pesky job) is a dream AND a firm strategic plan about how you can get from point A to point B. This is where hiring a business strategist or consultant comes in handy. I spent YEARS teaching myself business crap and “going it alone” in my first business before I coughed up the dough to work with someone to help me with my biz. It was worth it and I should have done it sooner!

A part of this “strategy process” is defining what your freelance or business income needs to be. If you don’t know what you are shooting for, you will likely never reach it. So figure out how much money you need to make to have a clean transition from your job and then create a strategic plan for you to help get you moving!

Not sure what this magic number is? Well it’s different for everyone, but it is probably less than you think. I recommend signing up for the free online budgeting and tracking software like Mint to get a very good visual of what your average expenses are and what categories are necessities vs. luxuries. You can plan to quit your job when your freelancing or business provide you with enough to meet your necessities (which could be sooner than you think).

Are there benefits to staying a little longer at my job?

Staying at a job you dislike can suck, but there are some great benefits to sticking it out until you are ready to take the leap. Here are just a few:

Creativity- when you have steady money coming in you tend to be more creative. If you are really stressed about finance (i.e. you leapt wayyy before you were ready), then your creativity may be negatively impacted. This does not apply to all…some people LOVE the pressure and this time of deadline only increases their creative capacity. You know which one applies to you and I suggest you consider this when deciding when to quit and under what circumstances.

Resources- When you have steady money coming in, you also usually have the ability to put some of that money towards very useful things that you NEED when starting your freelancing gig or business (like a website, courses, or consultants…the list goes on!) You don’t have to spend a billion dollars, but you do have more flexibility in paying to strengthen whatever your “weak” spots might be.

You call the shots- One of the things that I was proud of with my old skincare biz was that once I figured out my target client and how much I wanted to charge, I could be picky about who I worked with. Unlike other estheticians who were slashing their prices or marketing like frenzied monkeys, I was able to stay calm and invite the RIGHT clients to work with me.

This allowed me to create a cool little niche business working with awesome clients and making good money. If I HAD to make a lot to cover my expenses in the very beginning I might have resorted to street corner banana suit tactics! So if you aren’t in a huge hurry to quit your job, use this time to set very good foundations to make sure that you are attracting the RIGHT people to work with you (and pay you what you are worth)!

So in conclusion, everyone’s circumstances are different and ultimately only YOU will know when the time is right to take the leap. Hopefully the points above get you thinking from all angles! And in case you are curious…the month after I left my “steady job” I made more in my biz income than I ever had in the job.

We all love learning from each other’s experiences, so if you have any insights or advice about taking the leap, please share below in the comments section!

Thanks for reading and sharing!

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