How To Know When To Quit Your Job and Start Freelancing

You’re wanting to leave your employee job and start freelancing. 

You’ve got a family to support and this transition is giving you some anxiety. 

If you haven’t already, check out the previous posts as part of this Employee to Freelancer series where I talk about how to figure out what to do as a freelancer and how to convert your resume into a portfolio. 

Today, we’re focusing on the next step which involves finding those first clients and working your way to quitting your job. 


What do you need to do before you quit your 9-5? How do you start finding clients? 

Before you quit your job, you need to start earning some income. You may be lucky enough to completely replace your income before having to quit your job but that’s definitely the exception and not the rule. 

Most people will have a gap where you don’t have enough income from your side hustle yet and in order to keep growing that, you have to quit your 9-5 to simply have the time. 

I quit my job when I had 1 client. I may have jumped the gun a little too early because it took a few months before I found some more clients and actually replaced my full-time income.  I had no savings to buffer me during that time so I sank into tons of credit card debt. 

That doesn’t have to be you. 


The first thing you need to do is sit down with your spouse and create a financial plan for how you’re going to transition. 

If you’re able to get a 3 months emergency fund in savings then great. If you’re barely earning enough in your employee job to pay the bills then you won’t get to have savings to live off of and instead will just need to accept a more gradual process into freelancing.

Your financial plan should include how much money your day job is bringing in and whether there is any extra. A budget, so that you’re limiting your spending and saving for the leap instead. 

It should also include how many hours you’ll be putting in per week to build up your freelance business on the side. It’ll also have what steps you’re taking to build up that business. For example:

Step 1:  Could be just getting educated for a couple months on how to do it.
Step 2:  Could be investing in a small online course or joining a coaching program.
Step 3:  Could be actually starting the process of finding clients.


The easiest way to start finding clients with the least amount of time invested is to get set up on a freelancer marketplace like Upwork or Fiverr or

Launch an account, set up your profile and start submitting proposals to jobs. You should be submitting several proposals every day because your close rate will be low to start until you build up sales skills. 

From those proposals, you’ll get some interviews, you’ll get a lot of practice getting on calls with potential clients and eventually one will hire you and then another. I’ve got other videos on how to sell yourself in these interviews and close deals with clients so go watch those on our YouTube channel, or read the blog. 

Episode 17 of the podcast is one of those where I go into detail in enrolling clients, be sure to read or watch that. 


Besides submitting proposals for job posts on freelancer marketplace sites, start spreading the word through friends and family about what it is you do. 

Don’t rely totally on friends and family: sometimes they are the most unreliable when it comes to building a business because they don’t treat you as a business owner, they treat you as their friend or son or brother. 

However, it could help you get some initial gigs under your belt that can help build your portfolio. Just know, you’re unlikely to grow your business through only working with people you already know. 


Audit your network and think about anyone that may be a business connection, it doesn’t have to just be friends or family. 

Who are you connected to on LinkedIn that could be your ideal client or likely knows them? 

Definitely update your LinkedIn profile because most clients will check you out there even if they don’t find you there. Have it reflect your current freelancing ventures. 

Now you will have to be careful with this because if your employer is connected to you on LinkedIn and they see you updating your profile to say you’re freelancing, they might confront you about what you’re doing and whether you’re planning to leave, which could end your job prematurely. So you have to make that judgment call in where you advertise your freelancing. 


The goal during this transition process of preparing to quit is to get as much education as possible on freelancing so at least that learning curve is done while you still have income. 

Definitely learn how to sell, learn enrollment skills, and be submitting proposals and practicing getting on sales calls. Even if you lose your job before getting your first client, if you have those skills, you won’t be far off from finding that client. 

This transition also largely depends on the type of freelance work you’re doing. Chances are you only have time in the early morning or at night to do your side hustle. That means consulting will be difficult since most clients will want to get on calls during normal business hours. 

But if you’re pursuing gig based work to start, like graphic design, editing videos, writing, blogging, or anything else that you can do without being on calls with the client, that’s better for a typical 9-5 work schedule. 


One of the best ways to start making time to build up your freelance business on the side is to start waking up early. 

Evenings were always hard for me because I needed to help with kids and dinner and my family needed me so I woke up at 5 or 6am before they woke up and spent 1-2 hours working on my freelance business every morning before my day job began. 

I was fortunate enough where my second employee job allowed me to work at home so it was easier to put some time into my business during the day and move my schedule around.  But my time was still very limited in what I could do for my business so I had to put time in early in the morning and also get to bed early enough so I got good sleep.

If you’re in a similar situation as me, and also have a family, I recommend the early morning. Some people will just work late at night after kids are in bed but I don’t recommend that. Your brain will be sharper in the early morning after having had sleep before midnight then it will be late at night when your head is full of the day's stresses and you’re tired.

So after a couple months of getting educated, gaining the skills you need to not only provide the service you’re providing in your freelancing, but also the sales skills, and find your first couple clients, that’s when you ask the big question:


How do you know when it’s time to pull the plug on your normal job? 

It’s going to totally depend on your unique situation. How much money do you have in savings? That will impact how soon you can quit. Again, there will always be a gap in most instances where you won’t be earning enough yet through freelancing to replace your employee job because you’re simply not giving it enough time. 

So you’ll have to make this decision with your spouse and make sure you have timelines in place for when you have to fully replace your employee income after quitting. 

By this point, a great number to have would be how many proposals you need to submit per week to get X amount of clients or gigs. To know that you need to know how proposals lead to how many interviews lead to how many clients. 

Then you make sure you’re committing to that number until you have the luxury of decreasing how many proposals you’re sending because you’re closing more deals, and your time is starting to fill up with client work and less doing sales. 

One option is to have a backup plan to go get a part-time, (not full-time), job during the process if it’s taking longer than expected to get enough clients after quitting your full-time job. 


Don’t go back to get a full-time job unless you’ve decided you’re giving up on freelancing. I did that. 

I gave up after 9 months on freelancing because I didn’t have any of the skills I’ve discussed with you, didn’t know how to sell, didn’t know how freelancing even worked and so I got another full-time job only to be right back in the same boat a year later of quitting and having to start freelancing all over again. It just delayed the inevitable. 

I barely had time to work on freelancing during my full-time job, most people don’t, especially when they have a family. You’re already working 40 hours per week. 


Ultimately you’ll know because you feel peaceful about making the leap. 

There isn’t a perfect formula for knowing when to quit your job but I gave you some indicators today to help you know when you’re ready enough: you have enough education on freelancing, you’ve submitted a bunch of proposals and have practiced your sales skills, and hopefully have found a couple of clients and been able to start building a portfolio of client work even if only occasional. It’ll give you a head start for when you quit your job. 

Just make sure you and your spouse are totally on the same page before you quit your job and you have a solid plan to navigate the transition. 

That’s it for today. Be sure to subscribe on YouTube if you want more content like this and head over to to see show notes. I wish you the best on this transition from employee to freelancer. Reach out to me if you want customized help and I can plug you into some of my programs. 

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