How to stay fully employed at your 9-5 while crushing your new freelancing business

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If you’re anything like I was when I started freelancing seven years ago, you’ve got the idea stuck in your head that the only way to start your freelancing business is by quitting your job. 

Fueled by Gary Vee videos and early morning inspirational Youtube videos, I was convinced that in order to be a real business owner I had to burn the boats, take the leap of faith, and never look back. 

In hindsight, this was silly.

I had an excellent job, surrounded by cool people, with pretty good pay and I was learning the skills I would eventually need to succeed in my business. 

Ultimately, things did work out in the end, but they were a lot harder than I think they needed to be. Sticking around at that job for 6-12 more months, with a steady paycheck and getting paid to continually level up, would have set me up for quicker and less painful success. 

This guide aims to help you consider everything you’ll need to know when it comes to working your 9-5 and freelancing, and hopefully you can make a more informed decision than I did. 

Let’s get into it.

Is freelancing even worth it? 

I say yes, a million times yes, freelancing is worth it.

This woman says it’s complicated. 

For you? It depends. 

Ultimately, you’ve got to sit down and ask yourself why you’re thinking about freelancing in the first place. What goals do you have in life that freelancing will help you achieve over your existing job situation? What are you prepared to sacrifice to achieve those goals?

Everyone is going to have a different why for what attracts them towards the freelancer life, and it’s up to you to decide if it’s “worth it” to you. 

That being said, here are some pros and cons to help give context to your decision making process. 

Pros and cons of freelancing while you’re still working your 9-5 job

As with any big decision, you’re going to come to a crossroads with which direction to go in and there will always be pros and cons.

Becoming a freelancer is no different and that decision gets just a little more complicated when you think about staying employed at your 9-5 while embarking on the freelancing journey.

Here are the most important considerations:


  • You have a stable income while you figure out how to secure your first few clients. 
  • If you don’t have a ton of experience in your field yet, you can get paid to learn skills and then transfer those to your freelancing business. 
  • Health insurance and other benefits that you won’t receive as a freelancer. 
  • Take advantage of company 401k account matches for as long as you can to help your future wealth building goals (compound interest is amazing and your first year of freelancing will likely change your investment plans).


  • More hours spent working instead of other life activities. 
  • You’ll have to work at unusual hours to make things work, either earlier in the morning than you’re used to or later at night. 
  • If you aren’t seeing success or spending your time on the wrong activities (non income generating), you can easily burn out. 
  • Having a stable job can take away healthy urgency to make your freelance business work because you have the job to fall back on. 

How to balance your freelancing gigs without getting fired or burning out

Now is the moment you’ve been waiting for. 

Congrats on making the decision to do it, weighing the pros and cons, and confidently moving toward action steps. 

You’re a champion in my eyes already. 

When it comes to keeping your day job while working freelance gigs, the key to long term success is balance and intentionality. 

In the beginning, you might have tons of energy, confidence, and even motivation. But over time, if certain goals aren’t met, when things get hard, or when your day job and life start getting hectic, your freelance work is likely to get dropped if you don’t have the correct foundations. 

These action steps will ensure that you’re able to balance your 9-5 with your freelance work for as long as it takes to make the transition to full time freelancing, or at least until you reach your financial goals. 

1. Define your goals and timelines

THE most important step you need to take before embarking on this journey is to define two crucial things:

What is your desired outcome of this work? For example “I will start freelance social media marketing on Upwork until I make $3200 / month to replace my salary at the job I hate. 

If you’re not familiar with S.M.A.R.T goals, it’s a game changing framework to help you achieve your goals more reliably. 

What timeframe does this need to happen? One of the worst things you can do to yourself is not have a set check in point or endpoint for balancing full time work and freelancing. If the freelancing goes on too long without producing any income then you’ll lose motivation over time and be less effective. If you keep your job while your freelancing is starting to pick up, but keep it for too long, you run the risk of doing both things half as well.  

For example, “I will work my job for 8 months while freelancing, and then I will switch over to my freelance business full time”. 

Now that you’re equipped with the knowledge of when and where the finish line is, it will not only be easier to get there, but you’ll know that you’re there once you arrive. 

Sounds simple right?

You’d be surprised how many freelancers dive into this world head first without any direction (myself included). So you, my friend, are already ahead of the curve. 

2. Find a remote job or make a case for remote working at your current job

One of the easiest ways to ensure a smooth transition into job + freelance life is to already have a flexible schedule. 

If your job requires you to work long hours with a sporadic schedule and needing to be at attention at all times, it’s going to be hard to work in extra work. 

In that case, it might make sense to look for another job that’s remote or semi remote. With most remote jobs, it’s less important that you’re “showing up for work at the right times” and more important that you’re “getting the right work done”.

While looking for these kinds of jobs, be on the lookout for work environments that stress a lack of micromanagement, who flat out say that they care about your output more than politics, and who have a culture of only working a set amount of hours each week. 

Alternatively, you can have a conversation with your manager or boss and be honest with them. Let them know you’re trying to balance more aspects of your life and that you’d like to work remotely for one or two days per week. 

As an incentive, you can let them know that you plan on increasing productivity or some other benefit to them so it’s truly a win-win scenario. 

3. If you can afford it, ask for a slight reduction in hours

Another route to take, rather than transitioning into remote work, is to simply work less hours. 

Now, if you’re thinking to yourself “I can barely pay my bills as it is Ken, that would be unthinkable”, you should trust that thought. 

I am not suggesting that you completely give up your livelihood on a whim. 

However, if you can afford it because you have a little wiggle room in your budget or you plan on taking your freelance efforts seriously and have a plan to make back the difference, then working less hours at your job will allow you to dedicate that time and effort towards becoming a stable freelancer. 

This could look like working one less day per week, or coming into the office one hour later. The key is to negotiate with your boss or manager in a way that benefits them as well as you. 

4. Focus on income generating tasks and billable hours at first

It’s so so so important that when you first start freelancing you get as many quick wins as possible. 

Wins being defined as earning money. 

When you come out the gate getting paid, and most importantly, getting paid quickly, it builds your confidence and gives you hope for a better future. 

That progress and hope is the fuel you’ll need to carry you through the difficult times that you will inevitably face (happens to everyone). 

Here’s a list of activities that should make up 90% of your time when you start:

  • Telling friends and family about your freelance work and asking if they can connect you with work. 
  • Signing up for job marketplaces based on your expertise. 
  • Actively seeking out ideal clients and projects and sending pitches or proposals to earn their business. 
  • Reviewing job boards for freelance work. 
  • Billable hours on projects where you’re working hourly. 

And here is a list of activities that might feel like you’re working, but really should be very little of your efforts at first:

  • Fiddling with your website. 
  • Redoing your branding or logo. 
  • Creating business cards or flyers. 
  • Reading endless amounts of blog posts or watching inspirational youtube videos.

Go out and secure the bag as soon as possible. Focus your attention on that. It’s the most important thing you can do to set yourself up for success.

5. Use the weekends and early mornings

One of the easiest and most sustainable ways to get in your freelance gig while working your 9-5 is by carving out 2.5 hours of time a day. 

How, you ask? 


Wake up 1.25 hours earlier than you normally do, and stay up 1.25 hours later during the week.  

Now…I know some of you reading this have already flipped over your coffee table and are thinking of typing an all caps rage response to what I just said. 

But hear me out…

We already discussed that freelancing is going to be hard work and take some sacrifices. This is one of those things. 

But it doesn’t have to be miserable. Most people will do fine on 7-8 hours of sleep. So if you’re getting more than that, you can just drop it down a notch. 

If you’re already at that amount, consider what you do when you wake up and before you go to bed? Is it scrolling through your phone? Laying in bed staring at the ceiling? 

All of those things are fine on their own, but for you, that’s precious unstructured time that you can now dedicate to your side hustle. 

Good habits and a well structured routine will set you free and change your life. 

On top of mornings and evenings, it’s very doable to spend 3 hours on both Saturday and Sunday on your gigs. 

If you have a family and a partner, then make sure you’re working around your responsibilities and quality time with them as well. 

6. Have an open and honest conversation with your partner and family

Because you’ll be working on a slightly different schedule, dealing with a little more stress than normal, and prioritizing different things in your life, it’s critical that you talk with your loved ones. 

Ask them their opinions, be transparent about what you’re planning on doing and what it means to you. This should be a discussion and it’s wise to take their thoughts into consideration since you share a life with them. 

If anybody discourages you from doing it without a good reason or mocks you for wanting to try, that’s a completely different story. You aren’t obligated to please or take action on everyone’s opinion. 

The most important thing is that you give space for yourself to digest what’s about to happen with everyone, and use those conversations to design the best system for your life possible.

Big Takeaway

Freelancing while you keep grinding away at your full time job isn’t easy, but it’s worth it to build a better future. 

Remember to have clear goals and timelines for what success looks like to you and focus the majority of your time and energy on income generating activities in the beginning. 

You got this.

Ken Marshall

Ken Marshall is the Founder of Best Freelancer Tools as well as a husband, former freelancer, recovering foodie, mini Australian shepherd puppy dad, and serial entrepreneur (mostly failures, lots of lessons). He is passionate about helping others achieve their full potential.