Five Things You Need to Consider When Leaving a 9-5 Job to Start a Freelancing Business

freelance life

The number of freelancers in the US alone is threatening to hit the 60 million mark. The work-from-home trend that exploded during the early days of the pandemic gave many creative professionals the confidence to leave the comfort of their 9-5 job in pursuit of freedom and becoming their own boss.

Whether you’re a digital marketing pro, you offer virtual assistant services, or you bring some other talent to the table, there are plenty of lucrative freelancing opportunities available to you.

 Who hasn’t dreamed of re-enacting the scene from Jerry Maguire where Tom Cruise’s character (or Half-Baked with Jim Breuer if that’s more your style), makes an emboldened speech, convincing Renee Zellweger’s character to join him as he rolls out, ultimately launching his own business as a freelance sports agent.

Video: Tom Cruise as Jerry Maguire

Just like Cruise’s character, more and more workers are leaving the workplace and starting their own businesses. Freelance businesses where you get to choose your clients, be your own boss, and grow your business as much (or as little) as you like, are becoming more and more popular.

That’s all well and good, but before you steal the company’s pet goldfish and throw your hands in the air in defiance as a declaration of your new freelance intentions, be sure you know what you’re doing.

To help guide you on the hallowed journey of leaving your 9-5 in pursuit of freelance glory, I’ve put together a list of five things you need to keep in mind to ensure your success.

Let’s jump in.

Be open to a little help from a friend

Although as a freelancer you will be the only person in your business, that doesn’t mean you need to go the distance alone.

As mentioned earlier, there are nearly 60 million freelancers in the US alone. Each of you is facing your own freelancing challenges. Help one another out by building relationships with other freelancers and helping one another grow.

Share ideas. Make introductions to additional partners. Refer clients. The list goes on.

When you work together with other freelancers, you all grow. It’s the whole, “a rising tide lifts all boats” concept. When you help others rise, you rise along with them.

Charge the rates you deserve

One of the biggest challenges freelancers face is determining what to charge. Many freelancers struggle with this.

I see too many freelancers sell themselves short, charging far less than they really deserve for their work. Often, this is a product of fear.

Fear of losing clients. Fear of being overpriced. Once you get past your fears, you can truly grow your freelance business.

Stop making excuses for why you can’t raise your rates. Keep in mind, that people and businesses aren’t paying you for your work, they’re paying you for the years of experience and expertise behind the work that you do.

You’ve spent years fine-tuning and honing your craft. Don’t sell yourself short, and don’t be afraid to charge more. Businesses that truly understand the value of quality work are more than happy to pay your increased rates to get a boost in quality and ROI over hiring someone from a discount worker-for-hire website.

Upgrade your working conditions

Working in an office eliminates (most) distractions. You’re closer to your co-workers, and it makes it easier to develop a true sense of work-life balance, as you can leave the office and switch into personal life mode.

As a freelancer, your office is your home.

If your family is used to you hopping in the car each day and heading down the road to work – you’ve likely got the balance down. It’s understood that when you are at the office, you are unavailable. When you are home, you are fair game.

When you work from home, the line between work and play is blurred…a lot. For this reason, you may find it necessary to upgrade your freelance environment. And this may mean upgrading your home.

It may be a bigger home with space for an office. Or perhaps it’s a need for walls with better soundproofing. Whatever the case may be, if your current living situation doesn’t permit solid working habits and the ability to separate work from play, you’ll need to make a change if you hope to be successful as a freelancer.

Before you run out and buy that big mansion down the road, however, you’ll need to know how much home you can afford. The beauty of freelancing is that you can really live anywhere, so consider moving to a market that’s not in the higher end of the housing market.

Make sure you have all the space you need in your new home, and only move if you’re 100% sure you’re all in on the freelance life.

Prepare to wear multiple hats

As an employee, your role and responsibilities are well-defined. As a freelancer, however, that’s certainly not the case.

You’re now the business owner as well as the head of marketing, director of human resources, SEO specialist, the CFO, and essentially every business role you can conjure up in your mind.

Wearing so many hats can burn you out quickly if you aren’t prepared. As such, it’s important to go into freelancing with a plan to manage all aspects of your company. When you have a direction, you’re much more likely to succeed.

Fine-tune your craft for whatever the service is you offer for sale. Then look to become a sort of jack-of-all-trades in all the other areas to keep your business afloat and make sure all the important things are covered.

Understand success or failure is on you

Not that we recommend passing the buck, but in an office setting, there are plenty of other people around to take the blame when things go wrong.

As a freelancer, however, it’s all on you. You can look left, look right, spin your head around 360 degrees, but no matter where you look, the blame will fall on you.

Before you make the leap to freelance work, be sure you’re mentally prepared to shoulder the weight of the responsibility placed on your shoulders.

Your new freelance job doesn’t come with insurance or other benefits. That’s on you. You need to seek out and set up an insurance plan. And it’s fully on you to start saving for retirement.

When you send out invoices, it’s on you to track people down when they don’t pay. If you utilize contractors to help out with any work, you need to make sure you set aside funds to pay them when the job is done.

You’re the boss. You’re the owner. You’re the employee. Whether you win or lose in the end, that’s all on you. If you’re prepared to deal with the responsibility part of freelancing, you’ve got one foot forward on the road to success.

Wrapping it up

Freelancing is an excellent way to make a living. If you dread waking up each day and facing your boss, the freelance life may be right for you.

Making the transition from your 9-5 to freelance, however, should not be taken lightly. It’s not easy by any means.

You need to understand how freelancing changes things. No more waltzing into the office five minutes before start time and then checking boxes on your to-do list all day.

Freelancing success requires you to be fully present and all in. If you aren’t prepared to give it your all, freelancing may not be for you.

If you’ve gotten this far in the article and you’re still chomping at the bit to get into the freelance life, you’re ready. Put your plan in place and get started.

We’d love to hear about your freelance journey. Drop your notes in the comments below.

4 Responses

  1. Every tip is spot on Anthony. Employees need to think differently – sometimes radically differently – to be entrepreneurs who freelance. We do wear many hats, need help and also need to own that success or failure is our complete responsibility. No more boss or company to blame.


    1. So true, Ryan. It’s very freeing to found your own blog, freelance business, etc., but it also comes with many challenges that freelancing fail to consider when they set out on the journey.

  2. You are right! Starting to freelance is a big deal and there are many things you need to take into consideration when transitioning from a 9-5 job. All of your points are really good.

    Another point to consider is that it usually takes time to build a freelance income. For this reason it’s a good idea, if you can, to start freelancing as a side gig while you’re still working at your day job. You can then integrate your freelance work into your finances and your life while you’ve still got the security of your 9-5 job. Of course, this doesn’t apply if you’re new to the workforce and freelancing will be your first real job or if you’ve lost your 9-5 job already. But if you’ve already got a job, then keep it, earn some extra money with a freelance side hustle, then turn that side hustle into your full-time gig.

    1. Hey Sabina. Thanks for dropping by the site! You’re so right. Unless you have a serious stack of funds set aside and dedicated specifically to your freelance business, it’s important to jump in only when you’re ready. Walking that line of balancing the freelance life as a side hustle while you finish up your full-time gig is a great way to build up the safety net you need to have in place to run your freelance business as well as build up your portfolio to make it easier to attract new clients. Here’s an article I wrote for another blog a while back on this exact subject, if you are interested.

Skip to content
Share via
Copy link
Powered by Social Snap