The Pros and Cons of Freelancing

If you’re an independent freelancer or thinking about leaving a full-time position to strike out on your own, there are some things you need to know first before taking that leap.

The first thing to understand is being a full-time freelancer means you are self-employed, and therefore enjoy the many benefits that come along with this new freedom. But if you’ve always been an employee and are thinking ‘the grass is greener’ as an independent, you need to be prepared for a dramatic change in your work and personal life.

Whether your specialty is graphic design, writing, photography, web development or even social media management, there are many universal operational challenges you may experience when serving your clients. Some of these experiences may be similar to your role as an employee, but as an independent contractor, can take on more serious implications for your business.

Despite these challenges, there are many benefits to being self-employed that can be rewarding in ways a job could never fulfill.

Let’s look at the PROS

Work when you want and set your own hours
This is usually the first thing people think of when it comes to being self-employed — ‘I can work when I want to.’ While this is true in many cases and it definitely has its appeal, remember that your business hours may be determined by the communication required in your client relationships.

In some cases, if you’re more of a night owl and prefer doing work during late hours, it might be great to do your work overnight and provide client reviews that are ready for them in the morning. However, if you experience a lot of back and forth communication with clients, the reality is you may find yourself needing to work normal business hours in order to be accessible to your clients during the day. Still, being able to choose when you work is a huge benefit.

You decide who you want to work with
In addition to setting your business hours, you also have the flexibility of choosing who you want to work with — and who you don’t.

For new freelancers this may be a bit more challenging because you want to focus on growing your business and getting as much exposure as possible. Therefore, you may be hesitant to turn work down and being too selective with your clients. However, as your freelance business grows, you will find that certain clients aren’t worth the amount of effort you’re putting into the relationship, and it may come time to let them go.

Remember, being a freelancer is about setting your own terms, and that also applies to relationship expectations.

Very few barriers to getting started
If you’re a creative who does the majority of work on a computer or laptop, you likely already have all the tools necessary to start your freelance business. Setting up a consulting business and working from home is significantly easier — and cheaper — than starting a brick-and-mortar business. It’s also something you can ease into while still working at your full-time gig and building a client-base before jumping in with both feet.

You’re in charge of work/life balance
Many people who work in corporate jobs regularly experience burn out or frustration when it comes to taking PTO, or trying to balance professional responsibilities with family/life obligations.

Some freelancers take full advantage of their ability to travel whenever — and wherever they want while still maintaining client relations and deadlines. Most freelancers only need their laptop and high-speed wifi to take their business on the road, and this freedom creates so many benefits for mental health it’s often the primary reason people set out on their own.

You charge what you want to charge
Determining your billing or hourly rate is entirely up to you, and you can change it at any time or any situation as you see fit. You are the one who determines your self worth and the value you place on your time.

You also have the option of being as flexible as you want to be. If you want to donate your services as an in-kind contribution to a non-profit, or even give certain clients a reduced rate because you value their repeat business, how you price your services is totally up to you.

You have more financial opportunities
As a business owner (and yes, freelancers are business owners), you are viewed differently in the eyes of the IRS as well as certain financial institutions and banks. Your tax situation will change dramatically from being a regular employee who receives an annual W2.

Business filings can be structured many ways and have varying benefits to different types of businesses. It’s important to build a relationship with a CPA who can advise you on the best ways to optimize your financials and your individual tax situation.

Now let’s consider the CONS

There aren’t enough hours in the day
While it’s attractive to be able to work whenever and wherever you want, the reality can sometimes feel like you’re working all the time. A downside of being an independent contractor is that you will wear ALL of the hats.

Having the flexibility of working independently also comes with the feeling that you have to ‘always be online.’ Checking your texts or emails at all hours of the day to ensure you don’t miss anything is a habit that’s easy to fall into, and hard to break.

Being responsible for everything can make it seem like you’re always behind, so it’s important to build in as many efficiencies into your workflow and make sure you aren’t overcommitting yourself with every client.

Dealing with peaks and valleys
The inconsistency of work can sometimes cause a great deal of stress with freelancers. You could easily find yourself completely buried with work one month, then sitting around without much to do the next month.

Accepting this unpredictable ebb-and-flow of work can be a struggle for someone who’s been used to a daily, steady stream of projects. It can even cause some to have doubts and go into ‘panic mode’ thinking they aren’t going to get anymore work and things are over for them.

The reality of freelance is that this is a natural course for most independents, so learning to take advantage of (and welcoming) the downtime can give you time to market your business, make new connections, or get to things you’ve been putting off because you’ve been too busy.

The critical need to multitask
It’s one thing to work at an agency or with a team where you’re juggling multiple projects and deadlines, but it’s an entirely new level when you have to juggle every aspect of every project — and still find time to run all the other needs of your business.

In my own business, I take advantage of as many tools as I can that help streamline my workflows and project management. Further, I make sure to introduce all new clients to these systems and get them on board quickly so I’m efficient from the start.

Unexpected costs and cash flow
Things that you’ve relied on in the past when working for someone else can be the unseen costs of healthcare or contributing to a retirement account. These expenses are now up to you and can have considerable impact on your profitability.

Another huge impact on available cash is planning for estimated quarterly tax payments. Most LLCs (whether single-member or sole proprietor) will have to make estimated tax payments, and depending on your income, the checks you will have to write each quarter can be substantial.

Tax time is one of the most dreaded times of year for every business owner which is another reason you need to have a great CPA who can help with planning a cash management.

It can take time to succeed
Even though this can be perceived as a ‘con,’ this is the reality for any business — becoming successful doesn’t happen overnight. Many people jump into freelancing and think they’re gonna be up and running profitably in no time. This is hardly ever the truth. In fact, most small businesses fail in the first few years.

It’s easy to get blinded by all of the PROS when we think about being self-employed, but going in to it without acknowledging the potential struggles is a recipe for failure. Anything worth succeeding at is going to take time — often far more than you expect.

Have a plan

As with any venture there are going to be PROs and CONs, what’s most important is doing as much research up front as possible and creating a plan with realistic expectations. Network with peers, business leaders, find a mentor, or talk with others who have already created successful freelance businesses. The easiest way to avoid potential hurdles is by learning from those who have already made mistakes, yet found a way to get through them.

Being a freelancer isn’t right for everyone, especially for those who can’t handle the volatilities and inconsistencies that can come with it. But if you’re motivated and determined, you’ll find many more PROs along the way that prove you made the right decisions.



Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store
Curtis Jackson

Curtis Jackson

Curtis is a marketing professional and author of, a blog dedicated to helping entrepreneurs and small businesses succeed.