8 things to consider before becoming a freelancer

Freelancing is hard

Freelancing is hard, and my husband and I are accidental freelancers. Seems a strange thing to say, but it’s true. We imagined he’d stay with his corporate job until retirement, and freelancing didn’t enter our life plan until he was ready to change jobs. Before then, remote work options were limited and website development agencies in our city didn’t fit us. However, once it was time to leave the corporation, freelancing became the obvious choice. We’d been contracting for nearly 15 years, how hard could it be?

What we learned: Freelancing is hard.


Freelancing isn’t just full time contracting. The move to freelancing turned contracting into a business. Contracting nights and weekends for extra money had its own set of constraints that clients understood. Once contracting became our “day job,” clients expected us to act more like a business. Income was no longer supplemental, but vital, and every project was potentially the last. Taxes went up. Responsibilities shifted and communication requirements changed.

We learned through trial and error that the freedom of freelancing comes with its own challenges. It’s a job, no longer a hobby. To succeed, there has to be dedicated, intentional effort.

Freelancing might give you more choices in what you’re doing and how you’re doing it, but it’s also a move from having one boss to having many. Every client becomes your boss. When something breaks, you fix it, and when deadlines are looming, you’re alone in the office finishing up.

Before you decide to move to freelancing, take a significant look at your core self, your situation in life, and your life goals. It might be time for a change, but consider these questions before you take on freelancing.

1. Do you need a consistent income?

There are times in life when a steady income is a must. Paying child support? Have the kids in private school? College? How about some extra debt you were hoping to pay off? If you have inflexible demands on your income, it may be necessary to stick with your current job a little longer. It’s possible to make more money freelancing, but it can come in at unpredictable times. The stress that can erupt from waiting on a check can ruin the freelance experience and put serious pressure on the relationships around you.

2. Do you have insurance needs?

Freelancing Health Insurance

If you haven’t discovered this yet, insurance is expensive. For 10 years our previous employer paid our insurance. We knew when we decided to head out on our own that this would be an expense we’d need to compensate for. What we didn’t expect was the high deductible we would need in order to have a manageable monthly payment. If you have health issues or a young growing family, it may be better to stay with your current job. The added stress of trying to pay medical expenses can overburden a new freelancing career.

3. Are you too soft-hearted to be firm with clients?

My friend hated contracting. She liked the work, but she couldn’t stand up to her clients. She struggled to set limits  and be firm about payment. She found herself continuing to make changes beyond the original scope and was unable to take back control of the project. Eventually, she quit contracting all together and found a job where she could develop without dealing directly with clients.

4. Do you struggle to be organized?

Being poorly organized will ruin freelancing fast. Everyone simply ends up angry and frustrated. Clients feel cheated because projects aren’t delivered when promised. Payments don’t come in because invoices never went out. Without organization, you end up working all the time to make up for the distractions that have crowded into your day. If you’re someone who doesn’t want to deal with the details of a project, then find a job that fits that, but don’t try to freelance.

5. Do you dislike dealing with clients?

This isn’t just being soft-hearted; this is all the way.

Truth is, clients are a hassle. They need hand holding and speak a language all their own. They have wants. They have needs. If all you want to do is create, then freelancing isn’t for you.

A business can’t survive without customers — and if you’re a business of one, no one else is there to manage them.

6. Do you actually want to run a business?

Running a business has its own challenges. There’s a lot to remember, a lot to organize, and a lot of responsibilities beyond creating the product. You can find help (accountants, billing software, etc.), but you will still have work on your end.

Nothing can ruin a future faster than running a business poorly.


Legal issues can occur. Poorly handled taxes can lead to audits and large bills. If you’re not willing to take it seriously, walk away and find a job working for someone else.

7. Do you struggle to save money or manage finances?

One of the biggest struggles in the move to freelancing is the income flow. Work comes and goes. There are times when clients are beating down your door and other times when everyone is off on vacation. You’ll have months where you might pull in substantial revenue as you’ve closed out a big project and other months where all your time went into business development and project management.

If you are someone who just can’t save for the lean times, freelancing is going to be a consistent strain. Sure, some months you’ll have money to burn, but the next month you’re shaking out the couch cushions. Seriously, this happens.

8. Is your community supportive?

Freelancing is stressful. There’s constant pressure to finish the current project while at the same time establishing the next. Some days you work all the hours you can keep your eyes open knowing tomorrow will be exactly the same. It’s a lot to take on with a solid support system. If stress is also coming from the people around you, it can feel like drowning. Balancing work, clients, and family is going to be hard enough. If your community isn’t willing to be flexible, willing to be understanding, and willing to work with you, you could lose both them and your business.

Freelancing is hard — make sure it’s right for you

In the end, no path is right for everyone. Yes, freelancing offers more choices, but it also comes with more responsibilities. There are any number of tasks and demands that get overlooked when working for someone else. Consider who you are, what your current needs and goals are, and decide if you want to take on the challenges of freelancing.

Remember, having a skill isn’t enough to create a successful business, but if you’re willing and able to take on these new responsibilities, you can have the opportunity to shape your own future.

Image by: markus spiske via Compfight cc