10 Strategic Questions to Ask Before You Become a Freelancer

Becoming independent is going to be the best thing you’ve ever done for your career–if you do it right. Not everyone is meant for, or even comfortable with, working on their own. It’s important to figure this out before becoming enamored with all the freedom freelancing brings.

You don’t want to leave a good job and then realize too late that freelancing isn’t right for you. So, make sure you ask yourself these questions first in order to determine the answer to the most important question–should you freelance?


1. Are You Comfortable Working Alone?

Freelancing can be a lonely job, and for some people that can actually impede their workflow. You’ll quickly learn that you miss the camaraderie between co-workers. You’ll no longer have free lunches, picnics, or any of the social events that come with a job.

However, if you’re like me, you actually prefer to work alone anyway. I’m actually sitting in my husband’s office as I’m writing this post and finding it very difficult to concentrate because there’s always several people coming in and out of the office to ask him questions. This is a great reminder of why I prefer to work alone.

However, it’s smart to have a couple of backup places to work from outside of your home office. Regardless of whether you like to be alone or not, it’s healthy to get out and have some human interaction. Personally, I always schedule my blog writing days on Wednesdays, when I take my laptop to a bookstore, Starbucks or to my husband’s office.

2. Are You Naturally Motivated or a Procrastinator?

Freelancing is going to be very, very tough for you if you’re a procrastinator. One of the biggest complaints that my clients tell me about their previous freelancer is that they never met their deadlines and schedules. This is one of the most important aspects of running a business. If you can’t deliver work on time you become untrustworthy and unreliable and you’ll likely end up without any clients.

However, if you’re a naturally motivated person, you’ll find that freelancing is a much better fit for you than working at a job. You can go out and find your own work and schedule yourself to work at your own pace. Just remember, reaching deadlines is as important as the quality of work you bring.

3. How Much Money Do You Need?

Before you decide to jump into freelancing, you need to figure out how much money you need in order to make the minimum payment on all of your bills. From this, you’ll have to decide how much to charge hourly and how many hours you’ll need to work a week.

You’ll also want to look at how much money you want to make. One of the biggest perks of going freelance is that you can control how much money you can make. Just because you only made a certain amount at your previous job doesn’t mean you  have to be stuck with that amount as your income. In fact, you should aim higher–maybe even double the amount you made as an employee!

4. What Are Your Skills?

What are you going to do when you freelance? Are you going to still do the kind of stuff you do now at your job? Or do you want to try a different field? Figure out what kind of skills you have and what would really make you happy. Then hop online and do some research. Is there a market for your skills? If not, could there be a market for something you are good at doing?

5. What Kind Of Work Do You Want to Do?

This question will dictate how you run your business. While it’s possible to change your field mid-course, it’s always easier to figure it out in the beginning and go after it. What kind of projects do you want to work on? What kind of clients do you want to work with?

This is where you decide if you want to be a generalist or a specialist. Will you niche yourself into working in certain industries only? Or will you take any project that comes your way?

Another thought that normally doesn’t come up until you’ve been freelancing for a long time, but is certainly viable for a newcomer, is whether you’ll want any clients at all. If you’ve got the skills you can create as many businesses and products as you’d like and you may never even need to have clients.

6.  Are You Planning to Work Locally?

If you’re planning to have local clients, you’ll need to market differently than what you’d do if you’re planning to work with clients nationally. For local clients, you’ll need to actually get out of the office a lot more to attend local functions and meet with the clients.

If you plan to work nationally, you’ll rely on the internet for your marketing. Concentrate on getting your name in front of as many potential clients as possible.

7. Do You Have a Good Website?

Whether you plan to work locally or nationally, it’s 2011 my friend and you need a website. Nowadays, if a business (no matter what is it) doesn’t have a website, it’s almost like they’re not legit.

Not only is having an actual website important, but it needs to look good. It doesn’t matter if you’re a copywriter, developer, or some kind of freelancer that doesn’t deal with design. People will judge you and your work based on how good your presentation (the design) looks. Just like you wouldn’t go into a job interview or meet a client in shabby clothes, don’t let the first thing your potential clients see be a shoddy site.

8. Do You Have Enough Space to Work?

Where are you going to work as a freelancer? While it’s certainly possible to work off your dining room table or in a closet, I really recommended going with a real office. You need a calm, clean and nicely decorated space where you can close off the rest of the household and think. You need to be able to conduct phone calls, sit in concentrated silence or be able to blast loud music while you’re working.

9. Where Do You Want to Be in Five Years?

Is your long-term plan to remain a freelancer until retirement? Or do you want to run your own agency or hire some employees or make your own products? It’s okay to start at one place now and slowly work your way to another. Just be sure you always work with your end goal in sight. Just like you don’t want to wake up at 60 to realize you’d worked at a place you hated for 40+ years, you don’t want be trapped in a freelancing role you hate.

10. Should You Freelance?

Now for the final question–can you make it as a freelancer? Are you ready? Have you thought this through? While trying to get clients and having savings for the down periods is important, strategy is the most vital planning activity you should invest your time in. Your initial thought processes about freelancing will almost certainly determine whether you’re a success or failure as a freelancer.

Your Thoughts

What are some important questions you think people should ask themselves before they become a freelancer?

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