Six Questions To Determine If You Are Cut Out For Freelancing

Probably once a month, a colleague who is unhappy at work or recently laid off will contact me to ask what freelancing is like. Will it be lonely? Will they be able to make a living?

The answers to those questions depend on your personality, work experience and financial situation. Whether you are considering freelancing because you hate your job, you’re between jobs or you are looking to transition back to work from full-time parenting, here are some questions to consider. They’re based on years of working with freelancers as an assigning editor, conversations with freelancer friends and my own experience.

1. Are you willing to sell yourself and your work? If you can’t find a way to approach potential clients, you will not succeed as a freelancer. When you’re starting out in business, a steady flow of work isn’t going to land in your lap. It may take three to six months to build up a good volume of projects.

Look back at past situations where you have had to sell something and consider how you felt while doing it. Were you depressed, or was it a challenge that you could manage–and maybe even find ways to enjoy, because you knew it would lead to work you loved? Whatever your answer, that is likely how you will feel many of the days you are freelancing, especially in the beginning.

2. Are you disciplined–about work specifically? You may be very dedicated to your training for marathons or religious about keeping your volunteer commitments at your children’s school. However, if you’re not good at making yourself show up at your desk, ready to work, for at least a few hours every business day, your freelance business will not take off. Clients will not contact you regularly if it takes days to return phone calls or emails.

At the same time, it’s important to consider whether you are good at balancing your life. Chaining yourself to your laptop will not lead to success and can drain your energy. If you’ve spent three hours at your desk on a deadline project, getting out for lunch with a friend can be a good way to keep your energy flowing….as long as you’re back at your desk the next morning. Freelancers who take breaks when they need them seem to do better, long-term, than all-or-nothing types, according to my unscientific observations.

3. Do you need the money? This may seem like a funny question to ask, but from what I’ve seen, the pressure to earn enough to pay the bills or contribute to paying them is a powerful motivator to success in freelancing. I don’t know any creative professionals for whom the money is a primary reason for being in business. Most get their inspiration from their passion for their work, the subject matter it involves, the desire to give back or something along those lines. However, the survival instinct is what often pushes someone to get moving in any business and earn real money.

4. Can you live with gray areas in your career? In a staff position at a company, your role will be clear. You will have a certain title, a particular place to sit, a specific salary, etc. Not so in freelancing. Even if you’re part of a team, your role there will be temporary and somewhat fluid, compared to team mates who are on staff. You may be working alongside former colleagues who were junior to you — but now find that you have less clout than they do. You may not know where you stand financially, week to week, because the amount you earn from a project may depend on how much work the job ends up requiring.

Then again, freelancing means you will be almost free from the burdens of office politics. You’ll be able to move onto another gig if the people involved in a particular project are unpleasant, without a dramatic farewell meeting. And you will control the amount you earn, through the effort you put into winning business and delivering projects that make your clients happy.

There are other uncertain areas in freelance life, too. The big one is that you will not have corporate benefits, unless they are provided by your spouse’s employer or a part-time gig. Can you handle the legwork of buying your own health insurance, setting up your own retirement plan and figuring out how to handle issues like disability insurance? If you’re over 40, these benefits are likely to become increasingly important.

There’s no right or wrong way to feel about living outside of the structure of corporate America. But it’s important to consider how you will react before you embark on freelancing.

5. Are you flexible about the work you do? In some fields, like journalism, opportunities are drying up in areas such as newspaper reporting. If you are not willing to branch out into new, related pursuits in digital media and the like, you may not be able to earn enough to support yourself and your family. The same holds true in other creative fields, such as design.

6. Will you be able to plunge into unfamiliar areas successfully? Here’s one litmus test: Look back at your career, to see how you reacted when your company offered opportunities to pick up new skills. Were you one of the first to volunteer, or did you hesitate to get involved? Did you actually learn new “tricks” that you brought to your work going forward, or did you find that you returned to the way you were accustomed to doing things? Freelancing requires you to do a lot of on the job learning, so if you’ve found you naturally gravitate to “crash course” type situations and thrive in them, the freelance world is a good one for you.


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  1. Pingback: Confessions of a cookbook ghostwriter

  2. admin

    Hi Trey,

    We’re taking it slowly for now … but thanks for the offer and if you like send some examples of your work to