I’ve been a freelance technical writer since the start of 2014. I’ve learned quite a few things about the profession and myself in the last 4.5 years. Today I thought I’d share a few more of those insights (you can find other comments here and here). They might or might not help you with your decision to pursue a similar career choice.

Lesson 1: Hustling is Hard

The early part of freelancing is challenging because you might or might not have a solid idea of whom your customer base will be. When I metaphorically “hung out a shingle” as a freelance writer, I was trying to be anything to anyone. That was a mistake, as I figured out I’m more useful trying to specialize in particular types of clients. Working with fellow entrepreneurs–as I learned from trying to acquire multiple clients–was not an easy way to pay the bills. Small businesses and sole proprietors seldom have the money or the recurring business need to keep a single technical writer fed, which means acquiring a lot of clients and doing a lot of hustling and research and marketing to bring in the business. It’s not impossible, just very difficult. It turns out that I’m lazy.

Lesson 2: Work with Your Network

My time in the corporate world (20+ years) gave me exposure to multiple types of work and multiple types of potential customers. I moved to Florida with one part-time gig lined up and two potentials in the work. The part-time job I found through a friend of a friend; the other “potentials” were working directly with friends who worked for small or medium-size businesses. My current bill-paying customers are corporations and, again, the work came to me through people I’d worked with before on previous jobs when I was a full-time employee. Those folks reached out to me because I’d favorably impressed them on those jobs.

Lesson 3: You Will Never Take Benefits and Taxes for Granted Again

Most freelancers pay their taxes quarterly by writing checks, as opposed to full-time employees who have their taxes taken out automatically via payroll deduction. This is how you learn how much you’re actually paying to the government, and it has serious implications for how you save and spend your money. For one thing, instead of an employer paying half of your Social Security contribution, as a self-employed person, you pay the full amount.

Healthcare benefits are another thing you learn to appreciate–especially if you’re paying out of pocket. I got spoiled by the employer-supported health insurance plans and quickly learned to shop around if I found my rates going up (there are few discounts for individuals). I haven’t had vision insurance since 2012, dental since 2013. If I have to get glasses or a tooth cleaning, I’m paying out of pocket or waiting for a sale. Not ideal, but I’ve also learned to let my eyeglass prescriptions last longer and to take better care of my teeth.

Lesson 4: You Have Both More and Less Control Over Your Workflow

Full-time staff writers usually have a minimum of work they can count on regularly, if only because an employer expects you to be productive and feel they’re getting their money’s worth. If you’re a full-time worker, that also means you’re usually in a physical office 40+ hours a week. In addition to the actual tasks they give you (you don’t get to choose your work very often), you often have to attend weekly or daily staff meetings, client meetings, safety briefings, “team building” activities, and other corporate events that just don’t touch the freelance writer much. And the industrious technical writer will find things outside of his/her normal duties to become more useful/indispensable to the company.

Freelancers get–within a few guidelines–to set their working hours. They also can choose which clients they wish to support. And it’s been my experience that I don’t actually have to be at my desk for eight solid hours a day to get my work done. Mind you, I’m potentially on call during my business hours (currently any day of the week, 0900-2100, though that could change), but if I don’t have an actual task in front of me, that means someone else isn’t assigning me “busy work” to do to keep me occupied.

The most discouraging side of being a contractor/freelancer is the increased lack of job security. Contractors are easy and less expensive for companies to hire if they don’t need technical writing services all the time; however, that means they can also be easily dispensed with if the company decides it has to cut expenses. And if your contract is cut, there are usually no upsides, such as accrued vacation pay, pension, or severance pay–you’re just done.

Lesson 5: If You Learn to Love It, Freelancing Can Ruin You for Full-Time Employment

I’ve been very fortunate in my freelance career, as I’ve managed to acquire large companies as customers, which gives me the steadier paychecks without the required business hours, dress code, or meetings. My usual wardrobe usually includes a Hawaiian shirt of some sort. I haven’t worn a necktie for work in over six years. I’ve gotten rather accustomed to the freedom that freelancing gives me (grocery shopping at 1000 on a Tuesday morning or making a doctor’s appointment whenever it suits me are two things I still rather enjoy). I’ve taken to calling myself a “feral” employee, meaning like a feral animal, I’m a domesticated creature who’s gone wild. “Wild,” of course, is a relative term as I edge closer to the 50-year mark. I’m not throwing loud parties at the apartment, but I’m also less tempted by full-time jobs because of the shackles it puts on my free time.

Bottom Line: F * S = k

One of science fiction writer Larry Niven’s “laws” is that the product of freedom (F) and security (S) is a constant (k), meaning that in order to increase the amount of freedom you have, you give up some security as a consequence, and vice versa. The choice of pursuing a freelance career comes with many benefits in the form of freedom, but your personal financial security can drop tremendously, particularly if you find your contract canceled.  I’ve enjoyed the stability and perks of corporate life, but I’ve also learned to appreciate the freedom that freelancing provides. In the end, you have to choose which factor in the equation is more important to you.