Occasionally someone will say something to me like, “I don’t know how you do it [freelancing]. I wouldn’t know where to begin.” Lucky you: today I’ll take some time to explain just that. The good news is that it’s easier than it sounds: you need the right tools, the right customers, and the right attitude…not necessarily in that order.

The Right Attitude

I’ll start with this one because usually when I hear someone say “I don’t know how you do it,” there’s a little hint of fear in the voice. There’s a lot left unspoken in that statement, such as: I don’t know how you are willing to leave the relative security of corporate life. I don’t know how you’re able to function without the typical benefits of an established company. Or simply: I don’t know how you’re able to work alone. Some folks just need the comfort of other people around them. Fair enough. That doesn’t mean if you have those feelings you can’t be a freelancer.

First, corporate life is not 100% secure, either. I’ve worked for projects and organizations that have been downsized due to the economy, a change in corporate strategy, or a restriction of funding due to government shutdowns or budgetary sequestration. Some companies offer you a bit of severance and wish you the best of luck.

Second, if you set your rates properly, you can pay for things like health insurance the same way companies: out of your markup. The number I’ve seen on the internet is [X rate suitable for your work and market] X 1.35 [35%] to cover things like taxes and insurance that you have to pay for out of pocket.

Lastly, if you find you need people around to feel happy and productive in your work, coworking might be a good option for you.

In any case, there are options for functioning outside the so-called safety of someone else’s company.

The Right Customers

“Where do you find your customers?” is another common question I get. I was a corporate guy for 20+ years before I went out on my own. What I did is start reaching out to the friends I’d worked with before in the corporate world and asked if they knew anyone with technical writing needs. I don’t ask them personally for a job–that gives them the option of saying no without me or them losing face. Asking about “anyone needing help” gives them the option of referring me to someone else. Sometimes, former coworkers reach out to me.

One thing you’ll want to do when reaching out to previous contacts is to identify exactly what type(s) of support you’re willing and able to offer. My expertise and experience lies in engineering proposals and technical white papers, plus editing engineering documents. I also know what my specialties are not: science writing, attention-getting sales copy, or medical writing. In those situations, I would refer a potential employer to someone else, which is also good public relations.

Also, when it comes to customers, you have to find work that will meet your budgetary needs. You know how much you are willing to pay for rent, groceries, insurance, etc., so your work/income need to meet those needs. You might get lucky and find a long-term contract that covers all those with one customer. You might need to reach out to multiple customers. If you’re consuming too much time for too little return, you might need to rethink your market.

You also need to know what type of customer works for you. As it turns out, thanks to my corporate experience, I work better with larger corporate clients that are used to hiring technical writers, understand their capabilities, and know how to work with them. Some of my friends prefer to work with small businesses or fellow entrepreneurs because they are more likely to work with or have access to the decision maker; they can get a clearer idea of what the customer wants; and because the work is more about individuals than organizations. Mind you, you still have to maintain good relationships with the individuals you work with in large organizations, but there’s also a certain amount of bureaucracy involved, too. Regardless, if you’re going out on your own, you should make an effort to find work you like to do and people you enjoy doing it with.

The Right Tools

I’m sharing this section last because it’s the most likely to become dated in five years (or less). In 2019, my suggested minimum tool kit for the entrepreneur would be:

• Laptop with Microsoft Office and wifi (which should be standard by now).
• Email address. I have an email address for Heroic Technical Writing, though I admit to being enough of a dinosaur that I route all my email to one legacy account because I’ve been keeping stuff in it for 20+ years. Regardless, you should have one easy-to-remember, professional-sounding email address for handling business. SuperSexyWriter69@blahblahblah.com does not convey a professional image.
• Printer/scanner: I still find a need for hard copies…especially when I have to sign and send back tax forms, contracts, or non-disclosure agreements.
• Business website so people can find you.
• Mobile smart phone: a “dumb” cell phone is useful for emergencies, but smart phones (iPhone, Android, or other) allow you to access the internet conveniently; check or add appointments to your calendar; make/take payments; and still actually talk to people.
• Social media account: I’m not sold on this, but some of my self-employed friends do a surprising amount of business via Facebook, Instagram, or Pinterest. I have yet to learn of someone who made a business deal via Twitter, but that doesn’t mean it doesn’t happen. Also, be mindful of what you share on social media.
• Dedicated home office: If you’re working on site with your customer this isn’t as important; however, if you work from home, it’s much wiser and healthier to have a dedicated space (away from your bed, eating area, etc.) were you can focus only on work activities.
• Accounting software or some method of keeping track of your hours, billing, and finances. See this post for more details.

Again, this list might look quaint or outdated in a few short years, but this is my minimum toolset. Ready to take the plunge?