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The Freelance Life

It’s Labor Day here in the U.S., which means that some people (teachers, office workers, church secretaries) have the day off, while others (retail employees, police, firefighters, hospital personnel) are working at least as hard, if not harder, than on any other day.

In between these two extremes are those of us who don’t have a regular employer, a regular work schedule, a regular paycheck. Some of us may be working today; others may be tending to the chores that piled up during the last project; still others may be taking a day of leisure. Which category we fall into on this particular day is largely the luck of the draw, because

We are the Freelancers.

When I left my last regular job, I didn’t think I was embarking on a freelance life. With nothing more than a single client, a computer in a corner of the living room, and a box of business cards, I walked out of my old job and into what I perceived as a world where I would shed the anxiety and stress of a regular nine-to-five and embrace the freedom and peace of working on my own. Armed with a paperback copy of Money-Smart Secrets for the Self-Employed, I set out on my new path.

Two days later, when I’d finished all the projects my client had for me at that moment, reality hit: I needed money. My old job hadn’t paid particularly well, but at least I knew how much money was coming and when. Because I was still flush with the energy of novelty, I cast a clear eye over the situation. The two obvious components were income and outgo. I took them in turn.

I examined my monthly bills to see where I could trim. For better or worse, my expenses were already in good control. There was only one smidgen of fat, and so I excised it: I canceled my subscription to TV Guide, saving a princely $10.00. Even though I knew it was a tiny gesture and slightly ridiculous, taking a concrete step felt empowering.

woman triumphant

Emboldened, I moved on to income. The partners in my old firm had taken me out for a farewell lunch and asked about my plans. When I described what I planned to do, i.e., research and writing for other lawyers, they inquired whether I planned to place ads or send out mailings. After four years of litigation training, I knew better than to admit that I hadn’t actually thought about something. Instead, I asked which they felt they’d be more likely to respond to. A letter, they all agreed. So, possessing this nugget of market research and the 1996 Martindale-Hubbell for Connecticut listings, I began flipping pages in search of my new clientele.

I reasoned that large firms had stables of associates to handle their research and writing needs, but solo practitioners and small firms might need such help. For example, my current client had only one associate, and they both spent most of their time in hearings, depositions, and meetings. I reasoned further that trial lawyers were most likely to be in need of research and writing services, because if they were spending their days in court, they didn’t have time to be going to the library or crafting motions and objections. 

So I wrote my one and only marketing letter, pitching my services to litigators practicing as alone or in small firms in central Connecticut. Among the recipients were lawyers who’d been my opponents, but whose handling of the cases I found to be reasonable (as opposed to the ones who pressed ridiculous claims or made outrageous demands). Since I couldn’t yet afford a laser printer, I put my letter on a floppy disk and took it to the now-defunct Kinko’s, where I printed it on cream-colored paper (I also couldn’t afford official stationery). Then, I put everything in the mail, settled into my lawn chair with Money-Smart Secrets for the Self-Employed, and waited.

fishing - man - 2

The remarkable thing is that I didn’t have to wait long. Out of approximately thirty letters, I gained three clients, one of whom I work with to this day. The rest of my clientele has come through word of mouth. I’ve received many phone calls over the years that begin, “I was talking to Attorney _____, and she said that you do research for her sometimes, and I was wondering. . . .”

This is not to say there haven’t been bumps in the road. I’ve had clients who bristle at the notion that I can’t drop everything for their project because I have a deadline on something else. In one case, a client who hadn’t said when she needed a particular bit of research became upset when I didn’t deliver it promptly. Opposing counsel’s animosity toward the lawyer I work with has sometimes spilled over onto me. When I used to represent individuals directly in appeals, I ended up working almost as hard to collect my fee as I did on the appeal itself, which is why I am now exclusively a subcontractor.


And then, of course, there are the financial aspects. Single and self-employed, with no alimony or trust fund or lottery winnings to provide a cushion, there is never a day when I can forget that it’s all up to me. I pay my own health insurance premiums, malpractice insurance, legal research database, and technology. As best I can, I try to manage billing and projects so that there’s a fairly steady flow, although there are times when I can’t control the schedule. This summer has been a perfect example: I had two major briefs to do, one due at the beginning of August and the other three weeks later. Because I spent six weeks doing little besides those two briefs, the cashflow was barely more than a trickle until the first of those payments arrived.

Now, I find myself in the position of needing to revise my career path again. Many of my lawyer clients are also my contemporaries. Realistically, this means that in the next five to ten years, at least some of them will be winding down their practices. Younger lawyers who have come of age in the age of the internet are more likely to do things themselves than hire them out. Unless I want to be involuntarily retired, I need to adjust my focus.

lens aperture

It has always been my dream to write fiction. Obviously, unless you’re Stephen King or Nora Roberts, you probably aren’t making a living from writing books. But it is possible to earn a living as a writer. I know, because I’ve been doing it for more than twenty years. Whether I can transition legal writing into fiction writing . . . that’s another story.


If you’ve read all this and you’re thinking, “Sure, that’s great for you, but how can I make a living as a freelancer?”, the good news is that there are some things you can do that may increase your chances of success:

Figure out what you have to offer. Everybody knows something that other people don’t. Maybe you’re an ace knitter, or you build gorgeous tables. You might be the best golfer at your club, and people ask you for advice. Or you could be a retired airline pilot who loves to take people up in your little plane. If you’re interested in this stuff, odds are excellent that you’re not the only one—and those people are your market.

It’s important to know whether you’re offering a product or a service. If it’s a product, is it something people will buy frequently (toilet paper) or once every few years (a computer)? If it’s a service, will you charge by the hour, or will you assess a flat fee ($100 for ten lessons)? Maybe you’ll combine the two—sell a custom-made  computer and offer training or support services for a separate fee. It’s your business, and you can set it up however you choose.

Decide how to share your expertise. If I were starting today, I’d set up a website dedicated exclusively to my legal research and writing services. I might start a law-focused blog. I could cultivate an email list and develop a newsletter to send to these people. Because I started in 1997, I’ve done things a bit differently: in addition to my one and only marketing letter, I’ve attended bar association meetings and law school alumni events and continuing legal education events, always with a handful of business cards. This isn’t to say I would never consider a website or newsletter, but right now, these aren’t my priority items.

Evaluate the money. This is huge. About twenty percent of small business startups fail in the first year, and about fifty percent fail in the first five years. If you intend to live on your freelancing income, you need to figure out (1) what it’s going to cost to pursue this career, and (2) how much money you need in order to live comfortably.

As to #1: Will you need equipment? Inventory? Employees? Subscriptions to databases or services? Specific insurance coverage? Will the computer you have now suffice, or do you need to upgrade? (Emphasis on “need”: the fact that you might like to upgrade to a shiny new system isn’t the issue when you’re launching a freelance career.)

As to #2: Many freelance success stories seem to involve a supportive spouse with a steady job and good benefits. However, if you’re like me and you forgot to marry somebody who’ll serve as your patron until you’re established, you need to know how long you can survive until the money starts coming in, how much you can reasonably expect to earn, and how regularly it will arrive.

There are many books, blogs, and websites devoted to the financial aspects of freelancing. I urge you to look into them and consider their advice. From my personal experience, here are a couple of quick tips:

Don’t pay a lot for things you can get cheaply or free, such as websites and business cards. Shop the deals and sales. Ask for discounts; sometimes, even a simple “is this the best price you can give me?” may shave a few dollars off. On some websites, if you look at a product and don’t buy, they’ll follow up with an email offering you a discount, so don’t feel compelled to act if you can wait. As long as your materials look clean and professional, nobody cares if they’re fancy.

At the same time, don’t skimp on professional advice where you need it. Your cousin Leon may have done his own taxes and gotten a $5,000 refund last year, but that doesn’t mean he’s the one who should advise you on managing your business expenses. (Actually, if he got that much back, it means too much money was being withheld from his paycheck throughout the year, so unless you like the notion of giving the government an interest-free loan, you may want to think twice about following his advice.) A good accountant can tell you, among other things, which of your planned business expenses are tax-deductible.

Assess the best way of getting the word out. Field of Dreams notwithstanding, the fact that you hang out a shingle (literally or virtually) does not mean customers and clients will immediately flock to your door or website. If you’re a person who enjoys networking, great! Go to craft shows, fairs, chamber of commerce events, and wherever else you can meet people who might know people who might be interested in what you have to offer. Contact your local adult education department and offer to teach a class or workshop. (It probably goes without saying, but try to avoid bringing people to your home for these classes or workshops. Not only do you need separate insurance in case they fall on your front walk–homeowners insurance doesn’t cover business-related accidents–but you don’t necessarily want the world knowing your home address.) If you’re more introverted or don’t live someplace with lots of in-person options, you’ll probably rely much more heavily on your website, social media, and email lists.

Plan ahead as much as possible. In my case, “as much as possible” wasn’t much. Not only had my firm given me a “get out” date, but these were the pre-Google days, and I had no idea how to be anything other than an employee. 

Most professionals urge you to make a written business plan before starting your own business. That’s sound advice even if you plan to be a one-person business with no investors. You can find tons of articles online to show you how. Even if you never show your plan to anyone else, compiling this information and setting it down in clear, concrete terms solidifies what you’re doing, and how and why, at least at the start. You can always revise your plan later if you wish; after all, it’s your plan and your business.

Planning ahead also means doing your market research. Maybe you want to write about parenting. While your family will likely keep you well-supplied with material, a quick search of the term “parenting blogs” turns up more than 500,000 results. This doesn’t mean you shouldn’t try to sell your articles to periodicals about parenting, but you’ll probably have better luck if you can put a unique spin on the topic. For example, if you have a child with special needs, you likely have a wealth of knowledge many other people lack, such as how to work with the school system to get the services your child needs. Consider what you know, and figure out who will pay for that information.

Embrace the unconventional. Just because it sounds weird doesn’t mean it isn’t exactly what you want.

Case in point: my old firm informed me that I wasn’t going to become a partner. Unbeknownst to them, this was fine with me, because I didn’t want to be a partner there. The problem was that in those days, associates in law firms had two choices: become a partner, or leave. 

On the upside, this meant I no longer had to hide the fact that I was searching for a new job. On the downside, I didn’t know what kind of job I wanted. I knew I didn’t want to continue in trial work, but that wasn’t good enough. A chat with the career counselor at my law school was unproductive. Scouring the legal classifieds was fruitless. Finally, I bought a copy of What Can You Do With A Law Degree?, a combination book/workbook for people seeking career guidance. The author’s answer to the title question appeared to be “pretty much anything other than brain surgery,” which wasn’t terribly helpful. On the other hand, doing the exercises revealed a few things, such as what kind of work I liked to do (reading, researching, writing) and what kind of work environment I preferred (away from other people). I recall looking at the list and thinking, “There’s no job that will let me do this.”

And yet, here I am: I earn my living by reading, researching, and writing, and I do it in the privacy of my home.

Livy on desk 2008


As I post this, the long holiday weekend is drawing to a close. This evening, I’ll straighten my office, file completed projects away, input data on my Excel spreadsheets to show recent bills submitted and monies received, and update project lists and calendars so I’m ready for tomorrow. Then, I’ll sit down with a cup of tea and The Business of Being a Writer, and I’ll study Jane Friedman’s advice on how to draft a query for my novel.

Because when you’re a Freelancer, there’s always something new on the horizon.

woman in meadow

2 thoughts on “The Freelance Life

  1. A lot of thanks for sharing article : SEO is the practice of translating content that’s written and formatted for human eyes to something search engines can clearly understand. Doing this helps search engines know exactly how to surface your site in search results

    Liked by 1 person

    • You’re absolutely right. Luckily, there are plenty of articles and services available to help freelancers make their sites easier to find. As with anything else, do your research before hiring somebody to manage this for you (she said, speaking from sad experience ☹️).


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