I’m A Freelance Writer. Here’s How I Spent Today
Hello, Medium!
Long time lurker first time poster, as they say.
I maintain a sparsely updated blog on my personal homepage, but for the sake of mixing up the content a bit, I decided to add this one here (although, in general, I still prefer placing content on platforms that I can manage).
In other words, no dear friends, I have not finally heeded your advice and hitched a ride with the Medium bandwagon.
But this is a start and I might come back to cross-post some content in the future.
So, let me begin.
It’s Dinner-Time And I Haven’t Dressed Yet. (Not Quite)
Ah, the joys of freelance life!
Long days spent lounging around the internet (and the house) wearing a onesie while sipping a martini and trotting out some SEO content for a client on the other side of the world. All before nonchalantly firing out an invoice in time for dinner and enjoying an idyllic work-life balance from within … well, your own home.
If only it were that easy (spoiler alert: it’s not).
There are many misconceptions about freelance writing, but that’s probably close to the image that many have when they think of what a day in the life of a freelancer would look like.
Sometimes, it even seems as if even our in-house brethren — the Content Managers and Editors with whom we often work — don’t take their freelancers seriously!
Alternatively — oh, the cruel irony! — some think that freelancing is a euphemism for being long term unemployed, a description that can be simply slapped on a resume or LinkedIn profile to cover over an extended junket backpacking around Asia.
While I’m sure there are some freelancers who actually spend their time touring the world in such a manager, and others again that have gotten so good at what they do that they can live a life of relative leisure (no judgement — I’d love to be you!) for the vast majority of freelancers — including the author — neither description comes close to being accurate.
For the vast majority, freelancing is a tough but rewarding slog (although, somehow, for those of us that stick with it, it still eneds up feeling rewarding!)
So although I see — with some disappointment — that I’m neither the first not the almost-first writer to try give an insight into my daily workflow to dispel those myths (if you’re interested in reading more “Day in the Life of a Freelance Writer” style posts check out 1, 2, 3, and others), I will do my little bit to give the world at large, my friends, and my sometimes disbelieving family (!), a little bit of insight into what I do on a daily basis.
Firstly: All Freelance Writers Are Not Created Equal
Sometimes, when I’m not really in the mood to get into a robotic “so, what do you do for living” conversation at a dinner party, and am simply trying to evade the topic entirely, I tell people that “I’m a freelancer” (even though I generally try to avoid using the term — see my footnote at the end of this piece).
Of course, it’s the equivalent of an insurance salesperson telling you that they “work in an office” or “do a job” for a living.
It goes without saying that virtually any occupation can be conducted on an ad-hoc, contractual, at-will basis (which is the essence of freelancing).
Looking beyond the typical freelance ‘monoliths’, or at least those that have emerged as such in today’s market (freelance writers, Wordpress developers, graphic designers, and Virtual Assistants to name but a few), there are also more traditional occupations — such as lawyers — who often run their businesses as de facto self-employed freelancers. It’s just that we, and they, don’t typically box them in the same category.
My point is that freelancing — as a group of at-will workers who are neither employees nor classic entrepreneurs starting unique enterprises — is nothing new under the sun, even if there has been a surge of freelancers doing jobs that didn’t even exist just a generation ago.
Additionally, because there are so many freelance writers in the world — and all freelancers, in effect, compete and against one another in the global market — there are also categories and sub-divisions.
As I’m assuming that you’re not a freelance writer, let me trot out some of the main ones.
To outline some of the main subdivisions within freelance writing:
- You have copywriters who specialize in writing short-form copy projects such as landing pages, email campaigns, and ad collateral (that discipline is the modern incarnation of the ad agency writers of old);
- SEO writers who are skilled in keyword research and digital marketing and who specialize in authoring content explicitly to be found in search engines and to convert readers to buyers;
- Generic “content writers” who might do a bit of both;
- And those (like me!) who come from a journalistic background and write words for slightly different use-cases (mine tend to be used as assets by actual — and aspiring — ‘thought leaders’, and include articles, speeches, e-books, and books).
My work — in its totality these days— consists of ghostwriting.
Feel free to check out my website or simply understand that I write a variety of longer form content pieces (up to book length) for mostly technology clients that are then published under their name rather than mine.
Yes, dear friend or perplexed family member, that means that my name is not and will not be on that article I sent you in an attempt to explain what I do for a living. But also that I haven’t been Netflix-and-chilling for the best part of the last two years too.
And no (it’s worth noting!) that does not mean that I’m getting ‘screwed over’ or abused by some evil corporation — it’s simply part and parcel of the system that I am part of. The next time you pick up a trade magazine or hear a compelling speech from a politician that resonates with your belief, know that there was somebody behinds the scenes, like me, whose job it was to pen those words.
So — How did I get here?
Before I dive in and give you an insight into the not-so-scintillating details of my daily work routine, it might be interesting to know a little bit about how I — like many — ended up doing these kind of gigs rather than sitting in a cubicle farm.
For many (most?) — and particularly those in the writing world — the path to becoming (and ceasing to become!) a freelancer can be a circuitous one that often has nothing to do with one’s employment status, one’s status in life, or one’s immediate career prospects.
My evolution, which is always in train, has gone something like this:
–I set up a news website while studying Law in university in Ireland (I’m still not sure why I chose that as my undergraduate!) and caught the journalism bug while I was at it. The stakes were obviously incredible small, but I learned — and taught myself — the fundamentals of learning beats, interviewing sources, and putting together news and opinion copy;
— During my first summer in college, I interned at an Irish-American news website and then wrote for them, and the website’s sister print publication, The Irish Voice, for a number of years;
— I ran my news operation full time for a year and then sold it;
— I moved to London where I studied for, and finished a Master’s degree in, Political Journalism (at City University London);
— I came back to Ireland and worked as the Marketing Communications (MarCom) manager at a then-nascent political technology startup;
— I moved to Israel, something I had already been planning for the best part of ten years;
— I spent my first summer in Jerusalem working as a Copy Editor at one of Israel’s national English-language broadsheets, received a full-time job offer from its competitor, and then realized that there was no way I could survive in Israel either being paid $10 an hour or earning the alternative salary;
— I began job hunting and quickly realized that there were almost as many companies looking for freelancers as they were looking for employees.I opened a file (‘tik’ in Hebrew) with the Tax Authority and began hammering out my first freelance content marketing articles to keep myself financially afloat while I looked for a full-time opportunity;
— I found a job at a PR company and kept my freelance file open but inactive;
— I was headhunted from said PR company by a startup I had interviewed at prior to accepting their offer. I left very soon thereafter. It was a messy/ugly startup experience that is better left untold — but acknowledged;
— This time by necessity, I returned to freelancing;
— Just when that was gathering steam, I took another job because I thought it was the sensible thing to do, even though I wasn’t entirely sure which of the two ways was forward. I worked as the Marketing Communications (MarCom) manager at another startup;
— I left said startup voluntarily to pursue my current client work;
Wow — I’m feeling tired just writing that out!
Perhaps I’m simply a job-hopping millennial, but I feel like my trajectory is far from aberrant among who are trying to find their place in the professional world.
My career, as unconventional as it might seen to some, has thus been a meandering succession of major pivots (journalism -> MarCom), minor shifts (in-house MarCom -> external writer) and even smaller adjustments (generalist tech writer -> niche tech writer) that is slowly unfolding to this day to help me find my ‘path’ in life.
I used to fear (irrationally, I believe) that being a freelancer for any extended period of time would mean being confined to that employment status indefinitely — that companies would take one glance at my resume and heap it in the trash can along with all the other failed applicants.
Thankfully, experience since going out on my own has assured me that that isn’t the case.
As I’ll get into later, there are pros and cons for both forms of employment (for one, freelancing is a massive and often mentally draining workload; and secondly, after a while, I have begun to miss having colleagues!). But I don’t think that either course needs to be a path for life unless you want it to be.
My belief and mindset in that respect has swung 180 recently and I now firmly believe that as freelancing continues to rise in popularity and acceptability — and as remote working becomes more commonplace in conventional employment arrangements — that there will be a softer and more understanding border delineating between the worlds of freelancing and employment.
I hope — and expect — that moving periodically between the two as one’s life circumstances and priorities shift will not arouse as much attention as it might now.
Freelancers who go in-house are not failures — they’re usually simply talented professionals with worthwhile experience to contribute who might want a change in tempo.
And, exceptions aside, freelancers are not a band of misfits exiting the corporate world simply because they can’t stand the thought of working for a boss for a day (I think that this image is particularly damaging, especially when freelancers themselves proffer this as their main motivation to go out on their own).
But coming back to my day.
It Started With Light
I mentioned earlier that I ghostwrite for (mostly) clients in the technology world, although the smaller half of my business consists of public affairs writing (I do hold a Master’s in Political Journalism after all!).
It’s a pretty common arrangement given the preponderance of technology companies in the world and the fact that they are often early-stage and latch onto content marketing as the centerpoint of their inbound marketing strategy. Earned media and publishing content on-site and on blogs is cost effective compared to traditional methods like paid advertising, and their online digital equivalents such as Google Ads.
For me, and many others, though, it’s also a happy coincidence given that I love both writing and technology.
I like to try out new gadgets both as…well, a means of trying out new things… but also to keep up to date with consumer technology as well as products and services I sometimes write about for clients (which is more on the B2B side of the divide; CRMs, enterprise technology, etc).
I’ve recently come to realize that many of my personal technology interests (Linux being the major one) have come in handy at some point or another as I have profited professionally from that knowledge — although the opportunity to do has often arrived surreptitiously and long after I had discounted that body of knowledge as probably professionally useless.
(I feel that my interest in vexillology will probably remain in that category indefinitely, but if you are a flag company needing a writer, please feel free to hit me up!).
It’s a good reason to keep interests going simply because they are interests — without the expectation of future recompense — and to keep searching for best-fit clients and industries that complement what you’re naturally inquisitive about (because those are always the easiest articles to write).
This week’s minor dalliance in consumer technology has been (of all things!) with artificial lights for Seasonal Affective Disorder (SAD).
My new SAD light sits next to my trusty white noise generator and I began the day, at about 07:30, by basking in its artificial glory — checking my email in its unexpectedly invigorating 10,000 Lux of white light.
I don’t want to draw observations too quickly, but I have definitely felt more energetic and focused in the few days since I began using it.
(Working at home can be a dark and dreary experience during winter, particularly as freelancers often have less reason to get out and about into the limited light that there is. I thought it would be a sensible purchase although I have no idea if I actually meet the diagnostic criteria for SAD!).
And Then There Was Coffee
After completing my morning routine, I usually go about making coffee from my delightful Arzum Okka Minio automatic Turkish coffee maker that I bought in Turkey two years ago.
I’m obsessed with — and exclusively drink — authentically brewed Turkish coffee ground to less than 100 micron powder-like fineness and liberally infused with an equally pulverized and generous quantity of green cardamom (sorry to any Israelis reading this, but most of you are making Turkish coffee incorrectly; and yes, it matters!)
I keep a massive quantity of coffee beans in my kitchen and it’s my little way of thinking in terms of long term objectives rather than focusing on the small picture of daily successes (and losses).
What’s the connection between coffee and success I’m trying to tease out here?
I have enough coffee in my kitchen to last me many, many months and coffee is the reliable fuel that keeps me going when, quite honestly, I feel like throwing in the hat on freelancing.
It’s always there for me — even when, sometimes, I’m not. And, to be frank, both these feelings occasionally crop up.
As I think any freelancer who is being honest will tell you — particularly during the brutally tough formative years which I am currently transversing , during which lessons tend to be learned the hard way— freelancing is extremely tough both in terms of the sheer amount of work and hours it takes to realize success and upon one’s mental health in general.
The scale, and seriousness, of that second challenge has taken me time to fully comes to term with and accept.
If all my retainers were cancelled tomorrow, for instance, I would go into next month with a guaranteed income of zero dollars. That’s a pretty stark degree of fundamental financial insecurity that has a nasty habit of preying on one’s subconscious and which is more than many people would be comfortable existing with.
Additionally: those retainers could be cancelled for a far greater range of reasons than an employee might have to countenance:
The client may have hired somebody in house; they may be going out of business; they may simply have turned to Upwork and found someone cheaper to take my place. It’s a classic external locus of control which can feel disempowering until you learn and come to appreciate the other side of the coin (namely: assuming there are managing their book of business correctly, freelancers can also have far more diversified sources of income than employees, which actually gives them greater income security.).
I also have zero paid holidays, so it’s my responsibility to charge my clients enough for me to be able to take them (so far, I have frankly sucked at doing this and, again, I have vastly underappreciated the extent to which vacations vital for one’s health and happiness! If you need another reason to charge better and professional rates, let this be it).
And then there’s the famous isolation that freelancers face and the less well-understood but distinctively strange feeling of being virtually tethered to one’s work and clients but not really having a day-to-day real-world relationship with them. Even thought I try to periodically see those who work in the same country as I do, it doesn’t equate to the familiarity and camaraderie that comes from seeing colleagues at a water fountain and having an actual collegiate relationship.
I am pretty diligent about breaking up my days and weeks with errands, social meetings, etc, but this is one aspect of freelancing that I sometimes don’t love.
Freelancing Reality Two: You Need to Wear All Hats, All of the Time (At Least at the Start)
But here’s the biggie and the part of freelancing that I actually think dwarfs the other challenges that I mentioned and explains why — in the eyes of most salaried workers — I would probably be classed as somebody that is almost “always working”.
(In practice, I observe the Jewish Sabbath and never work from after sundown on Friday until the corresponding time on Saturday night. I have a strong feeling that, during the hardest of freelancing’s travails, this almost alone has kept me strong and sane!)
But about those hats which I’m always juggling around.
You see, as I’ve only recently come to understand, I’m not only the guy that has to get the writing jobs done for my clients (if I want to keep my clients: on deadline and on expectation — every time).
Rather, I’m also:
- The business development department responsible for developing my professional network, maintaining relationships with them, and exploring new potential clients to target. I’m also responsible, in particular, for finding creative ways for using tools such as LinkedIn to land more work — even when openings are not explicitly advertised as such. There’s usually an ‘in’ to be found if you’re creative enough, I have found.
- The sales department responsible for initiating outbound contact with prospective clients, holding phone calls and face-to-face meeting with them, and running some kind of funnel to steer them down by selling them on the value I can bring to their organization. As well as being the Sales Development Representative (SDR), I’m also, of course, supposed to be the ‘closer’ — getting them to actually sign off on contracts for a viable rate (the last part is the most challenging of all the functions described thus far; writing is an area with far too much supply and far too much exploitatively compensated work.)
- The marketing department who needs to write posts such as this (and Quora contributions like these) to show prospects that I actually exist and am at least somewhat competent at the service that I offer. (Given that my line of business expressly involves me not publicizing my work — and foregoing bylines that help other writers get their names out there — this dimension is particularly essential, and I need to do a lot more of it, although it can be hard as so much of my time is taken up writing anyway.) Most of my activities, however, remain more on the one-to-one sales and prospecting / outbound marketing side. Truth be told, I greatly struggle with self-promotion and selling myself and am naturally averse to self-promotion. Coming back to the underappreciated importance of the mental and mindset aspect of freelancing, this (self confidence and being okay with self-promotion) is another arena in which I have a lot of work ahead of me.
Outside of those classic functions, I’m also:
- The IT guy. I manage a hosting network of 24 websites (yes, 24!), including my writing one, and — in general — have an obsession with doing things that can scale — even if that’s not the immediate requirement. Thus, I’m continuously revising my sales and marketing stack, working on integrations between systems, and making sure that I have a viable and preferably automated system for everything from outbound sales contact (thank you, Klenty!) to having reliable electronic versions of key paperwork to streamline the new account onboarding process. This week, for instance, I succeeded in provisioning and QA-ing a staging site for the aforementioned business domain. I’m a long-time Linux user and tech geek so this is all stuff that I actually enjoy and tend to get engrossed in (often to the detriment of actually writing things!)
- The purchasing department and office manager: who needs to keep the printer supplied with toner, find a good laser printer for a reasonable budget, and figure out how on earth to get that dried ink stage off my scanner bed so that it doesn’t look completely ridiculous when I send back paperwork scanned with it. Speaking of which, I seem to be continuously scanning, signing, and stamping NDAs, receipts, contracts, and the other pieces of paperwork that I routinely need to digitize.
- The accountant: who needs to meticulously log and record every expense expensable for accounting purposes; who must ensure that I’ve set aside enough money for tax and met my social insurance contributions so that I’m not faced with a gigantic bill once a year; and who must ensure that my pension contributions are also on track — and submit tax returns and forms at the various junctures throughout the year when they are statutorily required.
So What I Actually Did Today!
I hope the above explains why, on a typical day, I’m not actually sitting in front of my delightful workstation and writing all of the time — or even most of it.
Besides being as vulnerable to procrastination as your average office worker (at least!), there are simply a lot of things to do!
It’s kind of like being a professional organizer.
There’s the bits that my clients see (the output, i.e., the writing what they pay me to write) and then a lot of behind-the-scenes activity that they are unaware of.
The chief and recurring daily actions center around making sure that I have enough sales pipeline to keep opportunities coming in (a lot of work!); attempting to raise my profile online (a slow but consistent burner); figuring out pragmatic business questions (What’s the best virtual phone number service for my current needs? Can I find a better SMTP provider for this email marketing campaign?). And, finally, there’s the fact that I try to set reasonable limits around the hours I work, even if they are lengthy.
So to finally get to that breakdown.
Today I was involved in the following activities:
08:30–09:00: Ingestion of caffeine.
Early Morning: Business Development
09:00–10:00: Still dealing with responses from a recent direct email campaign targeting a certain startup sector. Somebody wanted to set up a phone meeting so I spent an hour tweaking Calendly so that it becomes a self-service operation for the prospect rather than having a tedious back and forth to schedule it. They book a slot in my calendar just as I finish and the system works beautifully. Sometimes, things really do work out as planned!
Late Morning: Technical Project and Website Updating
10:00:-12:00: As I mentioned, this week I got a staging version of my business site up, running, and QA’d. So I’m now in the process of making all the inner pages I never paid much attention to look good. Soon, I’ll probably just redo the entire site, as it’s not exactly a work of graphic design art — but, at least for now, it gets the job done. Today, I made the payments options page look a lot better and updated the Transferwise Eurozone account as they are migrating accounts to Belgium this summer. PDFs have to be updated as well as the website and then I need to also update the content in an onboarding Mailchimp automation (remember what I said about liking scalable systems?).
12:00–12:30: Ingesting food.
Most of afternoon: writing work!
12:30–16:00: I spend the majority of the afternoon getting through client deliverables. Today, I wrote about 2,000 words for two separate clients. When finished, I either send them directly to the client or add them to another delivery system. I then itemize my monthly invoices with the projects.
16:00–16:30: I’m using ZohoCRM to handle sending out files to clients (I want to stop doing this manually altogether) so I work on a few templates for file delivery, estimated completion date updates, and acknowledging the receipt of briefs with a deadline.
To get the Calendly integration running properly, I set up a quick Zapier integration to copy the appointments automatically from my business calendar to my personal one (I’m always in fear of not showing up for a phone call!).
16:30–17:00: I manage to get hold of my pension company just before their support line closes.
I’m self-managing a fund and am on my fifth attempt at trying to get them to accept paperwork to transition a fund from an old employer.
Every tiny detail must be perfect. Persistence, and the helpfulness of the company’s representatives have paid off, and the form is finally accepted.
Sometimes, in addition, I will post in Facebook Groups also to source recommendations from the community. I’m trying to find a bank which is more friendly to the needs of small business as I had an irritating experience with a clerk earlier in the week that has soured my perception of my current one. I engaged in a back and forth about this with a few posters.
17:30–19:00: The “Day in the Life of a Freelancer” post idea has been swimming around my head, and on the back of my to-do list for the past two weeks.
Today is the start of the weekend so I often leave somewhat enjoyable projects until the very end of the week. (Also worth pointing out: today was unusually focused on administrative activities and less so on writing!)
Tomorrow:
Invariably, there will be more work to do tomorrow, even though it’s part of the weekend where I live, at least nominally.
- I’ve nurtured the latest round of leads and set up meetings. I want to keep going with the prospecting and really not let up on it. I haven’t had as much time as I would like for about the past year to work on freelancing for personal reasons. Things have finally settled down and I want to go at full pace, at least for a few months.
- As I’ve been working on client deliverables this week I haven’t had a chance to write the prologue for an e-book that I’m co-writing with a friend. I’ll need to refer back to the recording of our conversation too as it’s already been a couple of weeks in the past.This is a far lower priority than the client work and the prospecting but it’s important to do this kind of work to keep passionate about what you do, I believe.
- I see that a client in Florida is working again so I’ll probably get feedback about one of my last deliverables by the time I wake up. I’ll also try to work on one more piece for them before I go offline for a day — and then call it a week.
Freelancing Reality Three: It’s a Lot of Work (But I Like It!)
That takes me all the way up to now, writing this Medium post from my desk at about seven in the evening, so it seems like a fitting place to leave off this blog post.
I hope I’ve shed a bit of light on what freelancing is like in actuality.
Although freelancing is not for the feint of heart (or work ethic!) I’m a firm believer that it is possible to succeed, no matter what your definition of professional success looks like (although — by writing this — I don’t wish to hold myself out as some kind of success story! Rather, I’m learning as I go along, but wanted to share a little of the experience I have garnered to date.)
I also firmly believe that it takes a lot more work to get the ball rolling than to keep it going (I believe engineers would explain this in terms of static friction versus kinetic force).
And the longer I do this, and the more I understand about freelancing, the easier it becomes for me to spot decent opportunity, see red flags that signal potential pitfalls, and the more I can focus on the actual writing rather than the business and administrative aspects.
For a while, I was part of a well-known writers’ Facebook Group and attempted to find my way to success by asking every conceivable question that could possibly be asked about freelancing.
Questions such as: ‘How many rounds of revision is reasonable for a white paper?’; ‘Does this sound like a reasonable free for ghostwriting interview responses for a software CTO’;’ Why are there so many clients looking for ridiculously low rates in the world?’
I’ve subsequently come to believe that the best way to learn freelancing is by taking action and doing and that over time the lessons you need to learn will make themselves obvious to you — and often through what could shortsightedly be dismissed as ‘failures’.
So I come back to that massive bucket of coffee beans that I mentioned earlier in this post.
You need to work smart, to have or develop a good professional network, and ideally also have some good administrative systems to succeed, as much as you can, as a freelancer.
But ultimately your success depends primarily on hard work and putting in the hours to develop that network, impress those initial clients, and secure the referrals that will pave the way to ongoing work.
Any time I have done the above, I have invariably seen the results — although it’s important to remember that brutally hard work is actually a leading indicator and that there is usually a time-lag between it and reaping its fruit.
That’s why it’s vital (but can be difficult) not to fall into mental despair when you’re working hard but not seeing results yet, or any at all, or going through a dry patch (because there’s a very good chance that it’s about to turn into opportunity!)
If you’ve worked hard with a little helping of smartness on the side, success will ultimately come your way. You just need to keep pushing — against the resistance of the market and the resistance that sometimes comes from within.
Speaking of the wars we sometimes foolishly wage with ourselves, I’ve also learned (yes, the hard way) that it’s vital to take care of your mental health at all times — particularly when you freelance.
The very nature of the business and the ingredients it so often throws our way — rejection, instability, stress, all in plentiful and repeated doses — can be a potent recipe for anxiety and depression.
Keep a watch out — and if things get too tough, remember that there is always a path out.
Any feedback, comments, criticisms, etc about this would be much appreciated.
I can be contacted directly through my website.
And good luck — whatever stage you are at in the journey.
Some Extra Snippets — For The End
- I never describe myself as a “freelancer” or a “freelance writer”. Although “freelance” is one way of describing the nature of the working relationship, I think there’s an enormous tendency to devalue freelancing work. Rather, professionally, I refer to myself as a “business writer”, “ghostwriter”, etc. But for the sake of this post and helping people to find the article I have deferred to the more conventional terminology.
