After the paycheck is gone: Successful solo writers share their secrets

By any yardstick, the outlook is alarming — journalism, already slimmed-down after two decades of digital disruption, is now being ravaged further by coronavirus-induced cuts.

At least 38,000 US news company workers were furloughed, laid off or took pay cuts between March and June alone, according to a Financial Times analysis. In the UK, Enders Analysis warns of a “total collapse” in which a third of journalism jobs could be lost. Poynter’s list of staff cuts and closures is a depressing roll-call of the unfolding state of affairs.

For an industry that has been witnessing record online traffic, that is hard to take. But it is only the latest and most profound milestone after years of decline. America lost more than a quarter of its newspapers in the 15 years before coronavirus, 300 of them in the last two years — a quarter of jobs gone in the last decade, 3,160 in 2019 alone. And these numbers overlook the sizable freelance workforce. Even digital outlets have struggled to provide the growth once expected.

For writers like me, prospects for gainfully pursuing the craft we love appear to be diminishing.

And yet, in the rubble, something new is being built. From Ghost and Substack to Mailchimp, ConvertKit, Patreon and more, a new wave of publishing platforms and newsletter tools is empowering creators to launch their own vehicle — to write and directly distribute their valuable content to loyal audiences; crucially, with the ability to make money from subscriptions.

Whether it's big-hitters like Ben Thompson’s Stratechery, analyst Benedict Evans and Andrew Sullivan’s The Dish, or the burgeoning number of small and medium sized digital publications, we are seeing a growing number of writers go solo.

So, what do the experiences of journalism’s “solopreneurs” tell us about succeeding without a salary in the new world?

1. Solo success has pedigree

In 2020, we are seeing plenty of hype about this avenue. But going it alone is not a new or faddish prospect dreamed up to brighten journalism’s darkening outlook. It's a decades-long trend with real evidence of success behind it. “Journopreneurs” (not a new term) have been spinning-out and starting-up online for years.

Their poster boy is Rafat Ali. Laid off following the dot.com crash in 2002 by Silicon Alley Reporter, a now-defunct magazine covering the digital economy, Ali tried and failed to get another full-time job. So he made his own — paidContent, a blog and newsletter covering the digital media business that soon became the sector’s go-to source. Within a year, Ali was making $80,000 from paidContent, leading him to hire his own staff (disclosure: I was his senior editor, international) and, by 2008, he was able to sell the site to Guardian News & Media for between $10 and $15 million.

“Out of necessity is born this,” Ali, who remains a respected media commentator and is now building his second publication in New York, told me. “You’ve no choice but to reinvent yourself. In 10 or 20 years time, jobs there may not exist — at least you can be in control of your destiny.”

2. Autonomy for the people

That sense of control is a key motivator, both for reporters that have had joblessness thrust upon them and for those who want to make themselves more resilient.

When coronavirus canceled matches and a regular client pulled work in-house, Chloe Beresford, a freelance soccer journalist in Stockport, England, found her commissions dried up. After using lockdown to reassess her goals, this June she formally started Curva e Calcio, a subscription newsletter and podcast on Italian soccer that she had previously experimented with. Already, Beresford has 115 paid subscribers, earning her around £800 per month and counting. But it is the freedom she values.

“The aim was to avoid being at the mercy of each outlet's budget, to write what I want to write and to invest the time I would've spent pitching articles into building a quality resource,” Beresford told me. “There are lots of plus points. I have flexibility in my life.”

Whilst Curva e Calcio’s earnings are not yet a full-time salary, they are an important and dependable bedrock, allowing Beresford to follow other pursuits like consulting and meditation, as well as ongoing freelance work.

3. You need your niche

In an ever more cluttered media environment, the publications that stand out are the ones that cover a specific topic and serve a defined audience. There’s nothing new about that — any media venture has to be about something. In other words, although specialists may serve a smaller audience, they are best placed to succeed.

That is why we are seeing increasingly tightly-defined publications and communities emerging, on previously low-key topics like ethnic-minority diversity in PR, women’s NBA basketball, the climate crisis and the future of work.

Local news reporters, amongst the hardest-hit by layoffs, can be assured that their locality is, indeed, a niche ripe for coverage, especially if it is underserved. Everyone should focus on a specialized topic with a built-in audience of some kind.

4. Bring an audience to the party, or don’t

Imagine launching a new magazine but not having anyone to tell about it. For individual journalists, leaving the publication whose audience they have helped build and serve may seem like entering the wilderness. But those who have managed to build their own audience, through other means, have an advantage when starting their own thing.

When Jon Ostrower was laid off as CNN’s aviation editor, amongst 50 cuts in 2018, he considered a job offer to return to mainstream media — but rejected it to launch The Air Current, a $249-a-year subscription aviation newsletter and website, around the same time his second child was born.

Although he initially lacked the confidence of his friends that he could fly solo, the facts were staring Ostrower in the face — after a career spent covering his specialist topic for major outlets like The Wall Street Journal and Flightglobal, Ostrower had cultivated tens of thousands of social media followers, industry respect and a contacts book galore — a ready-made bridge to his next horizon.

“Knowing my audience came with me was huge,” he told me. “I don’t know if this would have worked if I had to start from zero — it would have made it much harder.”

But not impossible. Ostrower, Ali and Beresford all agree there is ample room for writers who have not yet cultivated a following to succeed.

“It’s not essential,” says paidContent founder Ali, who built his site through toil and long hours in the days before social media. “You can do it by sheer quality of work, though it is a longer route.”

According to Ostrower, who, like Ali, first built his name by writing a free blog that was later acquired by a major publisher: “If you have something to say that’s worthwhile, valuable or isn’t being done by someone else, you can do it.”

5. Work with your tribe

Having an audience isn’t enough. Knowing the audience you want to serve is essential for writers and editors who want to build a profitable following. Media enterprises of any size are about that relationship — but none more so than at the smaller scale of start-up self-publishing.

“It only works if you are willing to engage with readers,” says Curva e Calcio’s Chloe Beresford. “You can’t afford to be aloof. I like to interact with the people who read my stuff. I can ask them what they want in their newsletter. They hit ‘reply’, say what they have liked and not liked.”

But this cycle of community connection doesn’t just inform editorial, it also defines what, for many in this new wave of writers, is also a business. Ostrower, for example, knew his information was valuable and his audience had means to pay, pointing him clearly toward an annual subscription model.

6. Time it right

When is the best time to launch? As more reporters and writers announce their own layoff through social media, we often witness an outpouring from loyal readers and followers — not just of sympathy, but anger at their former employer and a yearning to continue reading them somewhere else.

In the days immediately following a layoff, there may be a window of opportunity when out-of-work writers can capitalize on the spotlight being shone upon them.

Even so, the most successful launches happen when a plan has already been formulated. When Ostrower announced his lay-off in 2018, hundreds of Twitter followers lamented “CNN’s loss” of “the coolest aviation reporter” — but it took him three months to launch The Air Current, an idea which had already been percolating for a while before that.

If possible, the optimum time to build the bridge is before you need to. Side gigs are more accepted as inevitable by employers today than in the past. Those who, whilst still in employment, can build an audience for a publication of their own are stood in good stead. They can begin to do so by framing their site as a live portfolio, a notebook for potential story ideas or an unrelated interest entirely.

7. Use the tools of the trade

The first wave of journopreneurs could only have dreamed of the ease with which writers today can create their own publishing platform.

When Rafat Ali started paidContent in 2002, he knew just enough PHP to install and host some blog software, then bolt on a rudimentary mailing list downloaded from a script repository. His hardware was an internet cable run from an east London cybercafe to his leaky apartment above, where a reclaimed desktop PC from a local market sat on an old desk. That is a technical feat for most writers. And, despite his site’s name, the absence of plug-and-play content payment systems at the time meant advertising was the only business model initially available to him.

“It’s not like I had a choice,” he says. “Micropayments were around, but they weren’t available for small publishers. Now, 20 years later, it all exists. It’s much easier, with platforms for publishing, payment and distribution.” It all comes together to make the opportunity far more effortless.

And that’s something Ali, now CEO of his own travel insight company Skift, is considering again, as he contemplates his third act in publishing — possibly a small-scale, personal travel newsletter in what would be a return to his grassroots.

Next time, however, he says he would want more control than is offered by some solutions. “I’m proficient enough on the technology, I would want to own the whole thing, particularly if it's open-source if that means it has a lot of plugins. That's the challenge — Medium just dropped publishers like a hot potato. I hope that doesn't happen with Substack.”

8. Learn how to wear all the hats

Memo to journopreneurs — you’re not just a writer anymore. In bidding your old editors goodbye, you also lose a valuable quality-control and direction-setting function. Beresford admits to “sometimes second-guessing yourself” and advises seeking feedback from friends and colleagues. But, she says, in a close community, readers can make the best editors, a natural check on coverage.

More than that, though, solo writers are also business owners and product marketers. Beresford has successfully used her close reader connections to articulate a clear product offering, including her publishing cycle, pricing model and subscriber-only features, ensuring the expectations of paying readers are transparent from the outset.

“When no-one gives you a job description for starting your own publication, you have to be really focused on what you want it to be,” says The Air Current’s Ostrower. “My first year was spent trying to figure out what was the best use of my time — you are a business owner, a beat reporter, feature writer, trying to break news, do long-form, trying to use social media. You have to understand what your audience wants, how they consume their media, how you fit into their routine. I’m constantly playing chess.”

He advises new soloists erect a “firewall” by allocating disciplined, ring-fenced time that separates out the two key roles — editorial and business operations.

9. Go for growth?

That second imperative, business, may become more important. As more self-publishers start up, some will find themselves making insufficient revenue progress, others will find themselves wanting to focus more on the product.

Either way, hard work will be required. Ali toiled “24/7” to build paidContent’s reputation. Like others, he fears the biggest risk in self-publishing may be burn-out, as struggling writers bust a gut to continue serving an expectant, paying audience.

“I could sink or swim based on what I could write,” he says. “I once boasted, ‘I’ll blog anyone to death’ — the volume of posts was very high.” Curva e Calcio’s Beresford says writers can plan for time off by scheduling features to run in advance, but her number-one aim is still to acquire a large number of subscribers as soon as possible.

And, if the new generation of self-starters is going to become as big as the opportunity suggests, the work that goes with growth is going to be required.

“You have to be thinking three, four, five moves into the future for how you’d like to evolve,” says The Air Current’s Ostrower. And Ali adds: “Human instinct is to grow — one-person newsletters will become two-, three- or five-person publications. You may see an initial revenue up curve, but you may plateau and have no sense of how long it might be. If you have a choice, be fully into it. No startup investor will invest in you if you are not 100% invested.”

Slow and steady to the future of media

Today, the emerging crop of solopreneur writers has incredible opportunities available, right at the time when troubled journalists need them most.

At a time when the old guard of media is vanishing, it is likely that some of these new, direct-to-audience upstarts will become the next major publishing enterprises of the future. Some of them will look nothing like journalism as we have come to know it.

But execution is one of the factors that will determine which of them realize that goal. Do the new self-publishers want to toil tirelessly to claim their place at the top of publishing? Or are they simply seeking autonomy, self-sufficiency?

Some are now beginning to recognize the importance of balance — of making an impact on the world, certainly, but in a calm manner that doesn’t cause the opportunity to over-heat before it has really got going. Today’s more-capable tech stack makes that more likely than before.

But the growing digital content diet of many readers also means writers may comfortably afford to produce a lower volume than they might expect. The Air Current publishes only two or three, albeit-meaty articles per week, because its editor knows his readers are time-pressed. “There is so much noise on the internet, I want The Air Current to be a quiet place for our readers,” Ostrower says.

Different audiences and topics may have different demands but, as Ostrower says: “Put yourself out there. You will never know if you don’t try.”