Technicians, Visionaries, and the Myth of Going Solo
To the uninitiated, "being your own boss" sounds pretty nice. Those selling the prospect of business ownership can make it sound downright glamorous. Of course, the moment you go into business for yourself, you realize the wide variety of skills it requires—skills that you yourself do not possess. Skills that you don't want to and have no intention of learning.
Many years ago, I wrote a blog post (lost to time) in defense of "going corporate." I wrote another (same deal) about the myth of solo entrepreneurship. Both of these pieces reflected the reality that working for yourself is never just working for yourself or even for your clients. It's balancing a host of functions within one corporate (that is, "body") system. You can address the variety of those functions in a number of ways. You can learn and learn to tolerate those functions yourself. You can build a team that specializes in different functions. You can design your business to minimize the variety of those functions. You can opt for some combination of those options.
Or, you can fight like hell and hope the problem goes away on its own. It won't, but that doesn't stop a heckuva lot of people from trying.
Today, I'm exploring how we think about who a small business owner or independent worker is, what mental models have informed that identity, and how that identity plays into economic reality as work in the knowledge and creative sectors becomes increasingly hard to come by.
First, we'll talk about a pair of influential books. Then, I'll take a look at recent layoffs at The Washington Post. And finally, I'll propose a different way to think about what "going solo" actually means and how it can help identify the trade-offs on offer.
At the end, I've got a brief coda about some highly relevant Grammarly drama.
The Myth of Solo Entrepreneurship
Two books have heavily influenced the identity of the micro-business owner and solo entrepreneur throughout my career. Even if their titles and authors are unfamiliar, the ideas are easily recognized in most business education aimed at small businesses today. Both of these books seek to make sense of a very true, very frustrating realization that most business owners go through in the early stages of their business. And that realization is that there is so much more to running a business than doing the work you enjoy.
The E-Myth by Michael Gerber was originally published in 1986 and republished as The E-Myth Revisited in 1995. The myth Gerber refers to in the title is the idea that an entrepreneur is a sort of superhero who perseveres despite the odds to bring their dream to life. No, he says, that may be the cultural narrative we share, but the reality isn't pretty. "Exhaustion was common, exhilaration rare," he wrote of the vast majority of small business owners he met at trainings and consultations.
Rocket Fuel by Gino Wickman is a more recent book, released in 2015. Wickman takes the entrepreneurial myth that Gerber aimed to dispel and doubles down. It's not that the superhero entrepreneur isn't real; it's that a superhero needs a sidekick.
In The E-Myth, Gerber details three roles that every business needs filled: the Entrepreneur, the Manager, and the Technician. The Entrepreneur is a future-focused, strategic thinker who delights in building the business. The Manager is a present-focused logistician who ensures things run smoothly. The Technician is focused on doing the work of the business. Most of us have all of these qualities, says Gerber, but few of us have them in equal proportion. He claims that "the typical small business owner is only 10 percent Entrepreneur, 20 percent Manager, and 70 percent Technician."
Technicians wind up starting businesses because they want to do the work they love without worrying about a boss or institution. He's not wrong. Regardless of whether you're a business owner or not, you've probably daydreamed about the possibility of just getting to do what you love without worrying that someone is going to check up on you or ask you to file some stupid report.
The example Gerber uses throughout the book is a baker. The baker craves freedom over their work, so they start a bakery. And even if that bakery is wildly successful, the baker can end up hating every moment of it because they're constantly pulled away from the task that they started the business to do—ya know, baking.
In Rocket Fuel, Wickman claims that businesses require a yin-yang pair of roles: a Visionary and an Integrator. The Visionary is the future-focused strategic thinker akin to Gerber's Entrepreneur. The Integrator is like Gerber's Manager, but with even more power. The Visionary is creative, innovative, bold, and always thinking about what's next. The Manager essentially puts boundaries on all that energy by creating order out of chaos, building teams, and maintaining systems.
Visionaries, Wickman argues, are most often founders who, in the course of business growth, succumb to the unique challenges of that personality type and need to go looking for a "second in command" to help them with focus and execution. "The Integrator is the glue that holds the people, processes, systems, priorities, and strategy of the company together," writes Wickman.
This is not the part of this tale where I forcefully debunk both of these mental models. I think they both have merit, though there are some very gnarly gender politics hiding just below the surface. I don’t think it’s a coincidence that Gerber’s main character is a baker named Sarah, nor that the Visionary/Integrator relationship sure seems to mimic the heterosexual dyad, with all the feminine-coded tasks always assigned to the second-in-command.
Here is where I explain that the Technician offered small business owners one way to make sense of their frustration, while the Visionary offered another. The influence of Gerber's model is perhaps larger but also more diffuse, whereas Wickman's model ripped through my online business world to the point that business owners would explicitly say they were hiring an Integrator or attribute their shortcomings to the fact that they were a Visionary. I was not immune to this phenomenon.
For what it's worth, I think Gerber's Technician character offers a better explanation for the typical problems small business owners experience than Wickman's Visionary character. The vast majority of people I've worked with over the last 17 years got into business to do what they love, not because they had a brilliant vision for a company and a passion for figuring out how to make it real. However, to the point of Gerber’s thesis, the mythic entrepreneur is an enticing character to identify with. And so that character has been central to how business courses and coaching have been marketed.
There's Always the Creator Economy
(There Isn’t)
What both Gerber and Wickman’s models have in common is their acknowledgement that starting, building, and growing a business takes multiple skill sets—skill sets that, most often, individual people aren’t equally fluent in.
From my limited point of view, it seems the whole “visionary entrepreneur” hype cycle has petered out a bit. I say “I think” because I’ve been out of loop for a number of years now. There’s more hype about becoming a creator now, whether as a YouTuber, a newsletter writer, TikToker, or a (video) podcaster. Of course, the packaging has changed, but the flavor is the same.
For example, Substack seems to use both the Technician and the Visionary as archetypes for its messaging. On one hand, they say, “On Substack, creators earn a living doing what they love,” and include a handy (that’s sarcasm) calculator that shows the modest amount of money you can make from 800 paid subscribers, reinforcing the idea that you’re doing this for love not to get rich. Very Technician of them. On the other hand, Substack proudly features media brands, including Bari Weiss’s The Free Press, more so than individual writers. The app’s business model depends on Visionaries building high-volume, profit-driven media businesses on the platform.
Speaking of Substack and high-volume media brands, let’s talk about The Washington Post.
Amazon founder Jeff Bezos purchased The Washington Post in 2013. In 2016, Bezos spoke out against the ways he felt Trump was “eroding” democracy. Trump hit back threatening both Amazon and The Post. During the first Trump administration, The Post took a defiant tone, adopting the tagline “Democracy dies in darkness.” Subscriptions poured in as anti-Trump news consumers saw the paper as the broadsheet of the resistance.
But a lot can change in eight years.
The Post’s anti-Trump bump petered out during the Biden years. When the paper scuttled the planned Kamala Harris endorsement and announced there would be no presidential endorsement in 2024, readers let their feelings be known. When Bezos announced in very early 2025 that The Post would only publish op-eds that aligned with the values of personal liberty and free markets, readers cancelled their subscriptions and staff resigned in protest, including the opinions editor David Shipley. Now, a year later, 300 editors, journalists, and staff—nearly a third of its workforce—are out of a job.
The New York Times reported the news with these devastating lines:
“The cuts are a sign that Jeff Bezos, who became one of the world’s richest people by selling things on the internet, has not yet figured out how to build and maintain a profitable publication on the internet. The paper expanded during the first eight years of his ownership, but the company has sputtered more recently.”
This massive downsizing at one of the nation’s biggest newspapers didn’t come as a surprise, but it was a major blow. It’s true that the economics of the paper weren’t good, and so there was a “business” case for layoffs. However, the journalists affected and media industry observers alike recognized the politics of this move.
I don’t want to talk (much) about those politics, though.
In the midst of speculation about the particulars of what Bezos might have been trying to accomplish, whether a wink and a nod to Trump or a cynical capitalist lurch toward AI-ifying news or something else altogether, we can easily lose track of the steep path ahead for the newly unemployed journalists. The day the cuts were announced, affected workers took to Bluesky to share their dismay—and start putting out feelers for their next gig.
Other journalists, many of whom had been laid off themselves at some point, did their best to offer support. They reposted, shared endorsements, and amplified the story across the platform. It didn’t take long for some to speculate that when 300 journalists lose their jobs, 300 premium newsletters are born. Some experienced independent journalists worked together to put on a free workshop to share what they’ve learned.
Whether going independent is a viable path forward for journalists without a media organization to call home, it may be the only path available. Battered by Facebook and Google and now ripped off by AI companies, both legacy media and new media organizations are in dire financial straits. Jobs are scarce. There are far more talented journalists looking for jobs than there are jobs to be had.
Working at a media organization allows you to be an unapologetic Technician ala Gerber. Sure, there’s more to it than simply reporting and writing all day. But the purpose of the job is doing journalism. At larger organizations, there is a firewall between the business side and the journalism side. Journalists shouldn’t be thinking like a Visionary or Entrepreneur because it can easily create conflicts of interest (see also: Bari Weiss).
Going independent means going without all of those safeguards and support structures.
Every headline you publish, every word you write, every post you push out to social media is a business decision. Or rather, a decision that your livelihood hinges on. If you’re not the Entrepreneur, Manager, and Technician, no one is. If you’re not both Visionary and Integrator, nothing works.
A media organization—and really, any company—should be an operational system that distributes the work of these roles efficiently among those who need their support. The organization is a kind of safety net. Beyond pay and benefits, workers plug into systems that help them do their jobs. For journalists, that’s systems like legal, fact-checking, and sales. By joining with an organization, they get to tap into these centralized resources. The organization gets to enjoy the relatively low marginal costs of providing these systems by distributing them among their workforce.
While newsletter service providers can make it easier to produce and distribute journalism from a technical standpoint, they don’t offer the critical, if softer, support systems that media organizations supply. And while there are incredible independent journalists defying all odds, there is no world in which disaggregating news and culture down to an individual level is a world with richer news and culture.
Great journalism, compelling cultural output, and engaging media are products of systems—systems of collaboration, cooperation, and mutual care. Can these be replicable by individual workers acting in concert? To some degree, yes. But managing all of those systems is yet another skill set to learn and deploy while you could be "doing your job."
Business Beyond Money-Making
The potential of the “solo entrepreneur” or the “company of one” has been much touted over the last decade. And while I won’t deny that there is potential to go independent and do well (as an journalist, artist, designer, author, consultant, etc.), the path to that goal doesn’t match the solipsistic framework those terms imply. It might be better to view the solo journalist or consultant as a “3-in-1 entrepreneur” or the solo artist or producer as a “company of multiple personalities.” A little less appealing, right?
As I note in Blank Slate, there are essentially two ways to think about business-building: (1) How will this make money? and (2) How will this meet [my/our/their] needs? There are millions of ways to make money—but the vast majority of them won’t help you meet your needs. Yet, for many reasons, that’s the question that gets asked most often. How can I do X and make money? What would it take for Y to make money? Can I make enough money with Z?
The distinction might sound semantic. I mean, making money is typically how we meet our needs in the 21st-century economy. But foregrounding the money-making goal rather than the needs-meeting goal kicks the can down the road on important work-life questions. You can end up making a bunch of decisions about how you'll make money without considering the downstream effects on what that means for how you spend your time and exercise your skills.
When you ask how a venture can meet your needs (and the needs of those you’re creating value for), you get a much better picture of what “going solo” actually entails. A journalist has a certain set of needs—the provision of which is labor-intensive and expensive on an individual basis. A consultant has another set of needs. An artist has yet another set of needs. The customers for each of those ventures also have unique needs that should be met. Addressing those needs in the DNA of your business is a good strategy.
Those needs form the foundation of what building an independent work-life actually is. The roles of the Technician, Manager, and Entrepreneur or the Visionary/Integrator pair become much more apparent. You can make more clear-eyed choices about what roles you take on, which you hire or outsource for, and which you allow to remain unfilled.
However, I do not believe the way forward is all of us working from home offices or kitchen tables, trying our best to meet our needs, and hustling to fill in the gaps that used to be the purview of organizations. That's not to say the solution is for all of us who've "escaped" to go back to the cubicle either. Both of those paths actually play right into capital's hand. It's the cycle of disempowerment through unemployment and survival through re-employment for less that further entrenches our current economic predicament.
Unsurprisingly, the best way forward is systemic change. That's the solution I propose to business owners when we talk strategy. But it's also a strategy for addressing needs socially and politically. In addition to asking how our own ventures (or even our jobs) can best meet needs, we should ask how our communities can better meet needs. That's the ultimate question of political economy and one that can prompt the kind of creative and strategic thinking required to build more liberatory work-life systems.
Coda
Last week, users of the updated AI-forward Grammarly interface, Superhuman Go, noticed that they had access to "expert reviews" of their texts. These expert reviews featured suggestions from editors and journalists like Kara Swisher, Nilay Patel, and Casey Newton. One might expect that these journalists had opted in (and been compensated for) the use of the name and digital likeness in these reviews.
Not only had they not opted in, there was no way to opt out. That is, until those journalists started to say, WTF?! Now, experts can opt out by emailing their request to the company. There was no apology or even an attempt at compelling reasoning other than a Superhuman VP stating, “The experts in Expert Review appear because their published works are publicly available and widely cited.”
I went to try it this morning and couldn't get the feature to work. I'm not interested in playtesting it enough to figure out whether the feature is down or whether it's user error.
[ UPDATE ] There have been two developments in the story. First, it wasn’t user error (thank goodness). Superhuman did, in fact, disable the feature on Wednesday, March 11. Second, journalist Julia Angwin filed a class-action lawsuit on behalf of all those whose identities were used improperly. Superhuman’s CEO issued a statement that did include an apology.
To add fuel to the fire, reports from those who have used the feature testify that not only are experts' identities used without consent, but also that their identities are attached to bad advice. I don't know which hurts more, frankly.
Look, Grammarly has gotten progressively worse in the AI era. I was a huge fan for years and have—til now—paid for a premium subscription. But the minute it started to incorporate AI features, its reliability and quality went down. Sure, it'll catch typos (most of the time), but I find myself disregarding nearly every stylistic or semantic suggestion it makes.
I'm moderately confident in my ability as a writer, and so disregarding those suggestions isn't difficult for me. But I know lots of people who end up writing quite a bit are far less confident. And not without good reason, the education system does not prioritize writing skills nearly as much as it should. If you appreciate Grammarly and find it helpful, I get it. I'm not going to tell you to stop using it! That's not really my style.
But this news is disconcerting on so many levels. It was a real "Wait, what?!" moment for me and many others. To me, this feels like an even more blatant disregard of the value of human labor and the integrity of creators' identities than the original theft of intellectual property that the whole industry is premised on.
For now, it's worth reevaluating your relationship with Grammarly. If you use automated editing tools, I don't know that there's a way to eliminate the influence of LLMs. But check out the tool you use (or the one you might want to switch to) and look for ways to use it in a way that more closely aligns with your stance on LLM-powered machine learning.
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