Why hourly work is more creative and flexible than ever

TikTok for retail jobs, nail technicians with Hollywood agents & tattoo artists on world tour

Over the last decade, hailing a ride through an app, getting your favorite meal delivered, or having new furniture assembled at your convenience has become an affordable convenience for the average American. 

While the services provided by these well-funded Silicon Valley startups have enabled massive productivity gains for busy working professionals and consumers on the demand side of these technologies. In recent years, “gig” work has received its fair share of criticism due to its opaque wages and unfair labor practices as companies aim to cut labor costs and maintain an affordable service for customers.

As we look ahead to the next decade, I take an optimistic view on new opportunities for hourly work in the Roaring 20’s as more creative work becomes readily available across all skill levels.

In the same way that influencers and celebrities are using social influence to launch their own podcasts, jewelry lines and venture-backed startups, we’re seeing modern tradespeople such as mixologists, hair stylists, freelance designers and self-taught software engineers build meaningful businesses off the back of social platforms like Instagram. 

The virtuous cycle for modern trades starts with the delivery of an Instagram-worthy experience that’s praised by others, studied by peers and attracts more opportunities for future work.

With the help of Instagram and other platforms, creative tradespeople are bypassing licensing and other limitations by connecting directly with top clientele on social media and creating scarcity through multi-cities tours to meet fans and offer their services via a pop-up experience or private bookings.

In this essay, we’ll discuss: 

  1. The backlash on policies meant to protect freelance workers

  2. The 4 categories of flexible work 

  3. The tech and tools to enable flexible work

  4. Three predictions for the future of flexible work

The backlash on policies to protect freelance workers 

As freelancing gains significant momentum with high-earning sectors, we expect Uncle Sam will be watching these new classes of work closely under the guise of protecting workers, without really understanding the work at all.

While many new startups will emerge to support freelancers and flexible work with accounting, scheduling/time management, flexible health insurance and more.

The state of California — home to two of the largest markets for specialized independent professionals: LA and SF — made the first real attempt to protect freelance workers by introducing limitations to employers in efforts to create full-time employment which left both parties annoyed and confused:

One section of California Assembly Bill 5 (A B5) caps submissions from any “freelance writer, editor, or newspaper cartoonist” to 35 per year. 

A recent study by Contently surveyed 573 freelancers about CA AB5 and found the following:

  • 88% oppose AB5’s provisions limiting freelance creative submissions

  • 75% freelance because they prefer it over a full-time work

  • 82% are opposed to a cap on freelance submissions of any kind

When the government takes aim at the gig economy, it’s not corporations or the services they provide that are under attack, it’s real people.

In Los Angeles alone, there are over 400,000 gig workers who collectively earned more than $18 billion last year.

Freelancers affected by AB5 are sharing their stories on Twitter with the #AB5stories hashtag. It’s independent musicians losing performing gigs, full-time caregivers who need flexibility, and individuals with disabilities making their own way. One freelance writer put their concern succinctly: “#AB5 makes me feel like collateral damage in the war against Uber and Lyft.”

Here’s what the bill missed: many people actively choose flexible work. When laws remove these options, they’re taking away economic and creative opportunities: temporary relief, supplementary income, flexible part-time income and more. They eliminate paid creative work and income in support of creative work. 

The battle cry for work that falls outside 9 to 5 is too loud to ignore. With it, we’ll see technological innovation and a new class of tools to support independent contractors, creatives, and anyone else searching for their next side-gig. The future of work is flexible; let’s take a glimpse at current and emerging trends.

The Four Categories of Flexible Work

Flexible work exists across four main categories: Classic Gigs, Modern Trades, Creative Experts, and Me as a Service (MaaS). Each category is distinct and has its own specific characteristics. Additionally, individuals can jump categories one as they develop particular skills or as they become more selective. 

Classic Gigs: offering time and some muscle for extra cash

Before the rise of peer to peer apps, we had the classified section of newspapers and then the emergence of Craigslist. Anyone from babysitters to handymen could post an ad offering their services. 

These gigs are tried and true classics that have served as a right of passage for teenagers first entering the workforce and a familiar archetypes for Hollywood’s answer to wholesome American culture.

Although we still appreciate the classics, they’re not fully protected from disruption – the ease and convenience of driving your own car with Uber and Lyft presents a new opportunity for flexible work on your own schedule. 

The barrier to entry is low and making meaningful money generally requires regularly accumulating a number of smaller paid tasks (e.g. x number of rides or x food deliveries). Individuals finding flexible work in the Classic Gigs category increasingly don’t need to advertise; the gigs flow to them in exchange for a flat fee per gig or percentage of your earnings. Additionally, you may earn tips.

  • A DoorDash delivery driver earns a fee for each food order they pick up from a restaurant and deliver to a customer.

  • A Handy service professional secures payment for services like home cleaning and television mounting.

Modern Trades

Skilled mixologists, make-up artists, and tattoo artists fall under Modern Trades.

The services they provide have a higher barrier to entry because they're trained in a particular field either traditionally through a school or apprenticeship or non-traditionally through hours of self-taught education through Instagram and YouTube. 

Today, rather than handing out business cards or attending trade shows, individuals in the Modern Trades category use platforms like Instagram, Facebook, and other social media platforms to build a following, connect with peers and access more work.

While they use online services to promote their work, they generally provide their services in-person and face-to-face. 

  • A specialized nail technician might pay for space to see clients in an established salon, but is self-employed and showcases their nail art through Instagram.

  • A magician for hire might post videos of their stunts and tricks on YouTube to drive bookings for corporate and private events.  

@thehangedit is an LA nail technician represented by NailingHollywood.   

Creative Experts

Creative Experts are who we generally classify as “freelancers” in tech – freelance designers, freelance software developers, or freelance writers. In this category, the barrier to entry and level of expertise can vary wildly. While a novice brand designer can get their start on Fiverr and producing a logo for a low fee, an experienced designer can command thousands of dollars for the same task if they have a portfolio of past work and a differentiated style that’s sought after.

To earn top dollar, specialization and differentiation is key: a known portfolio, peer recognition that leads to conference talks and industry press are all assets.

Generally, Creative Experts deliver their services digitally and their work for clients can be done entirely remotely.

  • Alice Lee (@ByAliceLee) is a freelance illustrator turned muralist who is credited for developing the people illustrations used by many enterprise companies today (see @HumansofFlat for inspiration). She’s worked with companies like Slack, Cruise and Philz Coffee and bounces between San Francisco and Venice.   

  • Aristide Benoist (@AriBenoist) is a freelance developer who specializes in motion graphics and interaction with clients including Epicurrence and Folio. 

@ByAliceLee’s original work with Slack.

See Taylor Swift as SaaS illustrations here

Me as a Service (MaaS)

Me as a Service (MaaS) is the newest entry to the flexible work spectrum. Under this category, people trade off their name and established brand by earning income through streams like Patreon, Substack, a blog, a podcast, or an online storefront. 

Here the “product” is the individual or something they’ve written, spoken, curated, or created. This category relies on influence and people caring about what you say or think in a particular niche. Customers, often “fans” or “supporters”, provide payments directly to their favorite creators as a one-off transaction or a regularly recurring subscription fee.

  • Cassidy Williams (@cassidoo) has a popular newsletter and Patreon and is known for her technical knowledge and funny quips on software engineering. 

  • Julia Evans (@b0rk) packages technical content into helpful web zines. While it was a side project for several years, she recently left Stripe to pursue creative work fully. 

This category is increasingly broad and spans across niches like productivity and self development, political commentary, or academic discourse. 

MaaS represents the only category where individuals shift from earning with their time to earning while they sleep. Patreon or Substack allow anyone in the world to subscribe to your content. These platforms are truly scalable and can generate true wealth through flexible work (e.g. writing a weekly newsletter or filming videos). 

While these four categories have always existed in some form, they’ve become increasingly democratized as tech tools can provide access to a steady flow of gigs, help you inexpensively build a website to showcase your talent, or enable a company of one to reach thousands of people with an Instagram snap and a few well chosen hashtags.

The Value of Flexible Work

The reasons that people opt for flexible work, and will continue to do so in the future, are diverse. There are four key reasons we can discern: the Chicken-Egg Dilemma, Lifestyle Flexibility, Antifragility, and Creative Expression. 

Chicken-Egg Dilemma

Flexible work is an opportunity to more easily acquire experience to put on a resume to leverage for full-time employment. This mitigates the “chicken-egg dilemma” in which you need experience to get a job, but need a job to get experience. For instance, flexible work can help students build portfolios to secure their first internships or new graduate roles. Employers increasingly want to see what prospective employees have done, not what they can do. Flexible work is low barrier and low permission. By choosing flexible work, individuals can quickly develop cross-functional soft and hard skills – stringing together daily gigs is time management and organization, while advertising your business online makes you a marketer. 

Lifestyle Flexibility

The mainstay of “work hours” from 9 am to 5 pm locks many people out of full-time employment. It’s often infeasible for parents, primary caregivers, or people with disabilities. Alternatively, many simply desire lifestyle flexibility, wanting to experience some semblance of the 4-Hour workweek, or at least a 4-hour workday. Flexible work enables people to break the constraints of the long commute and office day. Instead, they can earn an income while simultaneously raising kids, taking care of an aging parent, or travelling the world.


Flexible work provides a means to work with interesting people, build your network, and gain more skills. In a fast moving economy, the ability to develop a body of work that precedes you represents stability and freedom. It makes you antifragile. Increasingly “building a personal brand” isn’t for marketers or entrepreneurs; it’s advice for everyone – academics, technologists, and everyone in between. Having a website, portfolio, blog, or Twitter account to point to can spurn work opportunities and serves as insurance in the case of job or income loss. 

Creative Expression

People are disengaged at work. 

Gallup’s 2017 State of the American Workplace Report found the following about the country’s 100 million full-time employees:

  • 16% of employees are actively disengaged — they are miserable in the workplace and destroy what the most engaged employees build.

  • 51% of employees are not engaged — they’re just there.

This disengagement exists for several reasons. Here’s just one: many people are unable to align their passions with their full-time work. Flexible work is a way to seek out passion projects that serve as a creative outlet. These can permanently supplement full-time work (e.g. “side gigs”) or they can be a bridge to transition to creative work in the future.

Alternatively, flexible work can support creative work that doesn’t generate income or costs money. The trope of the struggling actor waiting tables is now the striving actor who manages brand accounts on the side in between auditions.

The Tech and Tools Enabling Flexible Work

There’s an expanding canon of tools that are enabling flexible work across Classic Gigs, Modern Trades, Creative Experts, and MaaS. More so, it looks like the market opportunity for work tools and platforms is only growing.

Platforms like Indeed are part of the present-day pack of successful work tools.

However, there’s room for a new set of well-designed workplace tools and platforms that provide an elevated user experience for both employers and candidates. Additionally, there’s an opportunity for freelancer and creator focused-tools that help flexible workers find their next big project. 

The “workplace tools category” extends far beyond the next Slack or the next Zoom – it’s a wide grouping that’s ready for disruption and newcomers. These are the categories of tools we can look forward to seeing.

New marketplaces for flexible work opportunities. Beyond rideshare and delivery, marketplaces will arise across different sectors. Tend (a WorkLife portfolio company), a marketplace for highly-skilled hospitality and entertainment workers, helps anyone from mixologists to cooks get additional hourly shifts in cities like San Francisco, New York, Miami, and more. 

Tools innovating on hourly work. Hourly work remains a prominent part of the economy, and an area where tech tools will bring new opportunities and experiences. Heroes (a WorkLife portfolio company) lets prospective employees create short personality-driven videos to apply to customer service roles at companies like American Eagle, H&M, and Jamba Juice. Think TikTok, but for getting hired at your favorite store like REI (if you’re outdoorsy) or Sephora (if you’re addicted to beauty). 

Tools enabling creators. We’re going to see more companies like Patreon, Podia (a WorkLife portfolio company), Substack, and Gumroad. While each platform has their own specific value proposition, their commonality is in helping creators monetize their knowledge and skills by helping individuals offer exclusive content through subscriptions or paid courses. We’ll see more companies like Beacons, an influencer marketing platform that lets creators monetize through short video interactions with their fans. Similarly, Bunches lets anyone set up and monetize a group chat about anything and represents a shift to more intimate communities. 

Tools for remote work. The rise of flexible work will correspond with the continued elevation of remote work. Flexible workers can increase their client base from a city to a country and beyond. Tools like Tandem (WorkLife portfolio company) will provide a means to connect remote collaborators through a virtual office. Additionally, collaborating with anyone you want, regardless of their time zone, is increasingly possible with asynchronous tools.

Communities will be the new professional networks. I’ve suggested that the next professional network will look nothing like LinkedIn. Communities like Dev.to, Elpha, Girlboss, Webflow Community, and Lunch Club (all WorkLife portfolio companies) will redefine what networking for a job and connecting with prospective employers and employees looks like. These communities will serve as a place to find high skill gigs, potential collaborators, and prospective clients.

Tools to showcase work. We’ll see more tools like Dribbble and Behance for showcasing design work and platforms like GitHub for documenting open source contributions. Aside from work specific tools, we’ll see new platforms that are co-opted to showcase professional work (e.g. Instagram). 

Tools unbundling Patreon. Currently the platform is a catch-all for creatives – visual artists, writers, gamers, and everyone in between. Offshoots of Patreon that are niche-specific will arise (e.g. “Patreon for Academics” or “Patreon for Singers”).

Tools to start a business, quickly. The rise of flexible work means more Founders. We’ll see services to reduce the overhead, cost and complexity of starting a solo business (e.g. Stripe Atlas for Creatives).

Three Predictions on the Future of Flexible Work

It’s not only novel tech that will emerge as fixtures of the flexible work revolution. We’ll see a renaissance that extends beyond SaaS tools and permeates into the economy, physical spaces and how companies do business.

  1. We’ll see innovative healthcare plans to support freelancers. One reason people cite for not starting their own business is losing their employer provided healthcare. Private insurance remains complex and often out of reach. New developments in health care plans for freelancers will provide a corresponding boost in the economy as people start businesses, find success, and go on to hire others.

  1. Physical spaces for creatives. As flexible work makes traditional offices less important, people will still want a place to connect with peers and network in person. Despite the fall of WeWork, franchise and independent creative spaces, like The Wing and Ethel's Club, will continue to pop up as less people work in traditional offices. Big events like ComicCon, Vidcon, and the Girlboss Rally will grow in significance and act as modern day pilgrimages where individuals can congregate annually with like-minded people to discuss their passions and find new inspiration.

  1. Traditional companies will compete more aggressively for talent. Both legacy institutions and startups will compete more aggressively for talent as the power shifts increasingly to highly-skilled individuals. Similar to the Screen Actors Guild in Hollywood, industries like software development and design are seeing their own guilds and collectives form – both as a professional network and a trusted source of information on fair pay and labor rights. Moonlight, a professional community for software developers, helps professionals find jobs and engage with other remote developers. Employers will need to offer greater schedule flexibility and soften non-compete clauses to allow for side projects. The 2016 Deloitte Millennial Survey found “75 percent would like to start to, or more frequently, work from home or other locations where they feel more productive.” We’ll see companies try to turn full-time employment into flexible employment by offering more remote work opportunities. Employers will also turn to services like Dover (a WorkLife portfolio company), to increase their talent pipeline and staff talented employees.

I’d love to hear your thoughts on flexible work and new tools enabling more creative and flexible work. Say hi on Twitter: @briannekimmel