A six-figure freelance coach shares how workers should prepare for the inevitable shift in side hustles

LinkedIn cofounder Reid Hoffman once predicted in an interview that the traditional 9-to-5, where workers have one stable job, would be extinct by 2034 and replaced with people working multiple roles across several industries.

Hoffman’s comments recently gained fresh steam on X, formerly Twitter, and are completely in line with many American workers, including Hannah Dixon. Dixon makes six figures as a virtual assistant (VA) and freelancer coach and has freelanced full time exclusively from her laptop for the last 11 years.

The 36-year-old business coach said she’s been gearing up for an “inevitable shift” in how work will operate since 2014. Essentially, Dixon believes that by building a side hustle, or portfolio career, now, people can develop skills, networks, and income streams that will serve them well in an uncertain future.

Freelancing and side hustles are becoming necessities.

Over the past decade, Dixon has trained around 35,000 people to build successful freelance businesses, whether full-time or as a side hustle.

“I’m preparing people for the shift we’re now seeing, where freelancing and side hustles are no longer just an option but a necessity for financial security and independence,” Dixon said. “All workers should be preparing themselves for the monumental shifts taking place by at least exploring a side hustle.”

Upwork’s latest data shows that nearly 64 million Americans — representing nearly 40% of the entire US workforce — have undertaken freelance work. Stats like these further reiterate the growing recognition of the importance of having multiple income streams.

Gig workers shouldn’t rely on a single platform for clients or jobs

While many who explore freelancing initially turn to gig platforms like Upwork or Fiverr, Dixon maintains it’s important not to be overly dependent on them.

“Just as I advocate for not relying solely on a traditional 9-to-5 job, I also teach side hustlers and freelancers to diversify beyond a single platform,” she said.

Instead, she advocates a strategy of decentralizing the work, which means building multiple income streams, honing a personal brand, and creating direct strategic relationships with clients and collaborators. This approach protects against the risks and limitations imposed by any one platform.

Dixon also uses this strategy in her freelance career. She’s worked with multiple clients on long-term retainers, which helped diversify and stabilize her income. She also offers consulting services, maintains key affiliate partnerships with relevant software, develops informational products based on the expertise she’s gained throughout her career, and is compensated for speaking engagements.

Digital side hustles are great for people who work in tech

While many of her VA students have been victims of volatile layoffs, particularly in the tech industry, Dixon pointed out that tech workers are particularly well poised to succeed with digital side hustles — like freelance web development, app development, tech support, product development, or starting a blog or YouTube channel — since these naturally align with their skills.

And there’s money to be made as a freelancer. Zip Recruiter reports that freelancers in the US earn nearly $100,000 a year on average, and some rake in as much as $275,000 in salary — good news for current and prospective side hustlers.

It’s never all smooth sailing as a freelancer

Dixon admitted that while it’s easy to talk about the myriad benefits of freelancing, “it’s never all smooth sailing.” The lack of benefits such as healthcare and paid leave, and the isolation that can come with working solo, top her list of cons.

“The main challenge is the discomfort of doing things differently and taking ownership of tasks that have been covered by 9-to-5s traditionally, like managing finances, taxes, healthcare, and client acquisition,” Dixon said.

However, she emphasized that there are solutions. For example, she partners with a professional who helps her freelancers and entrepreneurs obtain appropriate health coverage. And for freelancers who feel their lifestyle is too insular, Dixon encourages them to attend holistic events and experiences to connect with others.

Workers need to learn more to earn more as freelancers

In the short term, these colossal workplace changes will create new challenges, some of which we’re already seeing. As Dixon puts it, just getting an interview feels a little like “The Hunger Games.”

Also, the rise of AI and automation means that many traditional jobs may not exist in the coming years — particularly in service industries.

With this in mind, Dixon suggested leaning into reskilling and upskilling, knowing that in this field, the more you learn, the more you earn.

People without side hustles could struggle

Ultimately, Dixon stands by the idea that everyone should have a side hustle. The shift to a predominantly freelance workforce may be devastating for those who fail to explore a portfolio career and use their skills in new ways.

“If you’re not at least working toward a nice little side hustle for yourself, you’re going to struggle in the coming years,” she said.