Tech and the Gig Economy: Understanding Side Hustles vs. Moonlighting

For the past 10 years, Dannie Fountain, a senior software engineer sourcer at Google, has managed a full-time role and a side job as an HR consultant with differing levels of support from her managers.

“At a job I had previous to Google, my manager used to call it Dannie International, LLC, and it was like a running joke,” said Fountain of her HR consultancy, Focused on People. “Very infantilizing, which in hindsight is hilarious, but in the moment, sucked. All of my Google managers have been super supportive.”

Whether they like it or not, company leaders need to recognize that their full-time employees might want side hustles or moonlight gigs. One in three Americans have a side hustle, according to a 2021 survey of 2,001 employees by Zapier, and Upwork says that number is even higher with 59 million Americans — or 36 percent of the workforce — freelancing in 2021, according to its “Freelance Forward 2021” study, surveying 6,000 U.S. working adults.

Even as gig work becomes more commonplace, there are best practices that employees who want to side hustle or moonlight should consider in order to manage both their full-time work and side jobs. Experts in HR and business, as well as tech employees with side gigs, share their advice on how to take on a side hustle or start moonlighting.

 

What’s the Difference Between Moonlighting and Side Hustles?

Moonlighting is the concept of having a second job that you work outside your full-time job, typically at night. It can be another full-time job or a supplementary part-time job. Side hustle refers to work performed for income supplementary to one’s primary job – it’s more associated with contract or freelance projects. 

“Side hustle first existed as a term in the 1950s. [It] was a much more passive activity. Mowing your neighbor’s lawn on the weekend was a side hustle, and moonlighting originated as like truly holding a second job with the intent of producing income,” Fountain said.

Moonlighting and side hustles in tech were the topic of Fountain’s thesis for her PhD in human resource management. Through her research, she discovered that while the terms originated as two separate concepts, they are now essentially the same.

“More present day, the two get used interchangeably. Side hustle is now seen as what moonlighting used to be, and whether you’re doing something for the love or the money, both terms get used now,” Fountain said. 

Fountain’s side hustle mostly involves working with clients on employee engagement, but she also does speaking engagements and has a book coming out this fall. Fountain said she identifies as a side hustler, but if someone called her a moonlighter, she “wouldn’t even blink at that.”

Both side hustles and moonlighting are considered part of the gig economy, which the IRS defines as freelancers or contractors who earn income by providing on-demand work, services or goods (and would typically receive a 1099 tax form). Gig economy income can include using applications and websites like Uber, Instacart, Fiverr and Etsy to sell services or goods. It also can include short-term assignments like providing creative or professional services as a consultant, independent contractor or freelancer to a company.

“I think it’s just a way to describe individual transactions within that ecosystem … The gig economy incorporates all of this,” said Joseph Fuller, professor of management practice and co-director of the project Managing the Future of Work at Harvard Business School. 

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Why Do People Choose to Side Hustle or Moonlight?

Fountain has always viewed her side hustle as a secondary income generator. She relates to the increasing number of people who want to diversify their income sources, she said. 

“At-will employment is a scary thing … I never wanted to be ‘left holding the bag’ if I was terminated for any reason,” Fountain said. “It’s always been like a safety blanket that I really enjoy.”

Some people pursue passion projects as their side hustles. Lindsay Kopit, territory manager at CRM platform company, HubSpot, took advantage of the company’s unlimited vacation policy to spend three weeks pursuing her interest in film as a production assistant on the forthcoming feature movie, “Gemini Lounge.” 

“Every time I talked to people on set about how my job was supporting me through this, they were so impressed and shocked and had never really heard of a company supporting employees in this way,” Kopit said. “I feel just extremely lucky, and the fact that my pay and my job hasn’t been impacted by being able to pursue my passion, I’m so, so grateful for that.”

While filmmaking is one of Kopit’s passions, she’s happy to pursue it on the side and keep her full-time tech job.

“I really value the stability of my tech job. I think the film industry … you don’t always know when your next project is going to be. There’s a lot of unknowns. There’s really no benefits,” she said. “Things like having benefits, having a stable income, being able to travel — these are all things I really value, so I would be very hesitant to give up my job in tech. Also, I love my job. I really do, so continuing to pursue it on the side would be the dream as long as I can swing it.”

Others use their side hustles to shift their career focus or to gain exposure and share their expertise with a larger group of people. Like many people participating in the Great Resignation, Ricklyn Woods reevaluated her career in 2020. After spending 16 years in HR, she reflected on what was really making her happiest in her job, and she realized that it was career advising and coaching people.

So, in 2020 Woods launched her own career coaching practice and started a podcast called “So You Want to Work in HR?” Her full-time job is working as a career advisor at the University of Phoenix.

“Like a lot of folks, I was just overwhelmed with things during the pandemic, and I said, what am I really passionate about doing and really did a self assessment.”

“Like a lot of folks, I was just overwhelmed with things during the pandemic, and I said, what am I really passionate about doing and really did a self assessment,” Woods said.

In the past, Woods has moonlighted as a hairdresser. While she doesn’t style hair anymore, she keeps her license up-to-date as a backup way to earn income, if needed.

“I also think there’s an understanding that the economy that we’re just in right now, people need more than one source of income.” Woods said. “So, I think leaders are much more likely to be supportive as long as there is no conflict of interest because people have things that they need to do that maybe that one income won’t support.” For Woods, her side hustle helped her pay for her son’s tuition while he was in college. For others, side hustles can help them save for homeownership, she said, or moonlighting can help employees pay for activities for their children, for example, Fuller said.

Jodi Brandstetter, author of “Hire By Design” and founder of talent acquisition firm, Lean Effective Talent Strategies, said she’s always had an entrepreneurial spirit, so she built her business on the side while she was employed full-time. Earlier in her career, she also did event planning as a side job that her full-time employer supported, even offering her training in this area to support both her full-time work in this field and her side hustle.  

“I literally created my business while I was still full-time,” Brandstetter said. “So, I started building the foundation. I didn’t take on work, but I was building my foundation for my business, so that once I said I’m going to leave and do this, I already had so much stuff already ready for me to feel a bit more confident in pulling the trigger of becoming a full-time entrepreneur.”

Trading cryptocurrency can even be considered a side hustle, which is something Jason Palmer, co-founder and CEO of the ATS platform Bear Claw, does at night, in addition to recruiting for his second company, Next Level Recruiting. His employees have side hustles in crypto and sell NFTs on the side, too.

“I don’t think they realize how good they have it because it’s kind of a hobby, but it’s also a side hustle for them because they’re making money,” Palmer said. “Because of the way things have evolved since the pandemic, people are overall just even more connected with their devices. Technology makes it easy to engage in these activities right from your phone if you’re done looking at the computer for the day. It’s just a very, very perfect situation to happen.”

 

So You Want to Side Hustle or Moonlight, What Next?

Before pursuing side hustle opportunities, an employee should evaluate whether or not they have the time and resources to dedicate to a side job outside of their full-time job. Can they manage both opportunities without a conflict of interest, decrease in work performance or unsustainable impact on their personal time? 

“I think you have to really be honest with yourself. Do you have the capability of doing a full-time part-time job and moonlighting?” Brandstetter said. “If you have family, are you going to be willing to take time outside of your normal schedule to do that work? If you’re not, then maybe you need to have a conversation with yourself about, ‘Do I need to be moonlighting or should I be looking for a new job? Is this more of I need to change my full-time job because I’m not satisfied versus trying to add on to what I already have on my plate?’”

If an employee’s desired side hustle is at all related to their full-time job, they should let their manager know about the situation. However, if they spend their days coding and sell hats they knit on Etsy on the side, it’s probably not necessary to tell their full-time employer about their supplemental income. But if there are any doubts or they want to err on the side of transparency, it’s best practice to disclose.

“If you’re not sure, then you should ask. If you think baking cookies might be a conflict of interest with whatever you do — I imagine if you work for a cookie company, you might not be able to bake cookies and sell them on the side — so it’s really going to depend on what you do,” said Ricklyn Woods, career adviser and podcast host.

“If you are baking cookies on the weekend and selling them as part of your side hustle, I don’t think you really need to disclose that,” Woods said. “If you’re not sure, then you should ask. If you think baking cookies might be a conflict of interest with whatever you do — I imagine if you work for a cookie company, you might not be able to bake cookies and sell them on the side — so it’s really going to depend on what you do.” 

At Google, Fountain said there’s a trust and safety committee that evaluates employees’ intellectual property and outside engagements, which is common at tech companies. When talking to a manager and HR about side work, employees should be prepared to demonstrate how the side work they’re proposing won’t be a conflict of interest. Plus, they’ll need to show that it won’t take up company time or resources. The company’s HR or conflict of interest team will then evaluate whether or not there is any issue with the employee side hustling or moonlighting and then lay out any company policies around supplemental employment. 

“I think since there’s nothing to be embarrassed about, I think that on the whole, employees are better off asking what the company policy is and understanding that,” Fuller said. “If you start getting, ‘Absolutely you can’t do that — you have to be heart and soul to the company,’ then you’re learning something about your company, and maybe you don’t want to work there.” 

 

What Policies Should Side Hustlers and Moonlighters Expect From Their Full-Time Employers?

Full-time employers will typically have some standard rules around pursuing supplemental employment. 

For example, Woods isn’t able to consult with University of Phoenix students through her private practice. Fountain’s side hustle can’t be in the hiring space since she works as a talent sourcer for Google. That’s why she keeps her work very clearly in employee engagement — she can’t help her clients with executive searches or anything related to recruitment. 

“Who cares what someone is doing on Saturday or on Friday after four o’clock if they’ve done a good job for the week, and you’re happy with them? Just enough already. You don’t own them body and soul.” Joseph Fuller, Harvard Business School professor 

“I think if you clearly define what your policies are, it makes it really easy for both parties. If you set the conversation up as consultative not punitive, you’re encouraging your employees to disclose,” Fountain said. “So, it shouldn’t be a ‘you cannot.’ It should be, ‘We love seeing our employees grow. Here are the parameters.’”

 

How Do You Keep Your Full-Time Job and a Side Hustle?

Kopit was able to pursue her passion project in film and meet her sales targets with support from her manager. “He’s known this is a passion of mine, and he basically was like as long as you continue to perform and hit your number and hit your quota, then let’s figure this out.” 

Her manager helped close her deals that were on the finish line during her three weeks on set, and a teammate helped manage new leads that came in, splitting any deals that closed. Kopit occasionally took a call while on set, but generally, her three weeks working on the movie were treated as vacation. 

“I wanted to make sure our team and my specific target wasn’t impacted, and basically, the business wouldn’t know I was gone,” Kopit said. “I ended up hitting my target and still making my quota by just figuring out those logistics.”

Kopit stresses the importance of being transparent with managers about both personal and professional goals and creating a plan to show them how work performance will be maintained. 

It should be “church and state” between a side hustle and a full-time job, said Fountain. “Don’t do both activities on the same device,” Fountain said. “While it’s okay to have ‘bleisure’ like business trips that also are leisure, do not make a trip that your corporate employer is paying for splash into a conference for your side hustle. That you can’t be doing.”

Time management and maintaining a clear division of the time spent at a full-time job and a side hustle are key to making this sort of arrangement work. Fountain said she marks her working hours on her Google Calendar, so it’s clear when she’s spending time on her corporate job versus doing side hustle work.

“Be really clear about your time,” she added. “If you’re an hourly employee at your main job, this gets easier because your hourly timesheet says this is what I worked for you, and then you can say these are when I did side hustle activities. If you are salaried, it’s a lot harder because you’re just getting paid to get your job done.”

It gets even more complicated if an employee is trying to hold down two full-time jobs, which some people have been able to manage with fully remote work. Employees need to be able complete both jobs on separate schedules. 

“There are multiple instances that I’ve heard of people who have two full time jobs,” Fuller said. “They’re basically doing the same thing for different companies because it was distance work.”

As companies go back to the office, Fuller anticipates that it’ll become harder to be over-employed, but smart employers will be setting up policies in anticipation of these situations, so employees can know the rules they need to follow, he said. 

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How Can Companies Support Employees Who Want to Side Hustle or Moonlight?

Employers should be open and clear about their policies around moonlighting and side hustle opportunities, Fuller said.

“It should mostly be basic, very simple, commonsensical rules, and otherwise, just don’t sweat it,” Fuller said. “Who cares what someone is doing on Saturday or on Friday after four o’clock if they’ve done a good job for the week, and you’re happy with them? Just enough already. You don’t own them body and soul.”

Fountain said conflict of interest evaluations often aren’t neutral — the company has to look out for its business during an internal review process. That’s why it’s important for employees to be extremely clear about how they delineate their full-time and moonlighting gigs. 

“If you as an employee are working with someone employed by your employer to define whether or not what you do is moonlighting, they have a clear remit to decide more conservatively in favor of the business,” Fountain said. “So, an outside third party might say what you do isn’t a conflict, but the internal team might say it is.”

Tech companies could take a note from higher education where sabbaticals and leaves of absence are common practice and allow professors to pursue side projects. Hakim Weatherspoon, a computer science professor at Cornell University and CEO and co-founder of Exotanium, a cloud resource optimization and management platform, was able to use his leave from his professorial job to build his startup based on the research he conducted at the university.  

“It’s a lot of personal time in order to do that, but fortunately, the universities have a lot of support to convert research into practice in the business,” Weatherspoon said. “Creating this company now would never have happened had I not done the research and have taken some risk in actually creating that.”

 

Potential Mutual Benefits of Side Hustles and Moonlighting 

Employees might even be able to bring new skills and experiences from their side hustles to their full-time employers.

“If they’re wanting to gain experience, and it could benefit both the employee and the employer, there really shouldn’t be a reason why a company should be hesitant about it,” Brandstetter said. “If you give them that space to do it, they probably will stay with you longer.”

“If your employees feel like they can pursue a passion and really be themselves at work … if they’re happy, they’re going to stay,” said Kopit.

Kopit agrees that allowing employees to have side hustles plays a role in retention. Employees are less likely to leave if they feel supported to pursue their outside interests and feel free to have side gigs, she said. 

“If your employees feel like they can pursue a passion and really be themselves at work … if they’re happy, they’re going to stay,” Kopit said.  

An employee’s side hustle not only can help them gain greater exposure personally, but it also might end up helping the full-time employer with more publicity too.

“If the employee is building a thought leadership brand for themselves, that only benefits you,” Fountain said. “Senior leaders in companies so often go out and speak at conferences to build the company name. Someone lower level doing that hopefully is only beneficial.”

Side hustles can push people to get out of their comfort zones and to share their skills to make a difference on a larger scale, Weatherspoon said.

“In computer science, our students, they graduate, they make $120,000. That’s a lot of money … Why would you do anything else?” he said. “Something that I like to tell my students or people in general is that you need to go outside your comfort zone to maximize your potential.”

 

The Future of Gig Economy Work

Fuller predicts in the next 10 to 15 years that side hustles and moonlighting won’t be viewed so much as special situations that companies need to contend with — employees will have all sorts of different flexible situations.

“Most companies are going to have 10 or 15 kinds of archetypal employment relationships with people, which won’t be strange and exotic where HR is pulling its hair out,” Fuller said.

One potential example he gives is an employee near retirement who might spend Memorial Day through Labor Day with their grandkids while they’re out of school and is only available for calls one day a week during that time. Another potential situation could be a new mother who has complete schedule integrity — there won’t be unplanned travel, but they will be unavailable before 9 a.m., and certain days of the week, they will need to be offline by 3 p.m. due to splitting caretaking responsibilities with a significant other. 

“Your supervisor knows that and your team knows that, and everyone’s happy for you,” Fuller said. “The ability to be flexible is — for the companies that figure this out faster — going to be, I think, material in terms of getting people to join you and then stay.”

The reality is that people have interests beyond their full-time jobs, and part of work-life balance can be accepting that and supporting employees with their outside interests. Ultimately, if any employee really has an interest in earning income outside of work, they’re probably going to do it anyway. 

“If someone has a desire for secondary income, they’re doing it whether or not you’ve approved it,” Fountain said. “If your employee is doing DoorDash, you have the conversation, ‘Hey, outside work can’t affect inside performance.’ But unless you are Uber Eats, there’s not a conflict, so it shouldn’t be a big deal.”