Gigs, Moonlighting, Side Hustles, and Passion Projects in Jewish Professional Life
By Doron Kenter
A 2019 study found that nearly half of all millennial workers (48%) earn income through various “side hustles.” Although we can’t know for sure how many Jewish communal professionals have gigs on the side, it’s probably not pure speculation to suggest that it’s a meaningful (and likely growing) number. And perhaps the time has come to think more seriously about what that means for all of us.
Call them what you will: Moonlighting, after-hours jobs, side hustles, and passion projects are a reality of life in the Jewish community. There are benefits and drawbacks to this reality, as well as some steps that our organizations might take to protect themselves, stay on mission, and support their work force.
(But first a caveat: this discussion is limited to arrangements in which a person has one “primary” job and is or might be paid by another organization for additional “after-hours” work. Freelancing as one’s primary occupation may pose some of the same questions, but is sufficiently different as to warrant exclusion from most of this discussion (unless otherwise indicated). And volunteerism is an important value that may raise other questions, but it creates a different set of obligations and expectations, much the way that one who rents has different obligations from one who borrows – see chapter 8 of Tractate Bava Metzia, or wait for Daf Yomi in June 2024…)
First, the Benefits
There are real benefits to the existence of so many opportunities for side projects. Not-for-profit organizations can fill in the gaps of their ongoing projects via contract workers who may provide services for a week, a month, or a year, or on an occasional basis. This (together with freelancers more broadly) can allow organizations to be significantly more nimble, paying fees for services provided, rather than maintain ongoing liabilities on their balance sheets (or be forced to hire and fire employees willy-nilly). And some organizations/roles simply aren’t full-time jobs – Sunday school teachers, scholars in residence, teen engagement, etc.
Moonlighters can make money on the side, helping to support themselves and their families on a not-for-profit salary, and can take these projects on as and when schedules and life commitments permit. This supplemental income is often critical in making ends meet and should not be taken lightly.
Additionally, these side projects can also help employees to develop new skill sets, build networks, and get to know organizations outside their day-to-day work. And a “9-5” (or some other “primary” job) can help to pay the bills while employees develop coherent plans for their own new and exciting projects. Contract work can also help to support an increasing number of workers who prefer flexibility and autonomy over steady income and traditional work environments. To be sure, these are good things.
On the other hand, there are also important considerations to take into account in the Jewish gig economy. Some are systemic ills that may not be easily cured by one organization’s practice or policy, while others are critical challenges that should be faced head on by employers and employees alike.
The gig economy can enable not-for-profits to avoid paying living wages to their staff, instead relying on a cadre of quasi-employees who, on the whole, are forced to cobble together various jobs to make ends meet – some of whom may be full-time freelancers, and some of whom have “primary” jobs but need, or choose, to take on additional work. Moreover, an excessive reliance on contract workers may result in a not-for-profit regime with less job security and, in some cases, unavailability of health insurance, paid parental leave, professional mentoring, office space and colleagues, and technological support (among other things).
Moreover, moonlighters of all kinds need to be constantly hustling to line up the next project. Many of these “gigs” might not be listed publicly on job boards and might simply be channeled to people within a limited network, so the work only flows to those who have access to the right people. (Indeed, the issue of access is one that warrants its own investigation and discussion.)
While all of these side hustles can create significant flexibility in work and life, the constant hustle may be exhausting. Data not being readily available, it’s hard to know what effect this may have on duration of employment, but it’s certainly plausible that there is volatility in the part-time job market, yielding shorter terms of employment and more frequent searches for talent and any requisite onboarding or learning curves, yielding less overall stability in the industry. This may be true of both freelancers and those whose primary job necessitates taking on supplemental work.
Oversight and Accountability
The Jewish gig economy may also reduce the community’s ability to oversee various part-time employees and contract workers. Although it may be preferable in certain respects to hire contractors rather than employees, the distinction does not allow organizations to abdicate their legal and ethical obligations to ensure that its agents act properly. (Consider, for example, the troubling data about Uber and other ride share apps.) Even with background checks and reasonable oversight, it is inherently more difficult to ensure that suitable people are being hired and conduct themselves appropriately on and off the job.
Loyalty and Institutional Integrity
There is an inherent risk that otherwise “full-time” employees may leverage their primary employer’s brand, office space, or other resources in furtherance of various side gigs or unrelated, unsponsored passion projects. Indeed, Yuval Levin has suggested that this trend of leveraging an institution to advance a personal brand has compromised communal and collective faith in our core institutions. But we needn’t be quite so apocalyptic to recognize that an institution’s interests may not always align with those of its employees – all the more so in situations where workers wear multiple professional hats, where use of company resources may not always be in service of the company providing those resources or that platform.
Similarly, how should we be treating side projects, speaking opportunities, consulting, or other engagements? Even if those are done “off the clock,” those projects and appearances will likely be associated, to some extent, with the individual’s primary employer(s). Logistically speaking, if Leah, an executive at Organization A, does a scholar in residence weekend at Synagogue B, is that in furtherance of Organization A, or is it a side project warranting separate payment to Leah for services rendered? (Interestingly, if it’s in partial or complete furtherance of Organization A, should Synagogue B be paying Organization A? Paying the executive? Or is the project an investment by Organization A in furtherance of its own marketing, development, or recruitment goals, with the cost borne by A as a function of Leah’s professional responsibilities? These questions warrant further discussion in their own right and might warrant a separate analysis in its own right – do reach out if you have any thoughts or experience with this!)
Even worse, we should be careful to not create a regime in which an individual who is compensated by a third party organization feels explicitly or implicitly duty-bound to steer work, contracts, or partnerships to that organization. And even in the absence of a quid pro quo, we must be aware that these various paid engagements can put people and institutions in uncomfortable situations and, at a minimum, may raise the “appearance of impropriety” – even if, in fact, there is no actual impropriety.
Although there may be some insulation from such conflicts if a school teacher tutors students from another school district on the weekends, this fear of explicit or apparent conflicts of interest becomes that much more relevant in our relatively small Jewish world.
Creative Bandwidth and Professional Development
A significant amount of the work being done within our world requires meaningful investment of time, as well as mental and emotional bandwidth, beyond the formal project at hand. How do we consider growing our network and skill set to advance our careers while maintaining fealty to our employing organization(s)? Perhaps even more importantly, where are we devoting our creative energy? How are we using the “thinking time” that so many of us while waiting at a red light, out for a morning run, or sitting through a less-than-engaging seminar? When we’re reading the latest in best practices, are we considering how to use that for one job or another? These are thorny issues that we are must grapple with, but they become more pronounced in a gig economy where primary employment and side hustles may not be quite so distinct from one another.
It is not my intention to suggest that additional income is not absolutely essential to a great number of people working in the Jewish communal world. Rather, I am simply hoping to suggest that in this context, ignorance is not bliss. A “don’t ask; don’t tell” policy may inure to a given employee’s benefit for some period of time, but it is rarely a sustainable and responsible way to conduct business. Company policies might be flexible, but they should be clear, as should Boards with CEOs and managers with those who report to them.
To be clear, there is no one right way to address the burgeoning Jewish gig economy. Indeed, some considerations are best addressed through formal policies established by boards and managers, and some are best navigated on a case-by-case basis, or in each person’s exercise of their best judgment. Perhaps some policies or practices are suitable for senior executives, while others should be made applicable to employees who do not represent the foremost public face of an organization.
Merely to get things started, consider the following questions:
Are employees being paid fair wages for that which is expected of them?
- Is a particular position expected to be the employee’s exclusive [paid] job? If so, what does that entail? Is the employee being compensated fairly, especially given that she might be forced to forego other paying gigs or to direct honoraria to her employer?
- If funds aren’t available, can hours or days per week be reduced, while maintaining the same pay for the same (or better) work? If additional hours are made available, should there be parameters regarding the types of acceptable after-hours jobs?
When employees take on responsibilities outside normal business days or hours, are those responsibilities “on” or “off” the clock? For example, if an employee is hired to staff an Israel trip, is that considered time off? Work time?
- Who gets paid for this time and the prep work? What about follow-up work with trip participants?
Should employees be permitted to use their employer’s resources in furtherance of side jobs or passion projects? (E.g., computer equipment, printers, subscriptions, office space, etc.)
Does the employer want to create time and space for personal R&D for new projects? If so, does the employer have any rights to those programs, technology, research, or other materials? A right of first refusal?
For both paid and unpaid volunteer work, when should employees be permitted to use their titles and/or the names of their employing organization (in bios, on other websites, in written communications or marketing materials, social media, etc.)?
- What about political activism? Signing petitions? Making public pronouncements on issues related or unrelated to the employer’s mission?
Should the employer’s permission be required to participate in cohort programs, professional development, etc.?
What approvals should be in place to make these various determinations? Direct managers? Employees’ discretion? Is board approval required in certain instances? What about funders or other stakeholders?
This is, of course, only the tip of the iceberg. And many of these issues are not new – Jewish clergy, educators, and professionals have always worn multiple hats. It was not my intention here to lay out all of the opportunities and considerations inherent in the Jewish gig economy, but rather to continue a conversation and raise some questions that should be taken into account within this complex Jewish communal landscape. Tze u’lmad – let’s go and learn.
Doron Kenter is a Program Officer at Maimonides Fund.
 See Amanda Dixon, “Survey: Nearly 1 in 3 side hustlers needs the income to stay afloat,” June 5, 2019, available at https://www.bankrate.com/personal-finance/side-hustles-survey-june-2019/
 See Beth Braverman, “Starting a Side Hustle? Here Are 5 Gig Economy Myths You Can’t Afford to Ignore,” USA Today, June 20, 2019, available at https://www.usatoday.com/story/money/2019/06/20/side-hustles-5-gig-economy-myths-you-cant-afford-ignore/1508341001/
 See also Levin, A Time to Build, Basic Books (2020), especially pp. 117-136.