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Talent Tip #163: Dating and Side Hustles: It’s Complicated Part I

July 23, 2024

Not sure if you’ve noticed, but side hustles are having a moment.

An increasing number of jobseekers these days have or are considering side hustles in addition to full-time jobs. The proliferation of virtual work has provided fertile ground for budding entrepreneurs to take on more than one opportunity.

And we’re noticing that both job seekers and hiring managers aren’t entirely sure how to navigate these uncharted waters.

If you’ll indulge me for a moment, I think there are some pretty interesting parallels between side hustles and my favorite topic: dating. Perhaps considering these similarities will be helpful to job seekers and hiring managers in this brave new world.

In fact, there is so much good stuff here we decided to make this a two-part series. So pop some popcorn, sit back, relax, and enjoy the first installment of Dating and Side Hustles: It’s Complicated.

  • Sharing isn’t everyone’s cup of tea. At some point in a dating relationship, the conversation about exclusivity comes up. In Millennial speak, it’s called DTR (Define the Relationship).

    For some people, the DTR occurs pretty quickly because they are only interested in an exclusive relationship. Meanwhile, others are happy to play the field indefinitely.

    And so it goes with side hustles. Some hiring managers are simply not going to be open-minded about sharing a potential employee’s time with another employer (especially if there are other promising candidates available who don’t have side hustles!). Meanwhile, other employers are willing to consider the concept as long as the side gig doesn’t interfere with the full-time job.

  • Transparency is essential from the start. Imagine you go on a date with a lovely girl who purports to be single with zero baggage. But what if, after several dates, you discover from another source that she is actually thrice divorced and has more baggage than Southwest and Delta combined? If the thought of being Lucky #4 isn’t enough of a buzzkill, the realization that she wasn’t forthcoming from the start ought to be.

    Side hustles are no different. If a potential employer finds out multiple interviews into the process that you have a significant side hustle, that might be cause for them to stop pursuing you. (We’ve seen it happen!) And Heaven forbid the employer finds out AFTER an offer has been made! Eeek.

    The best course of action is to be straightforward from the start.

  • The substance of the job matters. In theory, you would be happy to date a wildly successful business owner, right? But what if I told you the business was a puppy mill or a pyramid scheme? Rather than date the person, you’d probably prefer to kick him in the shin and report him to the authorities.

    Understanding the substance of the side hustle is just as critical. Is the side job completely unrelated to the full-time work? If so, that’s going to eliminate a lot of concern on the hiring manager’s part.

    As one nonprofit executive said, “No one cares if your side hustle is dog-sitting, wedding photography, or mowing lawns…unless you’re doing it in the middle of the business day.” And that caveat brings us to the next parallel.

  • When the work happens matters. One of my girlfriends married a cop who frequently works the night shift. They are hopelessly in love, but she will be the first to tell you that conflicting work hours presented major challenges for their relationship. When she’s at work, he’s at home. And when she’s at home, he’s at work. Date night is a struggle.

    Likewise, it’s going to be a tremendous hurdle if the hours of the side hustle conflict with the full-time job. Case in point, I spoke to three different candidates recently who indicated that their side hustles require them to work (at least occasionally) during regular business hours. And it won’t surprise anyone to hear that all three candidates believe this has likely cost them job offers.

    On the flip side, I recently interviewed a candidate with a side job that was relegated exclusively to the weekends. She wasn’t having any problems getting interviews and offers.

Ok, there’s so much more to say on this topic, but we’ll save it for next month’s newsletter. Meanwhile, if you have any suggestions or questions about the topic, drop me a note and maybe I can address them in Part II.

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About Us

Claire Kittle Dixon
Executive Director

Claire runs the day-to-day operations of Talent Market, manages searches for clients, and oversees the organization’s fundraising communications, technology, administration, and cat-herding efforts…
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Katy Gambella
Director of Outreach

Katy oversees Talent Market’s outreach to young professionals and manages the outreach team. She also manages searches and executes outreach directly herself…
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Stephanie Keaveney
Senior Manager of Outreach
Stephanie splits her time between managing talent searches for free-market nonprofits, maintaing Talent Market’s social media presence, and engaging in outreach to young professionals interested in liberty-oriented careers…
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Bailey Drouant
Project Manager
Bailey assists free-market nonprofits with their hiring needs by helping them manage the search process from start to finish…
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Savannah Rupp
Project Manager
Savannah channels her expertise to manage searches for free-market nonprofits, ensuring they find the perfect match to drive their missions forward. She also supports Talent Market’s…
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Wait, You’re a Nonprofit?

Talent Market is a nonprofit. We’ll wait here while that sinks in. We know it’s a crazy concept, but it’s been working like a charm since 2009.

Talent Market’s mission is to promote liberty by providing talent for critical roles within the free-market nonprofit sector.

We provide consulting and recruiting services at no cost to 501(c)3 nonprofit organizations that clearly and directly focus on advancing the principles of economic freedom, free enterprise, free trade, free speech, property rights, rule of law, and limited regulation. (We do not work with political organizations, organizations with mission statements that do not clearly advance free-market principles, organizations that focus on social issues, or organizations that have a focus outside of the United States. We are not a job board. ) 

Talent Market believes that the road to prosperity is paved with freedom and that the success of our movement hinges on the talent that will take us there.

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