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

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Talent Tip #164: Dating and Side Hustles: It’s Complicated – Part II

August 27, 2024

Last month’s newsletter article broached the hot topic of side hustles. Among other things, we talked about how not everyone is okay with sharing and that transparency is critical from the start. We also discussed how the substance and timing of the side hustle can make or break a situation.

But there is more to discuss! So here we are with Part II!

  • You can’t be two places at once. Picture this: you are single and a cute co-worker asks you out. Naturally, you say yes. But what if the smokeshow from your dodgeball league (whom you’ve had your eye on for weeks) also asks you out for the same day? Now what?

    Now you have a problem, my friend.

    Ditto for side hustles. What if your side hustle boss wants you to be in Poughkeepsie for a big event on Thursday? And then what if your full-time boss needs you to be in Seattle that same day for an important conference?

    You can’t be in two places at once, and one of your jobs has to take priority.

    Understanding which role will get priority is a must for any hiring manager who is considering hiring someone with a side hustle. (Hint: most hiring managers aren’t going to want to play second fiddle if they are hiring you for a full-time role.)

  • Everyone wants more of your time, but unless you’re a vampire, you also need sleep. I remember talking to one of my single guy friends back when he was on Tinder, Bumble, Hinge, and Match. His dating schedule sounded more convoluted than managing a carpool for a herd of tweens. I truly don’t know how he had enough time in the day.

    Now let’s consider side hustles. Regular jobs require about 40 hours a week, right? But many of them will have busy seasons that necessitate more. And, of course, some jobs regularly require more than 40 hours…50, 60+ hours is not uncommon.

    Imagine putting a 20-hour-a-week side hustle on top of that. Or what if it’s more? A candidate recently explained that his side hustle job takes up at least 20-30 hours per week! I’m no math major (art major, if you’re curious), but 40 + 30 = 70. That’s a lot of hours. And during busy times, it’s going to be more like 60 + 30 = 90. I hope the candidate is a vampire because there won’t be much time to sleep.

    Job seekers with side hustles and hiring managers need to have very honest and open conversations about the hours required for both roles and how those hours might ebb and flow over time.

    (Pro tip for hiring managers who encounter job seekers with side hustles that require more than 30 hours/week: wear a garlic necklace and keep a crucifix in your desk drawer. Just trust me.)

  • Conflicts of interest can ruin a good thing. On one of our first dates, I learned my now-husband didn’t like dogs. I almost pulled the plug right there. How can someone not like dogs? Maybe not all of his neurons are firing? It’s almost worse than being a progressive!

    But it turns out that he didn’t actually dislike dogs; he just never had one growing up. So, he didn’t understand what he had been missing out on. I introduced him to my beloved beast and the rest is history. Thankfully, our canine conflict of interest was short-lived.

    But it’s a good reminder for hiring managers to explore potential conflicts of interest with job seekers (and for that matter, current employees!), especially as it relates to side hustles. What if your potential marketing director’s side hustle is to create marketing materials for similar organizations? Or what if your future event planner’s side gig is to plan events for other organizations in the liberty space? And what if your soon-to-be development writer’s side job is writing Shakespearean copy for similar organizations competing for the same donor dollars?

    Pro tip: organizations might want to consider conflict of interest policies as well as non-disclosure agreements to mitigate risks.

We hope these thoughts on side hustles (and dating!) prove useful as you navigate the job/hiring market.

And if you do run across any liberty-oriented vampires who require no sleep and can work 90 hours a week, please have them send us their information here!

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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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