Talent Tips - Talent Market

Talent Tip #168: What My Favorite Christmas Vacation Scenes Teach Us About Career Moves

December 18, 2024

My Christmas season isn’t complete without at least one viewing of Christmas Vacation. Clark taking a chainsaw to the newel post is a perfect metaphor for most of my holiday misadventures.

And it turns out that my favorite scenes provide some good lessons for job seekers. Just trust me on this.

Do some planning before you start your job search.
I love the classic scene of the Griswolds kicking off the fun, old-fashioned family Christmas by heading out into the country in the front wheel drive sleigh to embrace the frosty majesty of the winter landscape and select the most important of Christmas symbols: the Griswold Family Christmas tree.

Road trip? Check. Singing Christmas carols? Check. Trading obscene gestures with good ol’ boys and nearly colliding with a log truck? Check and check! Saw to cut down the Christmas tree? Of course not.

This reminds me of a call I got the other day from a candidate who was eager to talk about his next career move before he got too distracted with holidays.

Me: Let’s start with the basics. What type of role are you looking for?
Candidate: I dunno. I haven’t thought about that.

For the love of non-nutritive cereal varnish…how can your network help you find your next great job if you haven’t put any thought into it yourself? I’ll spare you the play-by-play of the rest of the call, but suffice it to say, he hadn’t thought about much beyond sipping eggnog from a reindeer-shaped mug.

Before you start tapping into your network and applying for jobs, be ready to answer these basic questions:
- What is your ideal next job?
- What are the skills you want to put to use in your next role?
- Why are you looking to make a move?
- When are you looking to make a move?
- When could you start a new job?
- What is your desired salary range?
- Can you relocate?
- What percentage of travel are you comfortable with?
- Who are your references?
Be patient.
There’s nothing better than Cousin Eddie showing up for the holidays (unannounced!) in his tenement on wheels. Whether it’s his dog Snots rifling through the garbage or Eddie emptying his RV’s black water tank into the public sewage, it’s more than enough to test everyone’s patience. Yet, somehow, Clark handles it with grace.

And if you’re job searching, you’re going to need Clark-level fortitude.

Job hunting can take months. After you submit an application, it’s likely going to take at least a couple of weeks, if not several, for the organization to make a decision about which candidates they want to pursue. And once the interview process commences, it can take several more weeks (or months!) for decisions to be made. And this doesn’t take into account unexpected delays, board meetings, organization events, holidays, hiring manager vacations, staff illnesses, etc.

But don’t get frustrated. Just because you haven’t heard from the organization within 48 hours after you hit send on your application doesn’t mean you’re destined to be a pixie-dust spreader on the Tilt-O-Whirl. These things take time.
Get it in writing.
Remember when Clark tells his family that he put a down payment on a pool before his holiday bonus came in…only to learn his bonus was a one-year membership to the Jelly of the Month Club instead of the big wad of cash he was expecting? Oopsy.

Well, I worked with a candidate once who was one of two finalists for a senior-level job with a nonprofit. Shortly before the organization made its decision, she withdrew because she had received a tantalizing verbal offer from the executive of a private sector company. Days later, the executive presented her with the written offer: a full $30k below what he said in the verbal offer.

Now, one might think that this executive is a cheap, lying, no-good, rotten, four-flushing, low-life, snake-licking, dirt-eating, inbred, overstuffed, ignorant, blood-sucking, dog-kissing, brainless, *******, hopeless, heartless, ***-***** bug-eyed, stiff-legged, spotty-lipped, worm-headed, sack of monkey***. And one would be correct.

Unfortunately, by the time this mess unfolded, the nonprofit had already filled its executive opening with another candidate.

Be sure you have what you need in writing before making a leap.
Appreciate what you have.
I’m not gonna lie to you: I get a little choked up when Clark gets trapped in the attic and watches those old reel-to-reel movies from his childhood. It’s such a good reminder of the blessings we have, even if it doesn’t always feel that way.

A couple of years ago, a friend of mine in the liberty space called to say she was frustrated with her job and was on the verge of leaving. I asked her a lot of questions about why she was feeling that way and made a few suggestions about things she might want to consider before jumping ship.

Months later, she called to tell me that our conversation had changed her perspective. She told me she had several key discussions with her boss and that a lot of things had improved — including her outlook. In short, she thanked me for helping her realize she was in an amazing place.

I know it’s really easy to get burned out in the nonprofit sector. And, of course, no job is perfect. But before you make a leap, don a (faux) fur coat, crank up a little Ray Charles, and think about the good stuff.

Happy job hunting, happy holidays, and Merry Christmas!

Talent Tip #167: Rizz meets Righteous: Finding the “Just Right” with Gen Z in the Workplace

November 19, 2024

Stephanie Keaveney

As the “middle child” on a five-person team at Talent Market, I get the best of both worlds—I equally enjoy my more senior colleagues’ Office Space jokes and my Gen Z colleagues’ daily contributions of slang and memes in the team chat. Working between these two groups has shown me just how different perspectives can bring out the best in a team.

But it’s not all smooth sailing. I’m often reminded of the story of Goldilocks and how it took a bit of trial and error to find the porridge, chair, and bed that were just right. In the workplace, the same goes for balancing Gen Z’s unique style with the needs of Boomer, Gen X, and Millennial managers. Here are some insights to help everyone find that happy medium—and work together like a team of fairy tale heroes.

Purpose, Not Just Jobs
Gen Z cares deeply about purpose and is motivated by seeing how their work contributes to the mission – in fact, a recent EY survey indicated that Gen Z ranks making a difference in the world and enjoying their work as significantly higher priorities than making a lot of money in their careers. And while they think titles and hierarchy are fine, what really drives them is feeling part of something meaningful, with their unique role highlighted as part of that bigger goal.

Goldilocks Tip for Managers: Be transparent with your Gen Z employees about how projects and roles fit into the mission. It’s not just about crossing tasks off a list—it’s about connecting each project to the impact your team is making. Remind them that even the smallest of tasks can be absolutely mission-critical.
Goldilocks Tip for Gen Z: Not every part of your role will be glamorous, fun, or have an immediate impact on making the world a freer, more prosperous place. Embrace a range of learning experiences, even if they don’t feel groundbreaking. After all, you are the most junior employees on staff and it only makes sense for your generation to handle a bit more of the gruntwork. Remember that learning every phase of the operation will be helpful for you down the line as you move up and expand your responsibilities.

Frequent Feedback, Not Constant Validation
Gen Z grew up in the world of instant notifications and validation in the form of Likes and Subscribes, so they often crave immediate feedback on both daily tasks and larger projects. And while it’s always been true that feedback is more effective when it’s timely and constructive, there is a difference between a good feedback culture and one of constant validation.

Goldilocks Tip for Managers: A quick check-in or comment can go a long way. Frequent feedback helps with course correction and keeps everyone engaged. And every bit of feedback and mentoring you give your Gen Z employees will hopefully make them more productive and valuable to the team.
Goldilocks Tip for Gen Z: Remember, feedback might not always come instantly, and that’s okay. Often, waiting allows for deeper, more meaningful insights that help you grow. And if you want feedback, ASK! But be ready for honesty. Your manager’s job isn’t to offer validation; it’s to achieve a mission (and ideally help you grow in the process!).

Efficiency, Not Shortcuts
Gen Zers might not be old enough to remember the origin of the phrase “There’s an app for that!” but they certainly have grown up in a world where there really is an app, tool, or platform to solve most of life’s problems.

That means our Gen Z colleagues are often quick to spot ways to streamline workflows, bringing a fresh perspective on efficiency. But sometimes, what seems like a shortcut can miss the bigger purpose behind an established process.

Finding the balance means appreciating Gen Z’s knack for innovation while ensuring quality and structure don’t get lost.

Goldilocks Tip for Managers: Stay open to Gen Z’s ideas on efficiency—sometimes a small tweak or using a new AI-powered tool can make a big difference. Just because you’ve always done it that way doesn’t mean you should keep doing it!
Goldilocks Tip for Gen Z: Before stepping in to tell your boss you know better and can speed things up, ask why a process exists. Understanding the “why” can reveal nuances that help improve your approach. And if you start with questions before offering solutions, you’ll not only come up with a better solution, but I guarantee you’ll impress the higher-ups!

Guidance, Not Handholding
Gen Z has grown up with basically unlimited access to tutorials and step-by-step guides at their fingertips. In 30 minutes or fewer they can master everything from how to beat the latest Fortnite boss to how to make Japanese Souffle Pancakes.

However, Gen Z’s easy access to guidance can often morph into a reliance. And while previous generations enjoyed tinkering their way through problems, Gen Z often prefers complete instructions from the boss, replete with a “Troubleshooting Guide” at the end. If you suggest “trial and error” to them, they might ask if that is a new series streaming on Hulu. So, while they value independence, they are often less excited to dive in without direction.

Goldilocks Tip for Managers: Provide an initial framework or point them in the right direction—this helps them get started without needing every detail. But be prepared for them to have questions. Once they understand the basics, they’re more than capable of running with it. Encourage them to work their way through the process (after all, this is how one learns!) and only come to you when they are stuck.
Goldilocks Tip for Gen Z: Embrace some trial and error. Not every project will come with a step-by-step guide, and the ability to figure things out independently is a powerful skill. And isn’t this where you get to show your boss what you can do that no AI tool can? (When all else fails, use your well-honed Googling skills to find resources on your own!)

Real Talk, Not Reality TV
Gen Z brings an honest, open approach to work, and they value a workplace where they can share openly and be themselves without pretenses. However, there’s a fine line between honest conversation and treating the workplace like a stage for every thought and feeling. Oversharing about your high-drama weekend breakup or detailing your favorite TikTok influencer’s open marriage may feel natural but can disrupt focus in a professional setting.

Goldilocks Tip for Managers: Foster an atmosphere that values honest communication while setting boundaries around what’s appropriate. Be clear about where the line is—encourage openness while defining “oversharing” so it doesn’t become distracting. A quick, respectful reminder that certain topics are better suited to after-work chats can help maintain a professional balance.
Goldilocks Tip for Gen Z: Bring your personality to work, but remember—this is still a professional environment, not happy hour with friends. Choose moments to share that build trust without overwhelming and save the play-by-play for after-hours. Remember, sharing appropriately keeps everyone focused on common goals and shows you’re serious about the mission.

Finding the “just right” balance between generations can feel like a fairy tale quest of its own, complete with a few detours. But when each generation brings its strengths to the table—and gives each other some grace along the way—the result is a team that’s stronger, more adaptable, and a lot more fun.

And if navigating generational quirks means mixing Office Space quotes with the latest TikTok trends? Consider it a storybook ending, where everyone has their place (and no one gets left with the hard chair).

Talent Tip #166: Hiring Horror Stories (Just in Time for Halloween!)

October 22, 2024

The Talent Market Team

In the spirit of Halloween, our team wanted to share our most hair-raising hiring horror stories with you. Names and identities have been changed to protect the innocent (and the ghoulishly guilty!).

———–

The Candidate from the Crypt

I once received an application that was riddled with typos and grammatical errors. The candidate’s cover letter read like a spellbook of strange demands. Her first decree? She refused to do any phone or video interviews. She would only accept an invitation for an in-person interview! (Oh, and because she was located 2,784 miles away from the organization’s office, the plane ticket wouldn’t be cheap!)

It got better. She insisted on participating only in “paid interviews” (which, she let us know, would be determined by a fraction of the target annual salary range for the role). And even more bizarrely, she made it clear that she preferred to receive a job offer without interviewing at all! After all, she was such a strong candidate that “engaging in interviews would be an unnecessary step.”

Not surprisingly, the hiring manager decided to avoid this specter of a candidate. If her ghastly demands were any indication, working with her would be a true fright!

———–

Ghosted at the DMV

As soon as the candidate answered the phone, I knew I was in for a treat…or maybe a few tricks?

She was in a very loud environment not well-suited for a phone interview and she sounded very distracted. Since we had planned the interview days in advance, I thought it was a bit unprofessional for her not to have secured a better location for our call. Trick #1.

Within the first few minutes, I learned that her current job was not a full-time, paid position as her resume implied. Rather, it was a part-time, volunteer role. Trick #2.

When I got to my last question, she started to answer and then, just like when the line goes dead in a horror movie, she abruptly hung up. Trick #3.

Hours later, I got a contrite email from her saying she was sorry about the hang-up, but that she had taken the call while….wait for it…. waiting in line at the DMV. And, naturally, a DMV staffer had let her know that she couldn’t use the phone whilst in line. Trick #4.

(My trick-or-treat score: +10 points for attempting to multi-task, -100 points for lack of professionalism, and -1,000 points for choosing a questionably run government department over a phone interview for a job in the liberty movement.)

———–

The Citation Slasher

Picture this: you’re a hiring manager combing through the latest batch of applications, looking for that perfect candidate. You spot one that immediately catches your eye. But as you start reading the writing sample, an unsettling feeling creeps in. You notice the candidate included two sharp-looking charts. They seem familiar… a little too familiar. And then it hits you: these aren’t just any charts—they’re your charts.

But something is horribly wrong. The branding and citations are missing, intentionally slashed away as though someone had taken a knife to your intellectual property, deliberately removing your organization’s identity from the work. And, just like the killer who returns to the scene of the crime, the candidate boldly submitted the altered charts right back to you as a writing sample.

In the end, you let it slide without a confrontation, but the damage was done. Like a classic horror movie twist, the candidate revealed themselves as the killer, and their only victim: their own chance of ever being hired.

———–

Disappeared

Once upon a time, I was managing a search that was going smoothly. We had several strong candidates moving into the final interview stage. It seemed like we were well on our way to helping someone find his/her dream job.

That was until the hiring manager disappeared like a ghost.

I emailed for news. One week passed. I emailed again. Two weeks passed. I called. Three weeks passed. I called again and texted. Four weeks passed. I sent smoke signals and then a carrier pigeon. Five weeks passed.

The candidates and I stayed in close communication the entire time, growing more confused and concerned by the day.

And then, just as I was about to pull out the Ouija board to ask, “Are you there?” the hiring manager reappeared like an apparition, wanting to pick up right where he left off as if nothing had happened. It turns out he had taken an extended beach vacation without telling the finalists or yours truly.

Unfortunately, by this point, two of the three finalists were spooked by the silence and had backed out. It goes to show that while ghosts are fun on Halloween, they can be a real nightmare in the hiring process.

———–

The Terrifying Typo

A while back a candidate applied for a role with a client of ours. Everything seemed fine until she accidentally entered her current boss’ email in the “contact information” field instead of her own. Naturally, after hitting submit, the system immediately sent a confirmation email—directly to her boss. Imagine the candidate’s horror when her boss called her into the office the next day, holding the email with the subject line: “Thank you for applying!”

The boss, now well-aware that his employee was job hunting, wasn’t too thrilled. Safe to say, double-checking contact info is now at the top of her list when applying for jobs!

———–

The Magic 8 Ball

A couple of years ago one of our candidates phone interviewed for a role and then received an invitation to fly across the country to interview in person. Now, one never knows how the interview process will go, but the Magic 8 Ball can be a helpful guide, especially during the Halloween season.

Does this opportunity seem promising?
Magic 8 Ball response: Yes definitely.

Given the nature of the candidate’s current job, he had to pull every trick in the book to secure days off work. Just as the candidate prepared to board the flight, he received an email from the organization telling him the interview was canceled.

Is the candidate upset?
Magic 8 Ball response: It is certain.

Shortly thereafter, the organization requested a time-consuming assignment in lieu of the in-person interview. While the candidate was upset, he understood that things happen. The candidate worked multiple hours over the course of multiple evenings and submitted the assignment early.

A couple of weeks passed with no word. Then, like a phantom appearing out of the mist, a non-personalized, form email materialized: “Dear candidate, thanks but no thanks.”

At this point, is the candidate really $%*^)#@ upset?
Magic 8 Ball response: You may rely on it.

The organization’s careless treatment left the candidate feeling like a forgotten spirit, wandering the haunted halls of the hiring process. And it’s a lesson that sometimes the most haunting experiences come from the interviews that never were and the promises that vanish like mist in the night!

But there is also a lesson for hiring managers:

Will the candidate share his negative experience with his friends and encourage them not to apply for jobs with this organization?
Magic 8 Ball response: Outlook good.

———–

Candy Can’t Buy My Love

Looking back on my childhood, one of the Halloween highlights was the haunted house in my neighborhood. Every year, one particular neighbor turned their home into a spooky masterpiece. Their efforts were so elaborate, we wouldn’t have cared if they handed out boxes of raisins instead of candy—just walking through that spooky setup was an unforgettable experience.

It was a far contrast from the houses with nary a pumpkin in sight that tried to win us over by giving out full-sized candy bars: they were clearly trying to overcompensate for their lack of effort.

Fast-forward to today. A hiring manager recently told me about an applicant who had submitted a very low-effort application with a generic cover letter. But get this….the candidate then made a small donation to the organization within minutes of applying for the job.

The hiring manager chuckled as he relayed the story. “Was that supposed to be a $5 bribe to get me to hire him?”

It took me right back to the candy bar houses from my childhood. Instead of putting in the effort with a strong application (amazing haunted house), this candidate went the pumpkin-less route. And, to make matters worse, he only gave out a fun-sized candy bar!

Talent Tip #165: A Bartender’s Guide to Professional Branding

September 24, 2024

Stephanie Keaveney

One of the most delightful parts of working at Talent Market is discovering that nearly every career topic can be explored with either a dating or cocktail-related analogy. And living with a former bartender means much of my time outside of work is spent as a taste tester for new concoctions. So it’s no big surprise that a recent discussion on building your professional brand got me thinking about the overlap with crafting a great cocktail.

Whether you’re growing your network or applying for jobs, a strong professional brand is essential to making lasting connections and standing out in the working world. So grab your shakers and mini umbrellas and let’s explore what we can learn about professional branding from your bar favorites.

Base Spirits – Your Values

Your values are the key ingredient behind your professional brand. They’re what ground you and guide every professional move you make. Just like a cocktail’s base spirits set the flavor, your core values set the tone for everything else. Without knowing your values, your brand will be about as convincing as a lukewarm bottle of O’Doul’s.

Embrace your base: Think about what matters most to you as a professional, what issues you’re most passionate about, and what type of organizational culture you want. When applying for jobs, make sure you’re only applying for jobs that promote the ideals you care about. And be sure to clearly articulate your values-alignment in your cover letter. Finally, don’t forget to dig into organizational culture in your interview. Just like you choose your favorite bar based on the attitude and the atmosphere, you want to find an organization that serves up the right culture.

Signature Ingredient – Your Unique Selling Point
Every amazing cocktail has a signature ingredient. So, ask yourself: what is the special skill or trait that makes you unforgettable? It could be your unmatched creativity with Adobe InDesign, expert-level knowledge of excise tax policy, or extensive experience with civil rights litigation and 1983 claims. Like the Cointreau in a Cosmo, your unique skills are what people will remember you for and what will make them want to hire you.

Highlight your signature splash: Hiring managers won’t know unless you tell them, right? If you are applying for an entry-level writing position and you were the editor of your university’s liberty-leaning newspaper, MENTION THAT! Or, if you’re applying for a data job and you once built an entire Salesforce database from scratch for your favorite cat rescue organization, serve that up with a cherry on top! Include these types of things in your resume/cover letter and you’ll absolutely stand out in a crowded bar!

Garnish – Your Style
Style isn’t just about dressing sharply or having perfectly coiffed hair (though it doesn’t hurt!). It’s how you carry yourself, how you communicate, and the energy you bring to the room. Just like a cocktail’s garnish ties everything together, your style enhances your professional brand. But remember, even the highest-quality Traverse City cocktail cherries can’t cover up the taste of a terrible Old Fashioned – it’s about substance, not just the shine!

Add Your Lime and Sprig of Mint: Dress appropriately for the occasion and be aware that your body language and non-verbal cues have a big impact on first impressions. If you get anxious during interviews or struggle with things like small talk, practice! And don’t forget about your digital presentation – make sure your LinkedIn and public profiles are a good reflection of yourself. Remember: your style should reflect the job you aspire to have, not necessarily the job you have now. (E.g. if you’re an intern and your style screams, “I’m an intern”, then you might be an intern for a long time! And nobody wants to be drinking Natty Light for longer than they have to.)

Mixing it All Together – Your Consistency
Circling back to my role as a cocktail taste tester, I remember one particularly terrible concoction that, in theory, I should have loved because I like all the ingredients individually. But the flavors just didn’t blend together and it fell flat. That’s what happens when your professional brand lacks consistency. You may have strong values, unique skills, and a polished style, but if they don’t work together, your message can come across as muddled.

Balance Your Flavors: Hiring managers are drawn to candidates whose professional journey makes sense. Incoherent choices like frequently changing jobs, applying for roles well outside of your experience level, and claiming expertise in your cover letter with no evidence of that skill on your resume all raise red flags. Make sure your goals and skills are clear to a potential employer and take advantage of your cover letter to explain anything that may leave a hiring manager bleary-eyed.

Barware – Your Audience
Whisky aficionados everywhere will be the first to tell you that even the best single malt scotch can underwhelm if served in a Brandy snifter instead of an appropriate tumbler. Your professional brand is no different. Your audience matters! Whether you’re interviewing for your dream job or networking at an event, it’s all about tailoring your message. Understanding your audience, and what will resonate with them, ensures you’re always serving the right mix in the right glass.

Choose Your Barware: When applying for jobs, tailor your application — especially the cover letter. During the interview, be ready to talk about their work and why it matters to you. And when it comes to networking, read the room. I once knew of a guy who stopped getting invited to allies’ events because he used them as fundraising opportunities for his own organization. No one will toast to that behavior!

Cocktail Price Point – Your Salary Requirements
One of the consequences of having access to my own personal mixologist is that I’m much less willing to pay a fortune for a mid-tier cocktail. If you’re going to charge me $24 for a drink, it better include 16th-century spirits imported from Madagascar and tiny chunks of gold bullion at the bottom of the glass. Similarly, having unrealistic salary expectations for your level of experience and the specific jobs you’re applying for can get you cut off more quickly than the stumbling college kid using his older brother’s ID.

Find Your Price Point: Research what’s typical for the type of role, your experience, and similarly-sized organizations. Take advantage of things like an organization’s Form 990 to make sure you’re not submitting a salary range that’s double what the CEO is currently making.

We hope these tips have helped in both leveling up your professional brand and your home bartending skills. While we don’t recommend pre-gaming your next interview, maybe the next time you’re sipping a cocktail at a networking event, you’ll remember how much it can teach you about building an excellent professional brand.

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!

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.

Talent Tip #168: What My Favorite Christmas Vacation Scenes Teach Us About Career Moves

Talent Tip #167: Rizz meets Righteous: Finding the “Just Right” with Gen Z in the Workplace

Talent Tip #166: Hiring Horror Stories (Just in Time for Halloween!)

Talent Tip #165: A Bartender’s Guide to Professional Branding

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

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

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