Your Holiday Hustle: How to Pick Up Extra Shifts That Actually Fit Your Schedule
- Rebecca Batisto
- 9 minutes ago
- 5 min read
The holiday season is upon us, bringing with it a whirlwind of parties, events, and, for many, the perfect opportunity to boost your bank account. If you are already working a full-time job, the idea of adding a “holiday hustle” might sound exhausting. However, with the right strategy and the right partner, picking up a second job in the hospitality industry is one of the most flexible and rewarding ways to earn extra cash.
At WD Hospitality Staffing, we specialize in connecting dependable, service-focused professionals like you with clients across Illinois, Wisconsin, Indiana, and Michigan; from bustling catering companies, restaurants, and corporate event planners to essential corporate kitchens. Our entire business is built on providing you with shifts that fit your life, not the other way around.
If you are considering adding a second job to your routine this season, the key to success is flexibility and finding an employer who values your existing commitments. Here is a guide on how to approach the holiday rush to ensure your extra shifts are a boost, not a burden.
Ready to Apply Already? Complete the application on our website: https://winedine.nextcrew.app/register
The Demand is High: Why Hospitality is Your Best Bet
The high demand for reliable, trained staff means that companies are actively seeking professionals who can jump in and deliver top-notch service. And that includes us!
According to a December 2025 CBS News report on the U.S. labor market, the leisure and hospitality sector added 13,000 jobs in November as establishments prepared for the busy holiday season (CBS News, 2025). This growth signals a strong demand for temporary and event-based staffing right now, especially as companies ramp up for holiday events and seasonal client needs.
Moreover, the entire industry is still working to stabilize its workforce. While some segments have recovered, the Accommodation and Food Services sector lags behind others in a return to pre-pandemic employment levels. In a 2025 report on hospitality hiring trends, Escoffier Global noted that, as of April 2025, the Accommodation and Food Services sector was still nearly 94,000 jobs below its pre-pandemic peak (Escoffier Global, 2025).
What does that all mean to you? It means two things that are important:
The hospitality industry (hotels, restaurants, bars, stadiums, clubs, and such) relies on people spending money. If the economy is not great and people are worried about making ends meet, they’re less likely to go out. For you, that means it's a good time to take on extra shifts. Make money now to protect you through times when jobs aren’t easy to come by.
You need to work with companies you can trust. By partnering with WD Hospitality Staffing, you’ll make a good connection with a local company. And if there’s one thing we know about Chicago, it’s that we look out for each other here. If you’re reliable and hard-working, we want to meet you!
Smart Scheduling: Finding Shifts That Fit
The number one challenge for anyone considering a second job is managing the schedule. You need a boss who understands that you have a primary commitment and are looking for supplementary income, not a replacement for your main job.
1. Define Your Boundaries Clearly:
Before you even apply, review your existing schedule and clearly mark your “hard no” times and “flexible yes” windows. Do you need to be free every Tuesday evening? Is your weekend wide open? Be honest with yourself about your capacity, including travel time and the necessary recovery time between shifts. This clarity is the foundation of a successful hustle.
2. Prioritize Flexibility:
In 2025, worker flexibility is non-negotiable for many job seekers. As a September 2025 report on staffing trends indicated, more than 70% of job seekers say flexible work arrangements are now “non-negotiable” when evaluating opportunities (StaffingHub, 2025). This is exactly where WD Hospitality Staffing excels.
Because we serve a diverse range of clients, from a one-night corporate gala needing a cleanup crew to a healthcare facility requiring consistent daily food prep staff, we can usually offer a wide spectrum of schedules. This allows you to choose roles that specifically align with your available time:
Weekend Warrior: Pick up Saturday and Sunday catering events as a server or bartender.
Evening Expert: Fill in as part of a clean-up or breakdown crew after corporate dinners.
Daytime Dedication: Take on food prep or janitorial roles in a healthcare setting that operates during traditional business hours.
3. Embrace Short-Term Contracts and Event Work:
Hospitality staffing is well-suited to a “pick up extra hours” model. Instead of committing to a rigid, recurring schedule, you can select individual event gigs as a bartender, wait staff, or set-up crew member. This project-based work allows you to commit to one major event per week, two small evening events, or whatever fits your financial goal and energy level for that week.
The WD Difference: More Than Just Extra Work
Choosing a second job is about more than just the paycheck; it is about choosing an environment that values your effort and professionalism. WD Hospitality Staffing, a family-run business founded in 2000 and based in Chicago, is dedicated to this principle.
We pride ourselves on hiring professionals who are not afraid to jump in and help out, and who are intent on delivering the best service possible. Whether you are a chef, a barista, a mixologist, or a janitorial staff member, you are the face of our commitment to our clients.
Furthermore, the hospitality industry provides valuable transferable skills. When discussing the labor shortage, Executive Vice President Erin Karim of LGC Associates (a staffing firm that specializes in hospitality) advises employers to focus on “soft skills and providing training to bridge the gap” (LGC Associates, 2025). Working with WD offers you on-the-job training in a variety of roles, which can boost your professional resume across any industry. You gain experience in high-pressure environments, customer service, and team collaboration, all while delivering exceptional service.
Ready to Find Your Perfect Fit?
The holiday season is an ideal time to capitalize on the high demand for reliable, skilled hospitality professionals. Stop trying to shoehorn your life into a rigid part-time job. With WD Hospitality Staffing, you gain the power to choose the shifts that genuinely work for you, your family, and your primary career. We are here to make your holiday hustle a success.
We are actively seeking talented, dedicated individuals for all our roles:
Wait staff
Bartenders, baristas, and mixologists
Chefs and sous chefs
Clean up crew
Janitorial staff
Food prep and food line workers
Set up and breakdown staff.
Take the next step toward a flexible, rewarding second income. Apply for a position with us today and start picking up extra shifts on your terms. Visit www.wdhstaff.com to learn more and complete your application.
Source URLs
CBS News. (2025, December 3). U.S. lost 32,000 private-sector jobs last month in https://staffinghub.com/submit-an-article/surprise drop, ADP data shows. Retrieved from https://www.cbsnews.com/news/adp-jobs-private-sector-lost-32000-november-2025/
Escoffier Global. (2025). 2025 Hospitality Hiring Trends: What Employers Need to Know. Retrieved from https://escoffierglobal.com/
LGC Associates. (2025). LGC’s Guide to Hospitality Staffing in 2025. Retrieved from https://lgcassociates.com/
StaffingHub. (2025). The Key Trends That Shaped the Staffing Industry in 2025. Retrieved from https://staffinghub.com/submit-an-article/