How do we build in time-off for the holidays (even as a contractor)?

Do these sentences resonate? 👇

• “I’m new here, so I don’t feel like I’m allowed to ask for time off.”
• “I’m hourly / contract, so if I don’t work, I don’t get paid.”
• “Everyone’s talking about holiday PTO, and I’m just trying to keep my job and pay my bills.”

You’re looking at the schedule, refreshing your banking app, and watching people post “out of office” selfies like it’s nothing. Meanwhile, you’re a new hire, on probation, hourly, contract, or juggling multiple jobs, and every hour you don’t work feels risky. This isn’t just about time off; it’s about navigating a system that was not designed with you in mind.

"Caring for myself is not self-indulgence, it is self-preservation, and that is an act of political warfare.” – Audre Lorde

Understanding our time off reality ⌛

Before we request time off, we need to know what kind of worker the system thinks we are. That label decides what we’re “entitled” to whether or not it feels fair.

• Hourly employee: We’re paid for the hours we’re scheduled and actually work. If we don’t work, we usually don’t get paid. Holidays might be paid, but only if our employer offers holiday pay and we meet their criteria (like working the day before and after).
• Salaried with PTO: We’re paid a fixed amount and may have access to paid time off that covers sick days, vacation, or personal days. But new hires often have a probationary period (commonly 30–90 days) where benefits (including PTO) are limited or delayed.​
• Contract / gig worker: We’re usually considered self-employed or “independent.” There’s typically no PTO at all, and no work = no pay. Research on young gig workers (16–24) shows we’re often excluded from traditional benefits entirely, especially if we’re BIPOC, women, LGBTQ+, or young parents.​
• Multiple jobs / patchwork schedule: Surveys show more of us are stacking side gigs, seasonal work, and part-time jobs just to cover basic costs, especially around holidays.​

None of this is a reflection of our worth. It’s a reflection of how work is structured and who that structure was originally built for (hint: not us).

We’re not lazy or “behind” for feeling stressed about time off. We’re reading a system correctly.

How to ask for time off when we feel disposable (we're not!) 🗣️

If we’re new, hourly, or contract, it can feel like asking for time off = risking our job. But timing, framing, and preparation can lower that risk.

When we ask:

• As early as possible (weeks, not days, if we can).
• Avoid peak chaos if we know our workplace has busy seasons.
• Check the handbook, onboarding docs, or ask HR / our manager what the process is before we need it.

How we ask (especially if we don’t have PTO):

We can sound responsible and honest without over-explaining.

This is career readiness disguised as survival: we’re showing we understand coverage, planning, and impact.

When time off means less money 💸

For a lot of us, the real question isn’t “Will my boss say yes?” It’s “Can our bank account handle it?”

Workers across the U.S. are picking up side gigs, overtime, and seasonal shifts just to afford holidays and basic expenses, because one job isn’t enough. If unpaid time off is on the table, we’re doing math, not just vibes.​

A simple way to think about it:

• Our hourly rate × hours missed = income we lose.
• Add any extra holiday or seasonal costs we’re expecting (gifts, travel, food, etc.).
• Ask: can we cover essentials (rent, food, bills) and still take this time?

This isn’t about “manifesting abundance.” It’s about acknowledging that our rest has a dollar cost right now, and giving ourselves permission to weigh that without shame.

Guilt, comparison, and internalized pressure 📲

• If we’re new, hourly, contract, or juggling multiple jobs, it can feel like everyone else is “off” while we’re grinding. But the truth is more complicated:
• Many workers can’t afford holidays on one paycheck, so they’re doing side gigs, seasonal jobs, and overtime, not just chilling.​

We might be carrying:

• Being first-gen or the main supporter in our family.
• Being BIPOC in workplaces where we already feel hyper-visible or easily replaceable.
• The pressure to prove we’re “grateful,” “professional,” or “low-maintenance.”

Reframe:

• Rest is something we plan and protect, not a reward someone else decides we’ve earned.
• We are not weak or uncommitted for needing a break, we are human in a system that runs on overwork.
• Social media skews what we see: people are posting travel and cozy pics, not their shifts, second jobs, or declined PTO.
• Gen Z, especially, reports high anxiety and discomfort around even asking for time off, leading to things like “quiet vacationing,” where we step away without formally requesting PTO because we’re scared to ask.​

“Rest is not idleness, and to lie sometimes on the grass…is by no means a waste of time.” – John Lubbock

Take a moment to reflect on your own experience with burnout. Here are five questions to help you explore your relationship with stress and exhaustion:

1. What kind of worker does the system see YOU as right now (hourly, contract, new hire, student worker) and how does that shape YOUr options?
2. When YOU think about asking for time off, what’s the first feeling that comes up?
3. What obligations (family, community, financial) are YOU balancing when YOU think about stepping away from work?
4. What would a realistic, not perfect, version of rest look like for YOU this season?
5. If YOU could change one thing about how time off works for people like YOU, what would it be?

“For fast acting relief, try slowing down.” – Lily Tomlin

Click on the dropdowns below to see the easy action items:

Some vibes to close us out

You are not behind.

You are doing logistics in a game with rules you didn’t write.

Every time you learn your rights, ask early, plan ahead, or create a tiny pocket of rest in a packed week, you’re building a different future for yourself, and for everyone watching you figure it out.

YOU got this. 💭✨

Happy Holidays!🎄🕎🎁

Sources

1. "What Young Gig Workers Say About the Future of Work." The Workers Lab / Hilton Foundation (2024).
2. "Green Key Unlocked: Generation Z: Promoting a Healthy PTO Policy." Green Key (2024).​
3. "The Employment Probationary Period: 2025 Guide." Factorial HR (2025).​

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