How to wind down with confidence in December and hit the ground running in January, without babysitting your business from the beach.
TL;DR (the “gift bow” on top)
- Use a Holiday Operating Plan (HOP): a short, one-page plan that sets what’s “on,” what’s paused, who’s on point, and how to escalate.
- Lock in cash flow (collections, payroll, vendor payments) before you leave, and automate what you can.
- Prep tax & compliance now: W-2/1099 lists, Q4 estimates, state filings, and January deadlines.
- Build a minimum viable dashboard that’s still monitored over the break with simple red-yellow-green rules.
- Schedule a January re-start sprint: week-by-week themes to regain momentum without chaos.
- Use the Holiday Readiness Checklist (below) two weeks out, one week out, last business day, and first two weeks of January.
Why this matters (besides eggnog)
December’s slowdown hits sales cycles, response times, and cash receipts. Meanwhile, January compresses collections, payroll, inventory restocks, hiring, and tax deadlines into a four-week sprint. The smartest move is not heroic 24/7 availability: it’s deliberate planning that keeps the lights on with minimal oversight and sets up a strong Q1.
As a fractional CFO and accounting partner would say: holiday readiness = liquidity + continuity + compliance. Get those three right, and you can actually relax.
The Holiday Operating Plan (HOP): Your one-page anchor
Before we dive into checklists, put your HOP in place. Keep it to one page and share it with your leadership team, your bookkeeper/accountant, and anyone on call over the holidays.
What to include:
- Dates: Last operating day in December; reduced-hours dates; first full operating day in January.
- Coverage: Who’s on point for Sales, Ops, Support, Finance, IT. Include backups and cell numbers.
- Escalation: What qualifies as an emergency, who decides, and how to contact (text + phone).
- Systems “on/paused”: What continues (e.g., customer support email triage) vs. what’s paused (e.g., nonurgent product roadmap).
- Cash cadence: Payroll dates, AR reminders schedule, bill-pay runs, and who approves.
- Security: MFA, device policies, holiday travel checklist for laptops/phones, emergency password vault access.
Tip: Store the HOP in a shared doc titled “Holiday Operating Plan – 2025” and pin it in Slack/Teams.
The Holiday Readiness Checklist (bookmark this)
Use this as a phased checklist you can run two weeks out, one week out, and on your last business day. Then flip to the January Ramp-Up Plan.
1) Cash & Liquidity
- Forecast cash through January 31 (include payroll, rent, debt service, taxes). Leave a 10–20% buffer for holiday delays.
- Collections push:
- Email statements to all open AR by Dec 15–20 with gentle holiday framing (“We’re aligning year-end books; thanks for helping us wrap up strong.”).
- Turn on automated reminders for invoices >7, >14, and >21 days overdue.
- Offer ACH/credit card options to reduce friction; consider 1–2% discount for payment before Dec 24 if margin allows.
- Vendor payments: Batch noncritical bills into one pre-holiday run and schedule the next for the first full week of January. Communicate expectations to key suppliers.
- Payroll & bonuses: Confirm funding dates and cutoffs with your provider. Schedule year-end bonuses if applicable and verify withholding settings.
- Credit headroom: Confirm available line of credit and card limits; request temporary limit increases if January will be inventory-heavy.
2) Accounting & Bookkeeping
- Reconcile bank/credit cards through November (and ideally mid-December) so year-end is tidy.
- Close Nov P&L and send a simple “Holiday Health” dashboard to leadership: Revenue YTD, Gross Margin, Operating Expense run-rate, Cash runway, AR aging, AP aging.
- Pre-close adjustments: Accrue major December expenses, book inventory adjustments, and finalize fixed asset purchases with your CPA’s tax guidance.
- Backups: Export a read-only backup (or enable provider backups), confirm user access, and set a holiday lock date for the GL to prevent stray edits.
3) Tax & Compliance (U.S.-focused)
- 1099-NEC & 1099-MISC:
- Pull vendor list; flag any non-employee comp ≥$600 (most contractors).
- Request W-9s now.
- Plan prep so you can file by January 31.
- W-2 & payroll reconciliations: Coordinate with your payroll provider; verify employee addresses and retirement deferrals.
- Quarterly estimated taxes: Individuals often owe Q4 estimates by January 15 (check with your tax pro). Calendar reminders for owners.
- Sales/use tax & state filings: Confirm due dates that hit early January; pre-schedule filings where possible.
- Entity hygiene: Board minutes, officer updates, and any state annual reports due in January/February.
*Consult your CPA to confirm your specific deadlines and forms.
4) Operations & Customer Commitments
- SLAs during holidays: Set realistic response times and publish them (website banner, autoresponder, status page).
- Customer handoffs: For open projects, send a “holiday checkpoint” email recapping status, next steps, and who’s on call.
- Fulfillment & inventory:
- Stock critical SKUs; confirm last ship dates with carriers.
- Create a “no-ship” window if warehouse closes; auto-update checkout messages.
- Support triage: Define what’s urgent vs. nonurgent; set auto-tagging rules and escalation response times.
5) People & HR
- Out-of-office (OOO) architecture:
- Standard subject line: “Out for the holidays—back [date]. For urgent issues: [on-call name/phone].”
- Calendar blocks: visible to all; mark time zone if traveling.
- Slack/Teams profiles updated with coverage notes and on-call contacts.
- Time off approvals: Lock in schedules; ensure overlapping coverage.
- Holiday pay policies: Re-share policy and observe local/state rules.
6) Security & IT
- MFA health check: Ensure MFA on email, accounting, banking, payroll, CRM, and cloud storage.
- Access audit: Remove leavers; downgrade elevated permissions; share emergency access via password manager with dual control.
- Devices on the go: Enforce disk encryption, auto-lock, VPN, and travel security tips; carry privacy screens.
7) Leadership Communication
- Share the HOP and this checklist with owners and team leads.
- Set two brief touchpoints: one mid-holiday (15 minutes) and one quick post-holiday sync.
- Decide what metrics (see below) trigger a call or text.
The Minimum Viable Holiday Dashboard (what to watch while you’re away)
Keep it simple. Choose 5–7 metrics. Put them on a weekly email or a read-only dashboard. Define R/Y/G thresholds so the on-call owner knows when to escalate.
Suggested metrics:
- Cash on hand (target ≥X weeks of OpEx).
- Collections received (weekly $ vs. target).
- Open AR >30 days (count and $).
- Support backlog (open tickets and average age).
- Critical orders (on-time ship rate).
- Payroll status (next run confirmed/funded).
- High-severity incidents (count; any open >24 hrs?).
Escalation rules:
- Red: Cash <X weeks or missed payroll funding → call owner/finance lead immediately.
- Yellow: AR >30 days grows by >10% WoW → notify finance; add extra reminders.
- Green: All within tolerance → no action.
The Last Business Day Ritual (60–90 minutes)
- Send final AR nudges with quick-pay links.
- Approve and schedule bill pay for anything due before Jan 10.
- Verify payroll is queued and funded (including holiday shifts).
- Lock GL through the last completed bank day; save a backup export.
- Turn on OOO messages + emergency contact details.
- Share dashboard link and R/Y/G rules.
- Snap a photo of your whiteboard to capture open loops then archive tasks into January sprints.
January Ramp-Up Plan (a calm, focused restart)
Week 1: Reopen & Reconcile
- Cash & collections: Process all holiday receipts; chase any missed ACH/card failures.
- Bank recs: Reconcile December through 12/31; flag unusual items.
- Support cleanup: Clear ticket backlog; close duplicates created by autoresponders.
- Team retro: 30-minute “holiday operations review”: what worked, what to change next year.
Week 2: Compliance & Payroll Accuracy
- W-2 previews and 1099 vendor finalization (addresses, EINs, amounts).
- Confirm any Q4 estimated tax payments (often due Jan 15).
- Review benefit elections and 401(k) deferral changes for the new year.
- Re-baseline your cash forecast through March 31.
Week 3: Revenue & Pipeline Sprint
- Pipeline scrub: Recontact stalled Q4 deals with a “fresh start” theme; add calendar links for quick demos.
- Pricing review: Sanity-check your 2026 (or current) pricing and discount policies; implement increases if planned.
- Collections sprint: Offer structured payment plans for aging AR.
Week 4: Operating Rhythm & Q1 Plan
- Roll out your Q1 operating plan with 1 – 3 focus outcomes.
- Refresh your weekly leadership cadence (agenda + 45 minutes max).
- Share a January scorecard to the whole team highlighting wins, cash health, and next priorities.
How fractional CFO, accounting, and tax partners help (so you can actually relax)
- Fractional CFO: Builds your HOP, sets cash buffers and line-of-credit strategy, designs the holiday dashboard, and leads January’s re-forecast and revenue sprint.
- Accounting & Bookkeeping: Reconciles through year-end, schedules payroll and bill pay, maintains backups, and keeps the GL locked and clean.
- Tax Planning & Filing: Preps 1099/W-2 workflows, aligns final purchases/bonus timing with your tax strategy, and manages state filings so nothing slips during the break.
If you don’t have these roles internally, this is exactly where a partner like CleverProfits keeps your business steady while you’re off-grid.
FAQ’s (optimized for snippets)’s
Q1: What should absolutely not wait until January?
Bank reconciliations through mid-December, payroll scheduling, AR reminder sequences, vendor payment batching for anything due before Jan 10, and confirming W-9s for contractors.
Q2: How much cash buffer should I hold going into the holidays?
Aim for 4–8 weeks of operating expenses depending on seasonality and receivables risk. Increase the buffer if your customers typically pay late in December/early January.
Q3: Do I need to file 1099s for agencies or incorporated vendors?
Often no for corporations, but yes for many contractors and certain legal/medical payments. Always collect W-9s and confirm requirements with your CPA.
Q4: What KPIs should I watch if I’m only checking once a week?
Cash on hand, collections received, AR >30 days, payroll status, support backlog. Use red-yellow-green thresholds to decide when to escalate.
Q5: How can I keep customers happy while we’re slow?
Proactive communication: publish holiday hours, set clear SLAs, and send a checkpoint email for open projects with who’s on call and when you’ll fully resume.
The Holiday Readiness Checklist (condensed for printing)
Two Weeks Out
- Cash forecast through Jan 31 with 10–20% buffer
- AR reminders on; confirm ACH/CC options
- Batch AP schedule; confirm payroll/bonus run
- Reconcile through November; close Nov P&L
- Finalize 1099 vendor list; request W-9s
- Publish holiday hours & SLAs; set support triage
- Approve PTO; set OOO templates; MFA check
- Draft HOP and share
One Week Out
- Second AR push to >14-day invoices
- Inventory & shipping cutoff confirmed
- Lock GL through last reconciled day
- Confirm line of credit headroom
- Backup accounting data; access audit
- Send customer project checkpoint emails
Last Business Day
- Final AR nudges + quick-pay links
- Approve/schedule AP through Jan 10
- Verify payroll funding
- Turn on OOOs; pin the HOP
- Share dashboard link + escalation rules
First Week of January
- Reconcile December; process holiday receipts
- Clean support backlog; short retro
- Confirm W-2/1099 details; Q4 estimates if applicable
CTA: Give your business (and yourself) the gift of a quiet holiday
Want this done for you? Our fractional CFOs, accountants, and tax pros set up your Holiday Operating Plan, automate cash flow, and manage 1099/W-2 prep—so you can actually switch off.
The Clever Writing Team
The CleverProfits writing team includes various team members in Advisory, Financial Strategy, Tax, and Leadership. Our goal is to provide relevant and easy-to-understand financial content to help founders and business leaders reach their true potential.
TABLE OF CONTENTS
- 1099 deadline January 31, AP run, AR collections, cash forecast, fractional CFO services, GL lock date, holiday autoresponder, holiday business checklist, holiday cash flow, January ramp-up plan, line of credit, liquidity buffer, outsourced accounting, payroll scheduling, Q4 estimated taxes January 15, sales tax filing, small business holiday shutdown, support SLAs, tax filing services, W-2 recon, year-end accounting checklist
