Stop Working Through Christmas, You're Just Bad at Business
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The Truth About Holiday Hustle Culture
I'm writing this because I'm tired of the lies.
Every December, my LinkedIn feed fills up with the same performative posts. Founders humble-bragging about working through Christmas. CEOs celebrating their "24/7 grind." Entrepreneurs turning basic human rest into some sort of moral failing.
And I've been watching this pattern long enough to see what actually happens next.
Here's what I've noticed:
The founders who publicly pride themselves on "no days off" are often the ones privately wrestling with the highest burnout rates. Not because they're working harder. But because they're working scared.
Think about it:
How many times have you seen someone post about their "unstoppable holiday momentum" in December, only to go mysteriously quiet in January and February?
How many "365-day hustle" advocates have you watched quietly burn out and sell their companies for far less than they could have because they’re tired and over it?
How many "I'll sleep when I'm dead" entrepreneurs have you seen make preventable strategic mistakes because they were running on empty?
I've spent over a decade in startup circles. I've built companies. I've advised founders. I've seen the real patterns, not the social media versions of them.
And I keep seeing something fascinating: The most successful founders I know aren't the ones bragging about holiday hustle. They're the ones who've learned that if you can't build it in 51 weeks, you can't build it in 52.
In the next few minutes, I'm going to break down:
What I've actually observed about holiday hustle vs. success
Why the "always-on" narrative is fundamentally broken
How real founders approach the December shutdown
A different way to think about strategic rest
The Reality Behind the Posts
The startup world has a confession to make.
We've created a culture where taking a break is seen as weakness. Where rest is viewed as a lack of commitment. Where basic human needs are treated as character flaws.
And it's not just wrong. It's destructive.
I see it play out the same way every year:
The Public Story:
"Grinding through the holidays while others sleep!"
"No days off! This is how you win!"
"If you're taking a break, you're falling behind!"
The Private Reality:
Preventable mistakes from exhaustion
Strategic blindness from burnout
Teams quietly updating their resumes
Founders losing their love for their own companies
The Truth About Sustainable Success
Here's what I actually see in the startup world.
The founders who sustain long-term success aren't the ones posting hustle porn on LinkedIn. They're the ones quietly building systems that work without their constant presence.
Think about the founders you most respect. The ones building real, lasting companies. The ones whose work you genuinely admire.
I bet they're not the ones bragging about their holiday grind.
The Real Patterns
When you look past the social media noise, you start noticing something interesting:
Pattern #1: Strategic Distance
The best founders I know don't just take breaks - they plan for them. They build their companies to run without their constant intervention. Not because they're lazy. Because that's what actual scale requires.
Pattern #2: Team Trust
"If you can't trust your team to run things for a week, you haven't built a business - you've built a prison and made yourself the warden."
I heard a founder say this last year. Haven't stopped thinking about it since.
Pattern #3: Clear Boundaries
The strongest leaders I've watched don't apologize for having boundaries. They don't glorify overwork. They don't treat basic human needs as weaknesses.
They treat sustainability as a competitive advantage.
The December Difference
Here's what I've noticed about how real leaders handle December:
They make decisions before they're exhausted
They set clear expectations with their teams
They build systems that work without them
They trust their people to handle things
They actually rest when they rest
Your company's ability to run without you isn't a weakness. It's the whole point.
Think about that for a second.
We praise founders for working through holidays like it's some badge of honor. But what if we've got it completely backwards?
What if the real achievement isn't being needed for everything, but building something that can thrive without your constant attention?
The Strategic Reset
Here's what I've observed about founders who do this right:
They Plan for Power Down
Clear communication about holiday schedules
Systems in place for emergencies
Trust in their team's capabilities
Real boundaries, not performative ones
They Actually Disconnect
No "just checking in" emails
No "quick calls" during family time
No pretending to be off while secretly working
They Return Stronger
Fresh perspective on problems
Clear mind for strategy
Renewed energy for execution
Better decisions from rest
The Wake-Up Call
Look, I get it.
Taking time off when you're building something feels terrifying. Trust me, I know that fear.
But here's what I've learned from watching this pattern play out year after year:
The founders who can't step away for a week aren't showing dedication. They're showing a failure of leadership.
Because if your business can't survive without you for a week, you haven't built a business.
You've built a job.
And you've made yourself the least replaceable employee.
The Decompression Blueprint
So what do you actually do with this?
After watching countless founders navigate this transition, here's what actually works. Not theory. Not wishful thinking. Real, practical steps that build better businesses.
First, The Reality Check
Start by asking yourself these questions:
If your company can't survive a week without you, is it really a company?
If your team can't handle things while you're gone, have you really built a team?
If you can't step away for seven days, what are you actually building?
Be honest with yourself. The answers matter more than the image.
The Foundation Work (Start Now)
System Documentation
Map every process that runs through you
Document your decision-making criteria
Create clear escalation protocols
Build response templates for common situations
Team Empowerment
Identify key decision-makers for each area
Give them real authority (not just responsibility)
Run practice scenarios
Let them make (and learn from) small mistakes now
Client Communication
Set expectations early (not December 23rd)
Create clear service level agreements
Establish backup contact protocols
Define what actually constitutes an emergency
The Pre-Break Setup
Two Weeks Before:
Complete all major deliverables
Run team readiness checks
Test emergency protocols
Clear the decks of any lingering decisions
One Week Before:
Set clear communication windows: Not "I'll be checking email" but "I'll be completely offline from [date] to [date]"
Hold team alignment meetings
Establish success metrics
Confirm backup plans and emergency protocols
The Actual Break Protocol
Digital Disconnection:
Remove email from your phone
Delete Slack
Log out of all work accounts
Turn off notifications
Set a true out-of-office
Team Empowerment:
No "checking in"
No backchannel communication
No undermining your own system
Trust your team (actually trust them, not pretend trust)
Give yourself permission to disconnect
The Strategic Return
First Day Back:
No meetings
Full system review
Team feedback collection
Strategic assessment
First Week Back:
Focus on learning, not fixing
Document what worked
Strengthen what didn't
Build better systems for next time
The Key Metrics:
Track what actually broke (not what you feared would break)
Measure team confidence growth
Document client satisfaction
Identify system improvements
The Permission Slip
Let me give you something I wish someone had given me years ago:
You have permission to:
Build a business that doesn't need your constant attention
Trust your team to handle things without you
Take actual breaks without guilt
Come back stronger
Remember: The goal isn't just to survive a week off. The goal is to build a business that gets stronger when you step away, not weaker.
Because here's the truth about those 51 weeks: They're not just about working. They're about building something that can thrive without your constant presence.
And that extra week? It's not just about rest. It's about proving you've built something real.
Your Move
Here's what I want you to do right now:
Block the dates Open your calendar. Block December 24-31 2025 (next year). Not as "maybe" time. As actual offline time.
Tell your team Not "I might take some time" but "I will be offline these dates"
Build the system Start working now on making yourself unnecessary for those days.
Because here's the truth about holiday hustle culture:
The real test of your leadership isn't how long you can work without a break.
It's how well you can build something that doesn't break without you.
Scott
This was a great read to start off the year!