The 30-Minute Career Exercise Every Tech Professional Should Do This Holiday

Most senior tech professionals will spend the holidays focused on family, rest, and disconnecting from work.

All good things.

But I'm going to suggest you carve out 30 minutes—maybe on a quiet morning, or between holiday obligations—to do one strategic exercise that could fundamentally change your career trajectory in 2025.

The exercise is simple: Answer one question honestly.

"If my job ended in January, what would I do?"

Not "will it end" (it might not). Not "should I be worried" (maybe, maybe not).

Just: What would you actually do if it happened?

This isn't about creating anxiety during the holidays. It's about doing strategic career planning while you're employed and have leverage—instead of scrambling when you don't.

Here's the 30-minute framework, why it matters, and what to do with your answers.

Why This Question Matters Right Now

Three reasons this exercise is particularly important during the 2024 holidays:

Reason 1: The AI Transformation Is Accelerating Into 2025

The restructures happening in late 2024 aren't random cost-cutting. They're structural transformation driven by AI capabilities.

What's happening in Q4 2024:

Companies finalizing 2025 org structures
Roles being evaluated for AI automation potential
Budgets being set with "AI-enhanced productivity" assumptions
Decisions being made about which roles survive

What this means for Q1 2025:

January-March will see significant restructuring announcements
Many roles that feel secure now will be eliminated
The professionals who planned will navigate smoothly
The ones who didn't will scramble

Reason 2: Q1 Is Peak Restructure Season

Historically, most corporate restructures happen in Q1:

Why companies restructure in Q1:

New fiscal year, new org structures
Budget constraints from previous year
Leadership changes taking effect
Strategic pivots being implemented
Post-holiday "fresh start" mentality

The pattern I'm seeing:

December: Decisions finalized quietly
January: Announcements begin
February-March: Restructures executed
April+: New structures stabilized

If you're going to be affected, you'll likely know by March.

Reason 3: Planning While Employed Beats Scrambling While Unemployed

Planning while employed:

Clear thinking (not panicked)
Time to build foundation (months, not days)
Negotiating leverage (have income)
Strategic choices (can be selective)
Network activation (from position of strength)

Scrambling while unemployed:

Panic thinking (survival mode)
No time to build (need income now)
No leverage (desperate)
Limited choices (take what you can get)
Network activation (from position of weakness)

The difference in outcomes is massive.

The professionals who use this holiday to do 30 minutes of honest self-assessment will enter 2025 with clarity and preparation.

The ones who avoid the question will enter 2025 hoping nothing bad happens—and unprepared if it does.

The 30-Minute Strategic Question Framework

Here's how to structure this exercise:

Set a timer for 30 minutes. Find a quiet space. Be brutally honest with yourself.

Part 1: The Core Question (5 minutes)

"If my job ended in January, what would I actually do?"

Write down your immediate, honest answer. Not what you "should" do. What you would actually do.

Common honest answers I hear:

"Panic and immediately start applying to everything"
"Call my network but realize I don't know who would actually help"
"Update my resume and hope for the best"
"Take a month to figure things out (burn through savings)"
"Have no idea—I've never thought about this"

Whatever your answer is, write it down uncensored.

This reveals your current level of career preparedness.

Part 2: The Self-Assessment Checklist (10 minutes)

Now assess your actual readiness across five dimensions. Rate yourself 1-10 (1=completely unprepared, 10=fully prepared).

Dimension 1: Financial Runway

Questions to answer:

How many months could you cover expenses without income?

□ Less than 1 month (Score: 1-2)
□ 1-2 months (Score: 3-4)
□ 3-4 months (Score: 5-6)
□ 5-6 months (Score: 7-8)
□ 6+ months (Score: 9-10)

Do you have liquid cash savings (not 401k)?

□ Less than $10K (Score: 1-3)
□ $10K-$30K (Score: 4-5)
□ $30K-$50K (Score: 6-7)
□ $50K-$100K (Score: 8-9)
□ $100K+ (Score: 10)

Your Financial Runway Score: ___/10

What this tells you: How much time you have to make good decisions vs. desperate ones.

Dimension 2: Network Strength

Questions to answer:

How many people outside your company could you call who would take your call and potentially help?

□ 0-5 people (Score: 1-2)
□ 5-10 people (Score: 3-4)
□ 10-20 people (Score: 5-6)
□ 20-50 people (Score: 7-8)
□ 50+ people (Score: 9-10)

When did you last have a meaningful conversation with someone outside your company?

□ 6+ months ago (Score: 1-3)
□ 3-6 months ago (Score: 4-5)
□ 1-3 months ago (Score: 6-7)
□ This month (Score: 8-9)
□ This week (Score: 10)

Your Network Strength Score: ___/10

What this tells you: Whether you'd be starting from zero or activating existing relationships.

Dimension 3: Market Readiness

Questions to answer:

Is your LinkedIn profile updated and optimized?

□ Not updated in 2+ years (Score: 1-2)
□ Somewhat current but generic (Score: 3-5)
□ Updated but could be stronger (Score: 6-7)
□ Optimized with clear value prop (Score: 8-9)
□ Optimized and attracting inbound (Score: 10)

Do you have documented frameworks/IP that prove your strategic value?

□ Nothing documented (Score: 1-3)
□ Some notes but not organized (Score: 4-5)
□ A few frameworks documented (Score: 6-7)
□ Strong portfolio of IP (Score: 8-9)
□ Comprehensive library ready to share (Score: 10)

Your Market Readiness Score: ___/10

What this tells you: How quickly you could present yourself effectively to market.

Dimension 4: Alternative Income Capacity

Questions to answer:

Do you have any income sources outside your W-2?

□ Zero alternative income (Score: 1)
□ Exploring but nothing active (Score: 2-4)
□ One small stream ($1K-$3K/month) (Score: 5-6)
□ One solid stream ($3K-$8K/month) (Score: 7-8)
□ Multiple streams ($8K+/month) (Score: 9-10)

Could you generate $5K-$10K monthly through fractional/consulting work?

□ No idea how (Score: 1-3)
□ Maybe but never tried (Score: 4-5)
□ Probably, with some setup (Score: 6-7)
□ Yes, have done it before (Score: 8-9)
□ Already doing it (Score: 10)

Your Alternative Income Score: ___/10

What this tells you: Whether your income drops to $0 or you have runway.

Dimension 5: Identity and Positioning

Questions to answer:

Can you introduce yourself without using your title or company?

□ No, my identity is tied to both (Score: 1-3)
□ Struggle without those anchors (Score: 4-5)
□ Can do it but feels awkward (Score: 6-7)
□ Yes, value-based identity clear (Score: 8-9)
□ Strong value identity, title irrelevant (Score: 10)

Do you have a clear, compelling answer to "What do you do?"

□ Generic/unclear (Score: 1-3)
□ Clear but not compelling (Score: 4-5)
□ Pretty good (Score: 6-7)
□ Strong and specific (Score: 8-9)
□ Immediately engaging and memorable (Score: 10)

Your Identity and Positioning Score: ___/10

What this tells you: Whether you'd have identity crisis or clarity during transition.

Part 3: Calculate Your Overall Preparedness Score (2 minutes)

Add up your five dimension scores:

Financial Runway: ___/10
Network Strength: ___/10
Market Readiness: ___/10
Alternative Income: ___/10
Identity & Positioning: ___/10

Total Career Preparedness Score: ___/50

What your score means:

40-50: Well Prepared

You'd navigate transition smoothly
Multiple options available
Strong leverage in negotiations
Minimal stress during process

30-39: Moderately Prepared

You'd be okay but with some stress
Need to strengthen 1-2 dimensions
Could navigate but would be tight
Should build more foundation

20-29: Underprepared

Would face significant challenges
Multiple gaps to address urgently
High stress during transition
Limited options and leverage

10-19: Highly Vulnerable

Transition would be crisis
Starting from zero on most dimensions
Desperation likely to drive decisions
Immediate action required

0-9: Crisis Mode

Completely unprepared
Any job loss would be devastating
No foundation whatsoever
Emergency preparation needed

Be honest about where you score. This isn't about judgment—it's about awareness and action.

Part 4: The "What If" Scenarios (8 minutes)

Now think through three specific scenarios. For each one, write down what you would actually do:

Scenario 1: Your Role Is Eliminated in February

The situation:

You get 3 months severance
Decent references available
No immediate financial crisis but clock is ticking
Need to land within 4-5 months to avoid stress

Questions to answer:

Week 1: What would you do immediately?

Update LinkedIn? (Can you do this now instead?)
Activate network? (Do you have one to activate?)
Start applying? (Is your positioning ready?)

Month 1: How would you approach the search?

Cold applications? (2% success rate)
Network activation? (If you have one)
Fractional work? (If you have positioning)

Month 2-3: What would your strategy be?

Stay course or pivot?
How do you create urgency?
What's your backup plan?

Write down your honest answers. Do you have a plan or would you be making it up as you go?

Scenario 2: Your Company Gets Acquired and Leadership Changes

The situation:

New leadership brought in
Uncertain if your role survives
6-9 months before clarity
Should you stay or start looking?

Questions to answer:

Immediate: What signals would you watch for?

How do you assess risk?
When do you start preparing?
What's your trigger to act?

3 months in: How do you hedge?

Start building alternative income?
Activate network quietly?
Wait and see?

6 months in: What's your decision framework?

Stay and hope?
Leave proactively?
Build parallel path?

Write down your approach. Are you reactive or strategic?

Scenario 3: You Realize Your Role Is Being Automated by AI

The situation:

Not immediate elimination
But writing is clearly on wall
12-18 months before impact
You have time to prepare

Questions to answer:

Assessment: How do you evaluate the timeline?

Can you reposition within company?
Should you start transitioning?
What's your runway?

Strategy: What's your 12-month plan?

Build fractional practice?
Pivot to AI-adjacent role?
Find new W-2 before forced out?

Execution: What do you start this month?

Build visibility?
Land fractional client?
Document IP?

Write down your 12-month plan. Do you have one or would you just hope?

Part 5: January Action Items (5 minutes)

Based on your self-assessment and scenario planning, what are the top 3-5 actions you need to take in January?

Be specific. Not "improve network" but "schedule 10 coffee chats with former colleagues in January."

Example Action Items:

If your Financial Runway score was low:

□ Set up automatic transfer of $2K/month to career safety fund
□ Calculate exact monthly expenses (know your number)
□ Build to 3 months cash by June 2025

If your Network Strength score was low:

□ Reconnect with 20 people in January (4 per week)
□ Schedule 2 coffee chats weekly with decision-makers
□ Join 2 relevant industry communities

If your Market Readiness score was low:

□ Rewrite LinkedIn headline and summary (Week 1)
□ Document 3 core frameworks by end of January
□ Create portfolio of quantified achievements

If your Alternative Income score was low:

□ Identify 5 potential fractional clients
□ Reach out with value proposition
□ Land first $5K/month client by March

If your Identity and Positioning score was low:

□ Write value-based identity statement
□ Practice introducing yourself without title
□ Test positioning with 10 people in January

Your Top 5 January Actions:

Put these in your calendar now. Block the time. Make them non-negotiable.

Why Doing This NOW Beats Waiting

The difference between doing this exercise during the holidays (while employed) versus during a layoff (while unemployed) is massive:

During Holidays (Employed)

Mindset:

Clear, strategic thinking
Can make rational decisions
Time to build foundation
Can be proactive

Actions available:

Build financial runway over months
Strengthen network gradually
Create alternative income while stable
Position yourself strategically

Outcomes:

Enter 2025 prepared
Navigate any transition smoothly
Multiple options if needed
Negotiate from strength

During Layoff (Unemployed)

Mindset:

Panic, survival mode
Emotional decision-making
No time to build
Forced to react

Actions available:

Burn through savings immediately
Desperately reach out to network
Can't build alternative income (need W-2 now)
Accept whatever you can get

Outcomes:

Crisis mode for months
Stressful, difficult transition
Limited options
Negotiate from weakness

The professionals who do this exercise now will have fundamentally different experiences in 2025 than those who wait until they're forced to.

The Real ROI of 30 Minutes

Time investment: 30 minutes during holidays

What you gain:

Immediate clarity:

Know exactly where you stand
Understand your vulnerabilities
See gaps you need to address
Have concrete action plan

Q1 2025 preparation:

Enter January with strategy
Start building foundation immediately
Proactive vs. reactive
Prepared for whatever comes

Long-term career resilience:

Systematic approach to career management
Regular self-assessment habit
Continuous preparation
Real optionality

If your score was 40+: You're prepared. Maintain what you've built.

If your score was 30-39: You're close. Address the 1-2 weak dimensions in Q1.

If your score was 20-29: You have work to do. Make Q1 about building foundation.

If your score was under 20: This is urgent. Start immediately in January.

What to Do After the Exercise

Step 1: Share your score with someone you trust

Accountability matters. Tell a spouse, friend, or mentor:

Your total score
Your weakest dimensions
Your January action items

Step 2: Block time in January for your top 5 actions

Don't just write the list. Calendar the actual time:

"January 7, 9-11am: Rewrite LinkedIn profile"
"January 14, 2-4pm: Coffee chat with former colleague"
"January 21, 10am-12pm: Document core frameworks"

Step 3: Review progress monthly

First Monday of each month, 30 minutes:

Review previous month's actions
Assess progress on weak dimensions
Set next month's priorities
Track improvement over time

Step 4: Retake the assessment quarterly

March 31, June 30, September 30, December 31:

Redo the full self-assessment
Calculate new preparedness score
Celebrate progress
Identify remaining gaps

The goal: Be at 40+ by June 30, 2025

The Bottom Line

Most senior tech professionals will spend the holidays resting and recharging.

That's important.

But 30 minutes of strategic career planning could fundamentally change your 2025.

The exercise:

One core question: "If my job ended in January, what would I do?"
Self-assessment across 5 dimensions (score 0-50)
Three "what if" scenarios
Top 5 January action items
Calendar and accountability

Why now matters:

AI transformation accelerating into 2025
Q1 is peak restructure season
Planning while employed beats scrambling while unemployed
Foundation takes months to build

What your score means:

40-50: Well prepared
30-39: Moderately prepared
20-29: Underprepared
10-19: Highly vulnerable
0-9: Crisis mode

The action:

Do the exercise this week
Share with accountability partner
Block January time for top 5 actions
Review monthly, reassess quarterly

The professionals who do this 30-minute exercise during the holidays will enter 2025 with clarity, preparation, and strategic advantage.

The ones who skip it will enter 2025 hoping nothing bad happens—and unprepared if it does.

Which one will you be?

Ready to Build Career Resilience in 2025?

If this exercise revealed gaps in your career preparedness and you want help building a systematic plan to address them, I can help.

Book a Strategy Call to discuss your assessment results and develop a Q1 2025 action plan.

Download The Headhunter's Playbook for tactical strategies that work in any situation.

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Happy holidays, and see you in 2025!