10 Questions to Review Your Career Before Christmas
10 weeks. 10 questions. One honest look at your career before Christmas.
Every year I watch good people make big career decisions at the worst possible moment: Christmas.
Think about the mix: you’re absolutely exhausted, you’ve been running on fumes for months – then you stop.
You spend time with family and friends, have plenty of long lunches, and your days are full of no Slack, and no deadlines. Add a few wines and a lot more food than usual into the mix, and you end up with a real false sense of how you actually feel.
That’s why I suggest keeping a journal for the next 10 weeks.
How the Journal Works
- Once a week, answer the 10 questions on the next page. Use the prompts to think it through properly.
- Give each question a score out of 10, then add them up for a weekly total out of 100.
- Log your scores on the tracker. 10 minutes a week or honesty. Nobody’s reading it but you.
- Before Christmas, look at the trend, not the feeling on the day.
The Questions
1) Growth: How much am I growing – personally and professionally – in this role?
- Technical skills: Am I getting better at my craft, tools and
- People skills: Managing up, leading, clients, tough conversations
- Confidence: Am I backing myself more than at the start of the year?
- Exposure: New challenges, or the same thing on repeat?
Rating scale: 1 – I am growing heaps, 10 – I have stopped growing.
2) The Business: Does the business I work for excite me?
- Direction: Do I believe in where it’s heading?
- Leadership: Do I trust the people running it?
- The work: Am I proud of the clients, brands or products?
- Momentum: Winning and investing, or treading water?
Rating scale: 1 – I love this place, 10 – This place does nothing for me
3) Career Progression: Is there a clear path for me, and is it where I want to go long term?
- Do I know what the next step looks like and what it takes?
- Do people get promoted here, or leave to move up?
- Is the next role something I actually want, or just the next box?
- Have I actually asked, or am I waiting to be told?
Rating scale: 1 – There is a clear path, and I want it 10 – There is no path, or there is one but I don’t want it
4) Pride: When someone asks where I work, am I proud to tell them?
- Do I say the name straight away, or play it down?
- Do I find myself explaining or justifying it?
- Would I recommend it to a mate looking for a job?
Rating scale: 1 – I love telling people where I work 10 – When someone asks where I work, I change the subject
5) Culture and Values: Does the culture of this business match my own personal values?
- How people are treated: Respect, honesty, fairness from the top down
- What gets rewarded: Results at any cost, or doing it the right way?
- The people: Would I choose to spend time with them?
Rating scale: 1 – It fits me perfectly 10 – We’re not on the same page
6) Flexibility and Balance: Does this role give me the flexibility I need to feel a good balance?
- Hours: reasonable most weeks, or busy season all year?
- Hybrid or WFH: real, or only on paper?
- Switching off: can I log off nights and weekends?
- Energy: anything left for family, friends and me?
Rating scale: 1 – I’ve got the balance I need 10 – Work is taking over my life
7) Industry Outlook: How is my industry performing, and is there a clear long-term demand for what I do?
- Is my part of the industry growing, steady or shrinking?
- Are companies hiring for what I do?
- Is AI boosting my role, or slowly replacing it?
- Am I building skills the market will want in 3–5 years?
Rating scale: 1 – My space is in demand 10 – My space is shrinking
8) The Sunday Feeling: How often do I get a sense of dread on a Sunday when I think about work tomorrow?
- Most Sundays, now and then, or never?
- Does it start Sunday night, or Saturday already?
- Is it one person or client, or the whole thing?
Rating scale: 1 – Never, Sundays are mine 10 – Every week
9) Having a voice: Do I have a say in how the business runs, and does that matter to me?
- When I share an idea, does anything change?
- Am I asked for my opinion, or just told?
- Can I disagree with my boss without it costing me?
- Do I actually want a say? If not, score this low.
Rating scale: 1 – I’m heard, or don’t need to be 10 – My voice matters but no one is listening
10) Financial Reward: Am I being paid fairly for the contribution I’m making?
- Do I know what my role pays elsewhere, or am I guessing?
- Has my workload grown faster than my pay?
- The full package: bonus, super, leave, training
- Have I asked for a review? How was it handled?
Rating scale: 1 – I’m well looked after 10 – I’m giving far more than I get
Your Ten Weeks
Fill in one column every Friday.
Add up the total at the bottom (10 = happy as Larry, 100 = I have to go).
Jot down the best and worst moments of the week next to your score each week.
Reading your scores
Look at your weekly totals across all 10 weeks, then at which questions keep scoring high. That tells you exactly what’s wrong, not just that something is.
Mostly 10s-30s: You’re in a good spot, enjoy the break.
Mostly 31s-60s: Some things need to change, but it’s probably not your whole job. Chat to your boss when you’re back.
Mostly 61s-100s: It’s time to look. You need to change jobs.
Before you make the final call
I hope you see a lot more 1s than 10s – but if you don’t, ask yourself: is there anything that can be done?
I often hear from talent that there’s no career progression where they are. When I ask what they’ve done about it themselves, I usually get a blank stare.Sometimes we’re just one slightly uncomfortable conversation away from a breakthrough. So be brave. Have the conversation.
An old boss of mine used to say something that’s stayed with me ever since:
“No one is awake at night worrying about your career.”
That’s your job.
Enjoy the break, and hopefully this helps shape your thinking before then.
Ryan Kelly
Founder, Creative Natives