The toughest review of your year should be the one you give yourself.
And right now - in the small window before Christmas - is the perfect moment to take stock, and think about what you might want to change next year.
Do it well - and you can go into the new year with a well thought through plan. Ignore it..and you’ll be left, at best, with the same old flaky New Year’s resolutions.
Here are six questions you should ask yourself.
Yes or No answers only!
Does my CV look stronger now than it did a year ago?
If I stay in my current role, will my CV look stronger a year from now?
Am I using AI to make me more effective in my role?
Am I stronger in one or more key product skills than I was 12 months ago?
Am I in a better financial position than I was a year ago?
Is my work/life balance where I want it to be?
If the answer is Yes to all six: brilliant, don’t take that for granted.
If the answer is No to all six… well, you already know something’s off and you’ll need to change things quite fundamentally.
But the most common situation, for most of us, is a mixed bag: a few Yes’s, a few No’s.
That’s where this little exercise becomes useful.
Because the point isn’t the number of Yes/No answers you collect.
The point is the shape of the picture they paint, and whether you’re actually OK with it.
But first, let’s look at why these six questions matter.
They’re actually in three groups of two.
Group 1: Your CV as a litmus test
Your CV is a brutally efficient test of what you’ve been achieving at work, for two reasons.
1. Achievements have a brutal half life. What you did a decade ago doesn’t matter. What you did five years ago - vaguely interesting. Two years ago? That’s relevant. In the last 12 months - now we’re talking.
2. The most impactful work (and the stuff that anyone looking to hire you will be most tempted by) can almost always be summed up the most succinctly. You did something that grew revenue, saved cost, massively increased engagement. Easy to talk about.
You implemented a new reporting framework that ensured much greater alignment between product, sales and marketing etc etc …well it may have been a real game changer, but it doesn’t really scream ‘hire me’.
And the forward-looking question — “Will my CV look stronger a year from now if I stay put?” — is the question I ask everyone who comes to me asking whether they should stay in their current role or not.
Very often it’s because they know the answer to that is ‘No’ - but there’s some other factor: they like the people they work with, the vibe of the company, or they have a good work-life balance that’s keeping them there.
That’s fine - but just accept it’s a trade off. And that trade of is potentially ‘creature comforts’ vs ‘market value’.
Group 2: AI + Skills — are you developing or drifting?
The next pair of questions asks something even simpler: Are you actually getting better at your job?
Right now, that has to include a dimension of AI: but it’s not about acquiring expertise or its own sake, or in the hope of landing some massive job in the future (both of which are just fine btw but not relevant right here). It’s a bit more pointed: are you using AI now to be measurably better at your job?
And this is the nub of it. AI has lots of potential, and lots of limitations. What you need to be doing now is taking all of that on board and then applying effectively to your day to day work. That cliche of ‘you won’t lose your job to AI..but you will use it to someone who uses AI’ is a bit melodramatic, but right now - it’s an essential part of skilling up and staying relevant in the market.
But, AI is only one part of the story.
There are still huge parts of the craft — discovery, decision-making, cross-functional influence — that AI won’t magically fix. In particular, it’s the human stuff that becomes more important as your career progresses that’s hardest to delegate to Chat GPT: how you manage a relationship with a demanding sales team; a reluctant engineering manager; a relentless CEO. How you perform in an exec meeting.
Every year there needs to be things you’re getting better at.
Stuff that once seemed impossible should now seem routine.
Your commitment to yourself should be to both know where your gaps are..and what you’re going to do about them.
Group 3: Money + Having a life. The stuff that matters.
These final two questions are there to put work into context.
Because bluntly if work is going great, but you’re going financially backwards and /or your work/life balance is making your miserable…then actually, is work really going that well?
Money: Regardless of what you’re earning, or the enormous riches that might be in store for you on a hypothetical exit/ share vest…year in year out , the key question is: are you getting financially stronger?
A quick test of this is: If you lost your job tomorrow, would you be more or less resilient than you were this time last year?
Now, there are times when you will go backwards financially (having children; moving house; investing in the holiday of a lifetime…are all valid reasons). As with all these things - that’s fine..but be aware of it.
Work/life balance: The only real judge of this is you. And you will know if it feels wildly off; off but manageable; or just fine.
As with money, there are times when you will knowingly go backwards - and you can be happy with it. You’re working on something massive and motivating, and it’s taking up a ton of your time.
At the same time, you can just be in a state of overwhelm and near burn out, and for everything that looks great about your job - the sense of relentlessness is telling you it’s just not worth it.
So what do you do with all this?
It’s not about whether you scored four Yes’s or two.
It’s about why each answer is what it is, and whether you’re happy about it. That’s the good thing with a self-assessment - you get to be the judge as well as the judged.
A No isn’t a problem in itself.
But a No that you really want to be a Yes is.
The value comes from tracing each No back to its root cause:
What’s getting in the way?
What have you been avoiding?
What would need to change for the answer to be Yes this time next year?
And how are you going to make that happen?
And the last one, of course is what matters. A plan. Action with a purpose. Get onto it now, before the first box of Quality Street make it into the office!
pearls of wisdom , love it 👍