The Uncomfortable Gift of Evaluate Your Life Day

(And Why Most People Will Ignore It)

Tomorrow is Evaluate Your Life Day. Yes, really. October 19th. Someone, somewhere, decided we needed an official day to stop scrolling, put down the crisps, and have a proper look at what we’re doing with our lives.

And I’ll be honest: my first instinct was to roll my eyes. Another manufactured holiday wedged between World Pasta Day and International Sloth Day, designed to sell us journals with inspirational quotes and self-help books that promise transformation in twelve easy steps.

But then I thought about it—properly thought about it—and realised something uncomfortable: most of us are terrified of actually evaluating our lives. We’re brilliant at numbing, distracting, and postponing. We’ll reorganise the kitchen cupboards, deep-clean the grout, learn Croatian on Duolingo—anything but sit still and ask ourselves the hard questions.

So here’s what I’m proposing. Not a corporate wellness seminar with breakout sessions. Not a vision board party with prosecco and Pinterest quotes. Just some honest, practical ways to use tomorrow (or any day, really) to take stock without spiralling into an existential crisis or pretending you’re going to become an entirely different person by Christmas.

Why We Avoid This Stuff

Let’s start with the elephant in the room: self-reflection can be bloody terrifying.

When you pause long enough to evaluate your life, you might discover you’re not where you thought you’d be. Or that you’re pursuing goals that stopped mattering to you three years ago. Or that you’ve been operating on autopilot, making decisions based on what you should want rather than what you actually want.

It’s easier to stay busy. To keep moving. To tell yourself you’ll “sort it out” after this project, after the holidays, after you’ve had a proper break.

But here’s the thing about never stopping to evaluate: you end up somewhere you never intended to go. You wake up one day wondering how you got here, surrounded by choices you don’t remember making.

Evaluate Your Life Day—ridiculous name aside—is giving you permission to stop. Just for a moment. Just to look around.

The Questions That Actually Matter

Forget the life coaching questionnaires with forty-seven bullet points about your “authentic self” and “core values alignment.” Most of that stuff is just noise that makes you feel like you’re doing something without actually doing anything.

Here are the questions that cut through:

What’s working?

Start here. Not with what’s broken or missing, but with what’s actually going well. What parts of your life would you fight to keep exactly as they are? This isn’t about gratitude porn or forcing yourself to be positive. It’s about knowing what matters so you don’t accidentally dismantle it whilst chasing something shinier.

What’s draining you?

Not just the obvious stuff like a soul-crushing job or a toxic relationship. What about the small things? The commitments you said yes to out of obligation. The hobby you started because it seemed like the kind of thing you should enjoy. The friendships you’re maintaining out of guilt rather than genuine connection.

What are you pretending not to know?

This is the killer question. The one that makes you squirm. We’re all walking around with truths we’re actively ignoring because acknowledging them would require difficult decisions or uncomfortable conversations. What’s yours?

If nothing changed, would that be okay?

Seriously. If your life looked exactly like this in five years, how would you feel? Sometimes the answer is “perfectly fine,” and that’s brilliant—you can stop feeling like you’re supposed to be endlessly optimising. But if the answer makes your stomach drop, that’s information worth having.

What tiny thing could you change this week?

Not your entire life. Not a massive overhaul. Just one small thing. Because grand transformations are intimidating enough that we never start, but tiny changes are doable. And tiny changes compound.

The Practical Bits (That Don’t Require Buying Anything)

You don’t need a leather-bound journal or a weekend retreat in the Cotswolds to do this work. Here’s what actually helps:

Twenty minutes and a notebook

Set a timer. Write without editing. Don’t make it pretty. Nobody’s going to see this. Just get your thoughts out of your head and onto paper where you can actually look at them. Thoughts that stay in your head just loop endlessly. Thoughts on paper become manageable.

The “stop doing” list

Everyone bangs on about to-do lists and goal-setting. Nobody talks about what you need to stop doing. Make a list of things you’re going to quit, delegate, or ignore. What meetings could you skip? What commitments could you politely exit? What subscriptions could you cancel? Subtraction is underrated.

The awkward conversation you’re avoiding

You know the one. With your partner about division of labour. With your boss about workload. With your friend who only ever calls when they need something. Evaluating your life without addressing the relationships that shape it is like trying to clean your house with all the furniture in the way.

A proper digital detox (just for a day)

Not the performative kind where you announce it on Instagram before logging off for three hours. Actually, delete the apps from your phone for twenty-four hours. See what happens when you’re not constantly consuming other people’s curated lives. See what thoughts emerge when you’re bored on the bus instead of scrolling.

Talk to someone who isn’t you

Your own brain will lie to you. It’ll rationalise, justify, and protect you from uncomfortable truths. Find someone—a friend, a therapist, a mentor—who can reflect back what they’re seeing. Sometimes we need an outside perspective to spot the patterns we’re too close to notice.

What This Isn’t

Let me be clear about what I’m not suggesting.

I’m not suggesting you burn your life to the ground and start over. Most of us don’t need a complete reinvention. We need to tweak, adjust, and realign.

I’m not suggesting you achieve some permanent state of optimised perfection where everything is sorted and you’ve reached peak self-actualisation. Life doesn’t work like that. You’ll evaluate, adjust, and then need to evaluate again in six months because you’ll be different and your circumstances will be different.

I’m not suggesting you compare yourself to everyone else’s highlight reel and feel inadequate because you’re not running an eco-friendly startup whilst learning Mandarin and doing sunrise yoga. Your life. Your metrics. Nobody else’s.

And I’m definitely not suggesting you spend tomorrow beating yourself up for every mistake, missed opportunity, or suboptimal choice. Self-evaluation isn’t self-flagellation. It’s curiosity, not judgment.

The Bit Where It Gets Uncomfortable

Here’s what usually happens when people actually sit down and evaluate their lives: they realise they’ve been lying to themselves about something.

Maybe it’s that the career they’ve been working towards for years doesn’t actually excite them anymore. Maybe it’s that they’re staying in a relationship because leaving feels too complicated. Maybe it’s that they’re living somewhere they hate because they’re afraid of disappointing their family. Maybe it’s that they’ve built an entire identity around being busy and productive because they’re terrified of who they’d be if they slowed down.

These realisations are uncomfortable. They create cognitive dissonance. They require difficult decisions.

So here’s what we tend to do: we avoid the evaluation altogether. Or we do a surface-level version that doesn’t touch anything real. Or we have the realisation, acknowledge it, and then… do nothing. Because doing nothing is easier than disrupting our lives.

But here’s the truth: the discomfort of facing reality is temporary. The discomfort of living a life that doesn’t fit you is permanent.

Small Shifts, Not Seismic Changes

The good news is you probably don’t need to blow everything up.

Most of us aren’t living completely wrong lives. We’re living slightly off lives. The angle is just a few degrees out, but over time, those few degrees take you somewhere completely different from where you wanted to go.

Small course corrections now save you from massive detours later.

So what could you shift?

Could you have an honest conversation about needing more support at home?
Could you block out two hours a week for something that actually energises you?
Could you stop attending that committee you joined three years ago out of obligation?
Could you set one boundary that you’ve been too scared to set?
Could you start saying “I need to think about that” instead of automatically saying yes?
Could you spend less time with people who drain you and more time alone or with people who light you up?

None of these is life-altering. All of them could change everything.

The Question Nobody Asks

Here’s the question that doesn’t appear on any self-help questionnaire but probably should:

Are you living your life, or are you living someone else’s idea of what your life should be?

Because most of us are operating on a script we didn’t write. Go to university. Get a good job. Buy a house. Get married. Have kids. Be productive. Be successful. Be happy (but not too happy—that’s suspicious). Optimise everything. Never waste time. Constantly improve.

Whose script is that? And more importantly: is it yours?

Maybe it is. Maybe you genuinely want all those things. That’s fine. But have you actually checked? Or are you just following the path because it’s there?

Evaluate Your Life Day is permission to interrogate the script. To ask whether you’re living according to your own values or someone else’s expectations. To get curious about who you’d be and what you’d want if you weren’t trying to please everyone, impress anyone, or prove something.

What Happens After Tomorrow

Right. So let’s say you do this. You spend tomorrow—or this weekend, or next Tuesday—actually evaluating your life. You answer the hard questions. You identify what needs to change.

Now what?

Because here’s where most people stumble. They have the realisation, feel momentarily empowered, and then… nothing changes. Life goes back to normal. The insight gets buried under emails and errands and the general chaos of existing.

So here’s what you do:

Pick one thing. Not seventeen things. One. The thing that, if you changed it, would have the biggest impact. Maybe it’s starting therapy. Maybe it’s having that difficult conversation. Maybe it’s saying no to the next thing someone asks of you. Maybe it’s applying for that job you’ve been stalking online for six months.

Do it this week. Not eventually. Not when you feel ready. This week. Because if you don’t act on the clarity while it’s fresh, it’ll fade. You’ll rationalise it away. You’ll convince yourself it wasn’t that important.

Tell someone. Accountability is annoyingly effective. Text a friend. Post about it (if that’s your thing). Put money on it. Whatever makes you more likely to actually follow through.

Don’t expect perfection. You’ll probably mess it up. You’ll backslide. You’ll have days where you wonder what the point is. That’s fine. Progress isn’t linear, and self-improvement isn’t a destination you arrive at. It’s just… trying. Adjusting. Trying again.

The Real Point of All This

Look, I know this is a made-up holiday. I know it’s slightly absurd to designate a specific day for something you could theoretically do any time.

But maybe that’s exactly why it works.

Because without a designated day—without permission, without a prompt—most of us won’t do it. We’ll keep deferring, keep pushing it off, keep telling ourselves we’ll figure it out later.

Evaluate Your Life Day is just a nudge. A reminder. A moment to pause and ask: is this working? Am I where I want to be? If not, what needs to change?

You don’t have to overhaul everything. You don’t have to become a different person. You just have to be honest with yourself about where you are and where you’re going.

And then—this is the crucial bit—do one small thing about it.

That’s it. That’s the whole thing.

So tomorrow, when October 19th rolls around, maybe don’t ignore it. Maybe sit with it for twenty minutes. Maybe ask yourself the uncomfortable questions. Maybe write something down. Maybe make one small change.

Your future self will probably thank you.

Or at least, they won’t be quite so confused about how they ended up here.

What’s one thing you could change this week? I’m genuinely curious. And also procrastinating on my own self-evaluation by writing this, so we’re in this together.

Until Next Time