What would make you cry on your 80th birthday? …

…. And other questions to help you get clarity when you’re stuck

I’m an overthinker. I don’t know about you, but I often get myself confused over seemingly simple questions.

For example, now that I’m looking for work again, I keep second-guessing my life choices:
What do I really want to do? Can I manage another big project without burning out? Do I want more seniority or an easier life? Is it time for me to change careers, or even move back to France?

These questions are all worth exploring, but they can also lead to inaction and anxiety if I let them. (And as I found out reading Herminia Ibarra’s Working Identity, clarity always comes from action, not the other way around).

That’s when I need a quick reframe.

If this happens to you too, here are five powerful questions I have come across that help me find clarity when I’m stuck in my head:

1. What would make you cry on your 80th birthday?

This one comes from Suzie Welch, the author of Becoming You.

It may sound brutal, but what better way to start with the end in mind and laser-focus on what truly matters?

Just pause to think: what is it you need to do, so that when you come to the last part of your life, you know you’ve made the most of your time on Earth? Is there anything you must try? Anything you must stop? How can you begin now?

This question may seem abstract when you’re young, but once you reach midlife it hits closer to home, as you likely know you don’t have unlimited time.

If you’ve ever read Bronnie Ware‘s Top Five Regrets of the Dying, you will know that the thing most people regret on their deathbeds is not pursuing what they secretly wanted.

If you don’t start now, you will find more excuses. So what’s stopping you?

2. If you knew the answer, what would it be?

I sometimes find that my brain defaults to “I don’t know” rather than give an imperfect or risky answer to introspective questions. Especially when the stakes are high, for example if asking “what do you want to do when you grow up?” or “should I stay of should I go?”.

The truth is I sometimes spend so much time weighing pros and cons that I completely lose touch with my inner knowledge or preferences.

So this is a surprisingly simple hack. (I came across it in a guided meditation, unfortunately I can’t remember which one so I can’t credit it):

If your brain gets stuck on “I don’t know”, you can try to ask yourself what the answer would be if you knew it. The results might surprise you. Once you remove the need for certainty, you’ll usually get a tentative answer, which can be enough to move you forwards.

(Although, if this doesn’t work, “I don’t know” isn’t the end. It’s just a sign that you need to find out more until you can see more clearly, so keep going).

3. What is the smallest step you can take today?

Sometimes we’re clear on what to do but still find ourselves unable to start. If you’re an overthinker, or even a bit burnt out or depressed, procrastination is real.

I could write a whole article on this (there are many out there), but there is one thing in particular that helps me day to day: lowering the bar until action becomes easily doable.

These days I struggle to start writing posts, or job applications, or even reaching out to a friend. In those cases, I find the smallest next step I could take, that doesn’t fill me with dread or trigger resistance.

It may be creating a document that I can write tomorrow, or drafting a text to my friend to send later. Or even just turning the computer on.

Some days that’s enough to give me momentum to do a lot more and maybe even complete the task.

On others, if this small step is all I can manage, I don’t berate myself for not moving faster (as this would make resistance even worse). Any move in the right direction, however small, is progress.

Bonus points if you give yourself encouragements as you go.

4. Do you really need to do this?

There is sometimes a good reason you don’t want to do something.

Do you need to apply to jobs that aren’t a good fit, just for the sake of sending more CVs? Do you need to spend so much time editing your writing, just because you feel like an impostor?

If you’re being honest, why do you need to do that thing you’ve been avoiding?

Maybe you are doing it out of habit, people-pleasing or a guilty conscience. Sometimes cancelling does make sense.

It’s worth questioning yourself. Is it possible that you’re not getting the results you want, because you’ve been doing too much of the wrong thing?

5. What would you tell a friend in this situation?

This one works for when I need to give myself guidance and perspective, but also when I need a bit of kindness and compassion.

Would you tell your burnt-out friend that they are lazy and need to try harder? Or that they must take the first job that comes along, because it’s all they’ll ever get? Hopefully not.

But you also wouldn’t tell them to stay on the sofa for days if they don’t feel like going out. If they were stuck in a pattern of avoidance, you’d gently nudge them into action. Not in a bullying way. Maybe in a gentle way, or with a sense of humour – whatever works for you.

Speaking to ourselves as a friend doesn’t mean giving ourselves permission to opt out. It’s just that sometimes we get tangled in our own situation, and shaming ourselves out of it isn’t going to work (or it would have worked already).

What do you think? I’m hoping these help next time you need perspective.