10 Of The Most Important Questions To Ask Yourself

That you’re almost guaranteed to answer wrong at first

1. How are you?

Like, psychologically. Are you ok? Are you only pretending to be okay? Are you covering up some serious “not okay”-ness with other things, like anger or travel or alcohol or shopping? Are you always tired? Are you reluctant to just… sit with yourself? Do you feel like you always have to be on the go?

The thing — all of us have a neuroses of some sort. Some of us struggle more than others, but we all have a part of our lives that we’re overcompensating for.

So. Are you okay? And if no: do you wanna be?

2. What do you care about / want?

And, more importantly: do you accept we often don’t know?

Life is very often a series of guess and checks — we try things, some work out, some don’t.

And if you want a secret, here it is: nobody nails it. Nobody is always 100% sure of what they want 100% of the time.

We all make mistakes.

So the real point is: keep moving. What’s your best guess?

3. Are You Pursuing What You Want?

If yes: is it actually improving you or your life?

If no: are you sure that’s what you want.

I want to make one thing clear: I lived in Chicago for five years, and the whole time I lived there I told everyone I didn’t want to live there, and one day I would leave. (Dating serious long-term partners who lived there, though, complicated this. That, and the serious of other, smaller excuses I made for the delay.) Anyway, sometimes when I talked about leaving, people would point out, “the problem isn’t Chicago — it’s you.”

And I knew then that they were wrong. And years later, in a different city and now looking back, I am even more sure: sometimes we are just in the wrong city. Or the wrong relationship. Or the wrong job.

4. Are you happy?

It’s different than the first question, because it’s more specific. I’m not just asking if you’re bumping along or “not suffering.” I’m asking about lightness, contentedness, joy, bliss, warmth, etc.

If no: do you want to be? Do you want something else more?

Very often in life, we trade in one “type” of happiness for another. We may forfeit travel or eating out, for example, in order to save. We choose one job and turn down another.

We make decisions, and sometimes we don’t eat the marshmallow even when the marshmallow looks a hell of a lot like “happiness,” which means we may not feel “happy” in that moment even though we are investing in eventual wellbeing.

Very often, people don’t truly want “happiness,” in an amorphous sense, as much as they want to satisfy their other values — support, stability, status, adventure, control, peace, etc.

People often bastardize what they think will make them “happy” and bundle it into these things, and when they don’t find happiness at the other end of pursuing them, they’re often at odds with it, feeling they were shorted the deal. And for the most part, we don’t give up our real values (like the list above, though it’s not comprehensive.) So the better solution is to decouple or redefine “happiness,” and better understand how it looks to achieve.

5. Do you accept that happiness is a bit allusive, and doesn’t always look like happiness?

Sometimes when we’re pursuing the thing we want most, it looks a lot like sacrifices and patience. Few parents would say the first few months with a newborn are enjoyable, but when they look at the experience of raising a child overall, it’s often worth it.

6. Do you accept that happiness often requires relinquishing what we hold as our deepest, most-defended needs (e.g., neurosis) and even our identity?

The thing with happiness is that it’s not at the end of ceaselessly chasing things — whether that’s home renovations or travel or brunch or a new job.

Sure, sometimes we do have a bad match. But if we keep running without answers, the reality is that it’s us, and not it.

The dirty little secret is that we are capable of happiness. And for the most part, we are in control of our emotional wellbeing.

7. What are your blind spots? Do you accept that you’re still blind to some?

Most people don’t.

8. Are you facing your demons? Do you know what they are?

It’s likely that you don’t — most of us don’t. But if you do know that you struggle with something — anxiety, attachment, avoidance, etc. — then: are you facing it? Like, really doing the work here? When you look at it over, say, a 6 or 12 or 24 month period, are you making measurable headway?

9. Are you growing?

And: do you want to grow? (If no, why?)

We are always either growing or dying. There is no “stagnant” — at least not for long. The universe is always in shift, moving and changing, and if you’re not using that to your advantage, it’s likely not in your favor.

10. Do you accept that you are in control?

The number one differentiator between “successful” people — regardless of how you define that, whether it’s career or entrepreneurship or money in general or physique or personality or love — and those who struggle is:

Effective people, who get what they want and need most in life, are always those who take responsibility for their lives, especially their responses to things.

Ineffective people, they blame things outside themselves.

It’s their parents’ fault. Or their boss’ fault. It’s because “everyone else” is an idiot. Or because they have some disease, or disability, or a death in the family.

Look, bad things happen to everyone. No, not everyone gets dealt the same hand, and some hands, yes, are worse than others. But it still stands true: effective people focus on the end goal, and overcome hurdles. Ineffective people park themselves in front of them, or haul them around like Boy Scout badges.

You are always in control, and being able to take agency for your own responses to things is the number one most important thing in life.