The Six Core Questions.
Over the past few years, I’ve had conversations with countless people.
People in all sorts of careers, paths and lives.
People who are still working; people who are retired.
People who are about to have kids; people who are tired of having their own kids.
People who are just starting out at a new job; people who have been in the same job for what feels like forever.
And, they all seem to have the same 6 questions running through their minds when we speak.
Now, before you say anything, yes - these questions are the underlying questions. These are not surface questions - at least not immediately.
But, they are no less fundamental to the value of the conversations we are having, and I think more importantly, to the power that each of these people have to change their own trajectory, or make an important decision in life, or, to just know more about themselves.
Because, really, that’s what these questions are about - knowing ourselves better.
Here’s what I hear most often, and what I think these questions really reveal.
Question One: “What’s wrong with me? I should be happy.”
Ah, yes. The classic “should”.
“It all looks so good on paper, so why doesn’t it feel so good?” Or, “I really have nothing to complain about - life is good!” Or, “I’ve done everything I was supposed to to be happy, but that doesn’t seem to be working - now what?”
It’s odd how the set of instructions we get in life are “supposed” to lead us to a specific outcome, and yet, when we follow those instructions, so often they don’t.
It’s not like IKEA furniture.
Or, maybe it is.
There’s a reason that companies like TaskRabbit exist (and do well). People are generally either: a) reluctant to follow instructions or b) not good at following instructions.
But, my sense is that it really has nothing to do with instructions. It has to do with outcomes. Specificially, controlling outcomes. We don’t want to engage in most things unless we know exactly how it’s going to turn out.
Now, with IKEA furniture, sure - if you follow the instructions to a “T” - or have TaskRabbit do it for you - you will almost certainly end up with that lovely Malm or Poang you saw on the showroom floor.
But, with the paths of our careers or lives, there isn’t any TaskRabbit. No one is going to do it for you.
And so, in that sense, maybe instructions just aren’t all that helpful and we need to fundamentally go off script.
By deviating from what is expected of us, maybe we actually create space for more possibility - and, other outcomes that surprisingly are closer to “fitting into the room” that much better. This might have been what my therapist was trying to get me to understand this week when she was suggesting to go after the energy, rather than any specific sort of plan.
Which, now that I mention it, makes think of…
Question Two: “What if I make the wrong move?”
Another way of looking at this is to ask “Why am I frozen?” We want to make the “right” choice - we see risk in all directions, so we stall - we get stuck and refuse to move simply in an attempt to stay safe.
And yet, in staying in the same place, the greater risk reveals itself - the risk of idling, languishing - rotting if you really want to take it that far.
That’s not to say there is no value in idling. I love the work of Tom Hodgkinson and The Idler, which is fundamentally about a philosophy of “inaction being the wellspring of creation”. Which is true - how much good art has come from not being bored?
But, idling in the face of potential risk is something different - that is less a choice to be idle and more a sympathetic nervous system response to just stop - like a deer in the headlights - and we know how that usually ends.
But, to draw on something from above, what if there is no plan - no predetermined outcome - no destination? What if it’s simply an experiment instead? You try something out - see what happens - learn - and decide to try again or try something else?
Sometimes I feel like that in the work I’m currently doing. That this is really not a planned thing, and in fact, is just an experiment which may or may not pan out. That takes some of the pressure off, for sure - and, also makes it easier to do more creative things like write this article, or take a photo that could be good (or terrible), or maybe even get around to making that video content that everyone tells you (read: me) you should be making and sharing.
I think that approach works well with big career and life decisions too - sure, you can have a hypothesis, but don’t be attached to the outcome. Just like a great scientist (or science student) conducting some grand experiment - it might not work out as you expected, and that could be the entire point.
And that leads to asking…
Question Three: “What’s the point?”
Great question.
To make a difference in the world? To take care of your family? To live a life of hedonistic pleasure, casting the concerns of all others to the wind while you live only for the moment?
Maybe. Or, it could be none of them. I don’t know.
Most often, I think this question pops up right around the mid or quarter-life point. What so often we would call a “crisis”. The point where we’ve ticked off a number of important boxes, and now, the other questions arise - I am a quarter/half/three-quarters of the way “there”. What will I have to show for it?
In other, darker terms - you realize you are going to die. And when that happens, you might ask: what has this all been for?
It’s a pretty uncomfortable question for most people. And, I think once people start digging in, that’s when there’s the invitation to tear it all down - as if everything up to that point has been meaningless because now - now that you’ve realized it - you can really make a change and have an impact.
This opens us up to what Shigehiro Oishi refers to in his book Life in Three Dimensions: How Curiosity, Exploration, and Experience Make for a Fuller, Better Life, as the “meaning trap”.
Oishi argues that while meaning (in the sense of “my life matters”, “I have a purpose”, “things hang together”) is often held up as one of the key pillars of a good life. But, it carries some hidden risks. The “trap” is this: you set out to live a meaningful life (which is good), but you buy into the mythic version of what “meaning” means - and that setup can cause unintended downsides.
Or, in other words, you can take drastic steps (or non-steps) to ensure your life really does have meaning.
So, what do you do instead? Oishi argues that pursuing happiness - and being more present to happiness - can help. But, also, adding in a third ingredient to life - psychological richness. Expanding and varied relationships; opportunities for creativity; learning and taking a more winding path; and, of course, finding ways to contribute that don’t necessarily change the world - but certainly impact your own world. These actions, large and small, can deepen and widen the sense of our own psychology - the sense that my life has been, at the end, simply interesting.
Like a good movie. Which you might notice, you watch - you don’t “do”. Which leads to asking…
Question Four: “Why can’t I just relax?”
Yes, why can’t you? Or I?
As in, “Why can’t I idle in an intentional way?”
Or, “Why can’t I allow things to unfold as they might without being so vigilant?”
As if doing something all the time is somehow proving something about our identities. Or our value. Our worth.
Yes, sure - you can chalk this up to family pressure, or social media, or how you were trained at school or at your first job to be a “good worker”.
In my own life, this is a constant - I actually feel unsettled when I am not doing something. I’ve tried so hard to get better at just sitting - and the harder I try, the harder it is. Which is the painful irony of it - how can you get better at relaxing if you need to try to relax?
I honestly don’t know.
But, I think it starts with getting your own system to recognize that there isn’t some threat out there, waiting to pounce, if you let go of control, even briefly.
Maybe this is why psychedelics can work so well for this - they can (although not always) interrupt the usual stress loops of the nervous system and temporarily shift someone out of chronic sympathetic activation (fight, flight, freeze) into a more open, parasympathetic, “rest and connect” state.
Not that I’m advocating you go out and take LSD right now.
But, sometimes, we need something - therapy, meditation, a stiff drink - to remind the body it’s safe to “rest and connect”.
And, anything that can safely allow you to “rest and connect” can’t be all that bad, right?
Maybe, but if you’re having a hard time relaxing, you might also be asking…
Question Five: “Why do I care so much what people think?”
Being alone is, sometimes, not so much fun.
I like being alone. I really value my alone time.
But, I will admit - being a lawyer (and often in my current coaching and leadership work) is fairly solitary. It can lack the camaraderie and friction that working with groups on a shared project can have.
And, that can wear on you.
Similarly, being rejected - not having the approval of friends, family or “society” - can have that same effect. The isolation and loneliness that can result from being cast out to the wilderness to endure the rest of our lives in solitary pursuit of food and shelter is certainly not appealing.
Extreme? Perhaps. Although there is research to back up the claim that, ultimately, we care so much about rejection because of the evolutionary fear of being thrown to the dangers of the world outside of the tribe.
And so, of course, when we choose what work to do/what song to sing/what to wear, we are concerned about fitting in.
Can that be suppressed? Sure, of course. Is it helpful to care what people think all the time? Of course not.
We know this. And yet, we care. We want to belong. We want to be safe. We want to be cared for.
So, how can we feel safe and also do what we need to do at the risk of disapproval?
One thing I do is actually try to disappoint one person a day. Weird, I know. But, it works. I realize that not being approved of is actually not so bad. My life has not fallen apart. The person I have disappointed isn’t actually that upset. I am not being torn apart by hyenas in the savannah.
Put in other words, I can stop performing so much. Who I am isn’t necessarily identical to what I do, and as a result, I can trust a bit more that people still accept me for me, separate from what my actions or choices are. Visibility and validation are, in fact, distinct.
But if so, then does one matter more than the other? And, regardless…
Question Six: “Who am I without the job/title/success?”
This is what I call the “jugular” question.
As in: “I am going to go for the jugular now and possibly kill you by asking you this question.”
I think, in many ways, this is what it all comes down to.
And, how many of us can honestly say we haven’t asked this question?
So many people I speak with are deliberating, torturing themselves, stuck with the question of what happens if they stop being the job/title/earnings/prestige they currently are.
I know I struggled with this immensely. I still do. This presumes, of course, that I had any to begin with (I say, tongue in cheek).
I’ll never forget a mentor of mine told me, when I told him I was going to go out on my own as a lawyer and leave the confines of the “big firm” - “Jordan - you might do well, but you’ll never have the prestige.”
I honestly don’t know whether he was right. But I do know that, once I took that out of the equation, it made it easier to make decisions.
Because it didn’t really matter. It wasn’t connected to what I really cared about - independence, freedom, a greater sense of control over my destiny.
That doesn’t mean that I couldn’t have honoured those values had I pursued prestige. It just meant that, at that time, they simply weren’t compatible with the track that I was on. So, I changed tracks.
Or, a different way of looking at it, is that I edited the story. The story that I wanted to tell myself, about myself, in the future had to be reconstructed in a way that was going to have to leave out the “prestige” part in order to be more interesting - and more true - when it was all over. Which, I hope, is a long time from now.
Walking with the Questions
Maybe these six questions aren’t meant to be answered at all.
Maybe they’re more like little friends that walk with us as we go through our days - nagging sometimes, yes - but also asking who and what is happening beneath the plans, the striving and the noise.
They remind us that meaning, happiness, rest, and belonging aren’t places to get to or to arrive at - they are ways of being with ourselves along the road to wherever we are going - which, we might not even ever know (a topic for another time…).
So if one of these questions has been tugging at you lately, don’t chase it away. Listen. See where it wants to take you.
And if you feel like it, tell me which one’s been slightly nagging. I help lawyers, executives and creative professionals get unstuck - finding clarity, purpose, and momentum in their careers and lives.
