3 Unusual Questions To Figure Out What To Do With Your Life


It’s been awhile since I released the manifesto about being a questioning engineer. I’ve not written much since then. Why?

Because I was quite challenged by the feedback I got from some readers. Some really good feedback.  People were fascinated by the concept of something being worth the pain. That you have to enjoy the pain the of the journey, not just the destination.

BUT. They wanted to know –

How do you figure out what is worth the pain?

Laptop lifestyle

How do you figure out what to be passionate about? Some people just know what they love – Brian Cox is incredibly passionate about science and communicating it (and music incidentally), Steve Jobs loved technology and creating new experiences, Michael Parkinson loves talking to different people about themselves… you get the idea.

But what if you are a run-of-the-mill engineer who likes life, but doesn’t love anything except going to the pub or online gaming?

So I asked myself – “what do I think is worth the pain? How did I figure it out?”

My brain responded:


Hence, I’ve not written in a while.

After much contemplation, here are my thoughts. I’m no self-improvement coach, this is an engineer’s musings….

So, you don’t know what is worth the pain?

Well, let me tell you what is not worth the pain:

[blockquote id=”” class=”” style=”” align=”none” author=”” affiliation=”” affiliation_url=””]an interesting job, a nice house, a loving family, good friends, nice holidays once a year, fun hobbies…[/blockquote]

These things are… ‘nice’.

But let’s face it. They are as bland as beige, and as generic as vanilla (I happen to like both beige and vanilla, but you get what I mean).

Everyone says they want an interesting job, to be financially comfortable, etc. But what does that mean?

And so here is the first question to ask yourself…

Question 1: What was wrong with last week?

What happened (or didn’t happen) that caused a knot in the pit of your stomach? What caused you to lose your cool?

Or – even worse – what happened that meant you didn’t feel anything at all? What didn’t happen that meant you didn’t even react to life?

Hold that thought – we are just going to do an exercise to get your brain muscles working.

[box_frame style=”” width=”” class=”” align=”center” title=”Exercise 1: The last time you…” inner_style=””]

Think of things honestly – preferably write them down and never show anyone:

Number 1 – Think of the last time you felt accomplished. The last time you felt on top of the world and had really achieved something you were proud of.

If you can’t think of a time, what is an achievement that YOU could be really proud of? Can you imagine yourself having achieved that goal, what it would feel like?

Number 2 – Think of the last time you laughed.

I mean hard. Were you laughing with friends and family or at YouTube? It doesn’t matter which, just think about what caused it – was it relief, or amusement, or connection, or sarcasm?

Number 3 – Think of the last Friday night you had that you really loved and felt it finished off the week well.

(Not the one where you flopped on the couch with pizza and beer and passed out before the second ad break.)

Were you having drinks with family or friends? Or watching a movie with a beer or wine? Or in a restaurant in some far-flung corner of the world after hiking?


There’s no right answer to these questions, they are giving you an insight into what makes you feel recharged, energised, inspired to keep living.

You may notice the answers to many of those questions are little things. They are probably not life-changing answers. But life is made up of lots of little things and you possibly won’t have ONE BIG THING that gives your life purpose.

The life you want

These little things are the details of the life you want. Once you know what your life will look like during and after the pain, it will be easier to identify what is worth the pain.

The more detailed your description of your life, the better. The more you can touch and feel the sensations of your dream, the better.

I know, I’m sounding all woo-woo. Stick with me here – here’s the next exercise.

[box_frame style=”” width=”” class=”” align=”center” title=”Exercise 2: Is it last week… or Week A or… Week Z?” inner_style=””]

Remember what you thought about last week? Remember what didn’t work?

Well, now you are going to imagine your ideal week. For most of us, it is not last week. So start imagining the details of your ideal week… What did you do each day, night and on the weekend?

Week A and Week Z are below if you need some inspiration.


To jog your imagination, I made up two very different ideal weeks. So, do you prefer Week A or Week Z? Or is your ideal week somewhere in between?

Week A – A working parent’s ideal week

Working mother

I worked 5 short days (school hours) from home and in the client’s office 10 min away from home. The work was a mix of teamwork and individual work and I had autonomy over most of my deadlines and workload.

Out of hours I looked after my kids and caught up with friends with kids, including neighbours who brought their kids over for playdates and we drank wine together. In the mornings before school, I cycled 25-50km each day and did some meditation. I enjoy cooking different dinners (regardless of whether the kids eat them or not).

On Friday night I had friends and family over for a low-key hangout session. On the weekend we went out to the beach where I went for long walks, read books, and the kids played on their bikes and in the sand etc. I also spend time organising the upcoming holidays with my partner.

Week Z – Laptop lifestyle

Let’s look at the opposite extreme – the ‘laptop lifestyle’ made famous by the 4-hour work week and other entrepreneurs:

Laptop lifestyle

I work each day for a couple of hours on my laptop, either beside the pool or beach, at whichever latest exotic destination I find myself. I exercise loads by snorkelling, swimming, diving, and bike riding with my partner.

I’m constantly meeting new people and making new connections that bring a real depth to my experience. I also experience so many different aspects to cultures, as I head off the beaten track and don’t just stick to the tourist trail because I can spend months in a country, as I take my work with me. I try loads of different foods and drinks and haven’t eaten ‘meat and 3 veg’ for months.

See – simple. Both much more detailed than “an interesting job, a nice house, a loving family, good friends, nice holidays once a year and some fun hobbies.”

They look quite different, no? Neither is right or wrong, they just will appeal to different people at different points in their life.

Rules for Question 1.

There is only one rule in this exercise – Don’t think about the constraints.

Do NOT limit yourself by thinking, “oh I’ll never be able to afford that” or “oh I’ll never be good enough at anything to command that flexibility and money”. Suspend reality for the moment AND DREAM…

Next step.

What is your ideal week? Is it last week? Or your Week L?

Write it down. Now.

There are two more questions you need to ask yourself… stay tuned while I finish writing them.

All rights reserved Salient.

The 3 Early Warning Signs You Aren’t Changing The World – The Questioning Engineer’s manifesto.

Find out what a questioning engineer is in this Free Ebook.