Most young people I know are grappling with their careers.
Sometimes they’re worried that they’re on the wrong path.
Sometimes they’re worried that the right path isn’t satisfying.

When there is so much conflicting advice out there, how do you make good decisions?
My answer is always: Ask the right questions - even if they’re not easy or comfortable.
Here are some of my favourites:

What is my risk tolerance?
I was lucky to have a few hours of career planning with Brad Graham, one of the best consultants I’ve ever met.
He started the session like this:

“Let’s look at the big life factors first: Do you have any kids on the way?”
“No”
“A mortgage?”
“No”
“Legal troubles? Family member in court?”
“No”
“So you have a high risk tolerance then?”
“……………yes?”

I had never looked at it like that.
I’d considered myself risk-averse (based on my personality), when in fact my life situation actually enabled me to take big risks; in a way that I couldn’t in 10 years’ time.
What is yours?

Am I looking to earn or learn?
Which is more important for your situation: money or experience?
Both of these are good, but one usually takes priority over the other.
Would you be willing to take less money in order to accelerate your growth?

Am I happy?
This is a deceptively simple question.
Right now, are you happy with your work situation?

It’s deceptive, because it can describe several different things.
Maybe you’re on the right path, but with people you can’t stand, or are burdened with a dud project.
Maybe you previously thought you were on the right path, but it’s not making you happy.
Maybe everyone tells you that your job is cool, but you struggle to get out of bed each morning.

Seth Godin has a great diagram called The Dip.

Lots of things tend to start out well, turn tough, then become amazing later on (e.g. learning an instrument, travelling overseas to study, creating an artistic project, etc).
Other things stay crap, and you need to cut & run.

The key isn’t to avoid hard situations, but to diagnose which scenario you’re in.
Which one best describes your position?
What would your friends and family say if I asked them instead?

What are you good at that other people struggle with?
What do you get specifically asked to help out with?
Maybe it’s an eye for design, or an ability to talk to anyone.
Maybe it’s your work ethic, sense of humour or ability to keep spirits high during tough times.
These are all valuable, and a lot of people aren’t very good at them either.

Employers can train you in new skills, but they can’t change mean, lazy or awkward people.

How much would it cost to replace me?
Most people find pay negotiations to be a nightmare.
This is a missed opportunity.
Not because you should make demands to your employer, but because you sell yourself short.

I’m not suggesting you pick a fight with your boss; just that you understand your value, and have a clear picture of what you could get elsewhere.

The first component is: what other role could I get next week, and how much does it pay?
The second component is: if I left today, how much would it my team cost to replace me?

A junior person might start on a low salary and build their skills, making them more valuable, but not better paid.
However, if you work out that it would now take a senior person to replace you, suddenly you feel more confident in asking for more in your role.

Remember, it might not just be cash – it can be travel, flexibility, more leave, better tech or the ability to choose projects you find interesting.
If your employer still doesn’t see your value, time to find one who does.

Would more money actually change my situation?
A red flag is when someone mentions that they’ll change jobs for a $5k-$10k raise, or would stay in a bad job for a promotion.
Really?
After tax, how much extra does that give you?
Per week?
What will you spend that on?

Generally speaking, if you’re not happy, then money won’t fix things – especially in small increments.

Money also matters less as you earn more.
The gap between $40k and $45k is much more significant than between $80k and $85k.

More importantly, if you’re miserable, money solves nothing.
Better to be happy on a train than glum in a BMW.
Time to go somewhere that makes you spring out of bed in the morning.

What skills will be in demand in ten years’ time?
I’ve mentioned this before, and it’s really important.

What parts of society will not change?
Businesses come and go, roles become obsolete, but some things are timeless.
Things like the skill of talking to people, the skill of design, or the ability to solve tough problems.
How can you build up these muscles now?

How does my boss measure success?
This is a common blind spot.
People have different ways of measuring success.
Maybe they value dollars earned, dollars saved, customer feedback, staff feedback, replicability of the work, or just how much they like the person.

By identifying how your boss measures success, you can tailor your work to tick their boxes.
Not being a smarty pants, just ensuring that you emphasise the things they value.
This proves that you’ve listened and you understand their viewpoints.
It can also transform the way you’re treated by them in the future, and make work a more pleasant place to spend your time.

What can I do on the side to substitute for my main job?
Instead of asking “How do I find a job that covers everything?” it might be better to look at supplementing the gaps elsewhere.
For example, it might be a side project that lets you be creative, or a volunteer role that fulfils you.

Maybe your dream job doesn’t exist right now. 
How can you assemble a dream overall lifestyle out of different parts?