So you want freedom, do you?
What do we actually tell our children about work now?
I’ve got kids at university. They’re smart, capable, good people. And when they finish, I’m meant to look them in the eye and explain the world they’re walking into.
A world where “a good job” doesn’t mean what it used to. Where careers don’t move in straight lines. Where even the adults quietly admit they’re making it up as they go along.
So what do we say?
We usually hand them the great big empty box called 'freedom'.
You can be anything.
You can do anything you want.
Follow your passion.
Don’t let anyone box you in.
Slap on the back. Off you go. Job done.
But I don’t think that's what my kids want to hear.
They want advice. Guidance.
But how to advice them when the world of work looks nothing like it did when we were 21?
Too Much Choice
Kids today step into the workforce and immediately feel uncertain: too many choices, too little certainty, and a constant hum of comparison.
Everyone else looks like they’ve got a plan. Everyone else seems to know what they’re doing. Meanwhile, you’re staring at a thousand possible paths and wondering which one will quietly ruin your life.
So they do what anyone does when the stakes feel high and the map's gone missing.
They freeze.
They drift.
They overthink.
They start collecting options like comfort blankets.
They keep doors open so long that they never walk through any of them.
You see I think the problem is that freedom isn’t the goal. Freedom is the tool.
It’s not a destination you arrive at. It’s the ability to choose what you will commit to, and what you won’t.
And without commitment, freedom doesn’t feel like liberation.
It feels like drowning.
Why “Do Whatever You Want” Feels Like a Trap
We keep giving young people advice that sounds kind but really isn't.
“Do what makes you happy.” “Choose the right path.” “Find your purpose.”
It sounds like we’re giving them permission.
What we’re really giving them is responsibility for an outcome nobody can guarantee.
Because now if they pick something and it doesn’t work out, it doesn’t just feel like a normal setback. It feels like a personal failure. Like they chose their life wrong.
So they avoid choosing at all.
They do one more course. One more internship. One more round of applications. One more month of “figuring it out.” One more month at the family home. Safe.
And in the background, social media whispers: Everyone else is ahead of you.
This is why I don’t love “follow your passion” as advice. It's not that passion is bad, but it makes purpose sound like a hidden object you’re meant to find. Like there’s a correct answer buried inside you, and if you don’t uncover it in time, you’ve missed your chance.
That’s a brutal way to live.
Freedom Is Not a Plan
Freedom is often sold as the destination.
Get qualified. Get independent. Get free. Then you’ll be happy.
But freedom doesn’t automatically deliver meaning. It just hands you the steering wheel.
And if you’ve never driven before, the steering wheel is not exciting. It’s terrifying.
Here’s what freedom actually is:
The ability to say yes on purpose.
The ability to say no without guilt.
The ability to choose what matters and then act like it matters.
That’s it.
Not glamorous. Not cinematic. Just a daily practice.
And this is where a lot of young people get stuck: they want certainty before they commit. They want a guarantee that the thing they choose will become “their thing.”
But life doesn’t work that way.
You don’t get the guarantee first. You get it last, if at all.
The Better Question: What Am I Willing to Endure?
When someone says, “I don’t know what to do with my life,” they’re usually asking the wrong question.
Not because they’re silly. Because they’re anxious. And anxiety always asks the biggest question possible, as if the biggest question will produce the safest answer.
It won’t.
A better question is smaller, more practical, more honest:
What am I willing to endure?
What discomfort can I tolerate?
What boredom can I handle?
What frustration can I live with without resenting my own life?
Every path has a cost.
Some costs are obvious: long hours, low pay at the start, studying while your mates go out.
Other costs are sneakier: status anxiety, loneliness, constant travel, being “on” all the time, living inside your inbox.
So instead of trying to find the perfect path, ask:
- What problems am I willing to suffer for?
- What kinds of stress make me feel alive rather than crushed?
- What am I willing to be bad at for a while?
Because here’s the truth nobody really tells you: your “path” isn’t discovered. It’s built.
And you build it by choosing your load.
Direction Comes From Constraints
This will sound backwards, but it’s the most useful thing I know:
Your life gets clearer when you reduce your options (on purpose).
Most people treat constraints like failure.
“I guess I’m stuck here.” “I guess I have to do this job.” “I guess I don’t have many choices.”
But constraints can also be chosen. And chosen constraints create momentum.
Try this advice for young people entering work:
Pick a small set of constraints for the next 6 months.
Not forever. Not your whole identity. Just six months.
Things like:
- Location constraint: “I’m going to live in this city for 6 months and build a base.”
- Skill constraint: “I’m going to get genuinely good at one thing that’s valuable.”
- People constraint: “I’m going to be around ambitious, kind, interesting humans.”
- Money constraint: “I’m going to earn enough to breathe, not chase a lifestyle.”
Constraints stop you spinning.
Constraints turn fog into a path you can actually walk.
And once you walk, you learn. Once you learn, you adjust. Once you adjust, you get somewhere.
You Don’t Need a Calling. You Need a Few Good Experiments.
One of the biggest lies we sell young people is that they’re meant to know.
Know what they want.
Know who they are.
Know where they’re going.
Most adults don’t know. They just got good at pretending they do.
So here’s a better approach: treat early work like a set of experiments.
Not in a flaky “I’m just vibing” way. In a structured, grown-up way.
Pick a direction.
Run a 90-day experiment.
Review.
Repeat.
A direction might be:
- “I want to build things.”
- “I want to work with people.”
- “I want to understand how businesses actually work.”
- “I want to help solve a problem that annoys me.”
Then the experiment is something real:
- A junior role in that environment
- A project you ship publicly (even if it’s rough)
- Volunteering somewhere that exposes you to the problem
- A short contract, internship, or apprenticeship
The goal isn’t to find the perfect job.
The goal is to collect evidence about yourself in motion.
Because sitting in your bedroom trying to think your way into clarity is like trying to get fit by watching other people run.
The Missing Ingredient: People
If I could change one thing about modern “career advice,” it would be this obsession with the individual.
What do you want?
What are your strengths?
What is your purpose?
What is your brand?
It makes everything feel like a solo mission.
But most people find direction through other people.
Through mentors. Friends. Teams. Communities. Colleagues who make them feel capable. Managers who give them responsibility. Environments that bring out something in them they didn’t know existed.
When I look back at my own life, the turning points weren’t moments of private insight. They were moments of connection. People who nudged me. Challenged me. Opened a door. Told me the truth when I needed it.
So if a young person is lost, I don’t just want to ask, “What do you want to do?”
I want to ask:
Who are you spending time with?
Because you become like the people around you. Not through inspiration. Through repetition. Through what feels normal.
The right people don’t hand you a map. They make you braver while you draw your own.
The Thing We Should Tell Our Kids (But Rarely Do)
If my kids ask me, “How do I know which path is my path?” I think I’ll say something like this:
You don’t find your path by thinking harder.
You find it by choosing something small and real, committing to it for long enough to learn, then letting the learning change you.
You will make wrong turns. That’s normal. It’s also useful.
You are not choosing your whole life at 21. You’re choosing your next chapter.
And the chapters add up.
So stop trying to design the perfect story from page one.
Start writing.
So What?
If freedom without direction feels like drowning, then the antidote isn’t more freedom.
It’s commitment.
Not forever commitments.
Not “this is who I am” commitments.
Just enough commitment to generate feedback.
Just enough constraint to stop the spinning.
Just enough focus to become useful.
Because usefulness creates confidence. Confidence creates momentum. Momentum creates options. Not the other way around.
The world doesn’t reward the most “authentic” person. It rewards the person who can show up, learn fast, work with others, and solve real problems.
And solving real problems, even small ones, gives your life purpose.
Until next time,
Jon "Empty Nesting Soon" Kaye
Choosing to live more deliberately