9-5 Millennials vs. Gen Z freelancers: which career plan is better?

Check out my brother’s Bucket Hat business here

One thing you might have noticed as a millennial over the years is this kind of baffling trend of really young Generation Z people making a lot of money doing really strange things, like creating YouTube channels or selling weird merchandise or streaming themselves playing video games online. And your brain can’t comprehend how that might be a career or you might make a living doing something like that.

Well, you got to understand as these young guys don’t have the limits that we have: That jobs have to be safe. That you need one permanent job as a career. That you must go into an office and can’t just work online. That art and enjoyable creative activities don’t make money.

In this video, I show you the counter-argument to these outdated ideas so you as a millennial can protect your career and make a decent income in the future just like any Gen Z youtuber… rather than get left behind!


  • 00:00 Intro
  • 02:42 “Safe” jobs
  • 06:34 Need one permanent job
  • 10:51 Need to work in the “real world”
  • 13:26 Art can’t make money
  • 19:51 Solution to these limiting beliefs

Dan’s Top Resources


Dan has 3 bestselling non-fiction books available in both written and audio form:

  • The Naked Truth, his latest release, shows you how radical honesty builds self-confidence and relationships
  • Nothing to Lose explores how to build confidence from the inside by correcting the programming in your brain
  • The Legendary Life is a very practical, action-focused guide on how to plan and execute a life plan that brings you your ideal lifestyle


Online courses

Dan continues to put out high quality online self-paced courses through the Udemy platform

Full transcript

I’m the oldest of three
brothers. And way back in the

day, I used to play the old Sega
Master System, that’s when the

first kind of gaming consoles
came out. And this weird thing

would happen, which was my
younger brothers would like to

watch me play. Now there was
often another controller

available, they could join in.
There’s two player games, but

they actually prefered to watch me.
In fact, sometimes they would

hide around the corner and watch
me play. And I always thought

was the most bizarre thing like,
why would you want to watch

someone else play? Nowadays, you
can make five or even six

figures per month, having 1000s
of people go online and watch

you play video games. When I was
a kid, I was being shown

information about a potential
career path that never would

have ever occurred to me.

In a recent video, I put it out
there that millennials are

limited in their beliefs around
careers, in a way that

Generation Z are not. And because
of this, millennials are missing

out. Millennials are kind of bitter
and scornful of the weird new

careers and jobs that the
younger generation have. And

because of this, they’re not
keeping up to date, in a very

critical way for how to manage
your income for the future.

Millennials believe that
something like being a YouTuber

is not a real job – that it’s somehow
unsafe, that even if you are

making money, it’s a temporary
phase that’s going to end

perhaps, and the recent waves of
YouTubers and streamers and

freelancing copywriters, and
drop shippers and all that

stuff, it’s an entirely
different idea of what a career

might be. And yet, my
generation, and of course those

older than us, are resistant to
this new idea. And I think it’s

costing us. See, millennials seem
to fight against the data that

proves that new career horizons
have opened up, that a new way of

working and making an income – in
fact, a whole new lifestyle – is

now available to us. And
instead, we insist on boring

nine to fives with the one hour
commute either way, and the

office and the desk and the boss
and paying taxes and doing what

other people tell you… we insist
on sticking to that model, on

doing a job we don’t like often.
And yet the younger generation

are enjoying what they’re doing
and getting paid more than us to

do it. So let’s talk about the
limiting beliefs that people

over 30 have these days that are
holding their careers back.

There’s four in particular I’m
going to tackle today. One is

that you need a safe job,
whatever that means, and that

the Generation Z jobs I’m
talking about are somehow unsafe.

Two is that you need to have one
job permanently, that a career

is essentially a static
position, you might move up the

ladder, but it’s in the same
place. Thirdly, that you have to

work offline, that a real job
has a place you go to, an office

to sit in perhaps, and that you
can’t just sit at your computer

or on your laptop in your bed.

Fourthly, that being creative
and being artistic doesn’t make

money. Those are the four top
limiting beliefs that my

generation have that I hope to
try and tackle a little bit

today. Let’s talk about so
called Safe jobs. My last safe

job was working in the
Department of Corrections. So

this is public sector; a government
position, working for

Corrections. It doesn’t get more
guaranteed than that.

And yet, due to some changes,
they had what was called a

restructure, a shuffling as they
started outsourcing certain

parts of Corrections to private
companies and so on. Now, I

remember there was this old lady
at my office, I didn’t like her

much. And she’d been
there for like 20 years, a real

sort of stalwart of the place.
But one day I heard her

shrieking in the office…
shrieking! – and when I went to go

investigate, found out she had
had a minor heart attack. Why?

Because she had just been told
that there was no longer a

position available for her, that
she had been restructured. She

actually had to get an
ambulance. She was so sure that

she was in a career for life,
that the shock of being told

that she’s one of the people on
the list whose jobs just don’t

matter anymore, almost killed her.
And I think she’s a great model

of what I’m talking about. The
idea that you have a safe job is

ridiculous. This kind of
restructuring and outsourcing

and losing jobs is happening a
lot now in the private sector

as everyone tries to get leaner.
Everyone tries to make more

profit for less cost, the
biggest cost of course, being

staff and now it’s even
happening in the

Public Sector a lot more. And
even when it’s not, the public

sector is disintegrating all
over the world. The quality of

the work is becoming incredibly
unsatisfying, as people are

being asked to do longer hours
and achieve more with less

resources, as a career-politician
based governments try

to make as much money for
themselves as possible. And this

is even in the non corrupt
countries like New Zealand. I’m

intimately connected to many
people in public services, and

they’re all reporting that it’s
going downhill, that it sucks to

work there now, even when they
get paid. Well, you’ve got to

remember that employees are the
biggest cost to any company. So

when they’re looking to make
more profits by reducing their

costs, where do you think
they’re going to go? Do you

think they care as much about
your career as you do? You think

they care about you as much as
they care about profits? How

naive are you? If you end up
becoming more of a liability

than an asset, there’s no leeway
for that. They’re not going to

wait around to see if things
turn around, they’re going to

get rid of you. And you’re going
to be unprepared. When we look

at the rise in technology, I
predict that nearly all jobs

as we currently know them – basic
nine to fives – can be replaced

by artificial intelligence or
robotics. So look at what you’re

doing, your classic job, and ask
yourself, Is it really not

possible for a computer to do
this job? A well programmed

computer? Or a well placed robot?
And if so, is that going to be

less expensive than I am? The
next limiting belief: we need one

permanent job. You ask any
millennial: Why don’t they start

their own business? So why don’t
they go try something else? And

they’ll say “I need this job”,
especially once they’ve got kids.

So what you’re saying when you
say I need this one permanent

job is I’m going to put all my
eggs in one basket. When has that

ever been a good fucking idea?
When has it ever been a good

idea to have all of your income
dependent on a single thing?

That’s never been a good idea.
And yet people are still doing

it. You ask any highly
successful investor: Do you have

all your stock in one company?

You will never hear the answer
Yes. Everybody diversifies. All

the smart people do anyway. So
why don’t we diversify income?

If you look at your job? and you
think: What would need to

happen for me to lose this job?
Like I can’t do it. Let’s say my

job for example: if you cut my
vocal cords, I can’t coach

anymore. Essentially, it’s that
simple to have all your eggs

taken away.

Does your job need you to be
able to see? Does it need you to

be able to walk? Does it need
you to be able to think clearly?

What is it that could be taken
away that ruins your entire

income. Now see, if you cut my
vocal cords, I become a writer.

Well I dial up the writing. I’m
already doing right now. I get

paid a little bit to do blog
writing. And if you take away my

coaching, I’m just going to do all
blog writing. So I can adjust

quite easily if something
happens to me. Can you adjust?

Right now my auntie whom I love
is having to do shit work at a

new job, in her 60s, after a
number of new jobs over the last

couple of years, because her old
job, that looked like a good

permanent fixture became a toxic
workplace environment and she

had to leave. Do you really want
to be scrambling around, sending

out resumes and CVs and your

Do you really want to be put on the
back foot like that. Because

it’s going to happen. There is
nothing that is guaranteed for a

long time anymore. Technology is
changing rapidly. Global

corporations are constantly
taking over each other,

we’re getting these
monopolies happening now where

one entity owns everything, and
constantly tries to own more.

And every time they do that they
restructure and they change

things, and sometimes they just
gut the company completely. It’s

only a matter of time until
wherever you work, even in

public sector, is going to be
consumed by another company. How

are you going to survive that?
You don’t know. You just don’t

know. They might be coming with
someone who’s going to do your

role better than you!

Are you prepared for that? Well,
if you’re a millennial, the

answer is probably not. You’ve
got all your money on this one

bet. All your eggs in this one
basket. Do you really think

that’s a good idea? Do you
really think that that’s what’s

best for your family? We’re
living in an age now where you

can learn through online courses
better than you can learn at

university. I could probably
send you about 10 hours worth of

psychology material that would
make you better at clinical

psychology than a degree would.
We’re living in an age now where

you can rapidly restructure,
upskill, or re-skill yourself

for very little cost and in the flick
of a moment. Look how easy it is

now to prepare yourself for a
pivot, for a

change. You can find your dream
job, reverse engineer the

education you need, go get that
education online within about

six weeks and then go apply for
that job. And you could do this

with multiple jobs so that you
could have a range of income.

You know, my younger brother,
one of the ones that used to

watch me play the old Master
System, he currently is editing

at a sort of formal company.
Then he does freelance

copywriting on the side. And he
runs a very popular, highly

successful Bucket Hat business
online where he sells these really

hard to find really cool hats.
He’s got three things going at once.

Once you can’t upset his career. If
you take away one of them, he’s

got two more, and he can just
dial them up to fill the space.

That’s a smart career. By the
way, you can check out his

Bucket Har business in the link
in the description. There’s some

awesome shit there. Third
limiting belief: You have to work

in the real world, so to speak.
You have to get in a car or get

on a train and sit in traffic
and go to an office and wear a

suit and have your breaks at set
times and then go home again. Of

course in the trades, this is
much more real thing. Like you

can’t fix a car with your
computer, though one day you


But for most people, their job
really doesn’t need to be in the

real world as they see it. I
mean, COVID taught us that if

nothing else. All of us were
forced to stay home. Most of us

just kept working. How’s that
possible if you have to go into

the office? Well, truth is you
don’t have to go in.

I had my world rocked a couple of
years ago, when I took on a new

client. He was only 17 years
old I think at the time, one of

my youngest ever clients, making
more money than I was, on

YouTube. There’s two things he
did on YouTube. One is that he

just filmed his dog doing random
things. He had like a million

subscribers for that channel.
And other one was he streamed

himself playing video games and
people paid and sponsored him to

watch plus he had advertising
revenue. This guy never left his

house. He didn’t even need to
hire the dog. It was literally

his dog.

This guy has been raised in a
different generation, he doesn’t

even understand the concept of a
boring nine to five, it’s never

going to be a path that he’ll
pursue. He sees the world

differently. That doesn’t mean
he’s going to be a YouTuber

forever. There’s some downsides
to being a YouTuber,

particularly the toxic community
that can exist there. But

this guy just sees things
differently. He looked at his

dog and just went like, Okay,
that’s a job. And that is a more

accurate way of seeing the world
than the millennials who say,

Only this very limited list of
activities can be paid and

everything else you can just do
for fun. You know, all my work

is online now. Everything I do
is online. I used to worry that

if people couldn’t see me
in person it wouldn’t work.

Well, it turns out a lot of people
actually prefer doing online

video calls, and it means I can
access the entire world. So

there’s no limits to my market,
so to speak. There are literally

seven, almost 8 billion people
available for coaching, I’m

never going to get through all
of my potential leads. Even my

psychologist mum was using Zoom
during COVID and still uses it

quite often. So she’s doing full
on psychology work, qualified,

following the conditions
of the government and

everything, and she can still do it
online. She doesn’t have to

commute if she doesn’t want to.
So the last limiting belief I’m

going to address is creative art
doesn’t make money, right? So

most millennials will take their
creativity, whether it’s

painting or dancing, or
building little robots for

fun, or writing, or sculpture or
whatever it is they enjoy doing.

They treat that as what they
call a hobby that can’t make

money. It’s either not allowed
because money will ruin it

somehow, which I don’t know how
getting paid for something ruins

it but let’s just say it does.
Or nobody’s gonna pay you, which

is the more likely belief like, I
have to actually pay to do this

thing. I have to pay to do rock
climbing. I have to pay to play

video games. The idea
that I could get paid to do it?

Ridiculous. Absolutely
ludicrous. I work with a lot of

artists – or wannabe artists –
and they can’t make money

because they believe they can’t
make money. And yet I’ve met so

many who can. I know one dude
who was making board games on

the side while he worked at
McDonald’s. He now makes seven

figures a year selling board
games to the very extensive,

very exclusive board game
community who absolutely loves

them. I know another girl who likes
to play drums, so she started

posting videos of herself
playing drums and now she plays

drums online as a job. All
entertainment is paid for. You

pay for everything that you
enjoy, and yet you’re not

thinking who’s getting that
money? The entertainers! Not all

money, of course, but the
entertainment community, the

entertainment industry,
everyone’s getting paid there.

Why can’t that be you?

Literally millions of people
getting paid to be involved in

the entertainment. And yet you
can’t? Why? It makes no sense. There

are more people in entertainment
than there are mechanics. There’s a

thing I learned about called a
journeyman actor. You know

those actors you see in just
about everything and you

recognize their face, but you
couldn’t name them if you tried?

They’re never the star of the
show. They’re always a

background character with a few
lines or whatever. Or they’re a

staple and a kind of typecast in a
TV series, that kind of thing. They’re

always the lawyer or whatever,
you never know who they are. But

those guys are making six or
seven figures a year just doing

steady acting work.

The journeyman style of creativity:
like I have a DJ client, and

when he’s not making his own
music, he does background music

for fashion shows or ads, and he
makes really good money doing

that. You know, there’s really
great money to be made as a

skilled artist. You don’t have
to be Beyonce. There’s this

whole huge range in the middle
of everybody who contributes to

most of the entertainment you
watch, in the background

especially. Why can’t you be a
part of that? Why can’t you be

selling your paintings to hang
up in cafes and hotels? I mean,

you’re using YouTube right now, and even though my channel

purposefully doesn’t have ads,
you’re used to seeing ads on all

the channels. Do you know where
that advertising revenue is

going? A lot of it’s going to
the person who made the video.

I know of a guy who literally
stares at people for a living.

All he does is make eye contact.
He does this in huge venues,

people pay him 1000s of dollars
to just stare at them. He’s

tapped on to an idea that
millennials are resistant to:

anything can make money! There’s
an audience for any service.

Almost anything is valuable to

And if you can figure out how to
get in touch with the people who

find what you do valuable, you
can make it into a career – a

really lucrative one. Whatever
your art is, whatever your

creative, enjoyable activity is,
somewhere out there is someone

who will pay you just to watch
you, or they’ll pay you for the

product, or they’ll pay you to
teach them how to do it.

Put it this way:

Let’s say you’re an artist. You
could be doing online courses,

teaching people how to paint.
You could be doing live classes,

teaching people how to paint.
You could be selling your

paintings to hotel chains and
cafes, as well as featuring them

in galleries. You could be
sponsored by paint

manufacturers. I mean, I’m
making this up off the top of my

head right now, I haven’t even
put any thought into it. Can you

imagine what you could come up
with if you put a week’s worth

of planning into it? Your real
fear is marketing and selling.

The so called safe job of the
millennial has one particular

theme. And that is: you’re not
the one whose job it is to find

the money. So those people who
work in offices, and so on and

so forth, one of the main things
you’ll notice that they have in

common is they’re not the ones
going out there selling the


And this is why people are
afraid of art, because art,

especially if you want to be a
self employed artist, you got to

go find the clients. You got to
go pitch what you do and sell

it. You got to go put it in the
galleries or post it online or

whatever it is. And that’s what
you’re really afraid of: having

to go hunt for your food. But
the beauty here is there’s only

one skill, you really need to
learn: marketing. Call it

marketing and sales. If you’re a
person who can build an audience

who loves what you do and sell
that thing to them, you can make

money doing anything. You don’t
even need to be slippery or

sneaky. I’m completely authentic
in my marketing. So don’t use

that excuse, like all marketing
is scammy and bullshit and that

you just want to be this
honorable person, as if that’s

your real reason. No, you can be
totally honorable, totally

authentic, totally honest. But
you have to be very bold and

brave and face rejection. See
what Generation Z are not as

afraid of as us: rejection,
failure, humiliation, getting it

wrong. They go out and do all
that stuff and that’s why they

succeed. It’s not because the
younger. It’s not because they’re

up to date with technology. It’s
because they’re not as cowardly

as we are. That’s it. That is it.
By the way, if you’re currently

doing client acquisition,
marketing, sales or whatever for

a big company, then you’ve
already got the skills. Leave

immediately and do it for yourself.
Right now. Go on! Pause the

video, go do it. So look, times
have changed, right? Technology

is accelerating. Old school
beliefs are simply barriers.

Now, don’t be a dinosaur. Don’t
stay out of date, out of some

sort of grim, stubborn need to
keep things the same, because

that’s just going to cost you
and your family. You don’t win

from that perspective, you’re
definitely going to lose sooner

rather than later. If you want
to catch up, you can contact me.

Tell you what, here is an offer to
anyone who’s made it this far in

the video. I will have a free
session with you

to pull apart your current
skills and strengths and

experience and talents and
especially your passions, and

help you figure out how that
could translate into better work

that gives you more freedom, that
gives you better income, that

makes you more flexible and able
to pivot to changes and opens up

a new lifestyle that isn’t the
classic nine to five stuck at a

desk. Get in touch with me If you want to

take advantage of that offer, it
will be for a limited time.

I just don’t know how limited.
Thank you so much for watching.

I hope that helped. Cheers.


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