An Open Letter to Frustrated 20-Somethings…

by / ⠀Entrepreneurship Startup Advice / May 7, 2013

Frustrated 20 year old

So I’ll be 25 this Saturday.

I’ve gone through a huge evolution in thought regarding careers, passions, the concept of “work” and life direction in the past 10 years.

My first job at the YMCA (at 15), I figured out within 2 weeks that I was great at “pitching” myself during the interview — and I’m a likeable guy…but the work was boring and tedious…and it showed. It’s hard to keep high enthusiasm during summer camp, trust me.

I thought it was the job that sucked.

So I moved through a series of other jobs hoping that I’d find one I liked: museums, retail, grocery stores,
restaurants…a ton of things. Each one had some element I liked — but within weeks I always felt like I was
literally an indentured servant working for pennies with no end in sight. The worst part about this was when
I’d see people who had been in these jobs for 30 years and were in a state of zombie-like compliant quasi-

Like moaning dogs laying on nails who are too lazy to move.

I remember during my training at Publix (grocery store), one of the assistant managers pointed to his boss
endearingly and said “Greg hasn’t missed a day or called in sick in 27 years.” As if this was some good
thing, a point to be proud of.

I just remember thinking to myself “What the fuck is wrong with these people?”

I quit that job faster than Kim K quits a marriage.

Eventually I came to the realization that I could job hop my whole life, I could go to college and get a
degree and hop around with that on higher paying jobs — but in the end, the problem wasn’t with the
employers…it was with me.

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I had the problem. It wasn’t about getting a better PAYING job. It was about having a job period.

I was having a major case of cognitive dissonance between what I wanted my life to be and the options
I saw available. Part of this was coming because at a very deep level, I was afraid to admit what I really
wanted. I was afraid I’d be called lazy, impractical, idiotic, etc. I didn’t want to be ridiculed.
I’m not afraid anymore.

You know what I want? I don’t want to work. Like…not ever.

I don’t want to be responsible for showing up anywhere, simply because if I don’t show up, I won’t be able
to feed myself/my family (in the future).

I don’t want to be told I can’t do something, that I “don’t have any ‘sick days’ left”, that I won’t be getting
a raise or I’m being laid off. I don’t want to worry that I’m late or not meeting someone else’s standards,
and as a result, might not be able to keep supporting myself. I don’t want to be forced to stay in a specific
location and never get away because I have to clock in somewhere.

You know what I hate?

When people ask me “what do you do?”

What do I do? I don’t DO anything. I AM somebody. I can do so much. I’m not narrowly defined by skills I
use to make money.

What you do to make money is completely separate from what you do with your time. Ironically, many
people spend all that time getting more money.

Am I the only one who sees the sick paradox here?

If it were up to me, you know what I’d do?

I’d spend my life traveling, learning languages, practicing martial arts, reading, programming, eating good
food and (eventually) raising smart, open-eyed children. All the other shit can suck it.

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I mean, can we just be honest here. It’s just you, me and this letter. If it was up to you, you wouldn’t go to
work tomorrow, would you? Even if you “like” your job, wouldn’t you much rather be doing exactly what
you want to do at the pace you want to do it?

And not because you’re lazy and don’t like putting effort into your pursuits — it’s because you’d rather put
your full energy into the things that really ignite you. Whatever those things are.

Now, 95% of people will say “But Daniel, you have to do SOMETHING for ‘work’. You can’t just be a
bum. You need to get a job or something and then do stuff on your free time.”

This is incorrect thinking based on the overwhelming cultural paradigm that says work should be placed
squarely at the center of your life, with any fun/recreation coming as an afterthought.

It’s the deferred life plan, where you save, save, save for 50 years, contribute to your 401k and when you’re
60 (that’s early retirement actually…), you hope to be able to finally stop working and live the last 20ish
years of your life in frugal quietude, clinging to a slipping middle class existence as inflation goes up and
your savings decreases.

At least now you have time to finally do everything you wanted to do…right?
Sounds bittersweet to me.

I propose another way.

We’ve seen what happens when work is your central focus. Working for work’s sake, spending all your
time making more money or obsessing about money instead of doing the things you really want to do
because you’re ashamed to actually admit what those things are for fear of being labeled different. God
forbid you don’t have “work ethic”.

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What if you were to make your life and the pursuits that interested you – traveling, learning, physical
activities, art, whatever- the center(s) of your life and fit work in like a planet in orbit, designed to support
your life and pursuits without completely taking over?

What if your presence wasn’t actually required to generate the resources that support you, and you were left
to roam the earth freely?

What would you REALLY do with your life?

Have you ever considered that in a completely digitized society this is a very real possibility?

This isn’t a popular way of thinking, and if you don’t have any friends or role models living like this, it’s
hard to imagine that this is even possible.

But as I’ve met more and more incredible people through my blog — people who are living that “fictional”
life — I realize that it’s not only very possible, but that there’s a formula to creating these circumstances. It’s
not luck, and it’s not voodoo or “positive affirmation”.

In the past 12 months I’ve gotten increasingly closer to this reality.

Are you one of the few who believes a better way is possible, not just for people in books or in the news,
but for YOU?

Leave me a comment below and let me know.

Daniel DiPiazza teaches young people how to stop doing shit that they hate and break free of 9 to 5 boredom by starting their own businesses at his blog Rich20Something. 

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About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.