I’ll Never Work for the Man Again Syndrome (When NOT to Quit Your Dayjob + How to Not Suck at Business)

by Alexander Heyne · 10 comments

“You know what? Fuck beauty contests. Life is one fucking beauty contest after another. School, then college, then work… Fuck that. And fuck the Air Force Academy. If I want to fly, I’ll find a way to fly. You do what you love, and fuck the rest. “

-Little Miss Sunshine

I recently got an email from a reader inquiring about the all-too-typical “my job sucks, I know what my passion is, and I really wanna quit to devote more time to my passion” type story.

Here’s my response as a story and a very brutal, personal, and honest 2 cents:


“Fuck this, I’m tired of working shitty jobs for people who are assholes,” I told myself one rainy Sunday.

“I’m gonna just hustle my ass and do whatever it takes to make some small revenue stream freelancing in the next 3-6 months so I don’t ever have to work for anyone else again. It’s self-employed by 25 or bust, baby!”

Two weeks later I promptly dragged my sorry ass back to Craigslist to look for jobs.

I can be a stubborn bastard, and a proud one.

I guess I’m like a lot of naive youth that have the “do what you love, and fuck the rest” mentality and often split work into this artificial two hemisphere thing:

“I’d rather be poor doing what I love, than rich doing something I hate.”

I used to say the same thing.

Until of course I was poor and doing what I loved, and realized I’d much rather have a little money because my options became zero.


Don’t quite your day job when you’re trying to get your first business going.

Because you’ll probably struggle and end up being twiced as pissed off (except broke this time around).


In the past year I’ve started 2 projects – both of which have slowly puttered off and never produced any real substantial income.

I got the entrepreneurial bug, the dreamer’s bug, and barreled full-speed ahead, working 3-10 hours a day on my projects, 7 days a week, for 9 months.

And then one day I sat down and went “Shit.  My projects were genetically wired for suckage from the start.”

In other words, I was screwed.

Like a lot of people working jobs that are less-than-ideal, I wanted to quit my job as soon as possible once I had a somewhat livable income.

I wanted to be able to cut off those pesky 40 hours a week so that I could re-invest that time into my projects and help the income grow.

However, and this is one HUGE however, I was never given the resources or guidance needed as a first time biz owner.

So I trucked along and hustled, had a business plan for every single month, had one big overarching business plan, put in my hours, read and learned EVERYTHING, tested, worked, applied. And still got screwed in the end.

You see, the funny thing about business is that the start is often the most important part — the foundations of a new business – positioning (your USP), your branding, and your marketplace (who’s buying) — often determine your success or failure off the bat.

But I never knew that. I figured you could just change or adapt, hop marketplaces, change audiences, try out different products, test and abandon ruthlessly.

I figured quitting my job would allow me the time and freedom to put more quality work into figuring out how to make my business work.

I learned that business is like love:

Business is like a fart too. (My analogies are really sucking these days, I know).

If you feel like you are forcing people to get interested in what you’re doing, you’re doing the wrong thing and it will probably never pay you enough.

I remember reading a couple lines by Jon Morrow a few months back where he said something along the lines of the following:

“Even if you do everything wrong, if you’re in a niche or market that people are interested in and will pay for, you’ll succeed. The opposite is also true – you can do everything right including bust your ass, but if you’re in a market that no one cares about, you’ll fail.”

So before you embrace your inner-overly-ambitious-20something in coming up with a biz idea, do some research.

Sounds obvious. Sounds easy. Sounds like common sense.

Well, it is. But like all “common” sense it’s apparently only “common” after you’ve learned it the hard way.

Finding in-demand biz ideas, not quitting your job/life prematurely, and other ass-kicking info

My first line of advice (having lived as the poor man doing what he loved, and having been the miserable man with enough money) would be this:

Don’t try to start something thinking that it’ll be paying the bills soon if you’re already struggling.  It’ll guarantee stupid money-oriented business decisions.

I know your job may suck, I know the temptation will be strong to just quit and from day 1 think you’ll hustle and do whatever it takes to pay the bills.

But the reality is this: you’re probably going to make a lot of mistakes your first time.

I made them all. At once.

Wait until you’re already getting paid from your side hustle to quit your job. As dreadful as that sounds. Unless you’re single and in your 20s and willing to eat ramen noodles for 12-36 months while living in a cave.

The following are my top 5 pieces of advice to someone who is looking to avoid making all the mistakes at once like I did:

#1 Don’t start with your passion unless you thoroughly research #2 

I see entire rooms of people at “get more clients” conferences who started with their passion but never started with its more important other half: what other people want.

The “follow your passion” simplistic career advice is one of the most damaging things I want to see removed from people’s business advice.

Unless its twin is included: “follow your passion…but only expect to get paid for it if other people like it too.”

It’s just like the majority of blogs that have ever existed: people go with the idea of talking about what they want and thinking others will miraculously  pay them.

It doesn’t (always) work that way.

Know for a fact people also like what you like. See below.

Image from $100 Startup.

Read: Passion Never Earned a Paycheck  over at Life Without Pants.

#2 Does anyone actually want to buy what you are selling?

See the sections below on seeing if anyone actually wants to buy what you’re doing.

Being a writer for example is tough — how do you know if what you’re writing about people will buy? Obviously you can’t know unless it’s something your readers have already told you is interesting.

#3 Why the hell would I choose you over anyone else?

This is another really obvious one that wasn’t so obvious to me. I figured “Hey I’m awesome, people that know me will definitely choose me over someone doing the same thing.”

Problem is, all your customers start as strangers and don’t know you.

I’ve met 534,234,402 life coaches in my time (all of which were starving, FYI) and not one said: “I’m a life coach for mid-life crisis people” or “I’m a breakup life coach” or “I’m a terminal illness life coach.”  Had they chosen one of those specific fields, they would have an insanely higher chance of actually having clients.

Assuming I don’t go through a friend to find a coach, and I go through google, “Life coaches” brings up 9 million search results.

You don’t want to be one of those. You want to be known already because you’re special. That’s branding and positioning.

#4 You’re going to have to spend most of your time getting the word out.

Even if you have stuff that works, how is anyone gonna find you? Sure you’ll have some people say “OMG your shit changes the course of human history!”

But then you’ll say “great.. so where are my clients?”

You have to put yourself in front of them. It takes effort and work. A shitload of it. It almost never works where you create some great song or some great product that is just automatically spread by word of mouth to the millions.

That just doesn’t happen unless you’ve already built a platform for that to happen (you’re famous, have a blog audience, you’re a speaker, etc.).

Think about the music industry — there are millions of talented musicians out there. Just look on youtube.

But the ones that are more often than not successful are the ones with either good connections or good business skills (aka MARKETING). Getting the damn word out. Getting exposure.

The sad truth of having a business is that you’re gonna need to spend most of your time invested in getting the word out. If you don’t like the idea of that, you’re in for a rude awakening.

Where the “million dollar ideas” (also known as “stuff people actually want” ideas) actually come from:

Alright, so maybe some of you have the itch to start a business but dunno where to get ideas from.

I struggled with that for a long time, and I mentioned it in my beastly business intro post: The Ultimate Resource Guide for Starting a Kick Ass Biz.

Here’s where I noticed most (SUCCESSFUL) entrepreneurs that I know got their ideas from:

Look at things that people bitch about:

Like music teachers who hate the chaos of the billing/scheduling process.

Voila! Music Teacher’s helper, which rolls in a multiple 6 figure income.

Look at a current product or service and make it better:

This is exactly what Benny Hsu did with his Photo 365 App which became App of the Day. Read the story behind his almost $5k weekend.

There are half a dozen flashlight apps on the iPhone app market, one of which simply turns on the fastest. It got the most ratings because of that dumb little tweak – it starts the fastest. And it rolls in a shit ton of money.

Make people feel insecure / instill lack and then produce something to fill it:

Hate looking fat in your clothes? Me too! Buy spanks (billion dollar business)

Wanna be cool and ultra connected all the time even though you don’t need to be? Wanna have a personal digital concubine (ahem, assistant) named Siri?  Buy an iPhone.

Ab exercises suck don’t they? Exercise is stressful and I can’t find time for it! Buy the Ab Chair and help me scam millions out of their money because they believe in quick fixes.

Find already in demand markets and position yourself differently: 

One of the safest ways to make sure people will buy your stuff is to see if people are already selling what you wanna be selling. This apparently never clicked with me the first time around when I was stubborn as hell and thought “This is a COOL idea, people will definitely pay for it!!”

Look around the blogosphere, or the bookstore, or amazon.com, or search keywords to see what people already buy.

Had I done this when I originally started my first 2 business projects, I would had never started them because I would have realized there was no guaranteed need of what I was doing. They were shots in the dark.

Once you find something already in demand, position yourself differently.

Instead of being another “weight loss” coach, be a weight loss coach just for nerds.

Instead of being another business coach, be a business coach just for gardeners looking to start a business.

Instead of being yet another personal development blog, be a personal development and de-stress blog for high-powered high-stress corporate CEOs.

Again, I’ve made all of these mistakes.  They’re easy mistakes to make when you don’t know what you’re doing. They’re also easy to avoid if you have some basic guidance.

Slavin’ for the man…

… Can really suck. I know.

And maybe some of you will decide to be the “proud stubborn type” who’d rather be poor doing what they love. That’s fine.

But all I’m saying is that sometimes money is options and money can buy a certain degree of freedom. Having no money limits your options severely.

So if you’re tired of being your boss’s bitch and you really are interested in getting into your own side hustle, just remember my simple advice (from experience):

It will be harder than you think, and it will take longer than you think – especially the first $1.00. Plan accordingly.

Don’t jump ship and burn all bridges, as tempting as that sounds..

Wait till your side job can prove to sustain you, then make the leap. I know, it sounds ridiculously obvious, but the “I can’t wait to tell my boss he should suck a fat one” passion can sometimes overtake us in the moment. (Not saying that from experience.. or.. anything).

Thoughts, ideas, comments?

Anyone else quit a job prematurely? Anyone else start a project with way unrealistic expectations? Anyone else quit the corporate world vowing never to go back again… and promptly go crawling back in 3-6 months?

Hit me up..




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