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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{ 10 comments… read them below or add one }

Shanna Mann May 29, 2012 at 7:36 pm

…Ahem. Spanx. With an ‘x’.

Yeah, I’ve started businesses both ways, doing something I wanted to do, or doing something that filled a need. Let me tell you, it is SO much easier to do the latter. But you’ve got to be looking for it. Listening to people. Not focussed so much on solving your own tiny problems of working at a shitty job.

Best business I ever saw is Patrick McKenzie at Bingo Card Creator. He was living in Japan, and a friend of his was an English teacher. He wanted to do bingo with his students using english words on a particular them. Patrick took an hour, made up a shitty little program to create bingo cards. His friend emailed the program to all the teachers, and the next day Patrick got 40 emails saying thank you.

So, he took that shitty little program, made a website for it, and started selling. And he just refined the holy hell out of that sucker, testing and tweaking, testing and tweaking. Never has so much been made out of so little.

And who would have known that teachers needed bingo cards? Seriously?


afheyne May 29, 2012 at 9:23 pm

Hahah woooops ;)

And yeah starting with a NEED is way way way way way easier. The only problem is that if you only start with a need (and not interest) then you’re just gonna be working for money.. and pretty soon will probably hate being self employed almost as much as being employed by someone else. That’s my biggest problem – finding the intersection between interest and need. I have pretty much no patience for work I could care less about, I can’t even really fake it to be honest.

And that’s pretty insane about the bingo card stuff. I guess it doesn’t matter how shitty or little the product is, as long as people need it eh?


Shanna Mann May 29, 2012 at 10:02 pm

Haha! Well, I like to make money. I mean, if it were terribly labor-intensive, I probably wouldn’t bother. Like SEO. SEO is way too boring for me, as far as the actual implementation is concerned.

But for a tiny bit of software like BCC, all he did was A/B test the UI and various marketing stuff. That’s the kind of niche I’m looking for.

Shayna May 29, 2012 at 8:28 pm

I’ve just experienced a cool little case study that proves all the specificity examples in your post. My first product was a pronunciation course for English learners… that’s gotten 3 sales in 5 months.

I got depressed, but picked myself back up and made my second product: I took the course, adapted it for Brazilian English learners (including rewriting it in Portuguese) and have made 8 sales in 8 days!

It’s still reeeeally far from paying the bills, but certainly a promising start. My next product comes out in June and is based on my far and away most-shared post of all time… fingers crossed that it’ll be a success.

Your million-dollar idea-generating tips are spot on. Do you have an idea for your next endeavor?


afheyne May 29, 2012 at 9:29 pm

Sweeeet that’s good news Shayna!

And yeah thats pretty much a perfect example – instead of an english class, an english class for brazilian english learners. That was one of my HUGE mistakes too — I didn’t take that one extra step to make it more specific.

Something I’m also going to have to remember to pay attention to in my next project —

Awesome news on your next product! Honestly in my mind if you keep trucking away the long you do you’re already further than most entrepreneurs get… it’s easy to write about it (ahem… hahaha) and it’s easy to talk about it or read about it, but saying you have officially *launched a product* (regardless of how much you got paid) is leaps and bounds ahead of most.

Keep me updated on what’s next! I’m extremely interested

Re: my next ideas, i have a lot. The only problem is that I’ve seen the need but I don’t really find myself very interested in a lot of them. That’s the hard part now. My last 2 projects started with MY interest (and no one else’s haha), my new projects started with obvious need and paying $$$ clients, but I don’t know if going at them 100% would have my heart in it. So it’s back to the drawing board to find a project I actually care about and has a big time need.

Otherwise.. .in my mind, what’s the point of being self employed doing work you don’t like? It’s not much better than employment by someone else except for added flexibility and freedom. Still not much better.


Clivant Yeo June 2, 2012 at 10:28 pm

For me, the main motivation to venture out on my own is more of wanting more control for myself than the pursuit of my passion. During days where sucky people were not around to mess things up, I felt that my passion aligned with my job and I had learnt a great deal of stuff.

But when I had to work with suckers who cannot make up their minds, who add more workload just because that competitor have a particular (useless) feature and still expected me to deliver on time, the “I’ll Never Work for the Man Again Syndrome” almost overtook me — “If I can create my own career, I can easily be a decision maker who don’t chase after the puck just for the sake of chasing after it, and tire my coworkers in the process.”

But alas, no money no options. Without money, it is hard to try out options. Without money, it is hard to bootstrap your creations. And without money, it is difficult to stand by your creations before they even have a chance to flourish.

I guess suckers are everywhere, suckers are there to make sure we don’t suck like them. For the moment, I just have to suck my thumb and learn as much as I can out of my day job.

Totally like this post. Thank you for writing this. :)


afheyne June 3, 2012 at 10:17 pm


Yeah that’s closely tied to #1 for me too. I’ve mostly worked a lot of jobs I couldn’t bear, which is the main motivation to work for myself, but also the flexibility of being able to work whenever, wherever is very attractive. The potential for travel too.

And for sure working with shitty people can ruin work. I’ve worked for hellish sent-from-satan bosses, and saints – people sometimes can make all the difference.

The sad truth, like you said, is that no money = no options. Which is why i encourage people (unless they have a crazy tolerance for risk) to not ditch everything and make the jump. The first time is always going to entail a ton of learning. I’ve made all the mistakes myself!

Thanks for stopping by!



Erin June 3, 2012 at 9:58 pm

I love this post. I often have trouble reading all the way to the end of super long posts, but I read this one.

I did just quit a retail job I abhorred. I did so with nothing else in place and knew it might not have been the most practical choice. But, I’m really lucky in that my husband can support us for now, so the making money ASAP piece isn’t such an issue for me.

I am only very, very recently feeling like I might want to try my hand at starting a business. I’ve never felt like it was something I could do. Even if whatever I start fails, I want to try before I go back to a more traditional form of employment. As I brainstorm and research, I know it’ll help to keep your pointers and cautions in mind. So thanks!


afheyne June 3, 2012 at 10:21 pm

Erin — I seriously loved the feeling of quitting a job that was truly soul crushing. I’ve had jobs where I needed to start drinking after working because it was so stressful dealing with people (And unfortunately I wasn’t even making a lot of money..).

And yeah you’re lucky you have that support! I’ve got something similar (ahem.. my childhood bedroom, hahaha).

Yeah I think many of us are getting disillusioned now, and when we see so many self employment stories we get naturally curious. My advice would be to seek out someone who has done it first. They can save you thousands of wasted hours and wasted dollars.

Let me know how it goes Erin!



Erin June 3, 2012 at 11:11 pm

That’s where I was with my job. It was sapping my energy, my enthusiasm, everything. I’ve stuck it out through bad/tough jobs before, but I was done.

I totally did the childhood bedroom thing for a while. Nothing wrong with that :)

There’s so much inspiring buzz going on right now about self employment and how glorious it is, how easy, how rewarding. I’m trying to give it a shot with more reasonable expectations, more so that I don’t find myself on my deathbed with not trying as one of my regrets than because I’m expecting instant glory. I’m learning to use other people as resources — something I’ve always found hard. I’ll keep my eyes out for a mentor of sorts :)

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