Working for the man ain’t so bad.

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As millennials, we have a curse. Doing a job for the paycheck isn’t enough. We’re supposed to follow our dreams and live our passions because those are the messages we’ve heard since we were kids.

From Steve Jobs’ commencement address at Stanford, to Tim Ferris preaching lifestyle design in the 4 Hour Workweek, our generation obsesses about living a different life than our parents and grandparents.

Do what you love. Find your passion. Find meaningful work. Find what you love, and you’ll never work a day in your life.

In fact, I think most of us would feel shame if we admitted to doing a job just for the money.

Why do we have so much angst? Maybe it’s because we are the richest children in history, relatively speaking. Our baby boomer parents grew up in poverty and found wealth later, so we grew up rich. When it came time to choose careers, we were the first generation who could disregard money. Most of us always had enough to eat, so money was never the pressing issue it was for our parents.

As a result, we’re entitled. Many employers report that Millennials are the toughest group to work with. We want our rewards now, and we’re not willing to wait or work for them. Previous generations put in the hours to climb the ladder slowly. But not us.

We’re more likely to leave the “man” behind and strike out on our own, supposedly finding infinitely more fulfillment that way.

On the one hand, these arguments make sense. The old model of retirement is tired and broken. Pensions don’t exist anymore and neither does lifetime employment. It’s unlikely that you’ll ever work for one place for longer than 5 years.

With a global workforce competing for your position, layoffs, and recessions, it makes sense not to trust the man anymore. Most career people in software development will tell you the best way to get a raise is to change companies. And usually it’s true. You’re lucky if you get a 3% raise each year staying with the same company.

But misapplied any advice can be dangerous, especially when we’ve rejected an old ideology, only to replace it with a new one.

The new ideas can be just as dangerous and unforgiving as their predecessors. As an example, let me tell you my story.


I worked for Google for 3 years. Suffering from early 20’s angst, I was bored out of my mind. I bought into the Silicon Valley mantra of building the next Facebook or becoming the next Steve Jobs. So in early 2012, I up and quit, to found my own company. And so began one of the toughest 2.5 year periods of my life.

Have you ever noticed how the first thing people ask you when you introduce yourself is “What do you do?”

I went from being “The Google Engineer” to the “guy smoking crack.”

We spent two and a half years building various products. One was a digital billboard that hung in bathrooms or coffee shops, and another was an offline webmail client written with HTML5. Cool products, but solutions looking for problems.

Like most engineers when they start a company, we didn’t focus at all on marketing or distribution. And you learn the hard way that the actual engineering behind a product is only ~20% of the business. “If you build it they will come” is definitely not true. Thanks Kevin Costner.

What was worse, we didn’t focus on things that could make money. We were under the illusion that if we built the next app and got 1 million users, we could sell it to Google or Facebook or whoever for 10-20 million, and then go off surfing for the rest of our lives. We didn’t realize how difficult it is to get that many users, or how much time it can take.

Or that you have to build a product that solves a problem, not one you think is cool.

After 2.5 years of this, I was running low on funds, so I went and found a job. There was no aqui-hire that materialized out of thin air. My founder and I had backgrounds from Google and MIT, but there was no “soft landing”, even though we had read about them again and again in the tech press. Actually most employers gave me no credit for having worked at Google or for starting a company.

Anyway, my point here isn’t to highlight my mistakes. I wouldn’t take back any decisions I made. Plus I learned a lot, and I won’t repeat those mistakes in the future. But I want to highlight how I was living for a fantasy, one hand delivered by venture capitalists, the tech press, and lifestyle design gurus. And I ate it up willingly without questioning anything.

I see so many entrepreneurs in Silicon Valley falling into the same illusion. Smart people, who could work for Google or Facebook, don’t because it’s not “the cool thing to do.” The cool thing is to be a founder, and the master of your own fate.

But here’s the irony: many times when you become a founder, you’ve never been so much of a slave.

You work for your employees, you work for your customers, you work for your co-founders, and if you’re raising money, you especially work for your investors.

Freedom? What a joke.

You’re at the whims of market forces or Google shipping a new product next week that will put you out of business. You’re at risk of your company imploding. Ever had a fight with your co-founder when they happen to be a family member? Good luck resolving that situation peacefully.

You’ll go without pay, and you have to pay for insurance yourself. Any unexpected life event is going to put financial and emotional pressure on you, as if you didn’t have enough stress and pressure already.


Flash forward a few years.

Right now, I work for a large company writing software.

I’ve never been happier.

Maybe I wasn’t cut out to be an entrepreneur. But then again, being an entrepreneur can be a huge pain in the ass. With a company, I get to work 40 hours a week and then leave the job at the office. I get paid to work on software puzzles all day, not sales or marketing. I get health insurance, and if I get sick, I still get money. My company actually pays me to take time off.

Compared to my old job, I basically have 0 responsibility. And I work for a bigger company, where the pay is good, and the hours aren’t nearly as bad as a startup. How awesome.

Best of all, my job no longer rules my identity. My entire personality is no longer wrapped up in whether my business succeeds or fails.

Looking back, I periodically see coworkers and friends falling into the same mindset that I did.

A buddy of mine quit his job as a software developer because he wanted to be a writer. Writing on the side wasn’t good enough, so he just up and quit.

But making it as a writer is hard, maybe harder than making it as a tech entrepreneur. So my buddy probably just set himself up for financial hardship and stress. And there’s a good chance he’ll be right back in the same situation in a few years, only poorer.

I’ve read countless stories of people doing similar things. There was the woman in New Jersey who quit her well paying corporate job to follow her dream of founding a Yoga studio. Unfortunately she knew nothing about Yoga studios or running a small business, and she had a family to support, so she wound up on food stamps. Ouch.

Contrary to the tone of this article, I’m not advising you to ignore your calling, if you have one. But many times “following your passion” is nothing more than becoming a sheep. And for me, doing the “Silicon Valley founder thing” was just another way to follow the herd.

It’s a different herd than the guy who sits at the same company for 30 years, but it’s still a herd.

Try to understand why you’re doing whatever you’re doing before you take the plunge. Personally, I had unresolved emotional issues I needed to work through. Working for Google wasn’t the problem. The problem was the deep existential hole I had inside of myself, and working on my “passion” wasn’t going to fix it anymore than winning the lottery.

Plus if you understand the risks of working for a big company, that path isn’t so bad.

Yes, you risk getting lazy. You also risk developing “golden handcuffs”, and you shouldn’t delude yourself into thinking you’ll have the job forever, or even that the company is going to consider your best interest. Always keep your ears open, and use the job to your advantage. Try not to go soft.

But despite the risks, that big company will be a better master than Tim Ferris. Under his system, you’re likely to go without pay, go without insurance, go without recognition, work on plenty of stuff you don’t like, and then wind up exactly where you started.

So be careful and use your brain. Try to figure out if you’re falling into the same traps that I did, and prepare accordingly.

I would never have found myself without my experience, so I have no regrets. But maybe I can get you through yours with less pain and delusion.

Photo Credit: Sean MacEntee