The 5 times I quit my job: The good, the bad and the ugly

“I quit the job … I hated it so much … I didn’t have a plan, I just said goodbye … no two week notice … I’m not proud of that, but — actually, I am kind of proud of that!”

That’s what I told Bloomberg News when they interviewed me at their San Francisco headquarters last year.

Everyone in the studio cracked up when I said it.

But quitting your job is a serious thing.

In some ways you can look at it as being more serious than managing your finances, or even your health. At least there are professionals who can advise you on those things (doctors, nutritionists, counselors, financial planners, etc).

But there are no “job quitting experts” who can help you figure out if it’s time to tell your boss to pound sand. And there’s good reason to be wary of anyone who tries to advise you in this area. (The one exception is a spouse or other family member who has a vested interest in your success — in other words, someone with skin in the game.)

While I can’t advise you on if/when you should quit your job, I can certainly tell you about my own lofty adventures in sticking it to the man. You may find it helpful, or be inspired by the fact that someone can do so many dumb things and still end up on top. Or maybe you’ll just be entertained by my follies, giving us something to talk about in the comments.

The first time I walked out on a job, I was 19 years old … and very stupid.

I was a waiter at a deli. I’d dropped out of college and had literally no idea what I was going to do with the rest of my life.

One night at about 10:30pm a stranger walked in and ordered several courses of food (a man after my own heart). I could tell from his order that he was probably on a low carb diet, so I gave him a friendly heads up that the chopped liver had some breadcrumbs in it.

He was very appreciative. From there we struck up a conversation and, later, we became friends. He eventually recruited me to join a Multi-Level-Marketing (MLM) scheme he was a part of.

The whole MLM thing seemed sketchy to me but I was hooked by their well-crafted message of “working for yourself, being your own boss, being an entrepreneur,” etc. I decided to give it a try.

I signed up and, after what I thought was some early success (which really wasn’t), I decided to quit my job to do the MLM full time.

Everyone warned me not to do it — even the other people in the MLM said it was a bad idea. But of course, I didn’t listen.

I started running out of money almost immediately. Not a big surprise since I had virtually no savings and my MLM activity was producing maybe a few bucks a month at best.

The only thing that kept me going was the fact that I still lived with my parents at the time, which artificially deflated my cost of living (while simultaneously increasing theirs).

After a long period of no income to show for my efforts, I was finally forced to get a real job. Suffering from a severe lack of confidence, brains, and imagination, I went back to waiting tables. Yup, right where I’d started many months earlier, and, sadly, none the wiser.

Looking back, it should have been obvious that the entire experiment was doomed right from the start.

Joining an MLM isn’t a good way to start a business, and, though I certainly could have worked smarter and harder at it, I don’t think that would have made much difference.

In fact, years later I found out that all of the people who I thought were making real money in the MLM ended up quitting and moving onto something else — often under very shady terms.

The second time I quit my job, it was to become a professional poker player — or so I thought.

I was now well into my twenties, still waiting tables and still clueless about what to do with my life.

I’d just seen the movie Rounders, and, like many young and dumb people at that time, I became fascinated with the idea that it was possible to make a living playing a “fun” card game.

This may or may not have been a worse idea than being a full-time MLMer, but it was definitely a bad idea nonetheless.

Poker is a great game, but it’s an awful job for so many reasons that are probably obvious to anyone not swept up in the romantic portrayal of the gambling lifestyle that only Hollywood could conjure up. On top of that, I made a lot of bad decisions that served to compound my failure at it.

For one thing, I was extremely overconfident. I read a few poker books, won a few hands in some very low stakes games, and quickly started to imagine that I was some sort of world-class player. This was in spite of the fact that I had absolutely no winning track record whatsoever. (In other words, I was a victim of the Dunning-Kruger effect.)

Even if I had been a better player, to say I was woefully unprepared would be an understatement. I just didn’t start out with the capital you’d need to succeed. Poker is, obviously, a risk-based game, which means you need to start out with a lot of money — say, tens of thousands of dollars at a minimum — in order to even have a chance at making it.

Whereas I started with a grand total of about eight-hundred bucks! Especially when you factor in my living expenses, that decision alone would have sealed my fate even if I was the best poker player on earth (which of course I wasn’t, by any stretch of the imagination).

Despite this huge disadvantage, I didn’t lose all of my money. What I mean to say is that I didn’t lose it all right away. That wouldn’t have been so bad, all things considered.

What happened instead was that I bled all my cash away slowly, over time … just slow enough, in fact, that I was able to fool myself into thinking I might be able to reverse the trend by putting in more effort. Which led me to play more and more hours in a misguided attempt to “work harder”…

Now, on top of being a not-so-great player with delusions of grandeur, I was also burning myself out, destroying any shot I might have had at improving my skills.

Eventually, statistics caught up with me, and I couldn’t deny reality any longer. I was out of money and had no choice but to once again return to the world of the not-so-gainfully employed.

The next time I quit my job … I was still very stupid, albeit a little less so, having at least learned that MLMs and gambling are both impossibly hard ways to make an “easy” living.

By this point I was working as a restaurant manager, which seemed like a step up from waiting tables, except for the inconvenient fact that I was actually making less money, both per hour and overall (as a waiter I at least had some influence over how much customers tipped me, whereas my managerial pay was a fixed amount).

On top of that, though I worked at a great restaurant, the job was painfully boring. Most of my tasks amounted to little more than following checklists. I imagine this would feel like fresh, unadulterated hell to just about anyone, let alone someone with my personality.

I remember waking up one Saturday morning…

It was beautiful outside, a perfect summer day on Long Island … and I just couldn’t bring myself to go into work.

I called in sick. Told myself I just needed a “mental health day” — but in my heart I think it was clear that I was over this phase of my life. For good.

It was around this time that I started flirting more seriously with the idea of starting my own business. Not a bullshit MLM-type business, but a “real” business (even though I was yet to discover what those words really meant).

The next day I went to the bookstore and bought a huge stack of books from the Business section. I read all of them in short order and came away convinced that I needed to come up with some “big idea,” write a business plan to show to investors, secure funding, rent office space, hire a bunch of employees, and so on.

I had no clue how to do any of that, but I did manage to come away with my first business idea — or what I thought was a business idea at the time: healthy cat food.

Go ahead, laugh if you want to. No really, it deserves to be laughed at. (Cat food is many things, but a business idea isn’t one of them.)

But that’s how far my mind could stretch at the time. I wasn’t born with natural business ability, and my entrepreneurial muscles had never been developed, let alone flexed or challenged.

What can I say? Humble beginnings are called humble for a reason.

With nothing but a half-assed (and I am being generous here) idea and no clue how to make it a reality, I called an acquaintance of mine who had owned a couple of businesses and asked him if he could give me some advice over dinner. (For the most part I didn’t hang around with successful people back then, but this guy was another customer from my waitering days who I’d grown somewhat friendly with; people tend to like you when you bring them tasty treats every time they see you — possibly a Pavlovian thing.)

We went to Lundy’s, a landmark restaurant (now defunct) in Brooklyn’s Sheepshead Bay area. My friend — we’ll call him Mike — listened to me ramble for a while, then gently explained that I didn’t really have much of an idea on my hands after all.

Nevertheless, he was a good guy, and he gave me a few tips on how to go about refining my preliminary idea into what could end up being an actual idea: Study the market, figure out a list of things I’d need to do in order to start the business, determine what costs would be involved — then we could talk about things like funding, he said.

But all of that sounded so overwhelming that I didn’t even try.

Instead I spent the next few weeks talking about my business fantasy to anyone who would listen, because I like to talk and also because it was 1,000,000 times easier than doing the hard work of trying to get good at something you currently happen to suck at.

One of the people who was forced to listen to this drivel was my sister-in-law, who responded with a great piece of advice: She told me that instead of trying to start some big cat food company, I should start a small cat food business, perhaps making specialty cat food for a few people in my neighborhood, or some such thing. If it went well, I could always expand it from there.

But I laughed her off because it went against the advice of one of the business books I’d read. Or at least I thought it did. In any case, she was right, and I was wrong — but to paraphrase Junior Soprano, “Sometimes you’re so far behind in a race, you actually think you’re leading.”

As you might have guessed by now, it wasn’t much longer before it became clear to me that my “business” was never going to amount to more than a pipe dream.

That would have been right about the time I started running out of money. Yes, again.

I didn’t want to have to go crawling back to some crappy job this time, but I was starting to get desperate for a way to pay my bills.

So what did I do? Tried my hand at poker again.

You know that old saying about the definition of insanity — doing the same thing over and over again, and expecting a different result? Yeah, that was yours truly.

Fortunately, the poker gods were more merciful to me this time. And by that I mean I lost all of my money very quickly, within just a week or two.

I was forced to go back to work yet again, tail between my legs.

The fourth time I quit my job…

A couple more years had passed.

I’d relocated from New York City to Omaha (if I couldn’t figure out how to win at life, I thought, at least I could cut my living expenses in half) and somehow found myself working for a local car dealer group.

The first few months were okay, but as I got more indoctrinated into the company I started to see more and more of the nasty tricks car dealers use to screw people.

At first I tried to rationalize it. I read that grocery stores had their own bag of tricks to maximize profits, so why shouldn’t car dealers?

But when I overheard one of the managers bragging about how they’d taken advantage of a disadvantaged U.S. veteran, charging him thousands of dollars above the sticker price for a car that should have been discounted, it made me sick.

That led to my first real business idea: What if I could do the opposite of what the car dealers did? What if I could help people get better cars for less money instead?

I stormed out of the dealership, skipped the exit interview with the creepy HR lady, and went home to start my first real business: A concierge service for car shoppers.

My business plan fit on the back of a napkin: I’d charge people $300, and help them save double, triple, or even 10x that much on their car purchase — while personally handling all of their interactions with the car dealers. Since I knew how all the shenanigans worked, I could easily stop the dealers from getting into their wallets in much the same way a former burglar can easily protect your house against intruders.

I used Weebly to create a free website, made an awful YouTube video to explain my service, posted a message about it to my 43 Facebook friends, and, finally, put up some of the ugliest flyers you’ve ever seen all around town.

None of it was pretty. But it was something.

Amazingly, all of this ragtag marketing managed to get me my first few customers! And not just from friends — I even got calls from a couple of total strangers.

But as awesome as that felt, it wasn’t all roses.

Yes, I’d done a few things right this time around. Like coming up with a specific, actionable business idea that offered tangible value to people, and proving the concept by taking action and getting my first few paying customers quickly.

But in terms of both my results and the real potential of this business, it was more of a “mixed bag.”

While most car shoppers could certainly benefit from my service, there were too many hurdles to overcome. The concept of a “car shopping concierge” confused people. Many were reluctant to try something so new and different, opting instead to do what they’d always done before (go to the car dealer and do it the “hard way”).

In the end, I learned a very hard lesson that seems like it should have been obvious all along: To succeed in business you need to sell something people want — not necessarily something you think they should want.

Unfortunately I was out of money by that point, forcing me to — you guessed it — go back to work.

I refused to go back to the car dealership, though. (Or any car dealership for that matter.)

Instead I went to Indeed.com and started applying to just about any job I could find.

Only now it seemed harder than ever for me to get a job.

I sent out a lot of applications, and got a few interviews … but couldn’t get anyone to take a chance on me. Even for the lowest skilled, most entry level jobs, the answer over and over again was “No.”

I got the distinct feeling that being 34, while certainly not old by any means, made it exponentially more difficult to find work — at least for someone as unskilled and unfocused as I was at that time.

But then I finally caught a break (or so I thought). I saw a job post for a “fee negotiator” who, as the title implies, could help an insurance services company negotiate fees with medical offices.

Now you might be thinking, “Danny, what the hell could a 34 year old who’d worked only a handful of low-level jobs (between very long stretches of unemployment) and never went to college know about negotiating medical fees?”

Well, mostly nothing. But in a weird way, also, a little.

See right around the time I was working at the car dealership, I became very interested in the art and science of negotiation. I’d even picked up a book about it — Getting More, by Stuart Diamond, a lawyer who’d famously taught Wharton Business School’s world-renowned negotiation course.

Now, I certainly wasn’t a world class negotiator by any means. Definitely nowhere near Samuel L. Jackson’s character in the movie The Negotiator (although weirdly his character’s name was Danny, too).

But after reading Getting More I became so obsessed with negotiating for things that I tried it everywhere I went. Here are some real examples of “everyday” things I negotiated using the techniques from the book:

• A 15% discount on grass fed beef at Target
• A $75 discount on a new phone
• A free $100 gift card from Amazon

So I filled out a bare bones application, wrote a cover letter, and emailed the whole thing over along with the news story about how I was so into negotiation that I planned to “negotiate on everything” for an entire year.

A few hours later I got an excited call from the hiring manager, who wanted to meet me right away.

When I got there, we barely even had an interview — she was already sold.

She then offered me the last “real” job I would ever have the pleasure of quitting.

I say pleasure because, while the company looked impressive from the outside, on the inside it was a rotting cesspool of corruption, cheating, and managerial incompetence that would make even a DMV worker squirm.

Yeah, turns out I’d jumped out of the frying pan, and into the fire — people in the insurance game are even dirtier than the folks who run car dealerships. Go figure.

During my short stay, I watched multiple employees cheat and even steal from the company … not only were they not fired, they were actually recognized and rewarded for their behavior by the geniuses who were running the show!  

I even stayed late one night to compile rock solid evidence against them, but when I brought it to my supervisor he brushed it off (he was likely in on the scam is my guess). Even the HR department didn’t seem to care.

The entire episode was sickening, and mind you this is a big company with thousands of employees and a large national presence. It was all straight out of the “you can’t even make this stuff up” file.

I lasted all of about 70 days before developing an incurable allergy to the place. One morning, I couldn’t stand it anymore, and just left. Hence the quote I began this post with:

“I quit the job … I hated it so much … I didn’t have a plan, I just said goodbye … no two week notice … I’m not proud of that, but — actually, I am kind of proud of that!”

Yup, not only was that quote about that job, but in a larger sense it was also about the end of one era of my life, and the beginning of a new one. Because the day I walked out of there was the same day I started freelancing.

Isn’t it funny how life plays out sometimes? If that job had been any less intolerable, I may have hung around for a while, instead of activating the ejection seat. Hell, I may have even gotten stuck there for 30 years, climbing the corporate ladder (or trying to and failing). Who knows.

I mean, by this point I was 34, married, with one young son, and a second one on the way. I also had virtually no savings, absolutely no investments or retirement fund of any kind, and as you already know, no college education. Not having a backup plan for feeding your family is a quick way to dampen your appetite for risk, I assure you.

So why did I decide to “leap”?

Maybe the pain of continuing along the path I was on just outweighed the fear of the unknown path behind “Door #2.” (Most of us hate the unknown, don’t we?)

Maybe I was acting incredibly irresponsibly.

Perhaps I’m just not built for the 9-5 lifestyle.

Or maybe my brother is right and I’m simply not “employee material.” (I think his exact words were “You’re a horrible employee” but he can be kind of an asshole sometimes.)

Does this mean you should quit your job too? I honestly don’t know. And even if I did have an opinion it would be irresponsible of me to share it with you, given the extremely personal and subjective nature of this type of decision.

I can tell you a few things you might want to think about, however.

The first is that many people do seem to succeed at freelancing while keeping their day jobs.

Some keep those jobs for a while, and eventually transition into full-time freelance work (or even part-time freelance work with a full-time income!).

Some stay at their job indefinitely, either because they love what they do, or they get some other benefit out of it that gels nicely with their freelancing business. For example, they may get a feeling of stability from having a regular paycheck. Or freelancing on the side might add creative fulfillment to their lives, even if their day job is less than ideal from a “passion” perspective.

For some, having a successful freelancing business on the side, along with the option to quit their job if and when they want to, provides tremendous excitement, comfort, and relief.

We all have our myriad reasons for making the most complex decisions in our lives, and it doesn’t always need to boil down to something that seems “logical” on the surface. Sometimes the best decisions are the most illogical. Pascal said, “The heart has its reasons, of which reason knows nothing.”

With that said, I have seen some people screw up massively trying to jump into full time freelancing. Especially when they do it too quickly.

See, in a sense, I had a couple of ironic advantages over many people who were smarter and more successful than I was.

Though they’re not the type of advantages I’m usually accused of, by readers who insist that I’m somehow so brilliant or gifted that “DUH, OF COURSE YOU ARE SO SUCCESSFUL AT FREELANCING…….”

To those people, my response is, “Did you read the 99% of this post in which I spend most of my adult life doing idiotic things and flirting with self-destruction?”

But to you I’ll point out that, in some ways, it’s easier to walk out on a crappy $30,000 a year job than it is to walk out on one that’s better, or that pays more.

Likewise, in a sense it’s also easier to take risks with your career when you don’t really have a career!

Both of these ideas are basic economics. Having less means having less to lose. And since crappy jobs are — by definition — all around us, they’re also easy to replace if you happen to give one up. (If you have a crappy job, please do not use what I just said as an excuse to quit it. Remember, nothing in this post should be misconstrued as advice of any kind, as no one can advise you on whether or not to quit your job.)

But just because these ideas come from economics doesn’t make them any less harsh. Being jobless is not something most people feel comfortable with, to say the least.

For some, like me, it can act as a healthy source of pressure, and incentivize me to do my best work. But for others the stress can be too much to bear. It’s like weightlifting — lifting more than you’re comfortable with can make you stronger, but if you try to lift too much too quickly you can easily end up hurting yourself.

This means that, for some people (like me), it may be better to have less of a safety net. While for others, the more outs they leave themselves, the better they’ll do.

What are your thoughts on all of this?

I want to start a real discussion in the comments section below. This is a very nuanced and complex topic that could really benefit from a true discussion, as opposed to tired tropes like “Just quit if you don’t feel fulfilled!” and other nonsense.

So if there’s ever been a time when you open up and tell me what is on your mind, I hope it’s today.

Have you ever thought about quitting your job?

Have you ever thought about going full time in freelancing?

Would you like to quit your job, but there’s something standing in your way? What is it?

Have you ever quit a job — and either thrived as a result of it, or later regretted it?

Do you know someone who serves as a cautionary tale for why you shouldn’t quit your job?

What else is on your mind about all of this?

Do you have any questions? Ask away and I will do my best to answer them personally.