“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.
A confession. I just quit a job I managed to get during the pandemic. I’m 23 years old, and landing something in my field seemed like the best use of my time after spending years waiting tables during University. I worked some marketing jobs in the meantime, tutored, and managed to scrounge up a fairly decent resume. The pandemic put a halt in all that, and hundreds of applications resulted in me trying something new. I began to draw again. I had graduated with an art degree from a very good high school and a set of skills I only… Read more »
Honestly, I have dealt with this before too as far as jumping too soon before the path is revealed. When I graduated from college, I quit my job as a server because I fully believed I would have a job landed within a few weeks of moving home. Fresh out and fully optimistic that the right job was waiting to be shortly discovered….. 2 months later, I was jobless and fretting about where I was going to live (in-state or out-of-state) with my future wife since we were to be married in a few months. I finally managed to get… Read more »
Loathing. Unadulterated loathing. That’s how I feel about my job.
I believe freelance would be perfect for me. But freelance in what? And how on earth would I make a sustainable life out of that? I could just quit my job and die of starvation and homelessness which seems less terrible some days.
Maybe I should just go to grad school, garner more debt, and put another break pad on having to deal with my seeming failure to be good at corporate life.
I am still doing master in laser (extended), with no income source (only survive on charity right now) and despite all the harsh conditions, I just really, reallllllyyy don’t want to work the office 9-5 job – it just not how I want my life to be. Maybe I have that “lazy entitled millenial” thinking, I don’t know but despite my family being dirt poor and I truly should starting to support my younger siblings’ education now as the older sister, I have had enough with all those horrible bosses and office politics (my current (master) supervisor is such a… Read more »
Thank you! I needed that! After working menial jobs and graduating with a master’s degree, I spent the last few years teaching in Japan. I recently returned to the UK and have been applying for jobs for nearly 3 months. I’ll be thirty next year. It’s the funniest thing, but everyone I love keeps telling me how surprised they are that I could fail in finding employment. Truth is, like you said, it’s tougher the older and wiser you get. For the first time in a while, I’ve been able to consider my options and I finally think I’ve discovered… Read more »
Danny, I never knew about all the crappy experiences you had. If there’s one concern, it is quitting a job that pays pretty decently (130k+ in California). Like you say, the less you have, the less there is to lose. I’m interested in freelancing, but I’m worried about having to deal with clients while I’m at work. What if they need something urgent, and I just can’t get to it? Or will I even have the energy to do great work for my clients when I’m so tired from my day job? These are some things I hope you’ll address… Read more »
I’m coming from a slightly different place. I have a job that I have really enjoyed for the last 4 years. The work is really interesting, and the pay is decent. Overall, I’m happy but I can’t help but feel that my growth (financial and otherwise) is limited by being in this job. My plan is to have a freelance income that can generate 60-70% of my current salary. Once I have that, I’d quit my job. But right now, the pain isn’t strong enough that I feel like needing to quit. I actually enjoy it. In a sense, freelancing… Read more »
Amazing Post Danny! It’s amazing how we can lift ourselves up when we feel we have ‘no choice’ . I also decided since 2016 that I will never return to be an employee (after 8 years working in airport operations), and after more than 1 year, it’s a mixed feeling of ‘desperation’ sometimes (what if everything go wrong?) and also a feeling of sureness (I will succeed working for myself, because It’s the only way) For all other readers, here is my experience : If you really decide that you will somehow succeed working for yourself / being an entrepreneur… Read more »
From what I can tell reading your story (very inspiring btw, thank you for sharing) my experience felt very similar to what you’re describing. My self-doubts were much stronger at first, and, while they persisted for quite a long time, the effect they had over me grew weaker and weaker until they finally became virtually nonexistent. For me, I feel that leaving myself fewer options has also been a blessing in many ways, though as you said it may not be for everyone. It’s a bit like weightlifting — lifting something that’s a bit too heavy can make you stronger,… Read more »
Haha. This is a great story, Danny! I love hearing about the “road of failures” before you started to succeed. Although I’m freelancing right now, I got a job for a different reason. It all started when I realized I didn’t have any marketable skills worthy for freelancing – so, I went to look for a company that I can learn from, and eventually get a good skill that clients would want to pay for. (This was a year before I found out about FTW). I worked for that company for about 7 months and learnt how to do some… Read more »
Great job Jason! There are many, many paths to success. And probably if we think about it only a few ways to fail. So avoiding failure is key, which it sounds like you’ve done well. Now you have options for the future, which is what winning is all about. Thanks for sharing your story and perspective with us.
This resonates with me, but for reasons different from those of the other commenters. Like Danny, I’m an INTP-A, so I really like the idea of forging my own path and working for myself. But I tend to end up working on multiple side-projects at once and doing a half-assed job on each when I should have focused on excellent execution of just one project. I also have a high-paying job, so I lack the financial desperation that forced Danny to become focused, even though we share the sense that our fulfillment depends on living life our own way. I’m… Read more »
Amazing insights, Steve. In my experience learning to understand yourself — your motivations, what drives you, what might hold you back, etc — is immensely helpful in figuring out what you need to do to reach your goals. (I learned a lot about this in Ray Dalio’s book, Principles.) Really interesting to hear where you and I are similar and also where our paths might diverge a bit (hearing others’ stories is also part of understanding ourselves better). I may write about this in the future, but, like you, I also tend to come up with many ideas and work… Read more »
Thanks for sharing Danny we all go down different paths and no two people ever go the same way!. Currently I am working on my side hustle, doing voice overs by night and by day I am a senior accountant for a major university, it’s not the worst job I’ve ever had for the most part it pretty good great benefits etc. It allows me to pursue my dream of voice overs at my pace, I am finally at a place in my life where my money story is getting better each day. I don’t worry about money. I’m a… Read more »
Yes, exactly, well said. Congrats on finding a creative solution to improving your life even more, 6 years to retirement sounds incredible and will open up many options for you while still young enough to enjoy it and/or be productive to the fullest. Thanks for opening up the dialogue and sharing!
Hey Danny, Thank you for the soul-baring post. My favorite FTW post. Ever! 🙂 I feel you. I have “retired” from the corporate life also at 34, with very little savings. And I have quit several jobs–and “businesses”–hoping my next venture would be my ever elusive lifelong mission! My decision was largely based on my dream to be a full-time, hands-on dad to my daughter, after having grown up with my father always abroad for work. Thank you so much for the sharing. Makes me appreciate and love you and your work even more! And, by the way, nice to… Read more »
Thanks so much Jeff. Being able to engage in conversations like this with you makes it all much more worthwhile as well. Logicians do indeed seem like nutcases, don’t they (er, *we*)?
Hi, Danny! How about a cautionary tale from the other side? You probably have a few readers in the same place I was, people scared to let go of the only things they know or worried about the wrong things. I should’ve quit my job and/or started a side hustle years before my job quit me (the company I worked for closed). By that point, I hated the work but told myself multiple stories to stick with it: I can help the company turn things around and stay afloat – Nope. Too small a cog in that machine, and nobody… Read more »
Oh wow. Yes I know many people would greatly benefit from hearing your perspective on this. I remember reading emails from you about this stuff a few years back and it’s amazing to see how you reflect on some of it now with a new perspective on things. This is what personal growth is all about — not necessarily doing a 180 but just being able to evaluate some of the beliefs from previous years and ask, “What have I learned?” I’d love to see an entire post about this. If you want to write one feel free to email… Read more »
Thanks for sharing your stories, Danny. (You may want to grab your favorite beverage before continuing (: ) Some things you said really stood out to me, or made me laugh! “Instead I went to Indeed.com and started applying to just about any job I could find.” Been there. Done that. Monster.com too. “Only now it seemed harder than ever for me to get a job.” Getting a job has been one of the most difficult things for me to do. And I know why. When it comes to getting a job, I’ve heard it a bazillion times: network, network,… Read more »
I said robbing a bank. I meant to say robbing a “casino”.
Hey Danny I feel your pain on that whole MLM thing been there done that got the T-shirt!! From Amway to other companies claiming not to be MLMs but operating exactly the same way, I’ve done that whole trying-to-supplement the income thing. (Usually when I was in between jobs). What I found is you have to be a special sort of person with a great support team, which I didn’t have. Now I’m calling myself a freelance writer, even though I’ve done very little in the way of paid projects, most of my published work is blogs and creative writing… Read more »
Thanks Kim–I overcame the fear using what I call the Crystal Ball Technique. The way it works, you never have to stress over whether or not those initial clients will love your work because it virtually guarantees that they will. You can search for it right here on the blog, it’s worked for me and many, many others.
Danny, thanks for sharing your experiences – I hope this will give others the confidence to start out adding value to the world through freelancing too.
To employees reading this who are sick of their boss/work environment – don’t let anything hold you back from starting a sideline freelance business. It could transform your life, if you are prepared to stick with it like Danny did.
Hey Rick, great words of wisdom my friend. Thanks for checking in!
Hi Danny,
I find this story quite a dramatic and adventurous one, with hardships and pains.
But I would prefer being on the safe side, and gradually shift to freelncing.
Awesome–and smart–approach. Thanks for sharing your perspective with us.
Hi Danny, and other people here, I would like to share with you different thoughts, which go in the opposite direction – meaning: going back to ”regular” job. It is not something that I want, but after two years on Upwork, I feel kind of stuck. My freelancing went up and down, but now for some time, it is mostly down. I write proposals which don´t receive answers, or communication with a potential client dies halfway. The idea of freelancing is a great one, but if results are far from satisfactory (even though I think I´m doing everything right, as… Read more »
Jasminka – I’m looking forward to hearing from Danny on this too. But wanted to share my experience as maybe it would help you in some way. I was a freelance Cinematographer for 7 years in New York City before I felt the exact same way you do – like I was getting nowhere. The jobs I got were pretty low pay compared to other super successful freelancers out there, and the work I got was pretty bland if it did pay well. I totally burned out and even resented the profession I had grown up loving since I was… Read more »
Hi Danny, While I did chuckle at your follies, it was more of a laughing with you in comradely commiseration. At least your insanity did not involve REPEATEDLY joining MLM after MLM, because the next one was going to be THE one. I quit my city job after 17 years. I hated the paycheck, hated the bosses and hated the hours. But, that was the most irresponsible thing I had ever done. I quit in the name of giving my family a better life outside of the city. It was ugly. I tried to make my last MLM work out,… Read more »
I actually did quit two jobs last year and tried my hands on freelance writing and transcription. So far things are working out but at a slower pace than I thought.
Regrets – never. I was so stressed most of the time.
I connected with this article a lot, mainly because I’ve had a good amount of quitting bad jobs this past year, though I’m. still far from figuring it out I felt way better reading that I’m not the first one to go through something like this. The first time I quit my job, i worked at a shoe store and was 17. They had offered me a Manager position but I said nah and went to art school instead. Then in art school after my first year I found myself not hitting even one little summer job and so I… Read more »
I made the decision to quit my job back in October 2017 after experiencing customer support and management politics. It wasn’t an easy decision, but I’m thankful for the choice. So much that I ended up writing an article on quitting my job and pursuing my freelance career as a writer and web designer. If this was me years ago, I wouldn’t had the courage to do so because of the fear in not providing any financial stability. Given with the headaches and the constant changes in management, I felt my heart telling me to take the leap. I’m glad… Read more »
Thank you Diana. I too am a “follow your heart” kind of guy when it comes to work/career/business. More power to you.
This post resonated with me so much! I’ve proudly quit more than 20 jobs since I was 16… including the United States Air Force and a “secure” government job where I made close to $75k doing what I loved… design. I even quit a job a week before Christmas (while married with two kids)… that was not wise. I’ve never had a plan and that has backfired more times than I can remember. However, zero regrets. Like you, I suck at being an employee. Always have. So, I refuse to stay any longer than I need to get back on… Read more »
Wow, quite an amazing story! I love it! Thanks for dropping by and sharing.
I like it Danny!
I have similar experience with MLM.
I get a question Danny.
As a fresh graduate that happen to have interest in freelancing. Should I go for 9-5 job and do freelancing as a side hustle or just go for full time freelancing? I still live with my parents so like your past the cost of living greatly decrease (but theirs aren’t).
Thanks
Great question Kevin. Since you’re unsure you might want to consider trying both at the same time. In other words you get a job, and freelance on the side (you can even get a part time job if you want to, instead of a full time one, so you don’t overload yourself all at once, depending on your personality). This will give you the maximum number of options…you’ll learn the most and you can always decide to give your full attention to either one at any point in the future. Plus you’ll have a better chance to become self-sufficient and… Read more »