I was watching a Q&A presentation at a conference a while back. Several questioners said something along these lines: “I was so inspired by what you say that I decided to quit my job and start a new business!” And then the whole room broke out in applause.
Seen this sorta thing elsewhere too. Someone says, “I quit my job to follow my dream of [starting XYZ business/acting/whatever].” And everyone oohs and ahhs and says how great it is.
My problem with that: Quitting your job is easy. That, on its own, doesn’t deserve applause. If you quit and start something new and persevere for years and make it happen, then you deserve hosannas. But just quitting? Anyone can do that.
And starting something is only a little bit harder. It’s easy to start something. Following through is the tough part. Just look at the landscape of abandoned blogs that litter the web for proof of that.
Contrast that to the reaction people who keep their day jobs and build something on the side get. Actually, they don’t get much reaction at all. There are no dramatic, sweeping statements about quitting so people don’t care as much.
Too bad. Doing what you love on the side means you don’t have to risk everything immediately. You have a steady income so you’re less desperate. You can build it slowly until whatever it is is such a success that it justifies quitting your regular job. It’s a measured approach instead of a toss of the dice. Plus, you can easily turn around if you go down the wrong path (or lose motivation).
Maybe these “keep the day job and build it on the side” folks are the ones who really deserve the applause.

Matt Linderman wrote this on Sep 22 2009 There are 63 comments.
Lloyd Budd 22 Sep 09
Quitting your job may be easier, but it’s not easy for many people—comfort and responsibilities ensure that.
Heiko Behrens 22 Sep 09
Agree with Lloyd, it’s the fear that distracts people from quitting their job. As with any changing steps you have to bring to self to do so first. Sure, silver wedding is impressive, but you have to marry first.
NewWorldOrder 22 Sep 09
I hear you in this post Matt, but like Lloyd has alluded to, quitting a job in the abstract is easy, but practically it’s very difficult.
I do however feel that the whole “I quit my job to start X” creates the false idea that entrepreneurs are big risk-takers when actually the opposite is true.
dan 22 Sep 09
Now that you mention it…. it’s sorta like a multilevel-marketing pitch, or a get rich quick scheme.
Александар 22 Sep 09
If those people had a great idea and implemented it then quiting their job would be natural. But I fear that they don’t believe in their idea strongly enough.
sean brady 22 Sep 09
37-signals inspired me to start a Twitter Analytics business, and NOT quit my day job. This allows the founding team to focus our energies on building a great product, without the distractions of raising start-up capital and worrying about feeding our families. Thank you!
Greg 22 Sep 09
It gets an applause because it’s a daring move. People love drama, so they applaud it. Staying with your full-time job while growing a business on the side is a smart and cautious move, but it isn’t fun to watch.
Which would an audience rather watch: A car chase or crawling traffic?
ML 22 Sep 09
It’s this idea that you need to risk everything that disturbs me. (And that we should applaud those who do decide to risk it all.)
Why not just start small and try out your idea on a tiny scale? See if it flies. See if you still love it after a few months. See what happens instead of throwing your life into a tizzy over what might just be a fantasy. Make that big, hairy decision when you have real data to support it.
You just don’t know until the rubber hits the road. It’s a fine line between “having a dream” and being delusional. The truth is a lot of these people are being applauded for following an unwise path. I’m more inclined to applaud someone who decides to experiment on a smaller scale first as opposed to someone who throws caution to the wind. Caution is a good thing to hang onto for at least a little while.
Chris 22 Sep 09
“Quitting your job is easy…..Anyone can do that.”
Actually, it’s not. Trust me – I’ve been yearning to do it for many years. It takes a great amount of guts (or naivete?) to kiss a paycheck goodbye.
“Maybe these “keep the day job and build it on the side” folks are the ones who really deserve the applause.”
That’s exactly what I’m doing. But please – hold the applause until I actually succeed at what I’m trying to accomplish. ;)
Lubo 22 Sep 09
If this person quit their job and convinced their spouse not to kill them…well, then they deserve applause.
Anonymous Nick 22 Sep 09
Thanks for the confirmation… I’m not a fool to burn the extra hours after work, away from the family, to pursue my dreams of self sufficiency without quitting my day job. I can’t justify quitting my job to pursue something that may fail… not when I have a family to provide for.
Doug Adams 22 Sep 09
How about “I got fired and my only alternative was to indulge my dream of [starting XYZ business/acting/whatever].”
That’s how I did it. Applause?
Anonymous Nick 22 Sep 09
@Doug :D
Anonymous Nick 22 Sep 09
+ clap clap clap
John 22 Sep 09
Man I totally agree. I’m living this reality now, for about 7 years I’ve had a ‘side business’ and a ‘day job’. I have an unusual situation now because I make a nice living from both of them, but I love them both too. I have been able to craft a lifestyle that I really love.
SO, actually, I don’t want to quit my day job. But, also I don’t want to be a slave to the man. So, if for some reason tomorrow my ‘day job’ came to an abrupt end, so be it, no big deal. It was when I hit that point of security that I realized that I actually really like going to the office and the people I work with and didn’t want to give it up completely.
It took years of really burning the midnight oil until my own company came into its own, and further work to really refine the profitability. Now I could do either one and be fine. If I had just ‘QUIT’ 7 years ago, I’m sure I would not have made it for more than a year based on what I know now.
DefuntOne 22 Sep 09
THANK YOU !!! Goodness gracious, finally!
The biggest myth about entrepreneur-ism is that you have to throw everything at a project (time, money, energy) within the first 6 months or else.
We are blinded by instant glory. In fact, most people fixate on instant glory because they are not willing to put in the steady 2, 3, 5, and 10 years it will take to make something work.
Great post and much needed.
Thank you
Austin Kleon 22 Sep 09
Keeping your day job (as long as it doesn’t totally zap your energy) also means that you can take more risks on your side project: if it’s not your steady source of income, you’re freed up to experiment.
To paraphrase Flaubert, “Be regular and orderly at your day job, so that you may be violent and original in your work.”
Erik 22 Sep 09
We applaud those who risk it all because they are doing what we all wish we could do, right?
Someone who does risk it all and succeeds is never the person who first says things like “small”, “tiny scale”, or “fantasy.”
Nathan Ostgard 22 Sep 09
I don’t think people aren’t applauding for actually doing the work of creating something. People are applauding because someone took a plunge for something they believed in, and put themselves at risk to do it.
The risk is the factor. Whether or not this is more or less intelligent, easier or harder, than building it on the side, is not relevant.
I also wish that the on-the-side people got more recognition, though.
Patrick Dennis 22 Sep 09
Well said Matt.
andycamp 22 Sep 09
Rarely do the right people get the right credit for the right deed. People quit their jobs, then advertise that they quit their jobs because it sounds ballsy and adventurous. People who just do the right thing, really aren’t that exciting to most people. Everyone knows hard work is what it takes, but few want to really do the hard work. It’s like when you see that guy/girl that is in perfect shape. No one wants to hear that they just work their asses off in the gym and eat right. Instead people yearn to hear that it really was some secret pill, or some secret diet. Well, secret’s out. Real success requires real effort; it waits not for accolade, nor does it expect it. Real success relishes in a job well done.
Robert 22 Sep 09
agreed!
Mike Locke 22 Sep 09
Great post! I currently maintain a full-time gig while running my web consulting biz on the side. Though I wanna go full-time one day, I have to keep the job to keep the boat afloat. Though I do get inspired by hearing the “I quit my job” stories, but then you bring up a good point, it doesn’t take much to quit. So true, so true. I have to agree with you 100%, keeping a job while slowly building my consulting business seems to be the best approach at this time. I take this post as our applause!!! Good stuff!
EH 22 Sep 09
Why not just start small and try out your idea on a tiny scale?
Because a lot of times the job gets in the way.
Mark C. Webster 22 Sep 09
People love dramatic stories, and the “risk it all” narrative draws people in. If you look at shows like American Inventor, Shark Tank, Pitchmen, they all focus on the people who are putting everything they have on the line for an idea.
I agree that building things on the side and growing a business over time is a smart move, but it isn’t very sexy. People will continue to be impressed by the people who take huge risks (even when they’re dumb risks).
Lloyd Budd 22 Sep 09
Thanks for the follow up Matt. Life is in the details, and risk mitigation is essential. Sure doesn’t make for drama and excite the tribe.
Geoff 22 Sep 09
I had the exact same comment some time ago on this post, but I think it’s worth repeating:
Before getting serious about a side career, ask yourself, “How would the person signing my paycheck (or the co-workers that count on me to help them do their jobs) feel about this? Better yet, ask them how they’d feel.
Consider the flip-side: How would you feel if your employer started outsourcing a component of your job to a contractor without telling you about it? Of course, they won’t fire you unless it turns out that their side project is successful.
Your job is a relationship. Treat it like a relationship. Respect the people involved and act toward them as you would want them to act toward you. If you both agree to an “open” relationship, then plow forward with a clear conscience.
ABasketOfPups 22 Sep 09
And yet, there’s the other side. The business-never-takes-off-because-there’s-no-real-NEED side. That’s a real problem too. Like most things, one size does not fit all.
Paul Graham says “Statistically, if you want to avoid failure, it would seem like the most important thing is to quit your day job. Most founders of failed startups don’t quit their day jobs, and most founders of successful ones do.”
Of course that doesn’t mean if all the failed startup folks quit their day jobs the business would have survived… but some of them would. Maybe a lot. Your motivation is going to be a lot stronger when you’ve got one focus and it’s do or die (or at least, crawl back to the corporate world…).
GeeIWonder 22 Sep 09
F’in A.
Jon 23 Sep 09
hear hear! I’m not saying that Guitar Noize is ever going to become my day job but I dedicate about 30 hours a week to it outside of my day job and I have a child and wife who I don’t want to neglect!
Derek Scruggs 23 Sep 09
I think the counterpoint is that a lot of people never get traction on their side project because their real job takes precedence, plus they’re in a comfort zone.
I get that you guys are all about the side project, and there’s nothing wrong with that, but I know my first company would’ve gone nowhere if I didn’t quit my job and focus on the new opportunity full time. I wish it would’ve been otherwise, but my personality (especially back then) is such that I have to go full-bore on something to move it forward.
Bruno Miranda 23 Sep 09
You totally missed the point. The applause is for the courage to make the leap, not for “quitting” or “starting”.
James 23 Sep 09
Quitting is hard, but it’s actually succeeding that’s praiseworthy.
I quit in March and launched www.listy.us just yesterday. I’m proud of it, but I’d agree it’s not really worth it until it negates the cost and starts actually pulling in money.
So I’d say kudos to those with the guts to quit, and praise and congrats to those who it actually pans out for. Me? My fingers are crossed. :)
Kevin Holesh 23 Sep 09
I agree with you, Bruno.
Quitting your job and eliminating your [perceived] job security can be a tough thing for someone who is used to a steady paycheck.
People that do something on the side deserve more applause for their follow through, rather than the courageous act of quitting your job.
RobyAva 23 Sep 09
I think quitting your job is a great challenge with a lot of troubling, but in some cases could be last chance to improve yourself knowledge and feel you better. When you’ve worked for many years in the same way, with same people and same habits, job is like a routine. I’m in this situation: I need some fresh air on my embedded software engineer role, and step by step i’m trying to build a dream. In my case, works on Apple technologies. And just with this starting project, i’m feel …. “new”!
Miguel Marcos 23 Sep 09
Quitting your job is easy?
SD 23 Sep 09
You are absolutely right..and this has been my mantra for the past 2 years or so…
Sandeep Shetty 23 Sep 09
The employment contract that you sign with your employer might not allow you to “start something on the side” or give them ownership of your work.
Richard 23 Sep 09
Leaping into the darkness is what scares most people, so seeing it impresses them. Of course following through would be the better, bigger task, but the bold step of committing is why you get the applause.
Me – I’m working on the app(s) while I do the day job :)
developingchris 23 Sep 09
Quiting is easier, but its not done a lot, so its remarkable. Bunjie jumping is easier than rock climbing, but you get more kudos for jumping, because it takes gumption, and is a remarkable feet.
I don’t disagree with the sentiment though. As a moonlight entrepreneur, I wish it were sexier to be stable.
Matt W. 23 Sep 09
Yeah … leaving the thing that has put a roof over their head and food on their plate, for some people decades, is SO easy.
Those wuss’s. And shame on the folks that applaud them, reinforcing their wuss behavior.
Don’t get me wrong, you are right in that sticking with the idea after you’ve quit and making it work is extremely hard, but doing that just deserves further applause. That part doesn’t exclude them from deserving applause for taking the first step, quitting.
Cormac 23 Sep 09
The applause is not for the job-quitters success, it’s for their story.
“I quit my job and failed dramatically” is a more interesting story than “I didn’t quit my job and succeeded modestly”
Pierre 23 Sep 09
“Beware the investment activity that produces applause. The great moves are usually greeted by yawns.” —Warren Buffett
ML 23 Sep 09
Those wuss’s. And shame on the folks that applaud them, reinforcing their wuss behavior.
If someone bet their house on a poker game, does that deserve applause? Maybe if they have six more homes. But not if they are barely struggling to get by. The idea that any big gamble deserves applause just seems off to me. Plus, how many of these people who quit wind up not following through or realizing their idea wasn’t right for whatever reason? I’ll save my applause for people who can swim, not those who just jump off the boat. OK, this is getting a bit analogy-crazy…heh.
Damien 23 Sep 09
I completely agree with that. I’m currently starting as an entrepreneur and keeping my day job. Many of my friends are already seeing me as a billionnaire when only declaring himself as an entrepreneur is in itself very simple. But keeping to it is the hard part.
Tony Wright 23 Sep 09
“Following through is the tough part.”
I disagree with the sentiment of this post, but THAT statement is absolutely true. So much so, that “hacking” yourself to do so is a really good idea. As you say, it’s easy to quit. It’s ESPECIALLY easy to quit if you’re doing it on the side. “Oh that side project? Yeah, I kinda lost interest in that” is easy to say and no one will care. It’s a LOT harder to say, “Oh, the idea I quit my job over? It failed.” because that makes you look like a failure.
Quitting your job is a similar psychological hack to fatblogging or announcing an engagement at a big party. Or burning the ships once you reach foreign shores. Being “desperate” is what can often push you through the crappy or boring parts of your startup.
Jo 23 Sep 09
Amen! I’ve been attending grad school in the evenings so I could keep my day job (and the security of a steady paycheque doing work I like)... Now that grad school’s coming to an end, I’ve started consulting with a group out of the UK while working my day job - which means getting up extra-early for consult calls and doing the bulk of the client work after my day job is done.
My plan is to build up my consulting business before quitting the day job. It’s extremely challenging in that it takes up so much of my time… but I feel good, as you say, Matt, that I’m both keeping the $$$ coming in and learning a lot about consulting so I’m better prepared (and less desperate!) to stick with it in the long run.
Darrel 23 Sep 09
if (person<=30&&kids==0){
quittingJobEasy=true;}else if (person>=30&&kids>=1&&savings>=substantial){
quittingJobEasy=true;}else{
quittingJobEasy=false; considerNightSchoolOrLongDays=maybe;}
Jonathan 23 Sep 09
Leaving your job takes guts. Making a success of it takes perseverance. Both deserve praise.
ML 23 Sep 09
Leaving your job takes guts and deserves praise.
Does leaving your wife deserve praise? How about betting your house on a poker game? How about committing suicide? Not everything that takes guts deserves praise. It really depends.
I’ve seen delusional people trot out this “I quit my job” line with no realistic prospect for what else they’re going to do and thought to myself, “Boy, you really shouldn’t have done that.”
That’s why this knee-jerk reaction of “quitting deserves praise” doesn’t seem appropriate to me.
Jonathan 23 Sep 09
“Not everything that takes guts deserves praise. It really depends.”
I didn’t say everything did. In the context of this discussion it’s leaving your job to pursue a new project. That can require the use of a decent set of balls. I did it recently and left a very good and well paid job to start my own company. For a while I tried managing a day job, a family with 2 young boys and my sideline project. After a while something had to go because there wasn’t enough time in the day. I believed enough in my talents and I had the support of my family so I left my day job. Financially it’s a tough one but now I have the time I need to develop my idea, meet people and do all the other stuff that needs to get done. When your at work “you’re at work” and your boss won’t be too pleased if you are taking phone calls about your new start-up.
Frank 23 Sep 09
So let’s consider my case:
My current job is exhausting and particularly annoying, unlike elsewhere. I go back home extremely tired. I try, however, to do my best to work on a startup project we’re bootstrapping with a friend.
We feel very excited about it but we’re making slow progress (yes, even with the minimalistic set of features). Working one evening a week and one day during the weekend is unfortunately not proving productive: not only we need to rest, we have to take care of those little thingies on our to-do lists and have a minimal amount of time for social activities.
Moreover, my current contract does not allow me to have any other work activity, paid or unpaid.
Given that my day job is quite irritating, and I’m feeling blocked by time, fatigue and legal obstacles… I decided to quit. I didn’t announce it with bells and whistles and I do not want applause. Begin a freelancer life (which I once had) and work a couple of days per week for the startup seems to me the way to go.
Is it such an unwise decision?
Jonathan 23 Sep 09
Frank, for what it’s worth I applaud you.
Matt, Have you ever worked on a project on the side that turned into a full fledged business? Or do you wish you had stared your own business but lacked the necessaries to leave your existing job? Just curious what your attachment to this topic is.
Rodge 24 Sep 09
I quit a job 8 years ago, it took me quite a while to find my feet and I had many times when it’s been really hard and I envied friends with secure employment. But quitting your job to work for yourself and trying to make it happen is really damn hard and scary and I think it deserves some credit. Also, moonlighting and turning a side gig into something also takes credit. Having a go deserves applause, and if you managed to make it successful, then that deserves even more.
Wytze 25 Sep 09
Quitting your job to go it alone is only easy if you’re just plain stupid.
Sane, responsible people don’t make this choice easily. So when they do, a sane and responsible audience should indeed applaud such a daring move on the assumption that it was well thought out.
pierre tournier 25 Sep 09
quitting a job is not that hard, come on guys. what if you start your company and fail. you get another job. simple.
i think we, in the western world, have our priorities and scheme of reference completely f* up. being in a third world country and having to support your family of 8 as a farmer earning 2 bucks a day….this is hard.
Harshit 25 Sep 09
What a co-incidence about the timing I have read this article. I just quit my job yesterday and today is the first day I am working on my own!
To be honest, quitting IS a really stressful decision. Especially when you have so many responsibilities on your head.
I worked as a moonlighter since quite few months before quitting. One thing I realised was that I would remain a moonlighter my entire life unless I took a bold step. To grow, you do need to take risks. But a calculated one. I decided to quit only when I knew that I was easily able to outsmart my boss in terms of business knowledge.
So here are my 2 cents: Quit only when you feel you know the business well and have had enough years of experience in it. It is not worth to shoot in the dark.
Cheers
Btw, I am now called Cubix Web Solutions :)
Andrew D 25 Sep 09
Good post, I can’t help but smile at the comments.
I see both sides of the coin but as someone who’s quit their job twice to work on software projects, I think that starting your own venture requires passion, self belief and commitment. And when these are strong we’re going to make some bold decisions and some of them will be mistakes. But all the books and blogs in the world can teach experience and sometimes that’s what it takes. They may not make it the first time round, but once they’ve broken that 9-5 routine once, they’ll have the freedom to think about what they’re really doing and whether it’s really for them.
I know too many people that are too stuck in a rut to even think about changing jobs or progressing, let alone quitting to find a new life.
As for me, I’m in full time employment and working hard on my startup and I’ve got a good plan to keep doing so until the time is right.
Dan Martell 26 Sep 09
This post reminds me of a great saying:
“Starting is easy, finishing is hard”
Found this online: http://hubpages.com/hub/Starting-is-Easy—Finishing-is-Hard
ben 26 Sep 09
Your right, there’s no applause necessary. It’s a decision, but working with your brain at a full time job (as I have done as a programmer for 10 years) really doesn’t leave a whole lot of hours of mental focus to get much done. I do think it’s necessary to quit for many – you shouldn’t need to have superhuman mental stamina to go into business for yourself, tenacity and a good idea are enough.
erik 27 Sep 09
Everything’s been said, just echoing the sentiment. :)
Like everyone else here, I’m trying to do the same thing.
Some people consider starting something easy / hard, while others consider finishing easy / hard…
But is there really an “end point”?
John 28 Sep 09
I’m thinking that the applause was NOT because people agree that quitting your job is the smart thing to do. Rather, they cheered because they’re envious – the cheering was a way of saying “Way to go, I’d love to do that but don’t have the balls/means to do so.”
Travis Campbell 29 Sep 09
You raise a great issue. Personal risktaking, is indeed personal, as risk tolerance varies greatly from person to person. Some who ‘quit’ and pursue their own business, would only ever succeed upon making that level of commitment. However, there certainly is a trail of regrets for those who quit their day job too early…not having that coveted follow through you speak of. Dreamers don’t survive long in the ‘quit my day job’ landscape, only those who couple the dream with targeted action do.
-Travis
This discussion is closed.