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Want To Be A Freelancer? Just Punch Yourself In The Face, Instead (terribleminds.com)
137 points by jamesbritt on Sept 17, 2010 | hide | past | favorite | 61 comments



Just for once I'd like someone to write something about X without using the conceit that all instances of X will be immensely similar to the author's immediate experience with X.

Everybody is different, significantly so even. They have different personalities, different educations, different ways of working, different skillsets, different passions, etc. That's why people have different jobs, different hobbies, different friends, different ways of living, and why people do their jobs in different ways. Saying "freelancing will be like THIS" is about as silly as saying that if one were to start painting their experiences would be identical to Van Gogh's, or Michaelangelo's, the likelihood is comparable. I've seen people of equivalent intelligence, equivalent education, equivalent cultural backgrounds doing the same exact job for the same exact salary and having experiences as different as imaginable. Working in completely different ways, generating completely different results, taking completely different degrees of personal satisfaction from their work, working different hours, and having completely different levels of work-related stress.

That's humanity for you. There's a huge degree of diversity out there, and that's true in every career path, don't insult us by pretending that freelancing or working a cubicle or any other human experience can be summed up in one tidy little package with minimal deviation.


You're absolutely right but like all opinion pieces I don't think it's meant to be taken as "advice". While some of it touches on real problems it's really just a bit of tongue-in-cheek fun.

Leaving aside the subject I really like the writing in this post. He created some great imagery. Good Friday reading.


As you nick is inclined plane, I think the title should be: If you are a free lance there is a statistical force that try to make you punch in your face. As is generally well known men are all different from one another, so this force can also make you punch in other parts of your body or hit someone near from you. So these experience can't no be summed up in one tidy little package since there is a wide deviation.


There is no such thing as freelancing. I mean it. There are insecure, short-term jobs and there are businesses. Freelancers are neither fish nor fowl. They don't have the security and legal protection of an employee, nor the efficiency and delegation of a business. If you consider yourself a freelancer, stop. If you have the inclination and the ability to delegate and manage, take on an assistant and start acting like a business. It is insane for a $100/hr worker to spend their time doing menial administration.If you just want to do a job of work without worrying about that stuff, you'll almost certainly be better off on a permanent contract with all the benefits that come with it.


This is a good post and accurate one; it also describes how my family's business basically runs -- as a business. We do grant writing for nonprofit and public agencies (http://blog.seliger.com/about/), and most of our clients and more than half of our revenue comes from shortish (6 to 8 week) clients. But it's run... like a business.

However, one thing I'd point out is that most businesses don't have the immediate cashflow to hire an assistant right out the gate, and many businesses that eventually charge $100+ / hour don't start that way as they try to acquire clients and get some amount of money going. When I was a little kid and my parents were starting the firm, my Dad routinely worked 80 – 90 hour weeks -- and that is not an exaggeration. He couldn't have hired someone else to do the scut work at the time.

I think there are two lessons to take from this, which isn't to discount your observation -- as soon as you can afford someone in a secretary / office manager type role, get them, but you might not be able to --

1) Do anything it takes to survive. pg calls this "maximizing your runway" and so forth, but that's the basic idea.

2) Do something that, ideally, everyone else isn't doing. We're basically the only non-specialist grant writing firm in the country. No one else works the way we do, from what I can tell. If you're a freelance writer for magazines and so forth... every third person in Brooklyn works the way you do. (That's one reason I never tried to be one, tempting though it was; I'm probably better suited for journalism than grad school, but here I am). If you're trying to be a freelancer, the competition is, to my mind, insanely fierce.


Is it less work to find a reliable, very part-time assistant than to just do the menial stuff yourself?

Serious question, because I'd love to be pointed to a way to do that.


If you're a freelancer who has a significant amount of menial administration, you're doing it wrong.


Common freelancer mistake is not charging enough or trying to compete with large companies on commodity markerts where margins are just too low. Not generating enough revenue is the direct cause of not being able to afford holidays, time off because of sickness, training, seminars or being worried about periods when work stream peters out.

It's hard for a freelancer to employ the economies of scale and hence they need to specialise n a niche where they can outdo big players and charge bigger premium to pay for overheads and cover the risks.

A freelancer carries more risks than even a small size company that aren't pooled: sickness, a spot of weak demand for a specific product, not getting paid. Certain overheads are also higher per "head": sales, bookkeeping, legal.

One need to charge a top buck and keep overheads low to maintain a sustainable freelance operation. I saw so many freelancers going back to permanent after 2-3 years just because they were not charging enough to compensate for the risks, extra work and flexibility of the service they were providing.


I'm an independent consultant.

I live within my means and never worry about money, much less have cash flow problems. Considering I get to do what I love in the process, every day is like Christmas when I put it in perspective.

I have health insurance. It's actually cheaper than what my contribution was the last time I had it "provided" as a benefit, for about the same coverage. Being part of a big risk pool is nice, but at least hedging against catastrophe with "self employed" insurance is too cheap/easy not to take advantage of.

If you don't make time, you'll never have time. The author seems to be falling into the all-too-common trap of equating long hours with productivity. You can find yourself on that soul-crushing treadmill regardless of whether you drink your morning coffee at a cafe or in a cubicle.


"If you don't make time, you'll never have time. The author seems to be falling into the all-too-common trap of equating long hours with productivity."

Not necessarily. It probably depends on the market you are in. The author is a writer: maybe it is a bit harder for him than for a software consultant: maybe he has to work more to earn enough money. Also I have a freelancer friend who is very productive just somehow he is trapped into a market where there is not too much money. (He (and I) lives in Eastern Europe, and works for not too big/rich companies.)


For what it's worth, paid writing projects are a non-trivial portion of my income. I've found time management and hard negotiation to be even more important in that area than in software development.


It's not the first time that I hear health insurance mentioned in stories I read on Hacker News. As a person living far away from USA I'm afraid I'm not getting the situation, and they don't seem to write about this sort of stuff often on the Net - because that's the way things are, except I think they are different in different countries.

For example, here in Russia every citizen including unemployed (which I am now) and retired has health insurance. It's of the basic type, you don't actually expect to get much good out of it, but at least you won't have to pay for a visit to physician. When you get a job, you receive health insurance from your company. It will be issued by different insurance company than when you are unemployed, but unless your company cares to provide you with extra health benefits, you will get the same benefits as unemployed person. I never worked at such a company though, and I started to think that maybe I should choose as my new job a company that provides a good health insurance end exercise some of those nice health benefits. Maybe pass some thorough medical examinations for free and receive whatever treatment needed (I have some issues with my health, but nothing that I can put my finger at and it nothing too serious to warrant the bother, up to this point). When I told about this to a doctor acquaintance, she said that in her opinion it is always wiser to get a high paying job and pay in cash instead, because that's the only way you can motivate doctors to treat you[sic]. So I keep wondering: do we have the situation so very backwards? I have really few information to compare.

Where can I read up on how health insurance works in the USA? Information about other countries is also welcome as well.

Why is the option of buying health insurance for a freelancer not even considered?


(I'm also from Russia)

The doctors here are much better and don't need "motivation" in a Russian sense of this word.. They will give you their best treatment, if you have insurance. For this reason, insurance here is very expensive. There's a lot of poor people here that don't have any kind of insurance.

The cheapest insurance in NY, for example is ~ $300/m, but you also pay up a large amount if you require serious treatment($5-10,000), and every time you come to see a doctor ($25-50). There are many other options for insurance - the larger the monthly payment amount (premium), the less you pay out of pocket for visits and other things.

A best situation you can have here is a company paying for you. To buy the same insurance that I used to have when worked for a financial company here would be $500-600/month.

So it's a big issue for freelancers and everybody who doesn't work for companies that provide it.

It's going to change in 2013 though after new legislation that Obama just passed this year, but there are different opinions here what the effects will be exactly (that's a different topic entirely though)


To buy the same insurance that I used to have when worked for a financial company here would be $500-600/month.

To put that in perspective, I pay a comparable amount of National Insurance every month in the UK, deducted from salary.

No such thing as "free healthcare".


Beyond that amount, however, in the US, we also all have to pay Medicare and Medicade taxes. Also, that health insurance at $500-$600 also almost certainly includes a deductible. And copays.

And, as a sister comment points out, National Insurance also includes government pension. I don't know if this is true, but if it is, also include our Social Security taxes in the cost.

All of these together makes our equivalent cost thousands a month.


If you're employed your national insurance also includes a large contribution to your state pension. Since I'm self-employed I only pay for healthcare at £32 per month. That's pretty cheap compared to the US.


2014 actually. 2013 was the House version of the bill but the Senate chose to make us wait another year.


> All life is work

So better make sure you enjoy your work! Otherwise doing more of it is going to make you feel miserable. Just like there are employees that are unhappy in their jobs because of the nature of the job so it happens that in freelancing if you don't like your job you're going to feel bad. Especially if you are doing more of it...

> The hunter lives in a hard world

Yes, but when you are kicked out, laid off, fired then work divorces you. Employment is paper-thin security, you are basically living at the whim of someone else. As a freelancer if you are not 'pipelining' your work you are doing it wrong. You need to set up your rates so you can afford some slack (you are that good are you?), and then you need to push a little bit too much work in to the pipeline working prospects and turning them in to customers. Over time you will find yourself with a portfolio of customers. Periodically you review them and you raise your rate in those cases that you'd rather be doing something else. As a freelancer that is good, work finds you.

> weekly paychecks are a luxury

Yep. So a freelancer saves. If you don't have the attitude that will let you save half of your income on the spot for taxes and rainy days freelancing is not for you. Suggest you get a dayjob in stead until you close the hole in your hand and you can plan ahead a couple of months to a year.

> Also a luxury: heartburn meds and that spleen transplant you really need

I have been self employed for as long as I care to remember and have on occasion paid cash for an operation I needed, but now have state required mandatory health insurance. Things actually got cheaper for me. This will vary country to country, and in some places it's really hard to find decent health coverage as a freelancer. But there are ways around that. Incorporate a company, hire yourself and your spouse as employees and sign up for a package with some health insurance provider.

> Hey good luck with that mortgage

Freelancing requires you to be in control of your own funds to a much larger extent than a day job will give you, and banks have learned the hard way that lots of freelancers can't do that. So don't look at a bank to provide you with a mortgage until you have a solid track record. Meanwhile, nothing will stop you from working a bit harder, saving a bit more and buying that house cash in 3 to 5 years time, staying in as cheap a place as you can get away with for the intermediate period.

> oh, and nobody else will get it either

So what. Who are you doing this for? Some audience? What do you care what other people think about you not having a 'job'?

> You might as well paint a face on a volleyball

Freelancing is the opposite of a lonely life for me! I've met more people than I would ever meet in a regular job. Freelancing has taken me all over the planet, caused me to meet some of the most interesting people. It's maybe time that you 'don't make money', but I've set my rates to compensate for that and am in enough demand that that still works out well. A bit of passive income doesn't hurt either, which is how a smart and savvy freelancers spends his 'idle time'. That way that time will still make you money in the future. $20 per day in passive income is definitely doable on a very low budget in terms of time invested. Much more than that will require you to work hard at a project for well over a year but that's something you will not be able to do in the beginning. Freelancing is a stepping stone to being independent completely, I think of it as a way to make money that has more freedom than a job will ever give you.

> So why do it? Because it's awesome

Then why bitch about it? I think the author should go back to a day job for a couple of weeks. Because if you really think it is awesome then any and all of the above is either 'speedbump' variety or lack of success.

Oh, btw, I did get that mortagage. Maybe find a better bank? The tax break made it worthwhile, otherwise I would have saved just a bit longer.


I dont think the author needs your advice, the post was half written as advice and half I expect a cathartic "bitch", at least thats how it came off for me.

people can enjoy something immensely and still feel the need to bitch about it once in a while, I think thats fairly healthy.


If he meant what he wrote he should get a job, seriously.

I love the freedom that being a freelancer gives me and I could write about the hard times but I'd still do it without a bitter aftertaste like this.

Of course everything has its good and its bad sides but this sounds like someone that is very frustrated but that has found nothing better than what he's doing.

Also I notice he's a writer, now writing code and writing books are completely different for the 'average' level. An average coder can bring in quite a bit of money if they play their cards smart (look at me ;)), but an average writer would have a very hard time to make ends meet.

Writing books is more like making music than it is to writing code. And music can be tough too, as long as you don't make it in the 'big league'.

Freelance writing is tough from a financial point of view, and that's something that you presumably know before you pick that particular poison.

I find this piece much more negative than just the facts presented, the undertone is such that I hope people do not take this as the 'average' outlook of freelancers on their work and their work environment as well as their financial situation. It is not representative as far as my experience and the free-lancers that I work with are concerned.

You can't negate the tone of that article with a single line of 'because it's awesome, duh' at the end.


the first few paragraphs are all about how much he loves his work, It sounds exactly like someone who loves what they are doing but wants to point out that it isnt all sunshine and roses for people thinking about doing the same thing.

he is obviously a very good creative writer, you probably need to read it a little less literally.

when I first seen the title I remembers pg's quote straight away "doing a startup is like being punched in the face repeatedly, but a 9-5 job is like being waterboarded"


Doing a startup is much more like running a marathon than it is like being punched in the face.

It's for people with stamina, and the will to fight back.

I've been doing this for many years now and the times that I got 'punched in the face' are relatively small, and most of the times they were simply setbacks that if I had thought a bit longer and had been a bit smarter I could have avoided. Being punched in the face repeatedly suggests that third parties are actively trying to hurt you as an individual, and I can only find two instances of that over the last 15 years, and in both those cases the counter-punch was a k.o., so I don't expect to see repeat performances from that corner.

Entrepreneurs as a rule are not from the soft side of life, they know the value of standing up for themselves.

Going out for funding and being turned down for instance is not being punched in the face, it is a learning experience that tells you that something about you, your product or your presentation needs work, or that the investors you've been talking to are simply wrong.

So you improve and you try again, such is the nature of entrepreneurship and the nature of life in general.

If you can't handle disappointment well then entrepreneurship may not be for you. Think of it as character building.

edit: the disagree by downmod crowd has it today it seems.


I feel compelled to mention that similarly to the OP, I am not having an existential crisis.

Its probably a cultural issue, At least personally I think if you cant have a proper bitch about something, you probably dont love it enough. Same as the british idiom that says you arent friends with someone until you can call them a [Insert crude insult]


What are some ways to get 20/day of passive income?


OP has a big problem and it's not freelancing. Just look at what he has written...

He talks about his office, his coffee, his pants, his computer, his commute, even his tax deductions. He talks about what he can do, what he wants to do, how he can structure his day, what he feels like, how he'd like to feel.

He talks about everything except his customers.

I don't care if you're a freelancer, a consultant, an employee, a founder, or a volunteer, it's not about you. It's about your work and the people you're doing it for. That's it. Everything else is just a detail.

Once you start thinking about what you give instead of what you receive, your begin to focus on the task at hand instead of the whine of the day. OP oughta try it sometime.


Geez, it was a light-hearted glimpse into the difficulties of freelancing. Not a tutorial, a how-to or documentary, just a slice of what daily life is like as a freelancer. Dry spells, unpaid 'vacation', no clocking out.

I for one enjoyed it.


I must admit, I can not even parse what you are trying to say. I am not a customer satisfaction machine. Is it really outrageous for a human being to be concerned about one's own happiness?


I completely agree with you, he comes off as unprofessional and unmotivated. If I had a person like that near me I'd avoid them like the plague, the negativity is just too much.

Focus on the task at hand, get the job done, don't whine. Rinse, repeat, watch the money flow in and the people around you getting happier.

This is a typical case of a victim mentality. If you want things to change then change them, don't sit and wait for the world to change around you for your sake. Go do something.


Seriously, that was an awesome take on freelance. I read a lot of these "how freelance is like," type of articles, and they're mostly focused on the freelancer not the work.

But I think he's just writing for that audience. The question isn't how can I be a successful freelancer, but how will my life be different if I choose to freelance. That's probably what most of his readers are looking for.


One item I disagree with. You are a freelancer, but you are also a company. You are employed under whatever name you are doing business as. If you don't have a business name, then it's just your own name as a sole proprietor. You can give yourself a real work history and paychecks, just like you would be receiving by working for any other company. Whatever is left over after your regular paychecks you can give yourself as a periodic bonus. Of course, if you don't make enough money to give yourself regular paychecks, or those paychecks are small, then you aren't making enough to convince a bank to give you a loan for a house.


You can't put yourself on salary unless the business entity is a corporation or an LLC taxed as a corporation. Even if you do payroll for yourself you still have to file a 1099 and a schedule c. For a freelancer a Corp is a bit overkill and you get taxed twice.


I was thinking more along the lines of building a history. Open a business bank account and a personal account. Give yourself regular payments (bi-weekly / monthly) from the business account. Perhaps then you could show your statements to the bank when asking for a housing loan. You would be demonstrating that even though the income of your business is up and down, you are able to provide yourself a steady living wage and that you have reserves to smooth out the bumps. Maybe this wouldn't help though, not sure. I'm a "freelancer" myself but I have never attempted to get a loan.


A lot of folks misinterpreted this and I can't edit it.

A sole proprietorship, a single-owner LLC and an S-Corp are all pass-through to your personal income taxes. Meaning that in the eyes of the government you are still self-employed and need to file a 1099 and schedule C, even if you put yourself on payroll instead of paying out on draw.

I learned this the hard way.

What I'm saying is that even if you have a business entity you are still technically self employed. That is unless you have a C-Corporation or an LLC taxed as a corporation, in which case yes you can put yourself on payroll and do tax withholding and can legally be considered 'employed' by the company, however you get taxed double and face a number of costly state and federal requirements not to mention new overhead costs for legal and bookkeeping etc which is in most cases not worth it unless you are earning quite a lot of money.

But regardless, I don't know how much a mortgage company would care about such things. Maybe regular issue of a check from one company would be enough to suffice and I'm overblowing the issue...


Which you should be if you are in the US. A freelance should be a S-Corp and pay themselves a "reasonable" salary. To not do so you are throwing a huge chunk of money away on employer FICA. Basically you are pissing away 8% of you income if you are not a S-Corp and that is just in taxes. When you factor in the tax deductions a corp can take the savings are astounding.

Someone up stream mentioned that a freelancer should hire a secretary and stop doing the office work for $100 hr. My though is the first thing a freelancer should do is outsource accounting to a CPA. These people pay for themselves, second should be legal counsel, at least a paralegal after that a secretary would be a good third.


That depends on what you're doing. If you're a developer or a sysadmin or something, you need to set up a corporation to provide you some level of liability protection. I'm not a lawyer/tax expert, but my understanding is that this is not something you could do without at least an LLC in place.

If I'm wrong about this, someone please correct me.


The point here is that if you are a single owner LLC, sole proprietorship or s-corp you can't technically claim it as your employer - at least for tax purposes. Yes you get liability protection and so forth, but you are in the eyes of the law still self employed.


You do need an LLC for liability protection but you don't need to pay yourself a salary. Instead, you take whatever you want as pass-through income distribution.


Ah, ok. That makes sense. Can you only pass through a portion? In other words, keeping some back for expenses like computers, cell phones, hosting, whatever?


Yes you would keep a certain amount of money in the company accounts for expenses. The company expenses would have to be paid by the company (as opposed to your personal income which is passed through to you) for these expenses to be tax deductible (right? I'm not a tax guru either.)

@rwhitman I wasn't necessarily referring to a salary. I know that you can't pay yourself a salary as an employee when you are the owner of the sole proprietorship. As the owner in such a case, essentially you are the company, not an employee.

As I mentioned in my other reply. I'm thinking that giving yourself regular payments from your business account would be a better way of showing a regular and steady income than showing the more crazy activity of the business account

I think the biggest problem is that he simply couldn't give a straight answer to questions. He could only say he is a freelancer and he works for himself. He could have said that he is a sole proprietor and that his company name is x.


You can pass through whatever you want but you should pay all the expenses through your LLC, otherwise you "pierce" the liability veil.

TIP: presuming you are in the US and you are married to someone who has a full-time job, you can save a large chunk of money if you sell 99% of your company to your spouse, have them be a passive partner, and distribute 99% profits to them. (Ask your accountant for details).


A properly managed S corporation avoids double taxation while providing the liability and legitimacy benefits of doing business as a corporation. That or an LLC should be in place any time someone is doing business; if you aren't working for one, make one. The benefits vs. the ~ $250 a Delaware corporation costs are huge.


There was a time when I thought freelancing means freedom. I no longer think that. In my experience the difference between a day-job and freelancing is much smaller than the difference between freelancing and starting a startup. Freelancing and day-job are almost the same for me: work for other people to earn money from month to month to support my family. Starting a startup (or doing a side project) is different. It is more about dreams, creativity and 'unlimited' possibilities.


Just wait until that startup starts feeling like a real job. Then come back and comment on how different it is. Personally I have found working for myself to be quite different then doing the same thing for someone else. I have to find the work, I collect 100% of the revenue and as a result the preverbal buck stops at my desk. I sleep well.


I don't know, maybe the problem is that my perception on freelancing is based on a non representative sample: For example I've browsed rentacoder.com for a while: my impression was that the market is extremely saturated, most of the tasks are quite boring, time consuming, low-payed and not much fun. Did not seem to be better than a day job. Being a well-recognized, top freelancer with special skills and good connections: that's good. But being an average freelancer does not seem to be very appealing. On the other hand at my startup I can create things which my bosses and customers did not even think of. Most fun software problems are not eceonomical to solve in very high quality for one client, but it is economical to solve if you can sell it as a product to lots of clients. This possibility of 'scale' makes startups very different. On the other hand the success rate it much lower. I have failed projects behind me, I know what failure is, but I've learned a lot from them, and still I try again (beside my day-job).


Rentacoder and elance are the absolute worst places a decent freelancer should look for work. Even craigslist is head and shoulders above them. I've found lots of $75 - 100 / hr gigs on Craigslist, but they'd laugh me out of Rentacoder for those rates.


One way to bring about a modest, regular payment is to not consistently withdraw almost everything you're bringing in. If you're getting paid to a business account, set up a small, regular transfer (even just $100 or $200/wk) when you're starting out and make that your dependable payment rather than getting $2k one day and nothing for the next couple of months.

Renting a desk in a shared office space can always help give you regular hours, social interaction, some networking opportunities, etc. (I currently rent a desk to a freelancer and have another space free - Adelaide, if anyone's interested.)

The rest is not unlike that stated. You have the freedom to get away for a holiday, but there'll be no one running the show while you're away. If you're big enough to have a couple of staff, but not big enough to have someone doing your accounts, prepare to get bogged down with tax, super, billing, etc - it's hell.


Yup. Everything he says is true. I've been self employed for 10 years and it never gets easier. I'd even say it gets harder every year. And I don't have a family or a mortgage to deal with, I can't even fathom trying to support a family as a freelancer.

Oh and try applying for a job after only ever being self-employed. That one is fun


What? What kind of freelance do you do? I've been doing this for just over three years and it's gotten easier every year. I can't imagine going back to a job, though I get offers every week (literally). Just curious why my experience is polar opposite yours :-/


Honestly 3 years in, everything was fantastic for me too.

I'm a web developer / project lead. Its hard to explain why things have been negative for me lately, there are a number of compound factors over time. I got too comfortable relying on certain clients. Credit cards are pure evil. Basically any prolonged reliance on debt can snowball. At some point you jack up your rate and its hard to knock it down when you start competing on price.

But the biggest pitfall - its very easy to splurge on business overhead when you are doing well. Nice office, bookkeepers, outsourcing basic tasks, top notch CPA, lawyers, furniture, fancy computers, memberships, travel expenses etc. This stuff puts you into awful debt when the work volume shrinks. Basically when you are feeling happy and comfortable, save money like crazy and don't splurge on anything. It doesn't last.


Aha - it seems you've been able to find your issues, and those have far less to do with freelancing specifically as they do with life/money management overall. I know plenty of people with regular f/t jobs that have gotten in debt to dangerous levels, faced layoffs, crises, etc. Freelancing seems to have little to do with it.

As for going back to a f/t job, freelancing for X years might be problematic for some employers, but certainly not all. I get approached on a fairly regular basis, and while I never say never, I've not had a serious offer that's been even remotely compelling, either from a responsibility or financial angle.

Gentle plug: these sorts of topics will be explored in more detail at http://indieconf.com


A must read for any would-be freelancer. Freelancing doesn't mean just sitting in a Starbucks with your MacBook Pro.


As I read this, I'm sitting in a Starbucks on my MBP. Now it doesn't JUST mean this, but it's not a bad part of it:)


Dude... You're a freelancer. Find a better coffee shop!


Neither is it a litany of misery.


I didn't see it that way. It was a bit negative but in a relaxed manner. I certainly didn't read it as a litany of misery. If you also read the comments you might find yourself laughing a bit or at least finding common patterns with your own experiences.

The reason I've said people should read stuff like this is because I see too much accent being put on the positive side of freelancing / startups and very little on the hard part.


I don't think the author suggested that. I found the article highly amusing, with several lovely laugh-out-loud moments.

You are taking the article too seriously.


A lot of this essay reminds me of the beginning of a startup. When days are long and sleep is optional and sparks are flying and people expect you to have cleaned the toilet because you've been in all day. (Except you've been sleeping, because you were up til 10am coding.)

The difference is the endless hand-to-mouth treadmilly cashflow problem transforms into something... well, similar and yet different, but I found it a lot more palatable than the idea of constantly writing blog posts for Calacanis^W^W^W^W^W chasing clients for tuppence a time.


Once you have some savings in the bank, it is a lot less stressful. For me then, a time without contracts is not a loss. I have enough other things to do, like working on my own projects that hopefully will eventually get me out of the consulting circle for good.

I also think as a freelancer it is easier to meet a lot of people. For one thing, you typically see more different companies. But there is also more incentive to go to technology meetups and networking events.


Wow. This pretty accurately describes my feelings as an "independent contractor."

"A vacation day is a day you’re making zero money." For anyone looking into becoming a freelancer/independent contractor/consultant/whatever you want to call it, I cannot emphasize this enough. I've been doing this for a little over a year now, and I cannot even begin to describe the feeling of "Hey, a day off! Wait, that means I'm making a big fat 0 today." Yes, you need to unplug and get away every once and a while, but vacation time starts looking very different when put in that context.

That being said, if you want to be your own boss, live by your own schedule, not be beholden to anyone else, etc start a business where you can make money when you're NOT at your desk.


If you have to work around the clock, can't take a vacation, and can't afford medical insurande, doesn't that mean your business idea is shit and doesn't hold?

Easier to bash the whole concept of starting your own business, instead of admitting failure I suppose...


Seems a bit ranty, but I'll agree that the mortgage thing is a bit of a PITA. I went through a broker and only needed to show 3 years of tax returns but I know of self employed people who've set up companies, employed themselves, then filtered their savings through the company as paychecks to qualify for mortgages. (The only downside being you end up paying taxes again on the money "earned" in this new employment in order to keep it legal.)

Why a few tax returns can't suffice is beyond me. A few years of working for yourself and making a decent income looks a lot better on paper than having held a job for 3 months to me.




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