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Ask HN: Should I go freelance? Right now?

34 points| maybeindie | 14 years ago | reply

I'm considering going the freelance/bootstrapping/contracting route. Currently very close to resigning a cushy salaried job as an Enterprise Java consultant. Would love your honest opinions on whether I'm in good shape for striking out on my own.

I have two reasons for doing so: A) I want to be able to call my own shots in how I spend my time. The commute is killing me, for one thing. B) I also want to bootstrap my own products. Have launched one web application a few years ago (didn't catch on, but I learned a lot.) I have a long list of ideas I'm eager to execute on, but unable to do so while working fulltime at a BigCo (I'd like to, and I've tried once earlier, but it didn't work out and probably won't while I work a fulltime salaried job.)

I'm 33 yrs old. Ten years experience as a paid developer. Competent Java/Ruby/JavaScript programmer. Frontend, backend and some mobile experience. I've done some speaking in the local developer community, got some open repos in GitHub in multiple languages and have a couple of public webapps/websites in my portfolio. I'm certainly no "rock star" though!

I have a decent network, but mainly composed of developers, not too many product owners/stakeholders/gatekeepers.

I'm a family man, but we've gotten our living expenses down to the point where we can live well if I pull in at average 3k each month (take-home pay). Have saved up a nest egg which will carry us for 6 months if I'm unable to get any contracting work at all. If I'm able to get work charging around 100-150$/hr I'd only need to work around 16 full weeks a year or on average 2 days a week to get by. This is a very rough calculation and subject to differences in currencies and living expenses from the US, but I think you get the idea: I've done my homework.

Oh and I live in a Scandinavian country, near one of the capitals (where most of the web/software work is going on).

So. How does my situation sound to you? I think this should work but I need some outside validation. What are my chances?

Really, one of the biggest things holding me back is a small fear that the current debt situation in the US turns into worldwide financial armageddon - would I be better off on my own or continuing work at a BigCo in that case?

37 comments

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[+] alain94040|14 years ago|reply
Very simple advice: don't leave until you landed one consulting gig.

If you have never been on the sales side of work, you may be shocked by how much time it takes to convince someone to sign a contract with you. Yes, you only need to work (code) two days a week, but on top of that, you need to find and convince new customers.

Just make sure you have been through the motions once. The coding part is not the issue here, it's landing clients.

[+] Jd|14 years ago|reply
Also, make sure sure your first gig is at least six months long and more than 20 hrs per week. The sales side of things is absolutely the worse part of being a consultant. You really have to be out there and not simply meeting other developers but meeting the people who hire developers.

Also, your ability to execute well in a 9x5 setting does not at all mean you can execute well independently, and anyone with experience working with contractors will know this and will want to vet you. So it may be rocky at first.

The worst thing is even with a good portfolio you have to be active active active seeking work, and that is just a completely different mindset than writing good code and one that, frankly, most developers would do better than to develop. I've learned how to market myself, etc., but frequently think that time would have been better spent elsewhere (e.g. learning new technology)

Also, you should know that the type of work you get may be quite different. There can be a lot of in and out, here and there, travel, etc.

I'm a couple years in with a good portfolio and can hit mid to high hundreds (USD) but it is such a pain in the ass I am actually looking for a "real job" again.

Plug: hit me up if you are in the Bay Area and looking for someone with experience with Javascript / Ruby / Java / Salesforce. I'm reasonably proficient in all of the above, won a bunch of awards, and just bored with what I happen to be doing currently.

[+] bennesvig|14 years ago|reply
Very, very good advice. Even if it's a very small gig, just getting the first job makes a huge difference.
[+] scrrr|14 years ago|reply
Coming directly from university I was earning about 45.000 Euro (+ Bonus) at a top-5 consulting firm here in Germany.

After one year I started to get very bored. In my free time I picked up Ruby and Rails and finally could not stand Enterprise Java and ABAP (SAP) any more and quit my job. I didn't have any freelance gigs set up yet, but I knew that I wanted to work with RoR.

Through a mailing list I landed a job at a Rails-startup and started to work there for about 300 Euro per day. Freelance. They didn't care if I was a normal employee or a freelancer, so I just said I want to freelance.

It was the best decision I have made in a long time.

First of all working for a startup you learn about 10 times as much as for a big company. There's just more stuff that needs to be done. From tweaking the database to writing front-end javascript. My colleagues were great tutors and especially through several sessions of pair programming I picked up some good skills that would otherwise have taken me a much longer time.

I also decided to work only 4 days per week, on average, which left me with one extra day for my private projects. While the jury is still out if we will succeed, it was a very comfortable situation, since I could work two days on my own stuff (Fri + Sat) and have the Sunday off.

Today I work for 500 Euro a day for a larger company that decided to use Ruby. They don't really care when I show up as long as the work gets done. I don't get called to as many meetings as the regulars and I know in a few months it will be over and I'll be working on something completely new.

Job situation: It's not "totally awesome" but by maintaining a network of other freelancers I'm never out of work. If one guy is engaged and gets an offer, he forwards it to the others, and vice versa. I'm not afraid I'll get in a financial crisis any time soon, because I have very nice savings and because I can always get a regular job for a big company, should I ever run out of offers.

I think it's important to stay up to date on new things (say the new RoR version or interesting ruby gems, nosql databases or caching methods), because a part of my job is consulting and offering suggestions, but that is easily done by reading blogs, watching some Railscast now and then and monitoring sites like HN.

So my suggestion is: Go for it. If everything fails, you're still a software engineer, a currently very sought after profession. (I assume it's the same in Scandinavia.) Remember: A regular job isn't very safe either. If the economy collapses you can still be laid off.

Todos: Find out about insurance and taxes. At least in Germany you're basically leaving the social security safety-net when becoming self-employed.

And yes, a long commute really takes the joy out of life. Quick tip: Get a kindle, use Instapaper to sync articles and read them on the train. ;)

[+] jordinl|14 years ago|reply
500€ sounds a lot, I'm based in UK and I've never heard of anyone getting paid above £400 per day (in Rails). I've been thinking for a while on moving to Germany, would you mind if I contact you?
[+] maybeindie|14 years ago|reply
Thank you. I'm also fairly certain I'll easily find new salaried work if all else fails and I run out of funds. Would feel like a big defeat though. :)
[+] babebridou|14 years ago|reply
In France we benefit from a system called "Entreprenarial Vacation" - anyone who spent 5 years in their company can ask to take a year off in order to start their own business. The company can accept or refuse. After 12 months, the employee can decide to leave the company for good (business works) or return to his former functions and keep his job/salary (business doesn't work, founder is not fit, crisis in the world- you name it).

I oversimplified it a bit of course, but basically you should check out if there are any system like this one in your country. I personally took this chance and I am freelance right now under these terms. I already had a contract ready to execute when I started, which helped tons.

Just one thing: expect up to 3 months delays in payments and expect administrative delays (at least three weeks, for me it was two months- don't ask) from the moment you have a bank backing you up until you can issue your first invoice: that's what it takes to incorporate a company. So worst case scenario is even if you start with a gig right away, you might have to eat all your saved up cash before seeing any money income.

Looking back at how it went for me, I would have rather started working on all the administrative details before leaving my previous company. Then again I'm talking about the French administration, I don't know the specifics in other countries.

[+] maybeindie|14 years ago|reply
Administrative details aren't quite as bad here, and anyway I've already got a company set up from my web app launch a few years back. Thanks for the input. Haven't heard about anything comparable to "entrepreneurial vacation" but some people do take extended, unpaid leaves of absence for various reasons. Maybe I'll talk to my employer about that, would make it far less risky - though it would also give me less of a fire under my ass :)
[+] sleight42|14 years ago|reply
My advice? Go for it. Let's break it down:

(1) Don't let fear rule your life (2) Given your ability to earn, your needs are modest (3) From your post, you seem to have a reasonable perspective (4) The added paperwork may be annoying

(1) Fear will tell you to stick with your "reliable" salaried position. I am unfamiliar with Scandinavian employment laws; however, in the US, job security simply doesn't exist.

What I tell folks: "Everyone is a freelancer -- some people realize it and most don't". What I mean: you are responsible for your career and for marketing your skills. You can't count on other people to do it for you.

You want to mitigate as many risks as possible to reduce fear.

* You already have a nest egg.

* You know how much you need to earn each month

* Do you already have clients lined up? If possible, I'd recommend having more than one at a time. This can get complicated, trying to satisfy 2 or more clients' needs while leaving time for your own (bootstrapping, et al). However, if you tell each client up front that "I can allocate up to 15 hours/week for you" and they're on board with that then you only need 2 clients. This will help keep the income steady.

* Even with a nest egg, burning savings while sitting on the bench is not good for the stress level (see the latter part of my previous bullet).

(2) Are Scandinavian businesses able to find (enough) full time hires with your skill set? If not, the market is ready for you. If so, you may need to be a little more flexible.

(3) You don't come off as an arrogant jerk (quite the opposite). WIN! ;-)

(4) Be prepared to do more paperwork. You will be your own business. Find out what this entails in your country. In the US, it means more taxes, finding and paying for my own health insurance, invoicing, and other tedium. This can take up 5-10 hours/week of your time at first. It gets better over time.

About me: I've been freelancing for a couple of years in the US and have been in the industry perhaps a little longer (just over 16 years). I tend to act as a "consultant" in addition to a "contractor": beyond just slinging code, I also providing "coaching" to individuals and teams. I've coached/mentored several friends as they've transitioned from salaried work to becoming their own business. Heck, maybe I should make a business out of that myself but I enjoy helping people. Feel free to drop me a line.

[+] mgkimsal|14 years ago|reply
The whole US debt ceiling thing - no one will know what the effect is - so much of the market stuff is driven by confidence/fear that there's no way to predict reactions to something that's never happened before.

re: freelancing - if you've got a family situation, I'd suggest getting two things in line before going freelance:

1. Getting a bit more savings - 9-12 months would be better imo (but I'm a bit conservative in that regard) 2. Getting some work lined up ready to go, or ideally that you can work on part time already, even if it's not quite your target of $100/hr. Once you quite full-time, you'll already have some income stream to build on.

I was in your shoes 4 years ago, and have had some ups and downs - an early client didn't pay (~$9k) and I filed a lawsuit - 3 years on its still pending. Be prepared to withstand 'feast/famine' cycles - that's where the > 6 months savings helps out. We've got 18-24 months (depending on how we spend) saved up in an emergency fund, and I'm now looking at expanding out - hiring someone, for example.

Your country may have better social safety nets than the US, but make sure your health stuff is taken care of, and you may want to investigate some business insurance. Will your tax situation change if you become self-employed? It does in the US - well, it doesn't, but the 'employer half' of FICA is something that bites a lot of first-time self-employed.

If it were you on your own, I'd say "go for it" - the fact that you have a family (just a spouse? children?) makes me a bit more cautious. You should also have your spouse on board with you emotionally before you do this - money/work fights can be a big problem if you're not both going in the same direction.

Ultimately, I suspect you can always go back and get another job someplace, although perhaps not as cushy as you have now.

Depending on how antsy you are, you could set a goal of 3 months from now (only 12 weeks) to have another month of runway saved up, and 2-4 paying client projects started or ready to start in October.

[+] maybeindie|14 years ago|reply
Thank you for the in-debth response.

My spouse is on board emotionally, we've talked thoroughly about it. Health insurance stuff will be taken care of if I do quit and is baked into my calculations (as is VAT, taxes, etc).

I start networking and pitching actively to my contacts for work/ the day after I resign, which means I'd have three months left in my job to find clients/contracts before I started working on my own - standard notice of resignation in my country is three months.

[+] stevenwilkin|14 years ago|reply
Having 12+ months of savings at hand has certainly bought some peace of mind in my own situation
[+] schme|14 years ago|reply
This is slightly off-topic, but I have a feeling the answer will be a short one. How would a straight out of university -student fare becoming a freelancer? One would have little to no contacts or enterprise experience (part from the degree and/or open source). I don't have a good understanding of what a freelancer contractor/consultant does, but I've always liked the word freelancer. This would be, as I assume, practically impossible?
[+] shimon|14 years ago|reply
You'd be challenged to demonstrate your ability to actually ship software. If you don't have a network of people who have worked with you and can vouch for you, you'll have trouble getting well-paying gigs. You'd likely end up starting with hard, poorly-paying jobs and working your way up.

That is difficult but doable. However, the bigger thing you'll be missing is the ability to work with programmers who are better than you. Freelancing is usually a lonely pursuit and you'll tend toward work that you can estimate accurately and execute efficiently. The need to focus on and master a domain is good for your consulting business but bad for learning. So I'd recommend against freelancing just out of university purely on that basis; you're missing out on the exposure and learning you'd get working in bigger teams.

That said, you don't automatically learn from people just by working in the same building as them, and you don't necessarily have to be a lone wolf when consulting. Whatever you choose, keep learning.

[+] mgkimsal|14 years ago|reply
Not at all impossible. However, most consultants I know get most of their work through word-of-mouth/network referrals. "Straight out of university" probably implies you don't have a large network of people that can refer work your way. And to the extent you can get work, it'll probably be on the lower end of the pay scale, but that'll probably be the case even if you go get a traditional job someplace.
[+] garethsprice|14 years ago|reply
A consultant is someone who can improve a client's situation for the better, applying knowledge or resources that the client does not have in-house.

A freelancer is more of an implementer whilst a consultant helps to decide what is implemented.

Simple to get started, just find clients who need your knowledge and will pay you for it. Simple, but not easy...

Be warned that as a recent ex-student, many will see you as a cheaper alternative to more experienced professionals ("looking for student or recent graduate" in freelancer wanted ads is usually code for "I pay way below market rates").

It's not impossible, but it might be difficult to make livable money at first. I was freelance straight out of college and in hindsight a year or two at an agency or startup would have given me a big step up as I spent the first few years re-discovering things that an agency job would've taught me very quickly (specialize, pick a profitable niche, don't be afraid to fire clients/turn work down, etc).

[+] LiveTheDream|14 years ago|reply
I think it makes sense to take a wait-and-see approach to the worldwide financial armageddon happens. However, 6 months of savings with a family seems just like the bare minimum. It doesn't give you a full 6 months of time to try the freelance thing; if you were to go 4 months with no income, you will by necessity start looking for traditional employment again.

You could try to leave BigCo on amicable terms, such that they would hire you back if the freelance thing doesn't work out.

Finally, before you strike out, have the first client lined up. You should be able to manage it such that your start date for the new client more or less coincides with your end date at BigCo. You don't want to spend the first days of freelancing life looking for work.

Good luck!

[+] base|14 years ago|reply
I was in your position 2 years ago but without a family to support. With a family I would be cautious, have a run away of 12 months salary or have some working contracts ready to start before leaving the work.

Also, expecting a constant flow of 100-150$ freelance work can be difficult, and although you might think that you just need to work 2 days a week, when you have a company you have lots of other stuff to deal that take lots of time like meetings, emails, social security, taxes, accountability, project budgets etc.

[+] davidamcclain|14 years ago|reply
I agree that some sort of cushion/runway is very important. But why do you suggest 12 months? Is the idea that you can spend 6-8 months making no money chasing around contracts and then you've got 6-4 months to find a job?
[+] maybeindie|14 years ago|reply
Thank you for your input. I'd try to put some work/contracts in the pipeline before I was done with the old job (and I'd have three months to do it: I have three months notice of resignation/termination in my current job.)
[+] meric|14 years ago|reply
You might as well. There's going to be a job thread on the 1st every month (tomorrow). Post on it and see what you get.

You won't have to quit your job now if you can find a small task to complete.

(looks like this http://news.ycombinator.com/item?id=2503204)

[+] rdouble|14 years ago|reply
I'm not sure what it's like in Scandinavia, but $150/hr would be an exceptional rate in the US for someone with the skills you describe. Most contract programmers with that resume are more like better paid temp workers who make $25-60/hr.
[+] babebridou|14 years ago|reply
I don't know about Scandinavia, but the typical beginner consulting gig in Paris, France is 40-50€/h. More experienced are at 60-80€/hr, vets are ~100€/h and super experts are at 125€/hr & more. Do the maths. That's before taxes of course. Then realize out that EUR->USD history: from 1:1 to 1:1.5 in ten years, and meanwhile wages in Euros have been kept relatively constant.

You can't survive in Europe if you get paid in USD, these days.

[+] maybeindie|14 years ago|reply
I based the 100-150$ number on couple of datapoints from people I know who have worked on freelance gigs and who are roughly equivalent to me in experience/rep. Wages (and cost of living!) seems to be higher in Scandinavia than in the US.
[+] gte910h|14 years ago|reply
I'd wait until after the debt thing, but it's not bad if you have enough savings.
[+] bahman2000|14 years ago|reply
the after the debt thing might take a VERY long time though
[+] feydr|14 years ago|reply
quit quit quit

like alain mentioned -- get 1 consulting gig first but it will do wonders for your self-esteem once you do

you'll also find that being a contractor is actually MORE safe than working for some random BigCo that can fire you at will

to anyone else reading -- note that he has 6 months of savings -- I'd say depending on your age and responsibilities you want at a bare minimum of 3 months -- I def. don't like having anything less than one year but each to his own