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Comment by jasonkester | Hacker News Reader

I don't remember ever taking a Leap.

I think it's because I moved from Employee to Contractor, to Consultant/Occasional Contractor before I really got deep into building products that it never seemed like I was in a particularly scary place.

I was already spending several months at a time voluntarily without work, and taking contracts when I needed to. The only real difference was that instead of travelling and rockclimbing full time during those breaks, I was parking it in one spot with the laptop and writing code. And I guess I started referring to those consulting gigs as "bootstrapping".

That might be a good path to look into if you want to make the transition from "guy in a cubicle" to "dot-com thousandaire". There's plenty of room to take it slow.

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I am really curious, can you go into a bit more detail as to what each those transitions meant for you, and how you went about doing them?

For example what exactly the move from employee to contractor entailed, or the one from contractor to consultant?

Moving to contract work is pretty straightforward. It's essentially just finding a new job. Lots of places prefer to hire contractors for individual projects, so it's not too tough to pick up a 3/6/9 month contract someplace.

Most contractors tend to try to move from one contract to the next with as little downtime as possible, or work for an agency that sorts it all out for them. For me, the downtime was the big payoff, since contracting pays roughly double what a salaried job does. If you have no attachments, you can spend a fair amount of time slacking off before picking up another contract. I used to push it as far as 9 months off between 3 month contracts and still put plenty into savings.

Repeat the above enough times, and you'll be able to break off work that doesn't require you to be on site, or pick up work from new clients from word of mouth. Some people refer to this as freelancing, but then they don't get to charge as much if they use that term in front of a client. Naturally, it's best to describe yourself as a consultant instead, and double your rate again.

The transition from full-time to contracting is what terrifies me. Having to constantly look for a new job every few months just worries me. Of course, it's probably because I am the sole breadwinner for my family but how do you overcome that sort of paralyzing fear? I've had thoughts that maybe I will do it later on down the road when everything is more settled but I don't know if things will ever be "settled".

It definitely helps to establish a reputation for yourself before you take off and start contracting. You should be at the point where you know without a doubt that you could send out a few emails (or respond to one of the standing offers in your inbox) and pick up another gig. As such, "paralyzing fear" never came into the equation for me or any of the successful contractors I know.

And of course once you've done it a few times, you'll have previous employers bringing you back in for more projects. So at most you might only need to go through that fear stage a few times before you've established yourself.

> "It definitely helps to establish a reputation for yourself before you take off and start contracting."

Does this mean moonlighting and taking side gigs? If so, can it be done without sacrificing personal/family life? Not to mention, possibly living with exhaustion.

No. Just work for a few different companies and demonstrate that you're the best guy on the team to the people who matter. Eventually you'll get a call from a guy who's putting together a team and got your name from one of your old managers as somebody who's good at that sort of thing.

Of course, it never hurts to build cool, visible things that you can point to when people ask what you're capable of.

I'm not sure where you're based (and I'd guess it makes a difference), but in the UK going contracting is incredibly easy once you make the decision.

Save up a couple of months salary if you can, make your CV all shiny, and send it out to every job board you can find, with your phone number, email and location at the top. At the same time, send a friendly email and your CV to everyone you've worked with, saying "Hey I'm available for contracts doing X, Y or Z. If you hear about anything, please let me know".

There's no need to quit your job early, you're just going to be leaving like you would for another permanent role.

When someone says they've got a contract for you, sign up for Parasol or a similar umbrella company so paperwork is at a minimum, and away you go!

I'm not hugely experienced at contracting, but since I started doing it a few years ago, another couple of friends have gone down the same route and it's worked out well for them too.

If you're good, learn quickly, and you're honest about what you can do, contracting is a great route for a few years of experience across a range of projects.

After the first couple of contracts, if you're happy with how it's going, then get yourself setup with your own limited company which means you'll end up with more paperwork, but more money in your pocket.

Build up savings. The traditional "have 3 months of savings in the bank" line you hear from personal finance gurus doesn't really apply when you're a self-employed breadwinner with a family. I'd suggest a min of 6 months with a goal of 12 months if you can. It will make those in between times much less scary.

Something I have always wondered about: how do you obtain/afford health insurance? (This is most likely a US-only problem)

Not surprisingly, health insurance isn't that expensive if you only want to cover the 'big' things. It gets worse as you get get older of course.

But if you're healthy, 20 - 30 type, and you're seeing the doctor once or twice a year and maybe using prescription meds occasionally for a bacterial infection, then you get the 'high deductible' plan, you end up paying for that stuff yourself but if you happen to be in a wreck or you get cancer or something the insurance will cover it once you get past your deductible.

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