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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 int

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.

vtanase 14y ago
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?
- jasonkester 14y ago
  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.
  - tixocloud 14y ago
    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".
    - jasonkester 14y ago
      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.
      - felideon 14y ago
        > "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.
        jasonkester 14y ago
        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.
    - 14y ago

vtanase 14y ago

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?

jasonkester 14y ago
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.
- tixocloud 14y ago
  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".
  - jasonkester 14y ago
    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.
    - felideon 14y ago
      > "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.
      - jasonkester 14y ago
        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.
  - 14y ago