The reason I came up with this poll is that I was thinking of all the time and steps it took me before fully automating my trading, since I started trading in the Fall of 1997. So I was wondering how long it took the others on this forum.
Since the Fall of 1997, I tried everything, failed many times and often had to keep on failing for years before realizing my mistakes. In this sense, my trading career didn't follow a steady progress, but rather very irregular, with many stalls and accelerations.
With a few constants. I never thought of giving up and I always thought success was around the corner. Also, I only focused - from the very beginning - on technical analysis, and before even knowing it was called "technical analysis", I thought I should just study the charts and try to predict the future. Lastly, I always thought I should only trade derivatives, because if I knew how to make money why not make more? (If I didn't know then why should I trade at all?).
The major milestones in my trading career since the beginning have been as follows.
1) 1997: Technical Analysis.
I realized , from the start, that I should only focus on charts and forget altogether about any news, budgets, balances of the companies (no fundamental analysis), and therefore also that I should only trade indexes, so my trading wouldn't be affected by news, insider info and similar things that there was no way I could ever learn and cover, or use in my predictions.
2) 1997: derivatives.
I realized , from the start, that if I knew how to make money, I should trade with leverage, that is, derivatives. And to people who said "what if you lose?", I replied "why should I be trading at all?" If you're planning to lose, then you just should not trade at all.
3) 2002: trading systems.
I realized that using approximate notions of technical analysis for picking trades was not good enough. I needed univocal rules, and therefore that trading systems were necessary. I started experimenting with Tradestation.
4) 2003: futures.
After years of trial and error, I concluded that the best and only derivatives to use were (liquid) futures. Options and other products were too complicated, unpredictable, too much work, spread, and basically not worth trading.
5) 2005: US broker.
After more years of mistakes, I concluded that I couldn't trade futures with a broker in Italy, where I live, because their commissions are too high, and service is too poor. So I finally opened an account with IB, that beats by far any Italian broker by any parameter.
6) 2005: automated systems.
I realized that trading systems implemented by a human are not good enough, especially for me, and that I needed an automated system, and started working on it, even though I lost focus of the backtesting in the process, and implemented an automated system that I couldn't backtest.
7) 2008: several automated systems.
Realized that the system had to both be backtested and automated. Also, realized that the more systems I had, the better. And started creating more and more systems, that all traded the same capital.
8) 2009: money management and full automation.
I realized (because of losing everything twice) that I couldn't have any part in my systems or trading even. I couldn't "help" them to make more money by adding some discretionary trading or second guessing their choices. I couldn't help them recoup losses faster. I had to fully automate them and this included money management. They had to take care of everything, even avoid financial ruin by not reinvesting everything all the time, as I had been doing. And I had to maximise the % of capital invested by non correlated systems, and by the best performing systems by "Return on Account" (instead of letting them all trade equally, as I had been until then).