Way back 2010 thats was the first time i read about bitcoin from the post in the site i forgot the name. I was interested enough to download the client and try to mine some coins. After running the client for a few minutes and being unable to tell if anything was actually happening I uninstalled it. To think if they just had some kind of estimate to next block mined or some indicator it was doing work I probably would have let it mine for awhile.
At the time bitcoin was worth about $.06 but I kinda disregarded it as a cool idea but didn't fully see the potential in it. Later when bitcoin reached dollar parity I began to take notice again. I don't remember the exact timeline but I bought some coins in the first bubble for around $5. I also started GPU mining around that time.
The highest coin count I ever got to was 500 BTC. I remember debating if I should have bought 500 more to get a nice even 1000 BTC but for whatever reason I decided I had already invested enough in it. I also had converted some of that bitcoin into litecoin and had 10,000 LTC that I later sold when LTC started going up.
After the first crash down to $2 / BTC I remember thinking, well that was fun and figured I would just hold on to the coins I bought and if they became worth nothing it would have been a life lesson. Once they started going back up above $10 I sold enough to set me even so anything after that would be pure profit.
I held most of my coins through the 2nd bubble above $200. When that crashed back down I was smart enough to realize this was history repeating itself and the price would rebound again. At the time I had more in cryptocurrencies than I did in any other investment, including 401k, etc, which was an odd feeling but I had faith it would bounce back.
When the third bubble came in 2013 I decided if the price got high enough I would sell about half of my coins to pay off my mortgage. This seems like a big enough life changing event that even if the price continued to rise I would be happy because I kept half my coins and if the price dropped I would also be happy I sold so many and now had no mortgage.
Luckily the price that would make me debt free was $1220 per coin. I watched with anticipation as the price continued to go upward. Once it got above 1200 and started to stall out I said close enough and sold enough to pay off my mortgage. Out of pure luck that ended up being the peak of the last bubble and I'd like to say I knew it was going to pop there but really I had just calculated how high I would need for the price to be to pay off my mortgage and capital gains taxes and that was the magic number.
I still hold a decent amount of coins, enough that even when the price goes back above $1200 I'll be happy because I still have a large investment in BTC. I probably wouldn't sell the remainder until it would be another life changing event like being able to retire completely.