Let me clarify my situation first. I didn't have a bunch of cash to buy stocks in March. I worked at Google for 4 years and had all my cash sitting in GOOG stock via RSU vests. I didn't hold any other positions. Over the course of weeks I watched all the gains that had accumulated over those 4 years evaporate to nothing. There were a few days where these savings actually went red. By the time the bottom hit I didn't have a bunch of cash sitting around. I had a bunch of stock that had lost substantial value. I remember thinking "I am now officially losing money I had previously earned from hard work". I got really scared. I thought I was going to _continue_ losing money. The bottom never really looks like a bottom when you are in the thick of it.
This is the _starting point_ for when I began to actively trade around my equities. I thought, the markets are wild right now and here is my chance to come out ahead. I can sell all this GOOG stock tax free since there was no capital gains any more (consolation prize for me). Let's get going. It was difficult because I was so used to the comfort of just holding the same thing and watching it grow. It was like the autonomous car just handed over the steering wheel as it was going off course and I needed to get back on the track and learn to race at the same time. I now have a balanced portfolio, with tons of extra cash with a lot less exposure to GOOG. I also quit working for them.
I do think what I've proven to myself is that I can read environments, react accordingly and have the conviction to make good moves at the right time. The world will be different going forward and the same opportunities might not exist. I built confidence but most importantly I learned that I absolutely love waking up in the morning each day and getting into it. This is something I didn't have working at Google, and whether I can sustain this or not, I know I am moving in the right direction (away from there!).
I still hold all my LEAPs. I am up 60-100% on those but they are unrealized and don't want to pay taxes on them this year. We will see where things land when I sell them. Anything can happen.
I put money into a mix of long and short stock positions as well as long call options (LEAPs). The shortest call options I would do are quarterly, where I will listen to the earnings call, watch how the market reacts in the next day. and then set a call option that expires after the following earnings if I think the stock has been unfairly punished. But I usually stick to call options > 1 year. I have about 2/3's of my total portfolio in stock and 1/3 in options just to get good leverage.
This is sort of where I landed at right now. I didn't have any strategy going into all this. I am the kind of person that likes to learn for themselves and I knew I would lose money doing it. I just tried to know my limits and not lose too much when I thought it might happen. Looking back there was a time when I had maxed out my margin account buying AAPL as it was tanking in September. I sold that margin off for a big loss. I made some really stupid choices. But I learned and processed everything I did.
I recommend just getting into it. Dip your toes in the water, it'll feel a bit cold, let it warm up and eventually you will be swimming in the deep end.