In fact, there is not too much optimism despite markets moving higher. Too many people are sitting aside expecting a crash, too many investors are pulling money out of the market (check equity funds outflows), too many pundits are speculating and competing in predictions who would nail the coming crash and recession.

All this is in fact a bullish behavior. At some point, these people who are now scared and pulling out of the market lamenting that they have missed the rally and they start chasing it coming back in. That will be the time when even a plumber in a small rural town in midwest America becomes a stock analyst and investing guru. Then you should start being worried.

However, I am talking about a major bull trend for which I expect additional +/- 18 years to last. But, that doesn’t mean it will be a straight run up. No, there will be pullbacks (up to 5%) corrections (up to 20%) and sideways moves along the way.

Too many people miss the big picture, many do not even look at the big picture, and then lose money (like those who are now pulling their money out of the markets expecting crash. Not only they will miss the rally, but they will enter back at the very wrong time when the market rolls over and crash and they lose again.

Here is a picture from 2016 where everybody predicted end of the bull market saying that it cannot go any higher. It must crash again. The market was going up for too long. This is not normal. Brace yourself… Well, look where we are today.
 

 
Because of the lack of the big picture, people tend to be trapped in their recency bias. All they know and remember id the previous crashes and tops. and there fore they are expecting crash and predicting a top as people did before them, just look at the picture above. When this recency bias end and is replaced with complacency, they you should be worried. But we are not there. if you keep monitoring news headlines, all you will see is who is predicting a crash and when, trade wars worries, economic slowdown and subsequent recession, slowing this and that… just watch it daily and you will get frustrated of how much pessimism is in fact out there.

Here is a big picture indicating that we are in a secular bull market which will last for some time:
 

If you want to be risky (which at your age is a great approach, because as you said, you have time on your side to make mistakes and repair them).

In this case, individual stocks are the way to go. Forget mutual funds or ETFs. These are average and many do not even beat the market. On top of that, they will charge you fees while stocks will charge you nothing.

Then your stock selection will depend on your strategy.

Are you planning to buy stocks and hold them until retirement?

Or are you planing to play a bit and buy and sell (note, excessive trading will however lead to losses over time)?

If you want to build a portfolio which will bring you income and allow you to retire early, then you need to choose stocks which have a great potential to grow steady, slowly, and safely. You need to look at stocks which will be around 20 years or 30 years later.

I would recommend you to open a margin account and start slowly buying dividend growth stocks. These do not require much work on your part and you can afford to buy them and forget about them and while waiting, collect dividends which can be re-invested back to grow your portfolio.

In this case, I would look into dividend aristocrats. They are relatively safe and grow and will most likely grow. You just need to monitor your holdings time to time to check that the stocks you have still meet the criteria for investing in them. If not, get rid of them.

Now, when I mentioned margin account, do not use margin at this phase. Your account is too small and if you leverage your account using margin, interest rates would not only offset the dividends and capital gains but may even eat your principal.

Then start saving money, so you can start trading options and that is when you use margin.

I personally use a strategy of selling cash secured puts to buy 100 shares of a stock and do this as long as I get assigned. Once I get assigned, I hold the stock, and then start selling covered calls as long as I get assigned. With this strategy you monetize your positions. You collect premiums when selling puts, you collect dividends when holding a stock, and collect premiums when selling covered calls. And with this strategy it is handy to start using margin.

Example: Let’s say, you want a stock ABC which trades at $60 a share. In a cash account you would need $6,000 to buy 100 shares. In a margin account, you will need only about $3,000 initial margin to buy 100 shares.

So, you sell a 55 strike put and collect 0.60 credit (or $60 premium). For this, the broker will collateralize about $1,100 of your buying power. If the stock stays above 55 by expiration, your put expires worthless, your collateral will be returned to you and you will keep the premium you collected. If the stock drops below $55 a share, you will be required to buy 100 shares at $55 a share but your cost basis will be 55 – 0.60 or $54.4 per share and your collateral will be added to the margin of $2,600 (since now you are buying for $55 and not the original $60).

While you hold your 100 shares, you start collecting dividends and start selling covered calls. By selling the calls, you again receive premiums. If the stock stays below your call strike price, the call expires worthless, you keep the premium, and you can sell a new call. If the stock goes above your strike, you will be required to sell your 100 shares (for example, you bought in at $55 a share, so you sell 58 strike covered call and collect 0.25 or $25 premium. If the stock stays below 58 at expiration, the call expires, it the stock goes above, let’s say to $60 a share, you will be forced to sell your 100 shares at $58 a share. Your profit will be premium received + the difference between the stock and strike, in this scenario additional $2 per share).

If your shares are sold, you go back and start selling puts again. Rinse and repeat.

This is as “aggressive” strategy as I would recommend to go. There are riskier strategies of course, but, with those, you can easily wipe out your account (my experience). Later on, as you get proficient, you can use other strategies to generate more income.

However, in order to do this, you will need at least $5,000 or more account and proper options trading approval from your broker. But you can start slowly, invest your first $2,000 and study the strategy until you raise money for more trading.

As far as the stock selection, I recommend using dividend aristocrats, Here is a link to a David’s Fish list of the dividend champions (aristocrats), challengers, and contenders:
Dividend Growth Stocks CCC list This list has enough stocks to pick from and if you study them carefully, you can even pick a real winners.

And what you can expect? Well, I have been trading this strategy (I also traded other strategies not so successfully though) and my average annual return on investment is between 30% and 45%. If you do your work, read, study, pick your stocks carefully, and do not deviate from the plan, you will be able to double your account every 3 years.

If you pick a broker who will charge you zero commissions so you can buy even 1 share of a stock and pay nothing to do so, then yes, you can still do it. Choose high quality dividend growth stocks (dividend aristocrats), 3 to 5 companies, buy few shares (choose stocks in the $40 – $50 range), set dividend reinvestment (DRIP) plan, and let it go. You won’t make much (meaning that in 20 years you still will not be able to retire on it) but you will still make more than in a savings account. Note that investing in stocks is a long run. So if you plan to buy today and plan on selling in a few months or even a year or two, then this will not work and you will lose money. This will work if you buy now and let it sit there for 5 to 10 years. A good example would be Mastercard (MA). I bought the stock a few years ago for $75 a share. Today, it sells for $303 a share. Do not worry about diversification. I agree with IBD and Warren Buffett on this matter who both consider diversification a myth. You can be very well diversified with 5 stocks too. If you do your homework, study the companies you plan on buying and know their business (for example, know how Mastercard make money – and it is not in lending money to people) then you will be safe.

Is this investment strategy good: allocate 75% in savings account with high APY(~2%), 20% in long term re-investing dividend stocks and 5% in short to mid term high risk stocks (kind of a swing trade)?

How old are you? If you are close to retirement or retired, and inherited a large sum of money, this may be acceptable (although not for me either). If you had saved enough throughout your life, it still would be a bad idea.

If you are young, let’s say 20’s then this is an incredibly bad idea. If you can invest money for the next 40 years then there is no better allocation than stocks. On top of that, if you have really 40 years time frame, you should go extremely aggressive (use leverage and as you age start deleveraging your account). A good book on this topic is Lifecycle investing by Ayres & Nalebuff.

So, if you have time, invest 100% in high quality dividend growth stocks, reinvest dividends, and use options to leverage your investments (as described in the book for example, or use a “Wheel strategy” – sell puts as long as you get assigned, then hold the stock, collect dividends, and sell covered calls as long as you get assigned).

Just look at the 40 years S&P performance and compare it to a 40 years savings account performance and try to convince me again why would you waste 75% of your money in savings accounts for the next 40 years.

I bet many people will tell you that you can’t because of diversification and other myths and misconceptions what all sorts of advisers tell general public to cover their backs and lack of deeper knowledge.

I started like that myself and built up a nice portfolio. It is difficult at first but doable, mainly today when you can trade commission free. That is a key. You must choose a broker which will allow you to buy a single share and charge you nothing for it.

The next thing is to choose a high quality dividend growth stocks (dividend aristocrats) to boost your income from your holdings, and reinvest that income. At first, use DRIP, later on I would recommend buying more stocks different than those which generated the income.

At first, choose only about 5 to 10 stocks and start buying them and accumulate.

Here is my portfolio I opened in April 2019 to do exactly what I preach. As you can see, even though the portfolio is small and generates small income, but it is growing. And given the size of the portfolio it is still sufficiently diversified as the point is not in owning hundreds and thousands of stocks but stocks which can hedge each other. So you can have only 5 stocks and achieve the exact same or even better diversification than someone who is buying hundreds of stocks.

Note, the stocks above are my holdings and not a recommendation or solicitation. If you decide to buy them, do so on your own risk and you must do your own due diligence and be aware that you may lose money.

Also, my broker charges me zero commissions so I can buy a single share and it cost me nothing. Before, when the brokers charged commissions I first had to save at least $600 dollars to buy a few shares to mitigate impact of the commissions so I was buying shares every 6 months. Today, you do not have to wait and you can start buying a few shares every month and slowly accumulate.