This is not about binary decisions. The problem is to pick two points in time: When to buy and when to sell.
If you went long, and lost money, going short instead doesn't mean you would make money, it means you could lose on the interest payments, you could lose on being forced to close, could lose on the different risk profile of having unlimited loss potential
Even more so with derivatives.
When you are long your loss is 100%. With a short it is theoretically unlimited.
Shorting is perfectly symmetric with longing (except linguistically -- because "shorting" is perfectly normal, but "longing" not): in the former you have unlimited downside risk and limited upside set by the price at which you sold, in the latter you have unlimited upside potential and limited downside set by the price at which you bought.
If you go exactly even before transaction fees, on a big enough number of transaction you loose everything....exactly because of transaction fees.
If your initial hunch is to buy a stock you don't own yet, you can't sell it instead.
You can (by selling on margin) if you have a margin account.