Hi Gigiti! I have a background similar to yours except that I am you plus 20 years and 100 cars later. I know I am going to get some arguments on this, but cars are not investments, cars are expenses. There are almost no exceptions to this, so anyone that tells you different is selling you a car or justifying their own garage full of toys by justifying your spending. So its said, I have spent a lifetime’s worth of money on cars, so I have a lot of room to talk.
The lease versus buy, I have yet to have a single car dealer or money guy show me how a lease is really better, so I would advise against it almost 100% of the time. Your commute is really, really rough. At somepoint soon, you are going to start adding up what you are doing to two cars in terms of expense and deprecation and its going to piss you off. I went through this a few times even recently doing the same drive in a new Range Rover. I decided that work started to not be as much fun as it used to be and you know what? I found a truck (Denali) for half the price, better gas mileage and all the same toys for half the price. It matters because now I am running the crap out of a 55k truck instead of an 110k truck, I am loosing half the money. The tirade here is to say don’t waste money and tear up nice cars driving that much, buy yourself a cool car to leave in the garage for the weekends. Invest what you are saving on the difference or buy yourself another cool car to drive on Sundays, but don’t waste it tearing it up going back and forth to work in it.
Everyone is going to say be careful with your money, invest, don’t spend it on cards, blah blah blah. That’s obvious and you seem to already know the answer to that question. So then its really a hard look at what makes you happy and what fuels your success. If you didn’t have these toys, would you be happy? Would your resulting unhappiness affect your success? Probably so. Would you retire later so you could enjoy the cool cars now or do you get buyers remorse after every deal? None of us need these cars, the word “need” and “Ferrari” do not belong in the same sentence or paragraph. We want a Ferrari because its cool, its exclusive and because we can. For some, there is some “FU” factor that’s involved too.
The bottom line is do what you want, you earned everything you have, don’t let people spoil your happiness and do whatever the heck you want to. I was pretty successful at the same age you are now and I am sure you have seen people that give you a hard time because of your age and that you have to work a lot harder for the same business & work as others because of your age. That treatment from people makes you more competitive with everyone most likely and want to outdo others, right or wrong.
If you truly think you aren’t being responsible and want to retire early, sell the toys! Maybe keep one to get stupid with on the weekends and save the rest, there will always be a new car waiting for you to buy it, there will always be a buddy that has a cooler car than you, it happens. When you are 40 and retired and that same buddy is still living paycheck to paycheck, you will be proven to have made the right decision.
Good luck and let us know what route you chose, you seem to make a lot of good decisions and the smart money says you will make another good one here.