Let’s think about this. You can clearly go back in your mind through all of your post-college jobs and remember every moment near the end of your time with an employer you were able to create a successful business plan that would provide endless rewards to your company or organization if only they would listen to you and put you into a position of power.
Meanwhile, you can also go back in your mind to every year you’ve lived in college and see that 80% of the time you were simply scraping by and not caring one bit about how you racked up debt and didn’t save money. It’s only in the past few years, with the help of a wife earning a full-time income that almost equals yours, that you have been able to get your debt under control and not completely find yourself $10K+ in debt after a year of carelessly eating and drinking whenever and whatever you pleased.
If you were a business, you would have failed completely at least three times, and come dangerously close to failing completely many more times over.
You have not taken much time to develop an online presence touting your skills, except when you are nearing a moment of transition to another job. If you applied the same diligence and persistence to prospective clients that you did to prospective employers, you would have more than enough work to keep you busy, and probably enough work to keep three other people under you busy.
There is clearly a reason for this reluctance to turn yourself into a business. You feel like you are participating in the root of all evil, and pursuing mammon instead of the things of the soul. But, that’s more likely to be the excuse for your laziness. You feel like when it is your own time, you should spend it relaxing and participating in consumer activities of self indulgence. You have never developed a mindset to be working all the time.
As much as you said you could never do it after college, you quickly embraced the 8-5 life. It’s easier that way. You know where your paycheck is coming from, you know who your bosses are to loathe and critique, and you know that you can pretend you are a free man at 5 PM every weekday. Meanwhile, at 5 PM, you consistently get to another kind of work: forging the shackles that keep you stuck in the 8-5 life.
At the most basic level, your situation is no different than it was for the sharecropper one hundred years ago. You are spending more than you make. As long as you are incapable of taking in a loan and converting it into something that is worth more than the loan, you are forced to pay the lender more for the loan than it was worth. You are incapable of viewing what you do at a macro level. If you borrow $50 to buy yourself and someone else a nice dinner and drinks, then you either have to accept that the dinner actually costs $50 + whatever time you take to pay off the $50, or you have to find a way to have that dinner return something of $ value that is worth more than the $50.
Is the hidden value of spending time with someone you love and enjoying the social experience of hearing the rumble of chit chat around you and having someone else cook for you and bring you your food worth the hidden cost of paying off the money you borrowed to do it? Most of the time it is not. There are, of course, special occasions that call for it, and you don’t need to end up like your parents who never went out to eat–who thought going through the Hardee’s drive through was eating out on a Friday. But, you are, for the most part, still putting down money on things that don’t provide even an equal $ return.
But why is it so hard to think about how you spend your time in money in terms of the $ value? You can easily rationalize that the extra $Ks you spent on your vacation to Rome helped cement a new marriage, creating lifelong memories and fostering moments of happiness long after the trip was over. But, you didn’t make a dime off of the trip, and had to settle for a smaller, older house a year later.