Killing Your Job

"All courses of action are risky, so prudence is not in avoiding danger (it's impossible), but calculating risk and acting decisively. Make mistakes of ambition and not mistakes of sloth. Develop the strength to do bold things, not the strength to suffer."
 -Niccolò Machiavelli, The Prince

Some jobs are simply beyond repair.

Improvements would be like adding a set of designer curtains to a jail cell: better but far from good. In the context of this chapter, "job" will refer to both a company if you run one and a normal job if you have one. Some recommendations are limited to one of the two but most are relevant to both. So we begin.

I have quit three jobs and been fired from most of the rest. Getting fired, despite sometimes coming as a surprise and leaving you scrambling to recover, is often a godsend: Someone else makes the decision for you, and it's impossible to sit in the wrong job for the rest of your life. Most people aren't lucky enough to get fired and die a slow spiritual death over 30-40 years of tolerating the mediocre.

Pride and Punishment

"If you must play, decide on three things at the start: the rules of the game, the stakes, and the quitting time."
 -Chinese proverb

Just because something has been a lot of work or consumed a lot of time doesn't make it productive or worthwhile.

Just because you are embarrassed to admit that you're still living the consequences of bad decisions made 5, 10, or 20 years ago shouldn't stop you from making good decisions now. If you let pride stop you, you will hate life 5, 10, and 20 years from now for the same reasons. I hate to be wrong and sat in a dead-end trajectory with my own company until I was forced to change directions or face total breakdown--I know how hard it is.

Now that we're all on a level playing field: Pride is stupid. Being able to quit things that don't work is integral to being a winner. Going into a project or job without defining when worthwhile becomes wasteful is like going into a casino without a cap on what you will gamble: dangerous and foolish.

"But, you don't understand my situation. It's complicated!" But is it really? Don't confuse the complex with the difficult. Most situations are simple--many are just emotionally difficult to act upon.

The problem and the solution are usually obvious and simple. It's not that you don't know what to do. Of course you do. You are just terrified that you might end up worse off than you are now. I'll tell you right now: If you're at this point, you won't be worse off. Revisit fear-setting and cut the cord.

Like Pulling Off a Band-Aid: It's Easier and Less Painful Than You Think

"The average man is a conformist, accepting miseries and disasters with the stoicism of a cow standing in the rain."
-Colin Wilson, British author of The Outsider

There are several principal phobias that keep people on sinking ships, and there are simple rebuttals for all of them.

1. Quitting is permanent.

Far from it. You can pick up your chosen career track or start another company at a later point. I have never seen an example where a change of direction wasn't somehow reversible.

2. I won't be able to pay the bills.

Sure you will. First of all, the objective will be to have a new job or source of cash flow before quitting your current job. Problem solved.

If you jump ship or get fired, it isn't hard to eliminate most expenses temporarily and live on savings for a brief period. From renting out your home to refinancing or selling it, there are options. There are always options.

It might be emotionally difficult, but you won't starve. Park your car in the garage and cancel insurance for a few months. Carpool or take the bus until you find the next gig. Rack up some more credit card debt and cook instead of eating out. Sell all the crap that you spent hundreds or thousands on and never use.

Take a full inventory of your assets, cash reserves, debts, and monthly expenses. How long could you survive with your current resources or if you sold some assets?

Go through all expenses and ask yourself, If I had to eliminate this because I needed an extra kidney, how would I do it? Don't be melodramatic when there is no need--few things are fatal, particularly for smart people. If you've made it this far in life, losing or dropping a job will often be little more than a few weeks of vacation (unless you want more) prior to something better.