If you’re gonna play the game boy

You gotta learn to play it right

Know when to hold em

Know when to fold em.

Know when to walk away

Know when to run

Of course, the song lyrics held truths and wisdom that went beyond the poker table. In the course of your career, there will be situations you will not be able to further your brand. Rather than choosing to die on this hill, you must know when to cut your losses and move on.

Nepotism means “not you”

Stay and learn what you can from family run companies, but leave when you are ready to become a leader in your own right. Understand that you are never going to be one truly in charge. At best you will be keeping the seat warm for the children. Do not think that because you are treated with love and as “one of the family” that you actually are family. The business will pass on to the children, regardless of their lack of qualifications or your abundance thereof.

Even if the children protest loudly that they have no interest in running the family business, chances they will still end up coming back once they realize how much easier it is in life to be the heir apparent. Even marrying in the family is not enough. There will always be a distinction by blood.

Worse, only 30% of family owned businesses survive into the second generation. This means that as the number of heirs increases, so does the likelihood of feuds and factions and infighting. You will eventually be forced to choose sides, and your career will be torpedoed if you end up backing the wrong horse.

If a gang controls the turf, set up shop elsewhere

D’Allesandro relates a story here about how he was working at a company when one of the senior managers took him aside and explained to him that the place was run by a Scandinavian tong. Unless he was a Midwesterner of Scandinavian origin, he would never be accepted and his career advancement halted. This book was published in 2004, and it mentioned that even then with all the laws against discrimination, that there still existed companies where you would be excluded from advancement on the basis of who you are.

The advice here is that you should recognize these situations, and not waste too many years in a situation where the existing people in power will be resistant to you. Besides race and gender, where you were born, what school you went to, whether or not you belong to old money, and other factors come into play here. It is an uphill battle to stay in such situations and try to be the pioneer that breaks through existing prejudice. If you do stay, don’t be in denial and recognize it as the gamble it is.

Don’t let the hazing go on too long

This is an issue with young people working at law firms, consulting firms, accounting firms, or architecture firms. The old make the young work difficult and brutal hours by dangling the hope of making partner as a carrot. The associates, eager to prove themselves, are forced to endure demeaning work and demeaning treatment from partners.

“Working for a partnership is longest hazing on record”.

This dynamic leads to young associates chasing older partners who are often not as smart. The old timer’s attitude is that since they put up with the hazing, the newcomers have to put up with it too.

Of course, there is a benefit of having worked at a prestigious firm and having it on your resume. Because these firms are prestigious, they also attract prestigious clients, and you will also learn a great deal there.

The problem is the young people are so focused on making partner that they become unrealistic in their expectations. Only 2-3 % of new hires ever make it to become partner. Existing partners don’t want you to make it, because that would mean giving up equity. The only way it would make sense for them is if you bring in a lot of new business. However, many people are not realistic about their own nature. Hunters make partner. People who skin the animals do not. So don’t fall into the trap of staying too long chasing a futile goal. At a certain point, you gain diminishing returns on the experience gained at these firms.

In fact, your brand will actually look suspect to many by the time you reach your mid thirties. You will be less willing to put in the long hours, as you have put in your dues at this point. You will have a family, so doing last minute travel all over the world becomes less appealing. Partners will want to replace you with someone younger and cheaper:

“People believe that the reason that middle aged men often look for trophy wives in their twenties has to do with looks. Actually, it is because young women are so much more pliable, wide-eyed and worshipping.

Parnterships, too, prefer pliable, wide-eyed, and worshipping.” Pg. 117

Don’t be the guy that stays too long at a firm hoping to make partner, only to get fired and replaced with someone younger. So be smart about it and give yourself a timeline. If people who came in around the same time as you make partner and you do not, make a note of it. If by next year you are still passed up, its time to leave. This advice is applicable to promotions at any company, not just at firms.

If you’re talented, expect to have your desk set on fire

Entrepreneurs are the ultimate narcissists. They tend to become paranoid under stress, constantly on the look out for enemies. As such, it is hard to remain in favor of such people. But don’t stay too long. To them everything is personal. They will do favors such as give you some time off or giving you a gift or a loan. But now you owe them. In addition, any sense of independence on your end is considered betrayal. Hence, at companies run by entrepreneurs, a cult of personality and worship grows around the leader. Employees will do anything for the CEO, including limit their own careers.

Entrepreneurs are insanely controlling. It is no coincidence that Elizabeth Holmes worshiped Steve Jobs. Both were incredibly controlling entrepreneurial assholes. Stories abound of Elon Musk terrorizing employees. While the best dictators like Steve Jobs and Elon Musk can get accomplish great things, the worst dictators are crackpots that ruin lives (check out the book, Bad Blood for a detailed look the horrors of Theranos). Entrepreneurs will be very picky about certain things and come up with arbitrary rules to enforce their obsessive compulsive whims.

Entrepreneurs do not like to share. They don’t want to share equity, and they don’t want to share credit for the company doing well and they don’t want to cede any decision making power. If you are good at your job and taking too much spotlight, your desk will be set on fire, such as John H Patterson of National Cash Register Company in 1884 was wont to do. Any power you gain at an entrepreneur run company can be taken away in an instant. The CEO giveth, and the CEO taketh away.

Entrepreneurs also tend to treat their employees like toy soldiers. Once they are done playing with you, you are abandoned. Worse in many cases they will attack your reputation or sue you and smear you. Again for a modern example, check out Bad Blood that documented Elizabeth Holmes and her reign of terror at Theranos.

So while working for an entrepreneur is a great way to learn, you will want to leave before you incur the entrepreneur’s wrath.

Regardless of whatever situation you find yourself in, if you no longer have a path forward for advancement in your career, it is time to leave and find someplace where you can continue to grow.