Hamilton Chan’s parents told him he could be a doctor or a lawyer. His “tiger mom” even had a mini breakdown when he deferred law school for a year to work for JPMorgan Investment Banking. He promised her he’d go back to law school after the year was up, and that’s what he did. 

Years later, his investment banking friends were making millions of dollars a year while he was slogging away doing due diligence as a corporate transactional attorney... and his mom asked him why he didn’t stick with investment banking. But Hamilton tells us you can’t blame anyone but yourself for your life decisions.

And Hamilton did experience outstanding success as a lawyer — he graduated from Harvard Law School, worked at a prestigious law firm in Los Angeles, represented Kobe Bryant, and worked at MGM Studios. But, ultimately, his legal career hit a dead end. He realized that he had taken what he was good at and polished it to such a point that it became something he no longer enjoyed. At one point, he was skimming hundreds of pages of documentation and writing about 15 pages of memos every day, without any time leftover to even pick up a magazine or read a book on the weekend.

Entrepreneurship was calling.

Hamilton wanted to be able to pursue creative endeavors, practice strategic thinking, and get out of corporate life. He told his family that he was very unhappy as an attorney, and his sister suggested he be a salesman at the family business, Charlie Chan Printing. After his whole family erupted in laughter, his mom and my dad said they could actually use some help. Although he had no experience in sales, he thought he could figure it out. Plus, he’d get to make business decisions and be involved in an enterprise that carried a lot of meaning and history for him.

After working in the family business, Hamilton went on to launch a tech startup. Then Loyola Law School approached him to start an executive education program, now called LLX. Hamilton was responsible for co-creating the vision behind it and coding a brand new interactive platform to host it on. He also teaches a six week class on negotiating, and really considers his role at Loyola Law School to be the culmination of his life experience and a true labor of love.

Hamilton’s tips from his off-the-beaten-path career are: 

• Learn to negotiate. You can leave a tremendous amount on the table if you are not skilled at negotiating. 
• Satisfy your curiosity and try new things.
• Realize that the business world is at least 90% networking. Hamilton used to see the world as super meritocratic and believed that, if you just produced the best work, everything would work out perfectly. Now he says that might be true for K-12, but not for the rest of your life.
• Make conscious choices to do the things that we should. The brain does such a phenomenal job of making sense of the world that it constantly discards contradictory information. And that's what helps us stay in a bad relationship, job, or situation.
• Craft the life that you want. Hamilton loves being able to spend time with his two daughters and his wife plus, have time for recreation, and work on...