1. We hear a lot about the five-year plan. That one should think about their goals for the next five years and chart the course? How really effective is that?

In my view, five-year plans, or any plan that stretches more than a year or two, are helpful primarily as career northstars. However, I suggest not making them too prescriptive. Being too exacting can backfire because life will throw you curveballs. It will not be a straight line. You or a loved one may get sick. Your employer may encounter challenges and not provide sufficient career promotion opportunities. Your startup may hit a rough patch and go out of business. 

Trying to stick to a very detailed plan may cause you heartache or even encourage short-term shortcuts at the expense of long-term benefits. For example, to get that big promotion before your 30th birthday you may go scorched earth and give your boss an ultimatum forcing them to let you walk. Later you learn that you shot yourself in the foot because you were actually on a promotion track but for your 31st birthday.

I would set your goals to be sufficiently broad such that they serve as guiding principles rather than strict edicts. As an example, when I was in my 20s, I would make sure I was always on track for the next promotion. On Wall Street, promotions typically happened in four-year increments so those would be good “mile markers” for me to note. If I wasn’t tracking, I’d make sure I’d diagnose the problem and course correct.  

On final tip: I would consider setting a few ultra long-term goals. These are great for achieving overall work-life goals. For instance, I set one for myself in my early 30s. I wanted to have the flexibility to leave the 24×7 life of Wall Street by age 40. This would require leading a frugal lifestyle and salting away substantial resources. So every year I’d check to see if I was on track for not only my long-term goal of being promoted in a few years but also my ultra long-term goal of being able to exit stage right at 40. Happily, I achieved it but I know that without that ultra long-term goal to guide me, I’d still be toiling away.

2. How should one set their career goals to lead a happy and fulfilling life?

Career goals are deeply personal and need to be considered in the context of overall life goals. Everyone is different and what may make you happy and satisfied may not make another. I have many friends who are billionaires but are deeply unhappy. They sacrificed everything, even their family life, to achieve unfathomable wealth. But they aren’t happy.

I know others who are stuck in dead-end jobs and feel similarly miserable. However, on the other end of the spectrum, I know some who lead happy and fulfilling lives because they are masters of their domain, well respected, and live good lifestyles. Many others I see view their career as secondary or even tertiary to their families, loved ones, and self.

In order to set your own career goals, particularly early in your career, I would observe and study many who have progressed before you. Mentors, bosses, elders. Anyone who you feel has trodden a path you would like to follow. Then learn from them. Take them for tea or coffee. Ask about how they mapped their career goals and achieved them. Collect data. Do due diligence.

Once you have an atlas of maps, chart your own course. Look deeply inside you and select what you admire most from each person’s path. Just remember, there are no free lunches in life. Time is the ultimate zero sum game and so you will need to make sacrifices to achieve your goals.

3. I’ve seen co-workers self-destruct when dealing with a boss. How can I avoid that?

Congratulations! You are doing the one key thing to prevent yourself from suffering the same fate. You are learning from other’s mistakes! Whenever I am learning, I recall the teachings of Confucius who said:

“By three methods we may learn wisdom: First, by reflection, which is noblest; Second, by imitation, which is easiest; and third by experience, which is the bitterest.”

Thankfully, by observing your co-workers, you can learn from their experience, without incurring it upon yourself. See what they are doing wrong. Are they too aggressive? Are they too passive? What emotional minefields do they trigger in your boss?

Reflection is really the best way to avoid the same fate. I am a big believer in behavioral economics and cognitive bias. These are fields of study that try to understand human behavior particularly as it relates to decision making. At its core, it tries to determine what motivates people. Once you decipher this you can build the right incentives. Reflecting can help you figure out what drives your boss. What makes them think less of your co-workers? Do they fail to help their boss achieve their goals? Meditating on these minefields and how you can avoid them is key.

Finally, seek out the co-workers who seem to have their bosses wrapped around their fingers. Figure out what they are doing right. Do they start off the boss’ day on the right foot with a compliment or a chocolate donut? If so, be sure to observe then emulate! Imitation is the highest form of flattery and we all know that flattery gets you everywhere ;-).

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About the Author

Dave is a seasoned executive and entrepreneur who founded several companies in entertainment, investments, and technology, and worked on Wall Street for almost 25 years.

He started his career by joining a fledgling investment bank, Jefferies, when it had less than 200 employees.  Today, Jefferies is a multi-billion dollar diversified public company (NYSE:JEF).  He rose from the entry level position of Analyst to Group Head of Internet and Digital Media and was one of the youngest Managing Directors in firm history.  As one of the only managing directors of color in the firm, he successfully broke through the Bamboo Ceiling. He not only worked hard but also played the corporate game. 

Hundreds of bankers have worked for Dave during his career. He has mentored many of them who have gone on to some of the best business schools and companies in America.  He is eager to share his knowledge with Asian Americans and other disadvantaged groups seeking to maximize their potential and achieve their career goals.

If you want some great career tips and insights check out Dave’s book, The Way of the Wall Street Warrior, at TheWallStreetWarrior.com.

You can follow Dave at Facebook@Liucrative, Twitter@Liucrative, Instagram@LiucrativeEndeavors, LinkedIn@DaveLiu, or TikTok@Liucrative.

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