Lessons I learned from HBS Alumni


Recently, I attended an alumni dinner, filled with alums that have been out of business school for a few months to 20+ years. I was half expecting this to be one of those hand-shaking, business card-swapping dinners, where you make spiffy small talk but not really get to know the person next to you: what’s your name, what do you do, where are you from, NEXT!

To my pleasant surprise, this dinner was much more than that. Many of these alums were astonishingly open and generous with their professional and personal experiences, lessons learned, challenges, and advice to others. 

I was inspired so much by them, so I’d like to share some of their wisdom here.

1. Move your goal post 

Since these are Harvard Business School alums, they were, of course, very driven and motivated, especially coming out of the business school gates. In a group of extreme type A’s who are all uber competitive, there is backbreaking pressure to snag a job with the most prestige, highest pay, and greatest promotion opportunities.

One alum shared her story about setting an aggressive goal to become Managing Director (MD) at her bank within 7 years after graduating. She worked night and day, even through social events and workouts. She even missed the first few years of her first born child’s life. Sacrificing all for work, she finally made it to MD within 7 years, but realized that she was utterly miserable.

The lesson she shared is that it’s so important to consistently evaluate your goal post and the cost of pursuing it. If the rewards of your goal and its pursuit cannot outweigh their costs, then it’s time to erect a new goal post.

2. Careers are jungle gyms and not ladders

I’ve heard this analogy before, but it’s refreshing to see alums actually climbing through the jungle gym. When companies recruit in business school, they tend to layout a nice and neat ladder heading to some prestigious sounding senior position, such as Managing Director or Partner or VP. Therefore, it’s great to see how many alums actively choose to jump off these ladders and climb elsewhere.

I sat next to an alum who had been climbing the investment banking ladder for five years or so. This alum became so frustrated and finally decided to switch to impact investing in a much smaller organization, with much less prestige, and probably a giant pay cut. However, it turned out that this was the dream job since “it doesn’t even feel like I’m even working”.

The lesson I learned is that it takes self reflection and courage to leave the ladder. It’s much easier to follow a carrot that’s always dangled in front of you than to leap into the unknown. But when the carrot is not appealing anymore, taking a risk is a necessary first step, even if it means you could be taking a step back.

3. Expand your opportunities with a portfolio career 

Before this dinner, I had never heard of the term “portfolio career”, which I believe is a collection of multiple careers. For example, a portfolio careerist may be a healthcare entrepreneur, education investor, and fiction writer at the same time.

One alum shared how she stumbled into a portfolio career. When she went to business school, her goal was to join a top consulting firm and become a Partner. During school, she fell madly in love with her current husband and followed him to Asia. At graduation, she made a choice between a consulting offer that required 90%+ travel and her life partner, and she decided to abandon her original goal. Instead, she became a media mogul in Asia…and then in Europe as well. Many years later, her husband was transferred to a tiny media market, so she decided to grow another interest – education! As a result, she successfully started and grew multiple business schools. Oh yes, between her career as in media and education, she also managed to work in a top tier consulting firm for some time. Amazing!

For me, portfolio career is such a mindset change. Since I was young, I was programmed to think what do you want to be when you grow up, what major do you want to choose, and what industry or function do you want to end up in. All these involve thinking in terms of a singular career (or at least highly related ones such as healthcare entrepreneur to healthcare investor). Thinking in terms of a portfolio career not only opens you to multiple opportunities but also stretches your development as a person and professional.

Management: a noble profession?


When you hear people complain about their bosses or watch movies like Office Space, you think: Wow. Managers are really the bane of everyone’s existence. As someone who currently has the word “Manager” in her title, that’s a scary thought. Would it be better to become a doctor (although I can’t stand blood) or a teacher (although I can’t stand snot)? Is becoming a manager a truly worthy profession or just a pain in the neck?

What is a manager? 

It’s a nebulous term, but I’ll give it a go any way. For me, a manager coordinates people, budget, and other resources to achieve certain business objectives. To do so, a manager needs diverse skill sets, but some key ones include:

  • Influence others: Motivate and move others to action. This requires not only good communication skills but also superb listening skills and high emotional intelligence. It’s not enough to tell people what to do. You have to convince them that it’s the right thing to do.
  • Problem solving: Address problems quickly and effectively by engaging the necessary stakeholders while keeping others focused on moving ahead.
  • Looking ahead: Identifying potential obstacles or opportunities in the short and long-term. Plan and act proactively upon them to either mitigate risks or capitalize on opportunities.
  • Maximizing team’s potential: Identifying strengths, weaknesses, and passions of team members and assigning them to roles that optimizes their chances of success.

Why managers matter?


Managers matter because they all impact our lives in profound ways (as anyone who has ever had a bad manager knows). The above infographic (albeit an advertisement and US-focused) is stuffed with interesting facts. To highlight a few…

  • 71% of employees aren’t fully engaged due to strained relationships with their superior!
  • Only 35% of people prefer a raise over a better boss, meaning most people value a better manager over more money.

If bad managers can make our lives so miserable, imagine how a good manager could not only improve your life but also our society by inspiring motivated and happy people to achieve great things.

Why have they become such a pain?

If managers could be so important, then why does the profession have such a bad reputation? I think a big issue is how managers become managers. We all start off as grunts in some function (IT, Design, Supply Chain, etc.). We spend hours getting good at doing really detailed work related to the function, whether it’s running Excel models, programming, or designing advertisements. We also get really good at managing up (since we’re grunts at this point and there’s no one to manage down). When we get good enough at our functional skill and when enough time passes, we eventually get promoted to managers. Now, as managers, we are expected to manage people below and budget, which are completely new skillsets that we need to learn.

Therefore, organizations tend to promote managers not for their management ability, but for their functional skills and expertise.

At this point, I think a manager’s success also depends largely upon a company’s performance management process. If a manager’s promotion depends on only his / her boss, then this problem will perpetuate. As this newly promoted manager has had plenty of experience managing up, then the company will continue to promote him / her even if the minions under the newbie manager hates him / her.

How can management become a noble profession? 

I think there are a zillion things to make this profession more (positively) impactful, but to (over)simplify here are so key ones:

  1. Attract more managers that could be good at managing others: They display EQ skills such as listening, compassion, and adaptability and not just high IQ.
  2. Conduct 360 Reviews: Evaluate managers based on feedback from people above and below.
  3. Don’t be a pain in the neck: Enough said.

MBA – a blessing or a curse?

For the last 1 year and 4 months, I’ve had an MBA. However, I often find myself keeping this information close to my chest (unless I’m with fellow MBA’ers). People usually have to pry it out of me with a conversation that goes something like this:

“What did you do before this job in Singapore?”

“I was a management consultant.”

“Where were you located?”


“So you moved from Texas to Singapore?”

“Uh….no….I moved from Texas to Massachusetts to Singapore.”

“Why were you in Massachusetts?”

“I was in business school.”

“So you have an MBA….where did you get it?”

“in Boston”

“Which school?”

“Uh…..[in almost a whisper]…harvard….”

“OH MY GOD!!!” (followed by a laugh that is usually either filled with mockery or fanaticism)

When an MBA is a curse

1. When people have unrealistic expectations:

Every time I hear: “You should be able to figure this out. You have an MBA.”, I just want to pull my hair out. Seriously? Just because I went to school studying business for a whopping 2 years, I can now solve all sorts of problems (such as predicting the weather or future political events?). A great perk about being young in your career is that you get to ask all the stupid questions without people thinking too much (unless they are really ridiculously stupid). However, with an MBA (especially from HAH-VARD), some people can be much less forgiving. As a result, often times you come in with a steep uphill battle, proving your worth and intelligence to meet some high standards.

2. When people don’t take you seriously:

On the opposite end, these are people that say / think: “Just because you have an MBA, doesn’t mean you actually know how to run a business.” These people discount the MBA heavily because you don’t learn business in school, you learn it through actually working. Therefore, those 2 years were a complete waste of money and time. Hrm…while I agree that most newly minted MBA’s are not ready to become CEO’s the day after graduation, most also don’t assume this position after school. To win over these people, I think it’s important to not only stress that you actually have pre-business school work experience (although these people usually discount management consulting as well, but that’s another story), but also to just roll up your sleeves and do some freakin’ great work.

3. When people think you’re stuck up:

This is the worst. Yes. Agree that some MBA’ers think that they are the best thing since sliced bread and make sure to communicate this loudly and clearly. They do so with comments like: “I work with morons.” or “So you work at a second tier bank?”. These select individuals are ruining it for everyone else. The other day, I went to an alumni event and met this alum who would only talk to my male companions because he thought they were the fellow alums. I guess he discriminates against women and non-MBAer’s?

When an MBA is a blessing

1. When you find yourself with some extra confidence:

In business school, it’s amazing how many execs and heads of state you could have access to. All of a sudden, you find the CEO of some Fortune 500 company in your classroom, and you’re asking him some question that (hopefully) sounds mildly intelligent. What happens is that you realize these people are just…people. During the first few weeks in my first job, I remember being terrified to ask the senior partner of my consulting firm a question. In client meetings, I was so timid, fearing whatever came out of my mouth would be gibberish. Engaging in intellectual conversations with high level leaders in business school makes you think that you can talk to anyone.

2. When you can develop and articulate opinions quickly:

This is particularly applicable for bschools that teach via the case method where a significant portion of your grade is participation.  When class discussions move fast and the room is filled with assertive ex-PE guys, you learn to quickly develop strong points of views and effectively communicate them. (You also learn how to adopt “power poses” to ensure the professor calls on you as opposed to the person next to you who’s about to jump out of her chair.)  I didn’t fully realize this benefit until after I graduated. In the business world, this skill becomes important in meetings where people with the most assertive and persuasive opinions heavily influence key decisions.

3. When doors are opened for you:

I reaped this benefit even before I received the actual degree. When I was job searching, countless alumni were willing to talk to me and help for no other reason than we went to the same school. Crazy, huh? But somehow it works. Now, I pay it forward as well, being as available and helpful as I can to others. However, this benefit doesn’t mean that great opportunities will descend from the heavens and land on your degreed lap. It just means you get pointed to the right (and sometimes wrong) doors and some doors may be left slightly ajar for you. Fully opening and walking through the door is still hard work.

Being young-ish in your career means your educational degrees still define you professionally. With more years and decades of experience, I think people will stop defining and viewing you based on your degrees and judge you based on the great work and reputation that you’ve built up. If an MBA can help you get a jumpstart to doing that great work, then that’s what matters.

Should I go to business school?

MBA definitions

As a relatively recently minted MBA, I am asked this question with some frequency. It’s a great and weighty question as business school is tremendously expensive (~$100K per year including tuition and housing + $XX(X)K in forgone income) and time-consuming (1 to 2 years of professional experience). Depending on where you go, you may all of a sudden disappear from the face of the earth as you’re transported to your business school bubble leaving your friends and family to wonder where you’ve gone for months at a time.

The right answer will vary by individual, but it depends on: Where are you coming from? Where do you want to go? 

People pursue MBA’s for numerous reasons, including: switching careers, moving to a position with more responsibilities / pay, acquiring business acumen, and even starting their own business. Since everyone’s circumstances are different, I’ll give a few examples and possible reasons for / against going.

Some reasons to go…

  1. Promotion: Your company highly encourages an MBA to get a job at the next level, a bigger pay check, more responsibilities, and a fast tracked career path. Most importantly, you want all of those things more than zombies want brains.
  2. Industry Switch: You’ve been stuck in an industry that makes you want to stab your eyes out and desperately want to switch into another industry that gets you jazzed.
  3. Function Switch: You can’t stand your “function” as an internal compliance officer or consultant or investment banker. You want to do something “sexier” like product management or “dirtier” instead of strategizing in your ivory tower.
  4. No idea what to do: Business school is a pretty costly way to figure things out. However, there are some benefits: you could (a) meet people from varying backgrounds, (b) learn about various companies / industries / functions through classes and professors, (c) buy time to test and develop your interests, (d) keep progressing on your resume.
  5. No business experience: There are some (but few) people from non-traditional backgrounds in business schools, such as marines or doctors or ballet dancers. They may have no business experience but aspire to get into the business world. Getting an MBA could be a great way to transition, gain some business knowledge (through classes), and some (not alot though) of business credibility.

Some reasons not to go…

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