Lessons I learned from HBS Alumni

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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.

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