Work for Someone You Respect

When I was a senior in college, I basically used three criteria to evaluate job opportunities: (1) Prestige - was the role desirable? (2) Pay - would I make a good starting salary? (3) Exit Opportunities - would this role position me for future success?

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At the time, it seemed like a thoughtful framework. But now having acquired five plus years of work experience (across a handful of different work environments), I realize I had a lot backwards.

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On Prestige: It’s only natural to want respect from others, but securing a prestigious job is the wrong way to do it. Real respect (the type that brings fulfillment) can only be earned through actions, results, and character - never a job title. [1] While it might sound fun to impress others with a cool job title, that momentary bliss is like a dangerous drug. It just leaves you empty and wanting more. 

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Lesson: Chasing prestige is a distraction.

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On Pay: Compensation is still an important criteria to me, but I’ve become more thoughtful in how I approach it. In college, since I was in a financially fragile position, securing a high paying job was a priority. Fortunately for me, I was able to land one. [2] But I soon learned there were reasons these jobs (e.g., I-banking and consulting) paid so well: they effectively rob you of your time and energy. The more long-term you are, the more sensitive you become to the costs of this trade off (as you’re left with little time to invest in yourself).

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Lesson: Be careful about exchanging your life-energy for incremental pay.

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On Exit Opportunities: In finance, because there’s so much competition for top jobs (hedge fund, private equity, venture), being strategic about career progression actually matters. So initially, my approach was to target jobs with high optionality - so that I could later pursue whatever career path I wanted. But after leaving finance in 2021, I abandoned this mentality altogether. Instead, I’ve adopted the view that as long as I keep my rate of learning high and continue to develop valuable skills, my “career development” will take care of itself.

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Lesson (still to be proven): It’s better to prioritize near-term learning and skill acquisition than over-optimize for exit opportunities and optionality.

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With each of these lessons, some expectation I had was proven wrong. I thought these criteria mattered for some specific reason but later learned this wasn’t true. 

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Over the last five years, I also learned there are certain things that mattered to me more than I would have expected. The importance of who I worked for is a good example of this both in (1) working for someone I didn't respect and (2) working for someone I deeply respected.

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On the former, I didn’t expect that taking directions from someone I didn’t respect would be so difficult. But it was. Even in cases where I was being asked to do something reasonable, if I lacked respect for the person, it was challenging to comply. Thankfully, I haven’t had to work for many people I didn’t respect. But in the few situations I did, the adverse downstream impacts on my attitude towards work and life were big.

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On the flipside, I was surprised by how much working for someone I deeply respected improved my work life. I’ve only had a few bosses I deeply respected, but I learned a lot from those experiences. I noticed that: I held myself to a higher standard. I became more ambitious with my work product. I derived a greater sense of meaning from the work I did.

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So, a few lessons here: (1) Avoid working for someone you don’t respect - even if other aspects of the job are compelling. (2) Don’t underestimate the value in working for someone you respect. (3) Work to become somebody others would feel privileged to work with / for.