Learning from your career crush

Issue 232: Taking admiration to fuel ambition

Admit it. You’ve had a crush in your life—the strong but temporary feeling of love or attraction for someone. Though crushes are typically attributed to romanic relationships, there are an array of crush types. Let’s take the brain crush as an example—an intellectual admiration of how a person views the world or thinks about it. As a person who is interested in art, computer science, and technology, there is no shortage of brain crushes for me. The most notable one was watching Bret Victor’s Inventing on Principle. As I watched the talk filmed in a crappy hotel conference room, the concepts and insights from the talk propelled my interested in working on creative tool.

The demo that launched thousands of careers.

There is also the career crush—a topic I’ve discussed with friends. This crush classification is the admiration of a successful person in your field. Perhaps they have a track record of roles you dreamed of having or inspired you during a podcast interview of how they approach the work. However, it’s important to remember the “why” of your crushes. The natural path is following a deterministic path as they did, but that is short-sighted.

You’re pursuing a unique path and it’s important to understand why you chose it. When you have a career crushes on someone, de-couple it from the person (for a multitude of reasons here). Instead, reverse engineer their career to understand what you’re seeking.

I’m not going to say any names of my career crushes. You probably can guess based on my reverse engineering techniques though. If you looked at their accomplishments at the surface level, it'd take me to a different path. Many hold the title Chief Product Officer and not even in Design. Taking the deterministic path would assume I need to be a co-founder, get acquired, and become a CPO.

My reverse engineering process highlighted what I admire about their careers. I realized all the people I admire in their career achievements are great parents. They are ambitious individuals who still have time to be a loving parent and partner. I would not have realized this if I only pursued their linear career path.

They are all high performing excecutives who have entepreneural backgrounds as a founder or formed their own business. Though they approached it from different paths such as an aquisition or moving up the ranks, the career crushes are high performing executives who sweat the details—never being detached from the their natural craft. Finally, they all are involved in the next generation of tech enepreneurs as angel investors and/or board members.

Reverse engineering attributes of career crushes confirmed I’m on the right path—my own. I don’t have to be a CPO. I can continue focusing on Design and Marketing, take the inspiration from the crushes, and resume my non-deterministic path. Now it’s your turn to reverse engineer your career crushes:

• Who are the people in my industry that I graviate towards their career accomplishments?

• What are the aspects of them I admire? Is it how they view the world? How they speak? Perhaps it's the work they accomplished?

• What are aspects in their career, though admirable, not what I'm looking to explore?

Take a moment this week to ponder your career crushes and excited to see what you reverse engineer.

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Hyperlinks + notes

A collection of references for this post, updates, and weekly reads.

• Congrats Ryo Lu on joining Cursor as Head of Design!

• The outputs of design are memetic, not visual by The Product Picnic

• Your AI Chatbot Is Stuck in the Past—Here’s Why That Matters

• Design Is an Activity of Research by

  Ha Phan

• Full Stack AI Agents by Sunail Pai