The Future of Generalist Work

Very, very many people at Stripe today are doing a quite different job to the one that they join for. In order to do that they've often had to learn a lot and stretch themselves into new areas.

Building a culture of excellence | David Singleton (CTO of Stripe)

While frameworks can offer valuable perspectives and guide decision-making, rigid adherence to them can lead to tunnel vision and unhelpful outcomes. Successful decision-making often requires a blend of framework-guided analysis and intuitive judgment, where the needs of both the business and the customer are carefully considered.

Lenny Rachitsky • Twitter’s former Head of Product opens up: being fired, meeting Elon, changing stagnant culture, building consumer product, more | Kayvon Beykpour

How to clarify a concept you can’t articulate:

1. Change mediums. Draw it. Photograph it. Sing it.

2. Change levels. Explain what is one level up (bigger picture) or one level down (finer details).

3. Change fields. What would this concept look like in different fields?

James Clear • 3-2-1: On hard conversations, how to ruin a good strategy, and asking for what you want

How great generalists think

This has been the core question I’ve sat with for the last decade—how to balance money and meaning on the entrepreneurial path. And there are three archetypal ways that I’ve seen people approach the question:

The deferred life plan

Being bivocational

Choosing to integrate

Casey Rosengren • The 3 Ways to Balance Money and Meaning

Here are eight imperatives—all of them drawing strength and sustenance from the humanities:

We need a way of defining and pursuing progress that doesn’t reduce that concept to something that only comes from a digital device.

We desperately need access to values and wisdom that aren’t corrupted by the relentless financial metrics and imposed

Ted Gioia • The Real Crisis in Humanities Isn't Happening at College

Collapse the talent stack every chance you get .

As I reflect on the teams I’ve led and hundreds of start-ups I’ve worked with, there is a consistent unfair competitive advantage i’ve witnessed when the talent stack was collapsed - when the lead designer was also the product leader, when the front-end engineer was also a designer, when the designer... See more

scott belsky • Tweet

Hiring generalists collapses the talent stack, thereby improving decision making and synthesis of information, and giving companies to act quickly when time and resources are limited.

Generalists have the advantage of interdisciplinary knowledge, which fosters creativity and a firmer understanding of how the world works. They have a better overall perspective and can generally perform second-order thinking in a wider range of situations than the specialist can.

Shane Parrish • The Generalized Specialist: How Shakespeare, Da Vinci, and Kepler Excelled

Taking a nontraditional path will force you to grapple with what matters

The greatest benefit of a nontraditional path is that you have to figure out what you care about. Rather than an employer telling you what you should value, you have to do the hard work of determining what you value for yourself. This may sound self-evident, but in a world... See more

Simone Stolzoff • In Praise of the Meandering Career

Mihika likens the role of a 0-to-1 team within a large company to that of Hestia in Greek mythology, who is the “keeper of the hearth.” It is Hestia’s job to always keep the hearth burning, even while other gods go out on separate quests. This means always keeping the 0-to-1 project alive and helping it spread to others, mostly through setting... See more