A generalist’s tools: a unique way of observing and navigating the world

A Generalist’s Guide to a Career in Tech (part 1 of 4)

Welcome, Smart Generalist

Jen Yip
Jun 11 · 7 min read

Back when I was working in policy in DC, I used to think of ‘tech’ as a sector. But in today’s world, tech is pervasive. It bleeds into every ‘sector’ and touches everything. Every shift in today’s institutions can be attributed to profound changes in our information systems. Simple tools have empowered new voices and transformed the political arena (Twitter in Egypt). New platforms have unlocked creativity (Kickstarter and the launch of the Pebble Time smart watch) and transmitted culture across borders (YouTube, Gangnam Style).

  • How are our systems of accountability and democracy and our notions of fairness being transformed?
  • How do we explain increasing polarization in public discourse?
  • How will artificial intelligence redefine international order?

Technology plays an ever-growing role in shaping the answers to these questions. These are the questions that shaped my personal interest in technology. These are the questions that opened my eyes to world of ‘tech’ beyond the new gadgets at the Apple store — the world of ‘tech’ as ‘the potential for human ingenuity to transform life.

I studied political science because I’m fascinated by the ways we humans choose to organize ourselves. Technology is affording us with new ways to organize and aggregate the power of groups. I think if you want to be involved with the most scalable levers of change in the world, you probably want to be here, in tech, and arguably, in the Bay Area.

The problem is that Silicon Valley has a lot of gatekeepers who won’t understand your value if you don’t have a CS or engineering degree. The commonly accepted narrative is that programming is the currency of innovation. However, there are important aspects to building new things that engineers may not be particularly good at or may not interested in doing. This is an opportunity for you, the non-engineer, to create value for the ecosystem.

I have a non-traditional background:

  • My undergrad was in political science and neurobiology and my graduate studies were in political theory.
  • I researched women’s entrepreneurship, ethnic identity, and domestic violence law while living in Cambodia, China, and Mongolia throughout my 20s.
  • I worked at The World Bank and was a political risk and energy consultant in my early 30s.

I’ve never written a line of code. Still, five years after moving here, I’m fortunate to be in the middle of almost everything interesting related to robotics and AI. I’ve been asked by many people how you break into tech with a non-traditional background so I wrote a guide for smart, driven people who want to join a startup here in Silicon Valley. I’m not touting this as the one ‘right’ way to build the experience and network you need to succeed…

But this is the guide I wish someone had given me when I moved here.

I hope that with this advice, you’ll be able to take advantage of some of my learnings to shortcut the circuitous, sometimes painful route that I took to launching a career in tech.

Technology needs more smart generalists. Building something new in the world requires tons of activation energy and all kinds of creativity, not just engineering chops. If you read this and parts of it resonate with you as a smart generalist, I would be happy to connect and see if I can be helpful. For the people who believed in me, made intros on my behalf, and referred me to incredible opportunities, this is my way of paying it forward.

PART 1: BE A SMART GENERALIST

“What do you do?”

“I have a research background. I’m a structured thinker. I’m a good writer.”

“Oh! So you’re in marketing.”

When I moved here, I had a lot of trouble communicating my experience to people working in tech. I agonized over job descriptions, kept a spreadsheet of phrases that seemed to describe the things I was good at, and felt inadequate because my background didn’t check the boxes. In retrospect, all of this was a waste of time.

Don’t spend too much time figuring out what startup title fits you best. Be a smart generalist and describe yourself as such.

If you’re resourceful, capable of asking great questions, and problem solving from core assumptions, you can add tons of value to an early startup.

Every early startup needs a smart generalist.This is someone who can dig into the many problems that a startup faces everyday. This is someone who approaches the world with creativity and epistemic flexibility.

**Note: Later stage tech companies also have roles that require strong non-Eng skillsets like UX research, Marketing, and Policy — but the tradeoff is less breadth in these types of roles.

All early startups have problems for which there are no right answers: How do we find our first few customers? How do we build a hiring strategy? How do we know what to focus on next? How do we differentiate ourselves from other people in this space? How do we get the best feedback from the market? What’s the next experiment we should try? How long should we push on something if it’s not immediately successful?

These are hard questions and no one has a roadmap to solving them. As my friend John Rector, cofounder of Dialpad, points out, “most startups need a lot of flexibility in how they think about things, because there’s a lot they don’t know. A smart generalist is someone who understands a little bit about what a startup is like, and someone with the flexibility to learn/wrestle with the stuff they don’t know.”

Familiarize yourself with best practices and bring your own set of experiences and observations about the world to solve problems. This is the essence of creativity — the ability to build on what exists, and bend, break, or blend what’s already known. **For more on this topic and to be inspired by creatives from all disciplines, check out neuroscientist David Eagleman’s latest movie, The Creative Brain.

Your unique experiences are the source of your creativity.

When the team is pushing on something, often, the most important thing you can do is ask “what is our core hypothesis? What kind of evidence would invalidate our hypothesis? How can we find high signal fast?”

Asking the right questions is valuable to an org because it’s so easy to waste time going down rabbit holes if you’re not hyper-vigilant about focusing on the highest leverage activities. If you have a CS degree, you might want to tackle a hard engineering problem just because it’s in your comfort zone. It’s an unspoken assumption in Silicon Valley that coding is a productive, high value activity. And it is extremely valuable. You can’t build technology without it.

But just because an engineer is at his desk with an IDE open and headphones on, EDM in the background, doesn’t mean you’re any closer to acquiring the necessary learnings to serve early customers. When faced with this challenge of divining user needs, sometimes engineers will focus narrowly on the coding problems. This is actually a form of avoidance behavior. The engineers are focusing on what’s natural for them and not what the customer needs. As my friend Andrew points out, “Just because the curveball is your best pitch doesn’t mean that the curveball is the best pitch for this situation.”

Check out those headphones!

Here’s an example of how a smart generalist can help an org prioritize by asking questions: Every startup should have a web presence at some point, but how much time do you want to spend on a discrete startup activity like building a website? Before you devote time and resources to hiring designers, photographers, and copywriters to building a website, have you identified what you hope to accomplish?

  • Are you trying to build credibility with customers or partners?
  • Are you trying to attract talent?
  • What are the chances that someone stumbles upon your website, reaches out via a contact form and converts to either a customer or employee? It’s easy to build a website but it’s hard to get people to navigate to it.
  • Would you be more successful at attracting new employees by inviting talented prospectives to a party?

In a resource-strapped startup, everything is a tradeoff, and a smart generalist can create a lot of value for a startup by asking the right questions that steer priorities.


Build your generalist arsenal. There are tons of free resources on virtually every aspect of building a startup: product, design, business strategy, branding, marketing, pricing, sales, and user experience research. Having some context for how to do these things can make you more effective.

Here are some of the resources that I found particularly helpful:

This is just a starting point. Let me know if there’s a topic that’s of particular interest to you, and I can provide pointers in the right direction.

Subscribe to newsletters to stay current on trends. MIT Tech Review is my favorite for robotics and AI news and Ben Thompson offers deep analysis on tech strategy. Reach out to great people you know and ask them what they’re reading — the blogs and Twitter influencers they follow, podcasts they listen to, etc. and start curating lists on different aspects of how to build a startup. If you need some pointers to get started, DM me and I’m happy to send you suggestions.

If you’re always adding to your arsenal of startup know-how you’ll have great frameworks for thinking through any problems you encounter. These problems pop up in regular patterns — and as you start recognizing the patterns, you’ll be able to quickly decide which techniques are applicable even if you still have to work out the details.

So now that you’re a smart generalist and you’ve done your homework, how do you actually find a startup role?


Part 2

In part 2, I discuss the importance of finding your tribe of supernodes and mavens, the connectors who are in the middle of the most interesting networks and opportunities in Silicon Valley.


Thanks to David King, Andrew Barkett, John Rector, Nodira Khoussainova, Anne Widera, and Doug Fulop for contributing thoughts to this.

The Startup

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Jen Yip

Written by

Jen Yip

Community builder, Robotics & AI. Deep appreciation for baroque silence, brainy bookworms, and rainbow sprinkles. Early to dinner, late to lunch.

The Startup

Medium's largest active publication, followed by +469K people. Follow to join our community.