The career arc of specialists and generalists

This post first appeared on Instagram over @radreadsco.

Ascending the corporate ladder can involve an alphabet soup of options. There’s vs. I-shaped professionals, a concept pioneered by design guru and IDEO CEO Tim Brown. For the wonkier free-agent types, there’s the semicolon-shaped person coined by blogger Venkatesh Rao. These frameworks all seek to reconcile the perceived trade-off between being a specialist or a generalist. And as someone who’s always game for a fancy cocktail, allow me to introduce my own framework: the career martini.

When the learning stops

RadReaders always ask me if the should quit their job once they stop learning. Yes, it’s true that as the years in a role accumulate, professional complacency and inertia can set in. Years of repetition of a task can make you feel like you’re on auto-pilot. Your manager may give you more autonomy, and thus challenge your ideas less. Or, the most common case, you may have a absentee manager who’s apathetic to your professional growth. If the goal is to always be learning, doesn’t this signal it’s time for a career change?

Not so fast, my friends. If you find yourself in this position, it’s tempting to point figures on external factors stunting your growth. And while the learning circumstances may be sub-optimal, I strongly believe that the ability, and more importantly, the desire to learn are independent of the circumstances around you. We all have the capacity for self-directed learning – blaming external circumstances is running from our own internal accountability.

Yo pass that Martini

So if you’re stuck in your role and looking to level-up, how should you think about the next leg of your career? Enter the three-stage martini glass:

Stage 1: The early days of a career

The base of the Martini glass is the newly minted college graduate. Let’s face it, despite your fancy degree and dope internship, you really don’t know anything. This foundational phase is all about consuming as much knowledge from as many sources as possible. During this phase you’ll:


  • Feel like you’re drinking from a firehose. Good, it means you’re learning.
  • Be told what to do. Listen to these people, they’re probably wiser than you.
  • Be a sponge. Try to draw as many inter-disciplinary connections as possible.


Stage 2: The specialist phase

When you hit the stem of the glass you’ll start to have a sense of what’s going on and specialization will kick in. Specialization is what makes you indispensable to an organization and can often help you earn more. In my experience, this is where the wheat separates from the chaff. In this phase you’ll:


  • Teach your skills to others as a manager or mentor. (Side note: the ability to teach others is a true test of one’s understanding.)
  • Need self-directed learning to deepen expertise. Your manager may adopt a more laissez-faire attitude.
  • Develop relationships with like-minded peers in your industry to facilitate knowledge sharing.


This is where the complacency often kicks in. The lack of immediate accountability makes self-directed learning extremely hard for people. Here are some tips I’ve offered to professionals who are stuck in the stem:


  • Understand the history of your industry or role. How did we get to where we are today? Were there any watershed moments? What crises or big mistakes can we learn from?
  • Get technical. Read white papers, original texts, and materials that are “off the beaten path.” Develop a set of first principles about your industry.
  • Learn how to be a dope manager. There is no greater leverage that investing in your team (and IMHO it’s one of the most personally rewarding components of work.)
  • Become the gatekeeper of truly unique information. This requires building genuine, mutually-beneficial and non-transactional relationships underpinned by trust, collaboration, and kindness.


Stage 3: The generalist, reinvented

Leaving the specialist phase leads us to the last phase, the inverted cone. Here’s where it gets fun. Despite being pretty seasoned, you’ll have to revisit the beginner’s mindset move away from the “trees” and back into the forest. This also entails:


  • Learning to ask good questions. The best leaders can cut to the heart of a topic with a simple question.
  • Rally a team (and possibly company) around a unified vision, crafting the narratives for employees, customers, and investors.
  • Recruiting. Knowing where the talent lies and how to persuade them to join your team.


This is far from the comprehensive guide to being an executive, but you get the gist – staying a specialist can limit the growth of your career. And for anyone stuck in a career who feels like they are no longer learning, remember that the levels aren’t clearly delineated – regardless of your experience, you can always prepare yourself for the next level of the martini glass.

S/O to @JulianMoncadaNYC for the inspiration behind this post.

I’ve started a coaching practice helping ambitious professionals make bold career changes. Together we’ll identify new types of roles, build a financial plan, and navigate the (perceived) loss of identity. Email khe [at] radreads [dot] co to learn more.

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