The ambidextrous career

It’s time to embrace talent mixing and domain hopping

Ann Bordetsky
5 min readFeb 1, 2021

I recently joined the venture world and as I go through the entry phase I am reminded once again of the amazing power of context switching in forging connection and collaboration between professional worlds.

(By the way, I’ve had an amazing first few weeks. The NEA team could not be more kind, collaborative and inspiring. This isn’t commentary on VC per se but a reflection on the importance of all manner of interdisciplinary careers.)

Me, right now in venture. The beginning of the beginning.

Starting at any new organization, big or small, is an assimilation process. We lovingly call it “onboarding” but really what we’re talking about is individuals assimilating into new tribes, cultures, norms and systems.

When we enter new institutions we naturally go through a steep learning curve. But it’s not just learning the job. We absorb into the language, lore and rituals (aka shared context) of the place.

This happens all the time, as employees join new companies, as execs take on new leadership roles and especially as we enter new professional domains.

I’m fascinated by the assimilation process because I’ve lived it many times.

My childhood was spent moving countries, states, schools and getting over the hump of new languages and culture shocks. As a kid these moments of assimilation were challenging and dramatic (ahem, that’s why immigrants are so resilient!). As an adult, the moments of assimilation were more subtle but still there with each career turn, organization and step on the ladder.

I like to throw myself into new arenas, so I’ve had many of these assimilation and context switching moments, for example:

  • From DC policy wonk to MBA program (fish out of water!)
  • From nonprofit sector to private sector
  • From lean startup to big company
  • From cleantech to consumer tech
  • From meme culture (Twitter) to hustle culture (Uber)

On the other side of the entry process, what you get is a deep appreciation for the unique context, customs and motivations with which different people, institutions and segments of our socioeconomic system operate.

It’s all of the hidden nuances you can’t read on Twitter, don’t find in books and media articles and can’t empathize with until you’ve experienced it.

Things like —

  • How different kinds of institutions make decisions (corp vs. nonprofit)
  • Structural and cultural incentives that shape individual behavior
  • What makes people tick and the unique tribal identity of that place
  • What it feels like to try to lead and create change in different environments
  • Facts. Reality vs the media portrayal of how certain arenas work

The nonlinear career path has its challenges of course (topic for another time) but I have to say, having worked in 3 of the 4 major “spheres of influence” in our society — companies, nonprofits, government — is priceless.

Now I’m on to #4! Capital.

We need more context switchers and sector “hoppers”

Moving across sectors what I’ve noticed and fascinates me to no end is this —

There is a wide chasm in mutual understanding between spheres of influence in our society, even ones that are in constant interface with each other (e.g. government & industry, nonprofits & private sector, investors & founders).

  • How many aspiring entrepreneurs understand investor incentives?
  • How many investors have spent time operating and building?
  • How many tech leaders have worked in government and public service?
  • How many regulators have spent time building tech companies?
  • How many activists have worked in the corporate world?
  • How many in academia have been practitioners in their industry?

We have so little cross-pollination of talent across sectors, industries and spheres of influence that we exist in different dimensions and speak different languages. Have you watched a Congressperson trying to cross-examine a tech a CEO? Things get lost in translation. Literally.

The digital media bubbles we live in only exacerbate that. And nowhere is that more evident than the day-to-day on social media.

Why is it then that policymakers struggle to understand technology businesses and startup people can’t wrap their head around government? It’s a simplistic example but the answer is more complicated than just politics.

Not enough of us are moving around to cross-pollinate expertise, norms and knowledge. We need to find more ways for individuals to move freely industry to industry, public and private spheres, sector to sector.

Why does this matter?

Well, human progress requires all manner of collaboration!

  • If we want to solve complex problems in our society, we need to bring together individuals from public, private and nonprofit to get it done.
  • If you want to build a fast-growing tech company, you will need to collaborate with many different stakeholders — investors, customers, employees, regulators, media.
  • If you want to build a diverse society with upward mobility, you will have to co-create with people who don’t think and talk exactly like you.

Our world is multi-faceted and it requires increasing levels of human coordination and communication to solve just about anything.

Take climate change for example.The most interdisciplinary problem of all.

If we manage to get it under control it will be because of unprecedented global collaboration between scientists, policymakers, innovators, company builders, civic leaders, activists and consumers all working in concert to make it happen. Like the Avengers final battle, we need ALL the superpowers working together to pull this off.

In almost every arena, we are in need of more individuals with interdisciplinary knowledge and experience. That requires breadth.

Yet our modern workforce rewards specialization and actively discourages career, sector and domain switching. Organizations are designed to elevate leaders that come up via functional tracks. Mastery of narrow band builds prestige and career equity faster than breadth. Niche dominance is the way to get noticed, whether you’re a scientist, academic or content creator.

The downside of that is tunnel vision. We lose out on working side by side with individuals who have different reference points, insights and context.

We need individuals bringing diversity of thought, experience and knowledge into established institutions. We need cross-pollinators as much as specialists.

As we reimagine the future of work (from education to workforce training to career progression and economic mobility), I’m interested to see how we can design for fluid careers, portfolio talents and cross-sector acumen. We need a generation that is capable of leading across and not just within institutions — and better yet having the span of talents to design entirely new ones.

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