On Being An Elder

I’ve been thinking more and more lately about the responsibilities of those who are elders in a given community or industry. This is perhaps normal as one approaches middle age, but is ironic to actual elders who don’t understand that within our industry you can feel positively ancient before you’ve yet lived four decades. I’m also thinking about this because we’re witnessing the most violent shift that’s occurred in technology in a very long time, and epoch shifts are generally a cause for reflection, if not concern.

While I might believe in Aristotelian ideas like virtue being exercised through guidance or other moral arguments for one’s obligations, I have a much simpler and more selfish aim. I want to share my ideals in the hope they inspire and shape others. If they do, I think it’ll make our small part of the world a better place.

The older you get, the more you realize how we have all benefitted from those who came before. Perhaps this is more true in our industry than in any other. One of the beautiful aspects of tech, historically, has been how its members help and invest in others without demand for repayment. ‘Open source’ is as much a community philosophy as it is a licensing concept.

So what are the responsibilities of an elder?

Pass down what otherwise would be lost

As fast as the hyperscalers are training LLMs on ever-expanding datasets, I think much of what matters lives in stories, mistakes, or habits of individual practitioners. This is wisdom; the judgement and ‘why’ behind decisions or ways of doing things that all-to-often fade with the passage of time. An elder should try to preserve these without confusing the past for a rote set of instructions lest we become a cargo cult.1

Speak up when something is wrong

I think modeling good behavior should be a given, but I think it’s equally important to admonish those demonstrating cruelty, dishonesty, exploitation, or behaviors that otherwise lead to a deteriorating culture or community. One reason why this is particularly important for those with seniority is that when you are young, it is much riskier for a variety of reasons to speak out. As the Good Book tells us, we must tend to the flock.2

Open doors for others

It’s easy to forget once you’re ‘in’, and can access anyone or any opportunity you want, what it feels like to desperately be in search of your first big break. I’ll never forget when my very first boss took a chance on a cold email from a teenager and hired and started mentoring me.3 Elders should use their access and resources to connect, refer, sponsor, and otherwise hold the door open rather than just offering advice from the other side.

Remain available

As you age, it’s natural to look more inward and focus on your family or tight-knit community. Time becomes more precious. Our industry is also a bit unique in that it’s not uncommon to achieve post-economic status and leave it while still quite young.

I’ll never forget as I was leaving Wealthfront to start something new, Andy Rachleff, the CEO and Co-founder and former co-founder and long-time general partner of the legendary venture firm Benchmark Capital, was more than happy to walk around Redwood City for a couple hours to listen, workshop, and share his perspective.4 Whether it’s answering emails, reviewing portfolios, or just listening and encouraging, elders should make themselves available to others.

Admit what we got wrong

Every generation inherits both the advances and sins of the one prior. I think it’s important to speak honestly about that, and humbly share what we got wrong and the mistakes we made so we can correct them and move forward rather than calcify the status quo into harmful traditions.

Let the young teach you

I have never been more inspired than this past year, seeing the amazingly creative and fun work that folks in their first few years of professional experience are creating, for both work and pleasure. It is far too easy to regard the knowledge you have as an elder as complete, especially with all of the rapid innovations happening now. Old dogs should still learn new tricks.

Being an elder is less about simply age, and more about turning that time, access, judgement, experience, and refined ability into a way of being that enables those who are coming next. It is this service, not seniority, that makes you an elder. And as I am fond of saying: it’s a pleasure to serve.

  1. I think this is why archival projects are so important. I am excited to work with a few good friends on History of Software. ↩
  2. A challenge with this one is that ‘righteous anger’ is a slippery slope. It can be easy to fall into the trap of enjoying calling out bad actors, but I think this can lead to a perverse desire to do this because it feels good or gets likes on Twitter. I’ve lately seen what I feel is an increase in egregious public behavior, but have to remind myself that the best way to effect change is rarely a scathing reply, as good as that might feel in the moment. I look forward to reflecting on this another decade or so into the future. ↩
  3. Allan Branch is now the mayor of his small hometown of Panama City, Florida, and is demonstrating the same ideas in trying to revitalize and invest in the next generation there. ↩
  4. No matter my protests, he refused to let me pay when we stopped at the local ice cream parlor. ↩