2020 in Review: The Year That Broke the Playbook

I’m writing this on December 28th and I can’t tell you what month it is without checking. That’s 2020 in one sentence.

A year ago I was heads-down building a cloud infrastructure company, convinced that the biggest challenge ahead was product-market fit. Then March happened and the biggest challenge became making sure the company didn’t die. Different skill set entirely.

The Company Made It

I’ll start with the thing I’m most proud of. The company survived 2020. But I want to be straight about what that actually looked like, because the LinkedIn version of startup survival stories is always cleaner than reality.

March and April were ugly. Two potential customers froze their budgets overnight. A partnership I’d been working on for months went silent. I spent a few weeks unsure if the company would make it to summer. The thing that saved it was that the product was a cloud infrastructure tool during the exact moment when every company on earth suddenly needed better cloud infrastructure. Lucky timing dressed up as strategy.

By Q3 I was shipping features faster than I was comfortable with. Some of that code is going to haunt me in 2021 and I know it. But the company is alive, and if you’d told me that in April I would have hugged you.

Leading Teams at Larger Platforms

The other big part of this year happened alongside the company. I spent 2020 as a tech lead at two larger platforms. Both taught me things a small startup can’t.

The biggest lesson: large organizations fail at decision-making far more often than at technology. I watched a team of perfectly competent engineers sit paralyzed for three weeks because nobody could get sign-off on a Kubernetes cluster configuration. The technology was the easy part. Getting six stakeholders to agree on a risk tolerance was the hard part.

I also learned that my founder experience translated directly. The problems startups solve with speed and scrappiness are the same problems enterprises solve with process and budget. Same problems, different constraints. Understanding both sides made me better at each.

Remote Work: What the Industry Got Wrong

I need to rant about this because the discourse around remote work in 2020 was insufferable.

Half the industry spent the year writing thought pieces about how remote work is the future and offices are dead. The other half spent it writing thought pieces about how remote work is destroying culture and we need to get back to the office immediately. Both camps were wrong in the same way: they treated remote work as a binary instead of a design problem.

Remote work is infrastructure: a set of systems and processes that either work or don’t. I’ve been running distributed teams since my days at a mobility startup. It works when you design for it. It fails when you take your office habits and paste them onto Zoom.

The companies that struggled in 2020 had never invested in written communication, async decision-making , or documentation. They replaced hallway conversations with eight hours of video calls and then blamed the format.

My company had been remote since day one, so the lockdown changed little about how I worked there. Not because remote is magic. Because I already documented decisions and wrote things down instead of keeping them in my head.

Office or remote won’t decide which companies thrive in 2021. The ones that design their communication systems will beat the ones that default to whatever they did before.

What I Got Wrong

I try to own my mistakes in these posts, so here goes.

I underestimated how much the pandemic would affect the teams I worked with. I spent Q2 optimizing for output when I should have been optimizing for sustainability. We shipped a lot, but a couple of people burned out, and I should have noticed sooner.

I also overestimated how quickly large organizations would modernize. Compressed timelines don’t mean compressed politics. Some organizations moved their infrastructure to the cloud in weeks but took months to update their security policies to match. The gap between technical capability and organizational readiness is wider than I thought.

The SolarWinds Wake-Up Call

I can’t write a 2020 review without mentioning SolarWinds . In December we learned that a major software supply chain had been compromised for months. Government agencies, Fortune 500 companies, the works.

This is the kind of thing I’ve been warning about for years. Your security is only as good as your weakest vendor. Most organizations treat vendor risk as a compliance checkbox. SolarWinds proved it’s an operational reality. I expect this to dominate security conversations well into 2021.

What I’m Carrying Into 2021

The company has momentum. The work keeps growing. I have a clearer picture of how enterprises and startups can learn from each other. Specifically:

I want to build better. The code I shipped under pressure in 2020 needs attention. Technical debt is a loan and the interest is compounding.

I want to write more. 2020 made everything feel too heavy to write about casually. But I think writing forces clarity and I need more of that.

2020 was the strangest year of my career. It broke every plan I had and replaced them with better ones. I wouldn’t want to do it again. But I’m grateful for what it taught me, and I’m heading into 2021 with more conviction than I’ve had in years.

Onwards.