Family Leave

Two New Additions

On 4/24/2026 my wife and I welcomed our twins, Clyde and Clara, and the day before that I started my paternity leave. Outside generously provides twelve weeks of paid leave, and during it there’s nothing I’d rather be doing than spending time with my family. Building bonds and routines, and watching my two children’s personalities begin to show, has been incredible.

The reality of a leave this long means that the return date looms close by and the tectonic shifts since taking off are a concern that clouds each week.

Extended time off means that while I was able to prepare a Q2 plan and the beginnings of a Q3 plan, I wouldn’t be there to see through Q2 or adapt Q3 to the reality of what we achieved in Q2. The scope of my role will likely be forever changed as colleagues forge new processes and relationships. I’ve been there since 2021 and risen up through multiple promotions. I look forward to talking to my coworkers as ever, but I know I’ll feel less ’needed’ and that will sting at first.

Missing out

Part of stepping away is the quiet fear of falling behind. The industry moves fast. The obvious thing I’ve missed out on is three months of development around LLM usage at work. Day to day, I think the momentum is still going in the same direction. LLM and agentic development has proven itself for developers. However, I’ve been anticipating more interest in lower-cost tooling and per-token models that keep their interfaces low-friction, especially since organizations were just hit with the reality of token-based enterprise costs and the newly discovered possibility of government restrictions on frontier models. Despite this, I don’t see most of those engineers ever going back to ‘hand-coding’.

In my experience, these three months are also where the year really begins. Ideas get in motion and start to blossom further. This aligns with our users’ patterns too. In the cadence of the year at Outside, the summer is one of the peak seasons. People are going outside, reading to be inspired, researching trail conditions, and tracking their routes to look back and reminisce. Projects are being ideated for the next few quarters, and while a strategy was laid out before my leave, the expectation is that reality led to pivots - ones I’ll only learn about once I return.

It’s a cliché that trust while delegating is one of the most challenging parts of delegation, but it consistently remains true. You surround yourself with an excellent team you trust, you agree upon a plan, and yet execution is still a skill folks ascribe to successful companies for a reason. It doesn’t come for free.

What to return to

When you’re hired to a role, the hiring manager has an idea of the problems you’re there to solve and the team you’re there to manage. I took a twelve-week leave doing that job along with the role creep that comes with promotions along the way. As tends to be the case, I was doing the work required of me by the job description, plus the work I thought I was uniquely capable of executing on.

For instance, I historically took it upon myself to get the most out of developer tooling, since it’s complementary to DevOps, and to focus on operational efficiencies like bringing many teams (and many more brands) onto shared services such as payments and identity - which is critical to maintaining a platform (vs a series of businesses under one roof). Those initiatives were delegated while I was away - either to engineers on my team or to IT - and the business hasn’t come crashing down as a result.

Aside: isn’t that always the case? You feel crucial until you’re gone, and then you realize people move on. You’ve probably done a better job of ‘working yourself out of a job’ than you give yourself credit for - which means you should probably scale up to bigger and better problems.

How to design it

So to wrap this up, what are my next steps?

1. Determine what I must do. What’s my job description?
2. Determine what I want to do. What fills my cup each day to allow me to keep doing the hard things?
3. Determine what I will stop doing. This was delegated but doesn’t go away. Someone is waiting to hand this back off to me.

Leave handed me a rare reset. I’m excited to come back thoughtfully.