The “In-Cation” Challenge

Make the most of your PTO when traveling is… complicated

Photo: Jessica Christian | San Francisco Chronicle | Getty Images

I love to travel. It helps me build great stories, and develop new perspectives that make me a better engineer and leader. However, it’s 2020. Everything is closed, we’re stuck at home, and if you’re on the West Coast, the freakin’ sky is orange. Given everything going on in the world, I decided this year, rather than traveling out, to focus inward and take an “in-cation” where I’d shut off all work-related communications and focus on completing some items in my ever-growing backlog of side-projects. If you also are looking for ways to get the most out of your PTO without wanting or being able to travel, hopefully you’ll get some inspiration from this post.

What I’m proposing isn’t all that radical. Bill Gates used to take solo “in-cations” where he’d turn his focus away from work and disconnect. What I did here and what I recommend is similar in spirit and doesn’t necessarily require a fancy cabin in the woods.

In this think piece I’ll lay out some of the rules for this challenge that I stuck with, what I sought to get out of this using the OKR framework (feel free to choose a different technique if you like) and what I actually learned along the way. Hopefully this won’t come off as a humblebraggy piece about how some geek spent his comparatively lame vacation (believe me, I’d rather have been in Hawaii). My point is to illustrate that there is opportunity to be seized in the chaos and success belongs to those who can harness the power of perspective to see those opportunities.

The Rules

Treat this like any other vacation. Turn off Slack/Teams and log out of your company email.

Define a handful of goals for yourself. They don’t necessarily have to be career related, but should involve areas in which you’d like to improve as a person.

Write a schedule and add it to your calendar. Make it sync with your internal energy, so if you’re a night owl, don’t try getting up at 5:00AM. Just start when you’re ready. Build in time for breaks and have a cutoff time each evening to avoid burnout.

Don’t take anything about this too seriously and burn yourself out; that’s not the point. There’s no shame in not meeting an aggressive goal; you’ll still learn something. There is only shame in not trying.

How I Approached It

I like using Objectives and Key Results (OKRs) so I found some goals I wanted to achieve that were reasonable for one week off, assuming I’d be focussed for a 30 hour work week. Then I converted them into OKRs. Here are mine as an example:

Objective: Improve Product Management Skills

Key Result 1: Read one new book on leadership in the tech industry.
Key Result 2: Re-read one book with renewed context.

2011 Martin Eriksson

Reading up on new ideas is always a great idea for product leaders. I read The Hard Thing About Hard Things by Ben Horowitz to get a deep understanding of how great leaders make decisions and delegate authority to people most capable of solving product problems. Revisiting previous ideas with new context is also great as the ideas take on new life in their updated backgrounds. I read Inspired by Marty Cagan when I first joined Microsoft as a PM and while it all made sense at the time, I really didn’t see these product discovery concepts “click” until after my tenure with Microsoft and partway through leading new product development at OneLogin.

Objective: Improve Engineering Skills

Key Result 1: Solve 1 Leetcode / Hackerrank question each day.
Key Result 2: Use a technology I rarely use (for me, TypeScript & Deno).
Key Result 3: Complete 3 bookmarked ML tutorials.

Silicon Valley | HBO

1 Leetcode a day was where most of my discipline was required since Leetcode is not something I take a keen interest to. For this, it helped to set the goal at 1 and do just that. Once doing 1 a day became routine I increased to 2. The trick to building this discipline is like increasing reps or laps at the gym. Gradually increase the number of reps so you barely notice the trend and you’ll be doing 5 leetcodes a day before you know it.

Objective: Learn a New, Non-Work Related Skill

Key Result 1: Memorize 2 scales and their arpeggios.
Key Result 2: Learn 10 new chords.
Key Result 3: Learn 1 song.

There really isn’t a direct professional goal tied to learning an art. This was just a fun thing to do that’s different from stuff I normally do. Having interests outside your professional domain makes for interesting conversations and interesting friendships to develop. If you’re living to work and your life lacks aesthetic, you’re doing it wrong.

Bringing it Together

What I learned, over the course of this experiment was this. The power of both newfound and re-contextualized perspectives, gives rise to new and interesting “0 to 1” type ideas that are more easily discovered outside the context of daily work. Applying techniques from unrelated areas such as fitness was pivotal in finding the discipline to hone my otherwise neglected leetcode skills. Finally, learning a skill that is totally outside the normal day-to-day life strengthens lateral thinking, increases metacognition (understanding how you learn) and makes you generally a more interesting person.

I saw an abundance of vacation days and increased travel friction as an opportunity to stop making excuses for not working through my backlog of professional learning and side projects. You might see different opportunities in the current climate and I hope you make the best of them.

Software Engineer | Product Leader