Resort swimming pool with umbrellas and palm trees

Doing vacation right

Tweet stating most people in tech dont do vacation well

The timing of this tweet made me smile. I had recently returned from 8 nights away in paradise (Khao Lak, Thailand) at an adults only resort with the love of my life. I hadn’t checked Outlook or Microsoft Teams once. I was in a pretty good position to comment on how to be someone in tech who was good at vacation.


Except, I knew the full story.

I’d jumped in to a new, full time role at Microsoft and, fairly quickly, into a busy travel schedule. Even with a supportive manager, a supportive team and the ability to manage my own time to balance out travel fatigue and missed family weekends, months like this were common:

Wellness report showing 2 quiet days
Yes that’s only 2 days out of the month that I hadn’t touched a work app outside of my regular business hours. This had been my life for 9 months. Not because I was being pushed too hard by my employer, but because I loved my job so much and the social interactions with my North American teammates. Time zones suck for that, not to mention the date line.

In addition to that, I’d come from being self-employed for 14 years. Running a business that my husband worked in too. Supporting small business clients who depended on us. We’d taken two major family holidays in that time which both involved taking phones & a laptop & checking emails or working on projects. That recent Thailand holiday celebrated 20 years of marriage and was the first non-conference related trip we’d taken without the kids, since we started our business.

So, I was hardly in a position to lecture people in tech on how to do vacations.

I did comment about my recent trip, but I felt like it deserved a bigger explanation here. It was a personal decision to delete all work apps from my phone the day I left the country and to not reinstall them until I returned. But it was a decision that I was in a privileged position to be able to make. None of my work was time sensitive. Nothing that came up in my new role would require my unique knowledge or skills to resolve. My colleagues could handle it all. I would not be at the risk of losing a customer and my salary would still be paid.

Add on my previous management and technical roles and it had been a very, very long time since I’ve been in a position like this. And I’m so grateful for it.

Taking a break as a small IT business owner is a long whitepaper in itself, so instead let’s focus on people in IT Operations roles, or software developers supporting production applications.

In my experience, people in tech are bad at vacations for two reasons:
1.  We love our work
2.  Our workplace doesn’t support it

I haven’t found an easy fix for reason one. In fact, I could even argue that in the past my stress levels felt better knowing that I could log on each day, tidy up a few emails, and log off again knowing everything was under control. How could returning to Inbox 380 be a good thing?

Reason two concerns me more. It’s usually immediate team leaders that want you to take a real break, but there’s some tie to you as an individual that can prevent that. Maybe it’s your knowledge of a process. Maybe it’s your history with a system. Maybe someone remembered that you were involved in troubleshooting a similar outage before so surely a quick phonecall wouldn’t hurt.

We’re good at working on systems resiliency. We plan for backups, business continuity and disaster recovery. We manage changes and backout plans. And yet, especially in IT Operations roles, we still rely on individual people. And there are a bunch of reasons why this happens. Missing documentation. Service tickets completed in a rush without enough detail. No time to transfer knowledge to someone else when you’re busy maintaining servers, supporting desktops and rolling out applications.

I hope you didn’t come here looking for an answer, because I don’t have one. What I do see though are organizations that seem to be saying the right things about mental health in the workplace, work/life balance, and protecting their people. And yet I also still see tech people who don’t switch off during their vacation. Or don’t take their vacations. That needs to change. I talk about “stomping out super hero statements”. We need a cultural shift where “around here, our staff take leave without work interruptions.”

By the end of my 8 nights away, I was feeling restless. I wanted to dive back into my work again. I wanted to play with technology again. I was glad to get back to my team, back to my routine.

Everyone deserves that kind of mentally refreshing break. What are you doing to make that possible for your teammates, for your staff, and for yourself?


P.S I’m a strong believer that there’s no one right way to do “balance”. If your picture of downtime does not involve a beach or a rainforest, you go and do you. Also in the interests of full disclosure, this is being posted at 10pm so by some metrics, I’m already failing again. But this was on my heart, and I’m glad I could write & publish it before I leave for a conference tomorrow.

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