Life after Startup – Pros and Cons of a “Workbatical”

Me getting up early to go to work before my family wakes up

Early morning work

It’s 02.00AM and I am wide awake. Probably it’s the 8 hour time difference between Rotterdam and Mexico City and a jet lag that I cannot seem to shake off.

I grab my phone and take the chance to get some work done before my wife and kid wake up.

By the time I am done with my tightly planned morning meetings between 07.00- 10AM, I have had a fully productive day.

Now I get to spend the rest of my day with my wife and kid exploring beautiful places and architectural highlights of Mexico City.

Obviously I would not recommend making this a full time way of living, however I was surprised how it’s possible to combine work with something I previously didn’t even dare doing: taking a sabbatical.

To be fair, it was not really the kind where no work was done for me. My wife had taken a 4 month break before starting something new.

And so we tried to make the most of it now that our kid was still in daycare and it’s easy to travel for a longer period of time.

For me this was mostly a “workbatical”, traveling with my family for 2 months, spread out over July and October, without losing much productivity.

Here is an overview of the pros and cons.

A bit of context: Working during holidays

During the past 15 years I got into the habit of taking longer holidays, but I always felt I needed to keep running a company with 20-35 employees, which would typically mean I would be on my phone at all times.

3 week holidays typically would look as follows:

Week 1: finish all work what I didn’t manage to finish

Week 2: actually relax

Week 3: ramp everything up to full steam working.

The only time in my life I actually put an out of office email was during my honeymoon, other than that I always managed to keep my inbox relatively empty by the time I got back.

As much as this made my working life more productive, it didn’t make me into a very fun travel companion.

Pros and cons of a Workbatical

Timing will never be easy I have learnt.

A sabbatical is a serious chunk of time taken out of your agenda, so it’s easy to keep putting it off.

But at the same time, taking time which would otherwise never be available, is what makes it so important to do this.

So here are a couple of pros, cons and coping mechanisms I came up with to make it possible.


My son had an absolute blast

⁃ I got to spend a great time with my family irregardless of whatever happened back home

⁃ Thanks to technology and wide availability of WiFi, I got to keep up a relatively high paced business with a team of people at the other side of the planet

⁃ I managed to travel to a completely new part of the world and really take the time to explore during the day

⁃ The 7-8 hour time difference allowed me to have most of the day relatively work free after 11.00AM.

⁃ I have a great team that thanks to clear OKRs (objectives and Key results) are relatively independent in pushing our goals forward.


Travel days were stressful

⁃ Even though you can plan for most things, I couldn’t really factor in last minute changes from projects that required my attention at odd hours.

⁃ Even though most fast paced work is possible to keep up with, larger deep focus work, like an extensive proposal, become pretty much impossible.

⁃ Time difference is your biggest friend and enemy. Having a 7-8 hour time difference meant I could switch off from 11.00AM onwards, but it also meant that within 1-2 hours I needed to communicate very quickly everything I needed before missing out to the next day.

⁃ Fitting 8 hours of work per day was extremely tough. I would mostly wake up at 3-6AM on average so I could at least get most work done before 10.00

⁃ This also overlapped with breakfast with my family, which made breakfasts short or distracted.

Coping mechanisms

In order to make it possible to be away for so long, especially in October, I came up with a couple of things that were necessary for me to keep the business running at high pace, without affecting it too much with my physical absence:

⁃ Clear OKRs: As mentioned earlier, my team is used to setting their own objectives and moving their own projects forward. This means that most of my emails or contacts could be limited to brief nudges in the right direction.

⁃ Tactical travel: after Mexico I needed to travel to New York for our next event, which is a relatively easy flight, and also in the same timezone, allowing for easy alignment.

⁃ Focus on quick nudges: when time is short, I mostly focus on providing clear and definitive answers to my team. Instead of providing long briefings, I would quickly connect them to the right people and let them resolve it directly with their counter parts.

Would I do it again?

This trip with my family has absolutely been one that I will always remember and cherish.

I also definitely would do another workbatical, as I do believe it can be hacked and perfected.

However I am not sure I would do another workbatical the way I did this one.

No matter how hard I tried to finish everything before 10AM, my wife still would notice me being distracted or tired during the day.

It’s not easy to keep up a very early schedule for a month, and also work requires those moments of deep focus.

Things I would definitely change for another extended “workbatical” abroad:

⁃ Have more balance of work for both me and my wife. If one person is completely on holiday while the other person isn’t, friction is bound to happen

⁃ Work more in “easy days”. If for instance you are staying on the beach and don’t plan to do much, it is easy for one of the two to take the morning to work, even on deep focus tasks.

⁃ Travel around less and stick to 1 place. As much as it can be fun to travel, it is also stressful in terms of keeping track of everything and it is super unstable and fragmented.

– Finally, also just plan a full week off in between, to give more focus on the sabbatical and the memories created.

This has been a blast, but now I am also looking forward to being back home with my family and our daily routines.

Also looking forward to hanging out in person again with my team of pirates!

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