KRISTEL KRUUSTÜK: The yearly Kruustük family winter escape is a lot like the early days of building a startup

Winters in Estonia are dark and cold. Seasonal depression shows up right on time. Our skin turns an impressive shade of blue.

My Zoom video stops looking good, no matter how much beautifier I turn on. Like nature, I feel an overwhelming urge to hibernate.

But I can’t.

Because the world is moving fast. And Testlio can’t afford to be any slower.

So I open Kayak, Booking.com, and Airbnb and start looking for flights and a place to live. We need to leave. Preferably next week.

First question: where?

Testlio is a global company with teams and community members in more than 150 countries. So we pull up a map, look for somewhere warm, ideally in the southern hemisphere, and check where our people are. Better time zone alignment with Estonia is a bonus, especially since Marko, my co-founder, works closely with teams in the EMEA region.

For me, time zones matter less. I can represent Testlio from almost anywhere, as long as I am not joining all-hands or leadership meetings at 3 am or 11 pm.

Since 2020, this approach has taken us to Dubai, South Africa, Mauritius, and now Florida. We usually stay for one to two months.

If you are building a startup and still reading, you might be thinking this sounds easy. You can work from anywhere. Worst case, you grab a backpack and make it work.

Now add two children.

We have two sons. Artur is five. Aaron is seven.

Until last year, both were in kindergarten, and winter escapes were relatively simple. But this year, our oldest started school, and I worried this might lock us into the next twelve winters. The usual concerns surfaced. Routine. Friendships. Falling behind. Being the family that is always away.

Then there was the upside. The memories. The exposure to different cultures. The kind of learning no textbook can offer.

As startups do, we took the risk.

I spoke with Aaron’s teacher, made sure we would keep up with schoolwork, and got the green light. The relief was real.

So how do we do it?

We do not over-engineer it. We decide, then figure it out. Just like in the early startup days, you can list everything that might go wrong. Or you can focus on what might go right.

Comfort has never really suited us. When life in Estonia becomes too predictable, I start to feel uneasy. The last-minute planning is stressful and joyful at the same time. We operate in controlled chaos. There are arguments, heightened emotions, and yes, the occasional “väike sõnasõda” (small war of words - editor). But we always come back together and laugh about it later.

And yes, screens help. A lot.

Marko and I are both building Testlio. Traveling with young kids without outside help is intense. No amount of colouring books, quizzes, pools, playgrounds, or backyards replaces the quiet that a screen can buy you when you need it. This is not a parenting philosophy. It is survival.

Early mornings help too.

In the end, our winter escapes are not really about travel, weather, or productivity.

They are about sustainability. About choosing a way of living that allows us to keep building, leading, and showing up without burning out or becoming strangers to our own family life.

This only works because of people who make space for it. A school and a teacher willing to trust us. A partner who shares the same values and carries the load when things get hard. A family system built on support, flexibility, and many honest conversations.

This is not a formula. It is not a recommendation. It is simply a choice we keep making, knowing it comes with trade-offs, discomfort, and a fair amount of chaos.

Startups teach you that there is rarely a perfect moment. Family life teaches you the same.

So we leave. We adapt. We argue, we laugh, we make memories, and we keep building. Not because it is easy, but because for us, it is what makes this life enjoyable and sustainable.