1. I Should Have Learned Estonian From Day One

My first and most obvious regret is delaying the Estonian language.

I did eventually learn it. I passed my language exams and met the requirements needed for long-term integration. But there were years in between where I became comfortable speaking only English. Estonia makes that easy, especially in international workplaces.

That comfort came at a cost.

Language is not just about communication. In Estonia, it is access. Even learning a few words daily would have compounded over years into confidence, belonging, and professional leverage.

I should have treated language learning as a daily habit, not a future obligation. Small goals. No pressure. Just consistency.

After living in dozens of countries, I can say this clearly: learning the local language is a cheat code. Even three phrases change how people treat you. It signals effort, respect, and seriousness. That matters deeply in Estonian culture.

2. I Should Have Prioritized Financial Independence Much Earlier

When I arrived in Estonia, I was on a scholarship. I was young, curious, and more interested in experience than money.

Later, I got a job. It was stable. It was international. But financially, it had a ceiling. While Estonia offers excellent work-life balance and safety, life in Estonia becomes expensive quickly, especially if your income grows slower than inflation.

I made a critical mistake: I focused on methods instead of outcomes.

I tried saving aggressively. I tried switching fields. I even attempted learning skills that were fundamentally wrong for me. None of that worked.

What worked was shifting my focus to income itself. Side projects. Consulting. Content creation. Experimentation. Most attempts failed, but each failure taught me something practical.

My regret is not starting that process earlier.

Financial independence is not about copying what others do. It is about solving your own income problem with whatever tools you have. Estonia rewards self-direction, but only if you start early.

3. I Should Have Bought Property When I Had the Chance

In 2014, property prices in Tallinn were reasonable. Areas like Kalamaja were just beginning to transform. Kopli was still considered undesirable.

I rented instead, assuming I would leave Estonia eventually.

Nine years later, I learned how wrong that assumption was.

When my landlord asked me to move out, I realized the rental market had changed completely. Meanwhile, people who arrived around the same time as me had bought apartments. Some rented them out. Others lived with stability and peace of mind.

Owning property in Estonia is not just a financial decision. It is psychological security.

Even people with modest jobs managed to buy homes. I could have done the same if I had prioritized it earlier instead of treating life as temporary.

If I moved to another country today and planned to stay, I would aim for ownership as soon as realistically possible.

4. I Should Have Protected My Mental Health From the Start

This is the regret that cost me the most.

Moving abroad looks exciting. In reality, it dismantles your support system overnight. Family, friends, food, climate, culture, familiarity—all gone.

Estonia adds another layer: long winters, limited daylight, reserved social behavior, and cultural distance. Over time, these things accumulate.

I ignored the warning signs. I worked harder instead of resting. I normalized loneliness. Eventually, I crashed.

Therapy and medication helped, but I wish I had been proactive. Sleep. Physical movement. Community. Travel breaks. Self-compassion.

Even Estonians leave during winter when they can. Expecting yourself to endure silently is unnecessary and dangerous.

There is no reward for suffering quietly.

5. I Regret Not Standing Up to Bullies Earlier

This is the hardest regret to admit.

As a first-generation immigrant, you carry something called immigrant guilt. You feel lucky. You feel replaceable. You feel indebted to the country that accepted you.

That fear makes you silent when you should speak.

I encountered discrimination. Racism. Unfair treatment. I often stayed quiet because I did not want attention. I did not want visa problems. I did not want trouble.

That silence empowers bullies.

Immigrants are not charity cases. They contribute economically. They pay taxes. They sustain systems. Estonia benefits from skilled immigration. This is not generosity—it is mutual interest.

Standing up does not make you ungrateful. It makes boundaries visible.

I eventually learned to speak up, but I regret the times I didn’t. Not just for myself, but for the people who came after me.