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Jonathan Wong
Jonathan Wong

Posted on • Originally published at blog.jonanata.com on

Sakura Migration   

Not long ago I visited UBC, where the Sakura blossoms were in full bloom again.

It reminded me of the first time I saw them decades ago in Japan, when I was working inside a 200‑person IT department. That was the on‑prem era. Everything lived in racks and server rooms. Everything felt stable, predictable, and physical. I thought my career would stay that way.

But life moves. Sometimes quietly. Sometimes without a plan.

Later I met Notey, and that was the beginning of my startup journey. I moved from enterprise structure to startup speed. From on‑prem systems to the cloud. From a single role to wearing multiple hats. That was my first migration, not geographical but mental. A shift in how I saw technology, teams, and myself.

I moved to Boxful next. Built an MVP that helped secure funding. Shifted from development to product. From proprietary stacks to open source. From execution to ownership. Another migration. Another environment. Another version of myself.

After that chapter, I joined venture builders, Flatiron, helping capital create new startups. Moving from building one company to helping many. From operator to enabler. From solving problems to designing systems that solve problems. Another migration.

Eventually, the Startup Visa program brought me to Vancouver. From East Asia to North America. From familiar ground to a new ecosystem. From the world I grew up into the world I chose. A migration across continents, but also across identity.

Walking past the students on UBC’s campus takes me back to when I was an undergraduate, excited about my first Yahoo email. At the time, I believed I would be happy coding every day. But the world kept shifting. We moved from desktop to cloud, then to mobile, and now to AI, where skills can be downloaded and coding itself is being redefined. Another migration. Another environment. Another identity.

Looking back, none of these migrations were planned. They happened one step at a time. Each one pulled me into a new environment and forced me to grow in ways I never anticipated.

There were migrations in scale. Migrations in technology. Migrations in geography. Migrations in identity.

Those who pause beneath the Sakura on UBC’s Memorial Road often say the trees were brought from Japan and replanted here. They blossom every year in a way you cannot find anywhere else. They did not choose the journey, yet they grew. And they became something unique because of the journey, not in spite of it.

Are you someone shaped by migrations.

What has been your latest migration.

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