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Josh Schachnow's Substack · Jun 17, 2026

The grass is always greener

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Josh Schachnow · Josh Schachnow's Substack

They say stereotypes exist for a reason. Boy do I agree.

As many of you fine readers know, over a year ago I expanded my law practice to include family law (the fun stuff like separation, divorce, etc.). I won’t go into full detail here but you can read my post here for more of the background.

One of the reasons was I got a bit bored of immigration law after about 8 years of it, lots of changes coming from the government, that kind of stuff.

And jumping into a new area of law was a fun challenge. I find family law to be very interesting and learning any new area of law usually has quite the initial learning curve to get over.

But a funny thing happened.

Around the exact same time I expanded into family law, I also had my first child, and boy has my life been different since then (for the better, of course). However, the more time I spent raising a very young family, the more time I spent thinking about how I wanted to go back to the area of law I knew well, felt more confident in and, believe it or not, was a bit easier and more “boring” to me.

Maybe the parents reading this can agree when I say that before I had my first child, work was the biggest part of my life and the meaning/passion/excitement from it was so important.

But now that our daughter is 17+ months old, running around the house and we’re planning to have more kids some day, I don’t mind if some of my work is a bit less exciting, more predictable and in some ways, boring.

Because my family time is anything but boring, and chasing around a 17 month old takes more energy out of this 35 year old than expected.

Don’t get me wrong, I still want to work on cool things, solve problems, build big businesses, all that fun stuff. But if some of the work is a bit predictable and boring, I don’t see it as such a bad thing anymore.

So all this is to say, I’m un-expanding my practice back out of family law, and mostly back to immigration. I don’t regret trying it because I learned a lot, met amazing people and scratched the itch I had, but found it wasn’t the right fit for me.

As they say, you live and you learn.

Have a great day,

Josh Schachnow

Canadian lawyer, CEO at Visto.ai

Who I can help:

  1. Anyone with Canadian immigration or family law matters in Toronto (separation, divorce, etc.), hit “reply” to see if I can help.

  2. If you’re trying to learn the basics of AI and how I’m able get way more done in less time, check out my course on how to build custom GPTs here;

  3. Family law firms in Ontario looking to do financial disclosure in half the time, check out Scio here;

  4. Immigration law firms in Canada looking to prepare immigration applications faster than ever before, check out Visto here.

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