Romesh Hettiarachchi
@romeshh.com
Toronto lawyer signallawyers.bsky.social
Chief lawtrepreneur.bsky.social
Web romeshh.com
Chief lawtrepreneur.bsky.social
Web romeshh.com
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Romesh Hettiarachchi
@romeshh.com
· Jul 15
Starting a daily writing challenge for next 30 days.
I'll be writing on the following
🤖 how businesses benefit from AI-enhanced legal advice
🧘🏼strategies that help lawyers build practices aligned with their wellness
🧠 the importance of financial/digital literacy for youth
Follow to learn more
I'll be writing on the following
🤖 how businesses benefit from AI-enhanced legal advice
🧘🏼strategies that help lawyers build practices aligned with their wellness
🧠 the importance of financial/digital literacy for youth
Follow to learn more
Three years ago, “vacations” still meant fielding client calls and checking emails every few hours.
Today, I take vacations where I actually disconnect - phone off, guilt-free, knowing my practice runs without me.
The difference: Running my business on an Operating System.
Today, I take vacations where I actually disconnect - phone off, guilt-free, knowing my practice runs without me.
The difference: Running my business on an Operating System.
August 4, 2025 at 1:38 PM
Three years ago, “vacations” still meant fielding client calls and checking emails every few hours.
Today, I take vacations where I actually disconnect - phone off, guilt-free, knowing my practice runs without me.
The difference: Running my business on an Operating System.
Today, I take vacations where I actually disconnect - phone off, guilt-free, knowing my practice runs without me.
The difference: Running my business on an Operating System.
Every successful business runs on two engines: a clear vision and systems that actually work.
But here's what most lawyers and business leaders get wrong: they build elaborate systems that fight against how they naturally work best.
But here's what most lawyers and business leaders get wrong: they build elaborate systems that fight against how they naturally work best.
August 3, 2025 at 6:04 PM
Every successful business runs on two engines: a clear vision and systems that actually work.
But here's what most lawyers and business leaders get wrong: they build elaborate systems that fight against how they naturally work best.
But here's what most lawyers and business leaders get wrong: they build elaborate systems that fight against how they naturally work best.
In less than a month, a new cohort of #lawstudents will start their first year at law school.
Here's my advice to them as they start this new journey:
Here's my advice to them as they start this new journey:
August 3, 2025 at 3:57 AM
In less than a month, a new cohort of #lawstudents will start their first year at law school.
Here's my advice to them as they start this new journey:
Here's my advice to them as they start this new journey:
At a time when so many are distracted by fads, Peter Drucker's insights on innovation and entrepreneurship continue to be relevant.
Key insight: Innovation is about spotting/exploiting opportunities that hide in plain sight.
Here's how to spot these opportunities:
Key insight: Innovation is about spotting/exploiting opportunities that hide in plain sight.
Here's how to spot these opportunities:
July 30, 2025 at 12:41 PM
At a time when so many are distracted by fads, Peter Drucker's insights on innovation and entrepreneurship continue to be relevant.
Key insight: Innovation is about spotting/exploiting opportunities that hide in plain sight.
Here's how to spot these opportunities:
Key insight: Innovation is about spotting/exploiting opportunities that hide in plain sight.
Here's how to spot these opportunities:
Most businesses struggle to explain why customers should choose them over anyone else.
Without a clear value proposition - an explanation why customers choose you over others - every business decision becomes expensive guesswork.
Here's a simple framework to answering the question "Why you?"
Without a clear value proposition - an explanation why customers choose you over others - every business decision becomes expensive guesswork.
Here's a simple framework to answering the question "Why you?"
July 29, 2025 at 12:27 PM
Most businesses struggle to explain why customers should choose them over anyone else.
Without a clear value proposition - an explanation why customers choose you over others - every business decision becomes expensive guesswork.
Here's a simple framework to answering the question "Why you?"
Without a clear value proposition - an explanation why customers choose you over others - every business decision becomes expensive guesswork.
Here's a simple framework to answering the question "Why you?"
Earlier this week, two Canadian legal luminaries argued that Supreme Court limits on lawyers for intervenors physically attending court deny "hands-on training in the advocacy crucible of the courtroom:" https://tgam.ca/3TTWRmM
Here's why their concerns reflect a profession removed from reality.
Here's why their concerns reflect a profession removed from reality.
It’s time to let lawyers come back to the Supreme Court of Canada - The Globe and Mail
Restrictions put in place during the COVID-19 pandemic have yet to be lifted, to the detriment of the court
tgam.ca
July 25, 2025 at 10:10 PM
Earlier this week, two Canadian legal luminaries argued that Supreme Court limits on lawyers for intervenors physically attending court deny "hands-on training in the advocacy crucible of the courtroom:" https://tgam.ca/3TTWRmM
Here's why their concerns reflect a profession removed from reality.
Here's why their concerns reflect a profession removed from reality.
When I started my solo practice, I thought having my own business meant finally controlling my schedule.
Reality hit differently.
For the first few years of starting, running a practice was full of challenges.
Here's how I shifted from grinding daily to creating momentum in my business.
Reality hit differently.
For the first few years of starting, running a practice was full of challenges.
Here's how I shifted from grinding daily to creating momentum in my business.
July 24, 2025 at 10:55 PM
When I started my solo practice, I thought having my own business meant finally controlling my schedule.
Reality hit differently.
For the first few years of starting, running a practice was full of challenges.
Here's how I shifted from grinding daily to creating momentum in my business.
Reality hit differently.
For the first few years of starting, running a practice was full of challenges.
Here's how I shifted from grinding daily to creating momentum in my business.
As a business lawyer, my success as a negotiator depends on having the most comprehensive and accurate information at all times.
The better my knowledge, the better outcomes I can achieve for clients.
I've found the same rule applies to running my practice. #ship30
The better my knowledge, the better outcomes I can achieve for clients.
I've found the same rule applies to running my practice. #ship30
July 23, 2025 at 12:13 PM
As a business lawyer, my success as a negotiator depends on having the most comprehensive and accurate information at all times.
The better my knowledge, the better outcomes I can achieve for clients.
I've found the same rule applies to running my practice. #ship30
The better my knowledge, the better outcomes I can achieve for clients.
I've found the same rule applies to running my practice. #ship30
Quick hack to use AI effectively:
Stop crafting prompts from scratch every single time. It's killing your productivity.
Use prompt engineering frameworks that deliver better results in less time.
My personal experience:
Stop crafting prompts from scratch every single time. It's killing your productivity.
Use prompt engineering frameworks that deliver better results in less time.
My personal experience:
July 21, 2025 at 2:00 PM
Quick hack to use AI effectively:
Stop crafting prompts from scratch every single time. It's killing your productivity.
Use prompt engineering frameworks that deliver better results in less time.
My personal experience:
Stop crafting prompts from scratch every single time. It's killing your productivity.
Use prompt engineering frameworks that deliver better results in less time.
My personal experience:
Law school taught me that meaningful sacrifice was the price of success.
A panic attack taught me the real price of success was my health, relationships, and sanity.
Here's why following all the right advice can read you to the wrong place.
A panic attack taught me the real price of success was my health, relationships, and sanity.
Here's why following all the right advice can read you to the wrong place.
July 20, 2025 at 6:24 PM
Law school taught me that meaningful sacrifice was the price of success.
A panic attack taught me the real price of success was my health, relationships, and sanity.
Here's why following all the right advice can read you to the wrong place.
A panic attack taught me the real price of success was my health, relationships, and sanity.
Here's why following all the right advice can read you to the wrong place.
The day I thought I was having a heart attack was when I realized law school had taught me to measure all the wrong things when it comes to success.
This is how I discovered the importance of reframing binary choices.
This is how I discovered the importance of reframing binary choices.
July 19, 2025 at 2:03 AM
The day I thought I was having a heart attack was when I realized law school had taught me to measure all the wrong things when it comes to success.
This is how I discovered the importance of reframing binary choices.
This is how I discovered the importance of reframing binary choices.
The older I get, the more I realize how often we are forced to choose between things we shouldn't have to choose between.
While these dichotomies may not be universal, exploring these false dichotomies have been integral to my growth over the last few years.
A few examples.
While these dichotomies may not be universal, exploring these false dichotomies have been integral to my growth over the last few years.
A few examples.
July 17, 2025 at 12:26 PM
The older I get, the more I realize how often we are forced to choose between things we shouldn't have to choose between.
While these dichotomies may not be universal, exploring these false dichotomies have been integral to my growth over the last few years.
A few examples.
While these dichotomies may not be universal, exploring these false dichotomies have been integral to my growth over the last few years.
A few examples.
This is my 3rd time going through Ship 30 for 30 - a cohort based daily writing challenge.
On each prior occasion, I did not complete the challenge due to my personal/professional commitments at the time.
Here's why I'm doing this challenge now & what to expect from my writing.
On each prior occasion, I did not complete the challenge due to my personal/professional commitments at the time.
Here's why I'm doing this challenge now & what to expect from my writing.
July 16, 2025 at 12:46 PM
This is my 3rd time going through Ship 30 for 30 - a cohort based daily writing challenge.
On each prior occasion, I did not complete the challenge due to my personal/professional commitments at the time.
Here's why I'm doing this challenge now & what to expect from my writing.
On each prior occasion, I did not complete the challenge due to my personal/professional commitments at the time.
Here's why I'm doing this challenge now & what to expect from my writing.
Starting a daily writing challenge for next 30 days.
I'll be writing on the following
🤖 how businesses benefit from AI-enhanced legal advice
🧘🏼strategies that help lawyers build practices aligned with their wellness
🧠 the importance of financial/digital literacy for youth
Follow to learn more
I'll be writing on the following
🤖 how businesses benefit from AI-enhanced legal advice
🧘🏼strategies that help lawyers build practices aligned with their wellness
🧠 the importance of financial/digital literacy for youth
Follow to learn more
July 15, 2025 at 12:29 PM
Starting a daily writing challenge for next 30 days.
I'll be writing on the following
🤖 how businesses benefit from AI-enhanced legal advice
🧘🏼strategies that help lawyers build practices aligned with their wellness
🧠 the importance of financial/digital literacy for youth
Follow to learn more
I'll be writing on the following
🤖 how businesses benefit from AI-enhanced legal advice
🧘🏼strategies that help lawyers build practices aligned with their wellness
🧠 the importance of financial/digital literacy for youth
Follow to learn more
Looking for support helping your child prepare for the future economy?
I'm creating a set of scenarios designed to help parents and educators develop tweens digital, financial and business literacy.
www.kickstarter.com/projects/law...
I'm creating a set of scenarios designed to help parents and educators develop tweens digital, financial and business literacy.
www.kickstarter.com/projects/law...
Lemonade Literacy: Turn Family Time Into Future-Ready Skills
Scenario-based learning that builds trust, strengthens bonds, and prepares kids aged 9- 14 for real life – no expertise required.
www.kickstarter.com
June 13, 2025 at 9:25 PM
Looking for support helping your child prepare for the future economy?
I'm creating a set of scenarios designed to help parents and educators develop tweens digital, financial and business literacy.
www.kickstarter.com/projects/law...
I'm creating a set of scenarios designed to help parents and educators develop tweens digital, financial and business literacy.
www.kickstarter.com/projects/law...
Reposted by Romesh Hettiarachchi
The great AI hiring pause is here, as a growing number of companies trade in human workers for bots to boost efficiency
The AI Hiring Pause Is Officially Here
A growing number of companies are using artificial intelligence to boost efficiency, sometimes at the expense of human headcount.
bloom.bg
May 17, 2025 at 1:45 PM
The great AI hiring pause is here, as a growing number of companies trade in human workers for bots to boost efficiency
Reposted by Romesh Hettiarachchi
Sharing this again for no reason whatsoever. Make sure your managing partner reads it.
commons.stmarytx.edu/cgi/viewcont...
commons.stmarytx.edu/cgi/viewcont...
April 11, 2025 at 8:07 PM
Sharing this again for no reason whatsoever. Make sure your managing partner reads it.
commons.stmarytx.edu/cgi/viewcont...
commons.stmarytx.edu/cgi/viewcont...
Reposted by Romesh Hettiarachchi
WH has now confirmed: this is insane nypost.com/2025/04/02/u...
April 3, 2025 at 12:17 AM
WH has now confirmed: this is insane nypost.com/2025/04/02/u...
Reposted by Romesh Hettiarachchi
Looking for an opportunity to better control the finances of your practice? lawtrepreneur.co/works…
We are hosting a workshop on Wednesday focused on helping lawyers better manage their money by leveraging the power of profit-first cash flow forecast.
We are hosting a workshop on Wednesday focused on helping lawyers better manage their money by leveraging the power of profit-first cash flow forecast.
March 31, 2025 at 7:46 PM
Looking for an opportunity to better control the finances of your practice? lawtrepreneur.co/works…
We are hosting a workshop on Wednesday focused on helping lawyers better manage their money by leveraging the power of profit-first cash flow forecast.
We are hosting a workshop on Wednesday focused on helping lawyers better manage their money by leveraging the power of profit-first cash flow forecast.
Are your innovation efforts focused on what excites you or what creates customer value?
My early experiments in integrating - and monetizing - AI in my practice was defined by how cool and advanced the technology was.
My early experiments in integrating - and monetizing - AI in my practice was defined by how cool and advanced the technology was.
March 26, 2025 at 10:23 AM
Are your innovation efforts focused on what excites you or what creates customer value?
My early experiments in integrating - and monetizing - AI in my practice was defined by how cool and advanced the technology was.
My early experiments in integrating - and monetizing - AI in my practice was defined by how cool and advanced the technology was.
Advice that applies to lawyers and business owners alike.
Struggling to grow revenue in your practice?
One reason for these struggles might be that your customers make purchasing decisions based on price alone - in which case you might need to find new customers.
It’s also possible you haven’t discovered what your customers value enough to pay more for.
One reason for these struggles might be that your customers make purchasing decisions based on price alone - in which case you might need to find new customers.
It’s also possible you haven’t discovered what your customers value enough to pay more for.
March 25, 2025 at 6:25 PM
Advice that applies to lawyers and business owners alike.
Reposted by Romesh Hettiarachchi
I helped build a government AI system. DOGE fired me, rolled the AI out to the whole agency, and implied the AI can do my job and the jobs of the others they've fired.
It can't. But, what DOGE accidentally revealed about themselves in the process is fascinating. 🧵
It can't. But, what DOGE accidentally revealed about themselves in the process is fascinating. 🧵
March 21, 2025 at 10:41 PM
I helped build a government AI system. DOGE fired me, rolled the AI out to the whole agency, and implied the AI can do my job and the jobs of the others they've fired.
It can't. But, what DOGE accidentally revealed about themselves in the process is fascinating. 🧵
It can't. But, what DOGE accidentally revealed about themselves in the process is fascinating. 🧵
Reposted by Romesh Hettiarachchi
Are you making enough profit to actually stay in business long-term (especially in a rapidly changing economy)?
Most law practices aren't.
Here's three reasons why management expert Peter Drucker believes profit serves three critical purposes and why that matters for your practice. #lawsky
Most law practices aren't.
Here's three reasons why management expert Peter Drucker believes profit serves three critical purposes and why that matters for your practice. #lawsky
March 22, 2025 at 2:09 PM
Are you making enough profit to actually stay in business long-term (especially in a rapidly changing economy)?
Most law practices aren't.
Here's three reasons why management expert Peter Drucker believes profit serves three critical purposes and why that matters for your practice. #lawsky
Most law practices aren't.
Here's three reasons why management expert Peter Drucker believes profit serves three critical purposes and why that matters for your practice. #lawsky
What if today's chaos is your greatest business opportunity?
Its easy to be overwhelmed with events/changes over last few months (years?).
I’ve maintained my mental health with the serenity prayer: serenity to accept things I can’t change, courage to change things I can, wisdom to know difference.
Its easy to be overwhelmed with events/changes over last few months (years?).
I’ve maintained my mental health with the serenity prayer: serenity to accept things I can’t change, courage to change things I can, wisdom to know difference.
March 21, 2025 at 12:23 PM
What if today's chaos is your greatest business opportunity?
Its easy to be overwhelmed with events/changes over last few months (years?).
I’ve maintained my mental health with the serenity prayer: serenity to accept things I can’t change, courage to change things I can, wisdom to know difference.
Its easy to be overwhelmed with events/changes over last few months (years?).
I’ve maintained my mental health with the serenity prayer: serenity to accept things I can’t change, courage to change things I can, wisdom to know difference.
Reposted by Romesh Hettiarachchi
Roses are red
Violets are blue
Violets are blue
March 20, 2025 at 5:43 PM
Roses are red
Violets are blue
Violets are blue