All Articles

July 2024

09-07-2024
174 - Do you work in an organization where everybody works one level lower than they should?
Career Design Leadership and Org culture
Micromanagement tends to roll down. Everybody works one level lower than they should—this is the cascade of micromanagement. Your boss’s boss meddles in your boss’s work; your boss does your work; and you do your report’s work; and so on. ...
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June 2024

21-06-2024
173 - The negotiating trick few talk about
Career Design Leadership and Org culture
Negotiations are won by whoever cares less. We know this in our bones, yet tune it out too often. ...
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11-06-2024
172 - The difference between informing and evoking
Leadership and Org culture Personal Development
This newsletter has talked about the difference between feedback and observations. Feedback, especially in professional settings, has got the air of walking on eggshells. It is hard to get it right and harder for it to be consistently effective. ...
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May 2024

11-05-2024
171 - Why is it so hard to say NO?
Personal Development
The difficulty in saying NO is a common one. I have family who’ve never refused a dinner invitation. Friends who would rip out a fingernail than turn someone down. ...
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April 2024

21-04-2024
170 - Essence of strategy, rationalization, and a question on processing emotions
Decision Making Personal Development
For anyone who has worked in Business Development or in Ops, they would be familiar with a tension that simmers all through the year. ...
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11-04-2024
169 - Feedback, observation, and coaching
Personal Development Leadership
Over the last six months or so, I’ve clocked hours doing, what I’ve come to learn is, internal and external coaching. At work, I’ve done consistent hours of mentoring/coaching and I’ve been lucky enough to have a few paid coaching clients. ...
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05-04-2024
168 - Are you solving a higher class of problems today compared to yesterday?
Career Design
No matter who you are or what you do, there’s a consequence to solving problems. It is inevitable. The problems you solve today will create opportunities tomorrow, no doubt. They will also bring you a new set of problems. ...
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March 2024

21-03-2024
167 - Skeptical and open-minded - operating in two modes at the workplace
Career Design Leadership and Org culture
At some point in my job, I started functioning in two modes. ...
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18-03-2024
166 - Learning from my younger selves
Personal Development
My eyes are shut. I’m wide awake in my head. I know it. I also know that at this moment before day break, as the darkness bleeds under my eyelids, on this already warm summer morning, I’m dead and buried. Before I’ve wrapped my fingers around my phone on the bedside table, I know. It’s another night of broken sleep, another one of those broken R90 sleep cycles as all those podcasts say. I open my eyes to check why. ...
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14-03-2024
165 - What's the big deal about being independent?
Personal Development Career Design
Seth Godin says in a recent episode on his podcast Akimbo that every big problem that seems to have been solved solo has actually been solved by a non-coordinated group. Even Einstein, Godin cites as an example, stood on the shoulders of giants before him to come up with a new paradigm for spacetime. ...
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11-03-2024
164 - Three questions for your work and life
Personal Development Career Design Miscellaneous
Here are three ideas to consider and three questions to ask yourself this week: ...
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07-03-2024
163 - What does your report likely mean when she says she wants to do new things?
Leadership and Org culture
Several times in my career, I’ve heard this and I’ve said this: “I want to do new things; I want to grow; I don’t want to just keep doing the same thing again and again.”...
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04-03-2024
162 - Laziness is exhaustion
Habit Building
A client of mine who’s a clinician recently told me she feels happy any time her first patient of the day (8am slot) cancels, but right after she feels guilty for feeling good about not working....
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01-03-2024
161 - SMART goals are doing your team harm
Leadership and Org culture
SMART goals can be counterproductive for your team or business unit. This runs contrary to popular belief. ...
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February 2024

27-02-2024
160 - “Do you think trying to adopt a leadership style that’s not your natural style could backfire?”
Leadership and Org culture
Last week, I published a piece on managing a transition in your career: role change, job change, or both. The piece made the point that the optimal leadership style is situation-dependent. A go-go-go leader who can see the firm through a...
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24-02-2024
159 - Tracking a lion, or a life
Career Design Personal Development
We adopted a rescue a couple of months ago. Before, we had Scotch, a British cocker spaniel, for fourteen years. He lived a full life, giving us no trouble with his eating or with his docile temperament....
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21-02-2024
158 - Managing yourself during a transition
Career Design
When Elon Musk took over Twitter, he swooped in like a hero. He didn’t wait to assess things, didn’t talk to the old-timers to get a sense of the history, he only saw fires that he wanted to put out....
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18-02-2024
157 - Searching for Originality
Personal Development
When Thomas P F Hoving, the late celebrated art historian, writer, and Director of the Metropolitan Museum of Art—the fourth largest art museum in the world, was a second-year undergrad art student (the Americans call it sophomore year)...
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15-02-2024
156 - How to spend your time in the first 90 days
Career Design
In a new organization or a new role or both, how should you spend your learning time during your onboarding? ...
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12-02-2024
155- Just knowledge does not change behavior
Miscellaneous
If you're anything like me, you're probably consistently late with your tax investment declarations or your reimbursement proof submissions. I ignore reminders, breeze past deadlines, and am generally notorious with these...
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09-02-2024
154 - Two stories about humility training
Personal Development
On Wednesday, I met a friend who was visiting town. Over breakfast, he shared a story with me. ...
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06-02-2024
153 - What we want from a job
Career Design
In what we want most from a job there’s a paradox: we don’t know what we want more—great work or a great work culture? ...
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03-02-2024
152 The “even more” strategy
Decision Making Leadership and Org culture
One year, at our annual offsite, the company leadership shared the mantra for the year: the Genius of the AND. ...
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January 2024

31-01-2024
151 Would you rather be disciplined or devoted?
Personal Development Career Design
Why do we value one at the cost of the other? ...
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28-01-2024
150 When working for free makes sense
Career Design
Why working for free during an internship makes sense ...
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25-01-2024
149 - Making the other person run out of things to say
Leadership and Org culture
The Drama Triangle and our roles in it ...
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22-01-2024
148 - Head without heart is a logic bully
Leadership and Org culture
The boss, a marketing director, has been pulled into an urgent one-on-one by his brand manager. The boss’s day is already packed but he’s made an exception for her....
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19-01-2024
147 - Shepard tone - how to run multiple projects in parallel
Personal Development
I’m working on a longer piece and that’s keeping me occupied far longer than what I had accounted for. I think there’s enough potential juice in that squeeze so I aim to keep going. Meanwhile, here’s a thought that’s ready for you....
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13-01-2024
146 - Why is the quest for mastery embarrassing?
Personal Development
The human cost of pursuing mastery: The hard apprenticeships of Robert Caro and Leonardo da Vinci ...
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10-01-2024
145 - Why AI may not leave us jobless, why Will Hunting should not lay bricks, and why Virat Kohli should stay away from aerobics
Career Design
from aerobics ...
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07-01-2024
144 - The power of putting first things first
Personal Development
After Christopher Nolan had finished the script for Oppenheimer, he first took it to his longtime visual effects supervisor Andrew Jackson. The fulcrum for the story, as Nolan calls it, was the Trinity Test. Nolan, as always, didn’t...
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04-01-2024
142 - The casually curious die early at the altar of pragmatism
Personal Development
It’s a December afternoon. I’m sitting in my living room, my straightened-out legs making a bridge between the couch and the coffee table, with the laptop balanced on it, when the thought occurs to me: I’ve been here before....
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01-01-2024
141 - The inefficiency is the point
Personal Development
Friction and intentionality ...
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December 2023

29-12-2023
140 - Be the only, not the best—the overlooked lesson in building a career
Career Design
I’m sitting at my desk in Mr. Ambrose’s class and I’m annoyed. I have before me a blank page I have to fill up. It’s only halfway through the term in grade nine, yet I feel like I’ve been here this term a million times already....
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26-12-2023
139 - Why do we hire talent like we’re buying a boring car?
Leadership and Org culture
How to reduce the problem of workforce homogeneity ...
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23-12-2023
139 - What you didn’t know about your emotions
Personal Development
How to get your brain to reconstruct reality the way you want it to ...
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20-12-2023
138 - What causes success?
Entrepreneurship Leadership and Org culture
‘And so you start to wonder—what correlates the most to success—team, product, or market? Or, more bluntly, what causes success? And, for those of us who are students of startup failure—what’s most dangerous: a bad team, a weak...
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17-12-2023
137 - Managing how people see you at work
Career Design
Setting your narrative and course-correcting ...
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14-12-2023
136 - Akbar, don’t worry about Birbal
Leadership and Org culture
How to overcome the loss of your domain-specific expert in your org or team ...
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11-12-2023
135 - Second-Order Thinking: The Seen and Oh, the Unseen (Part 3 of 3)
Decision Making
Part 3 of 3 in series on Visualization Techniques in Decision-Making ...
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08-12-2023
134 - Visualization Techniques in Decision-Making (Part 2 of 3)
Decision Making
Right then, on to a new week and a new year. Two weeks ago, in issue #132, I wrote about a trait that’s unique to us humans among all animal species: mental time travel. We can move back and forth in time, imagine possibilities, and...
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05-12-2023
133 - 2024 - a year in preview
Miscellaneous
Writing like cooking, learning like playing, and being helpful ...
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02-12-2023
130 - How about a career with (probably) the worst feedback loop?
Career Design
If the accuracy and frequency of the feedback loop came written on the label of the career you have chosen, would you have made the same choice?...
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November 2023

29-11-2023
129 - Why should we believe in the wisdom of the crowd? And when should we not?
Decision Making
1906. Plymouth, England. Country fair. Some livestock and poultry show, actually. A fat ox. A Joe-Biden-old statistician has an itchy idea that he wishes to scratch. But it’s not easy to pull off what he has in mind. So he comes up with a...
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26-11-2023
128 - How to Improve Your Ideas ~~By Working Harder Alone~~
Career Design
I outline the process of improving your ideas at work. This is a non-negotiable skill for knowledge workers in any creative market. We all have to build an air-tight business case for things we believe will make a difference. If we...
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23-11-2023
126 - The Stories We Tell Ourselves
Decision Making
Recording of last weekend’s session on decision frames ...
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20-11-2023
125 - Nine Tiny Thoughts from September and October
Miscellaneous
These tiny thoughts—most of them the words and ideas of luminaries in their fields—cover the themes of cognition, perception, and intuition; holding an opinion; and working with others....
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17-11-2023
124 - How to Escape Being a Rich and Wretched Entrepreneur
Entrepreneurship
Rethinking Rules: The Netflix Approach to Building an Innovation Culture ...
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14-11-2023
123 - Six rules that I follow as personal commandments
Personal Development
Part 1 of 2 on how to use rules to your advantage ...
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11-11-2023
121 - Getting Better by Goofing up (Intentionally)
Personal Development Entrepreneurship
How to Get Better by Going against Company Policy ...
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08-11-2023
120 - Two Kinds of Risk, Four Kinds of Luck and _That_ Worst Outcome
Career Design Decision Making
Managing your odds for career success ...
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05-11-2023
118 - Risk and Expected Value and the Mistakes We Make with Them
Decision Making
When making a decision, people tend to think too much of risk and not enough about the expected value. ...
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02-11-2023
117 - Should This, Not Can this, Product be Built?
Entrepreneurship
Startup-building is hard. New ventures operate in uncertainty. So it is inevitable that there’ll be waste but there are many levels of waste. The trick is to find the most acceptable level of waste by following a lean approach....
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October 2023

30-10-2023
116 - The slippery slope of hypothesis-less entrepreneurship
Entrepreneurship
For the last year and across multiple stints before that, I’ve worked toward getting pre-product-market-fit startups (products and services) off the ground....
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27-10-2023
115 - The Status Quo Trap
Decision Making Career Design
How to reduce the lingering power of the status quo ...
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24-10-2023
114 - TWO SELVES
Miscellaneous
Scotch ...
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21-10-2023
113 - Is this a success or a failure—the value of reference points in framing decisions
Decision Making
This is a now-famous example from a [1984 paper](http://courses.washington.edu/pbafhall/514/514%20Readings/choices%20values%20and%20frames.pdf) by psychologists...
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18-10-2023
112 - Bargains and Rip-offs
Decision Making
LI promo: We buy things we may not have use for just because they’re available at a price lower than we expect. We reject perfectly useful things we need simply because we believe their correct price in our judgment should be lower....
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15-10-2023
111 - Commander’s Intent and That Sweet Spot between Micromanaging and Abandoning
Leadership and Org culture
‘In a principal-agent model,’ writes Nobel Laureate Richard Thaler in Misbehaving, ‘the principal is the boss, often the owner of a firm, and the agent is someone to whom authority is delegated.’...
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12-10-2023
109 - Building for the Future: Investment in Loss (Part 2 of 2)
Career Design
Last week I asked a question. What do you look for in a hire for your early-stage startup, for your less-than-30-member unit, or for your tiny 0-to-1 unit? We explored ex-Meta and ex-CZI operator [Molly Graham’s...
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09-10-2023
108 - Building for the Future: The J-Curve or The Stairs? (Part 1 of 2)
Career Design
In the middle of 2021, I was heading a small business unit that was building a [smart writing assistant](https://paperpal.com/). The product was to be available as a web app, a plugin, and an online editor. We were...
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06-10-2023
107 - Chasing Greatness: Shoot for the Moon but Only If You Can Train the Monkey First (Part 2 of 2)
Career Design Personal Development
Henry VIII ruled over England with an iron fist for thirty-six years. For much of the second half of his reign, their king’s foul mood concerned Parliament. Word went that Henry VIII’s famed temper was down to leg ulcers. Painful and...
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03-10-2023
106 - Two proven ways of chasing greatness (Part 1 of 2)
Career Design Personal Development
You have permission to follow your curiosity (Part 1 of 2) ...
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September 2023

30-09-2023
105 - The Art of Learning
Personal Development
I faced a crisis at sixteen when I entered junior college. I was thrust into a period of intense preparation for competitive exams for undergrad admissions. A ranker through school, I was unsettled by the depth in competition. I...
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27-09-2023
104 - Odds and ends
Decision Making
What happens in groups happens to individuals as well ...
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24-09-2023
103 - The Truly Ambitious Hate False Progress
Entrepreneurship
If you have worked in operations (or taken an operations research course in business school), it is likely that you would’ve heard about the theory of constraints....
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21-09-2023
102 - Keep calm and be like Van Gogh
Career Design Personal Development
The perils of making up your mind too early ...
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18-09-2023
101 - Great leaders enjoy the deepest level of our permission
Leadership and Org culture
Learning permission marketing from an ex train ticket examiner ...
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15-09-2023
100 - Opportunity Costs: Have you thought of what you’re giving up?
Decision Making Career Design
Intrinsic motivation in a species is said to be correlated to the size of the brain relative to the body. Bigger the brain relative to the body, more driven is the species to exercise it for fun or for challenging things. That explains...
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12-09-2023
99 - ‘Real options’ thinking: Win the right, lose the obligation
Decision Making Entrepreneurship
(why firms are better off thinking like venture capitalists) ...
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09-09-2023
98 - How to build better decision frames
Decision Making
No frame is complete. So, don’t stop at just one. Mix and match. This essay shows you 5 ways to build new frames: ...
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06-09-2023
97 - Do your thinking frames serve you well?
Decision Making Leadership and Org culture
Some ways of looking at the world are unhelpful. One of them is imagining the world as opposing forces in a competing frame. I win, you lose. Locked forever in perfect competition....
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03-09-2023
96 - How to move from frame blindness to frame control
Decision Making
Imagine you’re one of the best at what you do. You get paid in millions. And suddenly you get dumped. You’re not fired but your services are no longer integral to the success of your team. If you haven’t guessed already, this happens in...
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August 2023

31-08-2023
95 - Practical leadership—lessons from…
Leadership and Org culture
Takeaways: 1. As a leader, it's ok to want to be on top of things. Don't let that make you anxious. Set up a system for fixing...
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28-08-2023
94 - Looking beyond dead ends
Decision Making
More than a decade ago I was at a company offsite where I was introduced to the phrase ‘The Genius of the AND and the Tyranny of the OR.’ I believe it was from Jim Collins’ Built to Last....
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25-08-2023
93 - How to resolve the stickiest conflicts
Decision Making Entrepreneurship
Every business leader, executive, senior manager, and founder has faced this question at some point, yet coverage of the topic is full of tropes. At least, I couldn’t find much beyond that in popular literature. So I looked deeper....
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22-08-2023
92 - How did Iceland get its teenagers to swap the high of drugs and alcohol for the high of sports?
Decision Making Leadership and Org culture
Plus: Why do organizations stop learning? ...
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19-08-2023
91 - The future is uncertain but in us we have a key
Decision Making
The paradox ...
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16-08-2023
90 - Power laws
Personal Development
Doing something the best way possible is 10X better than doing something in just a good way ...
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13-08-2023
89 - Decision categorization
Decision Making
The beauty of having a sound framework for decision-making is that it can clarify your approach to work both at a day-to-day and long-term level....
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10-08-2023
88 - Two principles I aim to follow moving forward:
Personal Development
The way to a (wo)man’s mind is through stories. ...
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07-08-2023
87 - Habit-building 15: Cashing out > Cashing in
Habit Building
I’ve been facing a challenge that you may be familiar with. The question of whether or not to stop mid-flow. ...
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04-08-2023
86 - Habit-building 14: Building a habit MVP
Habit Building
Product managers and designers are obsessed with reducing friction for users. It’s not unusual to find them laboring over the smallest detail, like the placement of a text field or the number of clicks to checkout. While to the untrained eye it may seem like making a mountain out of a molehill, the golden rule for any habit-forming product is to make it easy for users. ...
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01-08-2023
85 - Habit-building 13: The power of a motivation ritual and how TikTok does it
Habit Building
There’s a TikTok commercial doing the rounds. You may have seen it. It’s called Mystery Apartment Girl. ...
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July 2023

29-07-2023
84 - Habit-building 12: Habits at scale is culture
Habit Building
Imagine yourself, young and nervous. You’ve gathered the courage to sidle up to your mother and tell her that you’ve decided to drop out of college to start a T-shirt company. As you try and stitch the words right, your grandmother walks in and chimes “Like mother, like daughter.” Newsflash: Your mother had dropped out of school to start something on her own. Suddenly, a weight is off you. ...
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26-07-2023
83 - Habit-building 11: Building habits by hooking up with a crew
Habit Building
My mother believed kite flying to be a dangerous sport. She would go back years to recount all neighborhood accidents when kids, chasing kites, had fallen off rooftops. She also made this clear to my friends. I was thus forced to fly kites by myself on the sly. For those unfamiliar, kite flying needs prep (coating thread with powdered glass) and shared knowledge to succeed (kite-cutting, reeling in). ...
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23-07-2023
82 - Habit-building 10: How to make a habit attractive
Habit Building
What is common to Pepsodent, Febreze, and Dettol? ...
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20-07-2023
81 - Habit-building 9: Design your environment for good habits
Habit Building
Between my wife and I, we have a top priority. Make the milk sipper disappear. We agree that’s the only way for us to maintain a semblance of mealtimes for our 20-month-old toddler. The alternative is to have the day disrupted several times by the chirp of “Milk! Milk!” because of the sight of a stray milk sipper. ...
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17-07-2023
80 - Habit-building 8: A surefire way of starting a habit that will last
Habit Building
I’ve decided to start eating healthy several times in my life. Any success has only lasted a short period. And then, like a rubber band, I’ve snapped right back. This is called regression to the mean but you don’t need to know that to get what I’m talking about. Because we’ve all been there. ...
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14-07-2023
79 - Habit-building 7: Have you noticed your cue?
Habit Building
One doesn’t need to be a hypnotist today to convince anyone of the need to brush their teeth. But in the early 1900s, even such a person wasn’t enough. ...
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11-07-2023
78 - Habit-building 6: Hacking the habit loop
Habit Building
Every action has a cost and a benefit. You would think that you do something only if the benefit is more than the cost. But I will argue that you’re likely to do something, perhaps consistently too, even when the costs outweigh the benefits. By simply having the benefits first, you can be made to do something that is of net negative value. ...
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08-07-2023
77 - Habit-building 5: Understanding the habit loop
Habit Building
You now identify yourself as the person you want to be. With that as the kickstarter for the ‘New Me’ campaign, you start canvassing votes. Every action or behavior aligned with the ‘New Me’ is a vote you need. But with voting we know that even with the best intentions, it is too easy to forget or procrastinate. How do you stop yourself from flaking out? ...
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05-07-2023
76 - Habit-building 4: Identity is the root; behavior, the flower
Habit Building
How we see things affects how we feel about things and how we feel about things shapes how we act. ...
Read
02-07-2023
75 - Habit-building 3: Use fresh starts to change your identity
Habit Building
We tend to repeat any routine that makes us happy. Problem is lots of things feel short-term blissful while being long-term harmful. ...
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June 2023

29-06-2023
74 - Habit-Building 2: What’s your internal flywheel?
Habit Building
There’s a fundamental problem with how we approach habit-building. This problem arguably is the biggest reason for our failure to meaningfully change. The problem is this: we try to change what we do without first changing who we are. ...
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26-06-2023
73 - Habit-Building 1: If you want to build a lasting habit, ask yourself: ‘Who am I voting to power?’
Habit Building
I had good grades through school. Freshman year and they started falling. ‘I’m smart,’ I reassured myself. I waited for things to change. ...
Read
23-06-2023
72 - Tilt in decision-making and 3 ways to avoid it
Decision Making
Imagine a day where you open your inbox to a stinker. It’s the last one in, but there’s no doubt it has to be the first one out. You respond with a suitably charged email to refute the hideous allegations made against you. Thankfully though, from that point on, your day goes on to break even. ...
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20-06-2023
71 - Three practices to become a better decision-maker
Decision Making
Here are three simple practices to get you started on the path to better decisions. I’ve distilled them from a wonderful interview of neuroscientist and author Lisa Barrett on The Knowledge Project podcast. ...
Read
17-06-2023
70 - Deal with success or have it eat you up.
Decision Making
It may seem odd to worry about a positive outcome, but that’s exactly what we need to do to avoid being snowed under. ...
Read
14-06-2023
69 - Do you have a ‘local foreigner’ in your life?
Decision Making
I want to tell you about something that you understand but underestimate the value of in making your life better. And it’s not just you. I’m the same. That something is the idea of a ‘local foreigner’. ...
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11-06-2023
68 - Second-order thinking: carefully count what you see and find out what you don’t
Decision Making
Second-order thinking makes us imagine the unseen problems and opportunities created by every action we take. ...
Read
08-06-2023
67 - Introducing pause in rash decisions - the 10/10/10 method
Decision Making
If you find yourself making rash decisions or agonizing over decisions, this is for you. ...
Read
05-06-2023
66 - Mental models are keyboard shortcuts
Decision Making
What is different about how technophiles and power users use computers? ...
Read
02-06-2023
65 - Second-order thinking for organizational decision-making
Decision Making
When we think of a decision we look at the effect it may have. And then we stop. But the effect has an effect too. Second-order thinking is thinking about the effect of the effect. The need for it becomes clear when you look at how organizations design incentives. ...
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May 2023

30-05-2023
64 - The very powerful decision-hygiene habit of time travel
Decision Making
There’s a basic but powerful decision hygiene habit that few of us practice: time travel. It may sound outlandish, something you thought only happened in sci-fi dramas. It’s anything but. ...
Read
27-05-2023
63 - The power of thought experiments in making decisions in uncertainty
Decision Making
The difference between humans and other species on earth is that we can shift both back and ahead in time, while the rest can only go back. ...
Read
24-05-2023
62 - Premortems: why you should kill your dream project to save it
Decision Making
We agree that talking about failure is healthy, but we forget to think about failing ahead of time. ...
Read
21-05-2023
61 - Mental contrasting and the practice of WOOP
Decision Making
You’re brushing your teeth in the morning and imagining an important presentation later in the day. You picture yourself setting the table for the problem, laying out the options, and winning the audience’s vote for a desired solution. You’ve quick answers and there’s not a moment you go off script. What may actually transpire, the reality of it is something that you don’t consider. ...
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18-05-2023
60 - The Barbell Strategy for personal decision-making
Decision Making
Taking a number of small but extreme non-consensus risks means you’ll be wrong and pay a penalty for most of these risky bets. It’ll also mean two other things: ...
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15-05-2023
59 - The Forbidden Fruit Theory for org decision-making
Decision Making
Anyone who has had to hire someone will know this. You’ve a shortlist of candidates for a position. You’re undecided. Until you receive word from one of the candidates (let’s call him Dilbert) that he has received another offer. Suddenly, Dilbert’s value shoots up. Why? ...
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12-05-2023
58 - The young professional’s guide to persuasion
Decision Making
You’re probably going to scroll past this but if you ever have found getting alignment at work challenging, my Persuasion framework is just for you. ...
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09-05-2023
57 - Reverse-engineering the present from the future through backcasting
Decision Making
The problem’s that we plan looking forward but we can see more looking back. ...
Read
06-05-2023
56 - Using the Area Under the Curve Framework to categorize risk
Decision Making
All day, every day, you’re being bombarded with problems that need solving. Here’s a simple framework that’ll help put things in perspective so that you don’t lose sleep over an ant bite or sleep through a snake bite. ...
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03-05-2023
55 - Changing uncertainty to a risk range
Decision Making
You’re at the airport. You see a DELAYED against your flight on the display board. What would you think: Should I call and cancel the meeting I’m traveling for OR I’m sure this is nothing? ...
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April 2023

30-04-2023
54 - Why do we tend to go with the tried and tested for big decisions?
Habit Building
We often hawk ourselves like potatoes when it matters. Even when we’re zucchini or asparagus or anything but a potato. Why? ...
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27-04-2023
53 - What’s missing in how we hire?
Decision Making
Conversations around workplace diversity are often hot potatoes. But they miss a crucial ingredient: the potato. ...
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24-04-2023
52 - Deciding on normal
Decision Making
When moving between projects, teams, jobs, careers, have you ever thought about how what is acceptable often changes with the environment. ...
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21-04-2023
51 - The pain of sticking to commitments: inside and outside views
Decision Making
I was twenty-five and I was reporting to one of the co-founders. We were launching a new global website and my job was to collate/write news stories and populate the news section. I think it came to around 25 news pieces. I did some math, banking mostly on my writing speed, and committed to a date by which I would be ready with the content for the news section. Let’s just say I fell comfortably short and for a long time after I was worried I had made a fool of myself. ...
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18-04-2023
50 - The more people I talk to, the more confused I get. Help!
Decision Making
Ever wondered why this happens? ...
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15-04-2023
49 - How to earn the freedom to make decisions
Decision Making
Early career can be a hard time. You’re hungry to create impact. But you get bogged down by ‘micromanagement’, or by having to influence without authority, or even burn yourself out in the process of trying to prove your worth. ...
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12-04-2023
48 - How to run strategy meetings without authority (aka how to spark disconfirming analysis for better decisions)
Decision Making
When you’re running any consequential discussion among business leaders, as a young professional you may find yourself in one of two situations: the discussion converges too quickly OR it moves around in circles. The best way for you to drive the discussion is to steer it in the right direction. And that direction is away from preconceived position-taking AND toward open exploration. ...
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09-04-2023
47 - Better decision-making by asking better questions
Decision Making
If you had to improve your decision-making and you had 24 hours to do it in, you could do a lot worse than learning to ask better questions. Why? ...
Read
06-04-2023
46 - Decision-making with less: constraint is the seed for creativity
Decision Making
What does decision-making with constraints look like? Here are three high-stakes examples. ...
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03-04-2023
45 - How to help your team decide in your absence
Decision Making
Being a new manager shouldn’t stop you from being a good leader. ...
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March 2023

31-03-2023
44 - How to identify the most important thing
Decision Making
Some years ago, when my wife and I were beginning to think about homeownership, we spoke with recent homeowner friends. On one such visit, we marveled at the surrounding greenery (Sanjay Gandhi National Park in Mumbai). Our friend said that their decision to buy that place was based on a specific need. He said, “We knew what’s outside the walls was outside our control, and what’s inside we could fix. So we picked a location that was going to stay green.” ...
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28-03-2023
43 - How to change your spotlight to a floodlight
Decision Making
A common decision-making mistake is that we sincerely believe what we see is all there is. This happens nonconsciously. Before we know it, we’ve turned on our internal spotlight and are looking hard at what it has lit up. ...
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25-03-2023
42 - Why pros and cons won’t work for me (or you)
Decision Making
We all have unusual friends. I had a friend who was obsessed with flossing his teeth. No matter what, at the end of the day, he would pull out a piece of thread and run it between his teeth. The thing that didn’t make as much sense was that he was flexible with brushing. There would be days he would forget to brush, or just skip. ...
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22-03-2023
41 - The perils of problem solving
Decision Making
There’s an idea that is 10X as effective but only acknowledged a tenth of the time as it should be. I’m talking about avoiding problems–a far better approach to decision-making than solving problems. ...
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19-03-2023
40 - How to keep options open when waiting to decide
Decision Making
At the height of the dot-com bubble in the late 90s, Warren Buffett stayed out of the craze and looked like an idiot for a few years until the bubble burst and he was the one sitting on a piggy bank. ...
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16-03-2023
39 - How to know when to stop gathering evidence
Decision Making
By now you would know that the 2X2 decision matrix is really a prioritization tool. Its point is to help you strip down what’s on your mind to the most essential. ...
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13-03-2023
38 - How to know when to take a decision
Decision Making
As a leader, how do you know how much time you have to make decisions? Should you be quick or should you wait? Could you miss out on opportunities if you’re slow? Or will waiting out bring vital information that could decide the course for you? ...
Read
10-03-2023
37 - The secret to solving the right problem? Identify it first.
Decision Making
If you have a habit of jumping at a problem the moment it is presented to you, if you take pride in being action-oriented, you may want to read on. ...
Read
07-03-2023
36 - How we define a problem dictates the solutions we see
Decision Making
We don’t build cars that are sent to the museum after a trip, but we have always built rockets for single use. ...
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04-03-2023
35: How to break down a Lead Domino into smaller decisions
Decision Making
So you have identified what matters most to you and you’ve taken most other things off your plate. You have this (one or more) big consequential-irreversible decision to make. Think of it as your Netflix special. How would you approach it? There are two ways: ...
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01-03-2023
34 - How to differentiate between decisions using a decision matrix
Decision Making
I went from being stressed by too many daily decisions to having time for the truly important and big decisions with a simple change. You can learn the basics in two minutes. And like any good system it works everywhere–work and life. ...
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July 2024

174 - Do you work in an organization where everybody works one level lower than they should?

June 2024

173 - The negotiating trick few talk about

172 - The difference between informing and evoking

May 2024

171 - Why is it so hard to say NO?

April 2024

170 - Essence of strategy, rationalization, and a question on processing emotions

169 - Feedback, observation, and coaching

168 - Are you solving a higher class of problems today compared to yesterday?

March 2024

167 - Skeptical and open-minded - operating in two modes at the workplace

166 - Learning from my younger selves

165 - What's the big deal about being independent?

164 - Three questions for your work and life

163 - What does your report likely mean when she says she wants to do new things?

162 - Laziness is exhaustion

161 - SMART goals are doing your team harm

February 2024

160 - “Do you think trying to adopt a leadership style that’s not your natural style could backfire?”

159 - Tracking a lion, or a life

158 - Managing yourself during a transition

157 - Searching for Originality

156 - How to spend your time in the first 90 days

155- Just knowledge does not change behavior

154 - Two stories about humility training

153 - What we want from a job

152 The “even more” strategy

January 2024

151 Would you rather be disciplined or devoted?

150 When working for free makes sense

149 - Making the other person run out of things to say

148 - Head without heart is a logic bully

147 - Shepard tone - how to run multiple projects in parallel

146 - Why is the quest for mastery embarrassing?

145 - Why AI may not leave us jobless, why Will Hunting should not lay bricks, and why Virat Kohli should stay away from aerobics

144 - The power of putting first things first

142 - The casually curious die early at the altar of pragmatism

141 - The inefficiency is the point

December 2023

140 - Be the only, not the best—the overlooked lesson in building a career

139 - Why do we hire talent like we’re buying a boring car?

139 - What you didn’t know about your emotions

138 - What causes success?

137 - Managing how people see you at work

136 - Akbar, don’t worry about Birbal

135 - Second-Order Thinking: The Seen and Oh, the Unseen (Part 3 of 3)

134 - Visualization Techniques in Decision-Making (Part 2 of 3)

133 - 2024 - a year in preview

130 - How about a career with (probably) the worst feedback loop?

November 2023

129 - Why should we believe in the wisdom of the crowd? And when should we not?

128 - How to Improve Your Ideas ~~By Working Harder Alone~~

126 - The Stories We Tell Ourselves

125 - Nine Tiny Thoughts from September and October

124 - How to Escape Being a Rich and Wretched Entrepreneur

123 - Six rules that I follow as personal commandments

121 - Getting Better by Goofing up (Intentionally)

120 - Two Kinds of Risk, Four Kinds of Luck and _That_ Worst Outcome

118 - Risk and Expected Value and the Mistakes We Make with Them

117 - Should This, Not Can this, Product be Built?

October 2023

116 - The slippery slope of hypothesis-less entrepreneurship

115 - The Status Quo Trap

114 - TWO SELVES

113 - Is this a success or a failure—the value of reference points in framing decisions

112 - Bargains and Rip-offs

111 - Commander’s Intent and That Sweet Spot between Micromanaging and Abandoning

109 - Building for the Future: Investment in Loss (Part 2 of 2)

108 - Building for the Future: The J-Curve or The Stairs? (Part 1 of 2)

107 - Chasing Greatness: Shoot for the Moon but Only If You Can Train the Monkey First (Part 2 of 2)

106 - Two proven ways of chasing greatness (Part 1 of 2)

September 2023

105 - The Art of Learning

104 - Odds and ends

103 - The Truly Ambitious Hate False Progress

102 - Keep calm and be like Van Gogh

101 - Great leaders enjoy the deepest level of our permission

128 - How to Improve Your Ideas By Working Harder Alone