Shorts are small essays that I publish every day. They usually only take 2-5 minutes to read, and touch on all the same topics that my blog covers.

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How to Have Better Ideas

The best way to come up with good ideas: don’t get stuck on other ideas first.

Paul Graham’s excellent essay Keep Your Identity Small explores why thoughtful discussions about certain topics are difficult:

“I think what religion and politics have in common is that they become part of people's identity, and people can never have a fruitful argument about something that's part of their identity. By definition they're partisan.”

And he explains why that matters for idea generation:

“The most intriguing thing about this theory, if it's right, is that it explains not merely which kinds of discussions to avoid, but how to have better ideas. If people can't think clearly about anything that has become part of their identity, then all other things being equal, the best plan is to let as few things into your identity as possible.”

The link between your identity and your actions is so powerful that it’s a common habit-formation strategy. Simply saying you are a specific kind of person—the kind of person who exercises, for example—helps cement the habit. 

It’s something you can investigate for yourself. Next time you find yourself in an argument, try and slow down and examine how you feel when someone challenges your idea. You feel attacked! 

Even if someone asks a question about an idea, or a piece of your work, the visceral reaction is defensive. I feel it myself. It’s something that’s very hard to prevent, but we can learn to recognize and accept it.

If we have that kind of reaction in small arguments, it’s no surprise we react poorly when someone attacks part of our identity.

Keeping our identities small helps us have better ideas because we’re open to more possibilities. 

The reverse is also true. Allowing our identities to grow impedes our ability to think with clarity.

Thinking clearly is hard enough. 

We would do well to avoid anything that makes it harder still.

There Are No Absolutes

As humans, we like the world in black and white. But there is no such thing.

We like to simplify the world. It makes life easier. We would never be able to function if each day we had to re-learn whether something was dangerous or not. Or whether someone was a friend or an enemy. 

So instead, we learn once, form a model in our heads, and run with it. 

We learn that stoves can be hot and we should treat them with caution. 

We assume that people who look, act, and speak like us are friendly. We are cautious of those who don’t. 

The problem is that we form these models even when they aren’t appropriate. And we don’t know when they aren’t.

It happens in politics all the time. We assume a specific identity based on the political party someone supports. 

While they likely share some views with that party, they are individuals. They likely have nuanced views in different areas. 

But that complicates our model, and it takes effort and patience to engage with someone to understand those nuances. Instead, we throw them all in the same bucket and treat them the same.

We accept and reject beliefs the same way. 

If someone from a group we dislike or oppose believes something, we tend to oppose it. Yet if we tried, we can almost always find something we agree on.

That’s the problem. The world is not made up of absolutes, of black-and-white scenarios. There are degrees of truth to almost everything. We can interpret the same information and come to very different conclusions.

The world is not black and white. There are no absolutes.

The world is full of shades of grey.

Don't Believe Anything

One of the most important lessons I’ve learned: don’t believe anything completely.

As humans, we seek certainty. 

We are particularly talented at telling stories to help us maintain our certainty.

Justifying the purchase we made, our career path, our decisions.

We are storytellers, both in the way we describe things and how we remember and understand them. Linking events together in a logical way helps us remember things, and reassures us that we understand the world around us.

The problem is, none of those things are true.

Richard Feynman said “You must not fool yourself, and you are the easiest person to fool.”

The author Nassim Taleb agrees.

He’s shown repeatedly that as humans, we overestimate our understanding, constructing stories and narratives to fit events after the fact. We ignore extreme, unexpected events because they don’t fit our models of the world. 

There are a whole host of other studies showing similar psychological effects:

  • We don’t deal well with extreme probabilities. 
  • We don’t treat wins and losses the same. 
  • And we don’t do well accepting that we don’t know.

The solution? 

Don't believe anything with certainty. There is always a level of uncertainty, whether we can assess it accurately or not. Having a blanket rule is easier. 

Erring on the side of uncertainty is likely to cause some mental discomfort. But it opens us to the possibility of other options.

Believing something with a high probability is okay. In most circumstances, it should be accepted as good enough.

But believing something with complete certainty closes us to the possiblity of another view, another reason, another answer.

And it makes us vulnerable to a whole host of other psychological mistakes.

I'd rather accept a little mental discomfort if it means I fool myself just a little bit less often.

My Tech & Entrepreneurship Crash Course

My post-university years turned into a crash course in entrepreneurship and startups.

I opted not to do a masters in favour of attempting to build a startup of my own. 

That didn’t go that well, but it did lead me to Founder Institute, a program that trains entrepreneurs over the course of 4-6 months. 

Founder Institute gave me a group of entrepreneur peers, and a network of mentors willing to help.

It also gave me a wide base of entrepreneurship knowledge.

The new startup that came out of that program didn’t work out either, but the contacts I made there would lead me to my next job.

That job? An associate with Techstars Boston. Techstars is a well-known tech accelerator. They bring in 10-15 companies for 4 months and give them resources to speed up their growth. 

Along with 8 or so other associates, we handled some of the administrative stuff for Techstars, and did whatever we could to help the startups. 

That meant I got to see the struggles, try and solve problems, and learn a lot about different industries. We also got exposure to another exceptional group of mentors.

After Techstars Boston, I continued working with some of the people I’d met there, but it didn't last long.

I ended up joining one of the startups that had come out of Founder Institute—Lean Systems—in a cofounder role.

We got accepted to Techstars New York as part of their Winter 2017 cohort. We went through a similar accelerator program to Techstars Boston, this time as one of the companies.

It was another 4-month program of a lot of work, meeting amazing entrepreneurs, and learning and pushing hard to grow our company.

Eventually, that startup wouldn’t work out either. I moved on to join yet another company founded during Founder Institute called Unito.

In hindsight, my journey post-university seems well-planned. I got to see startup scenes in two major tech cities, get exposed to hundreds of different companies and founders, and learn while attempting to apply the lessons myself.

In reality, I had no idea what would come next, but I was choosing the options where I was most likely to learn.

The crash course I got in startups taught me all kinds of tactical things. It built a broad knowledge base of all the components required to build companies. It gave me exposure to the kinds of people that build successful companies too.

The main lessons I left with:

Everyone is figuring it out as they go. First-time founders almost always have one insight and specific skills, but quickly have to figure out things like hiring and finance. And they all do. They tackle problems as they come and keep moving forward.

Ruthless execution is the norm. Founders of venture-backed tech startups are obsessive problem-solvers. They're impatient, pushing the boundaries of how fast something can finished, or doing it themselves in the beginning. Once you get used to this kind of speed, it’s hard to do anything else.

You can choose what kind of founder/manager to be. The vast, vast majority of the founders I worked with, regardless of how successful, were extremely kind, considerate people. Some of them were more frank or brash than others, but very few fit the model of the domineering, bossy founder.

Startups are hard. There were a lot of brilliant people I worked with who had startups which didn't work out. So many things have to go right that are outside your control. 

I don’t know where my career will take me over the next 5 years.

But I hope it involves as much learning as my post-university crash course in tech and startups.

Money and Time

We use the same language for time and money: spend, save, invest.

So why are we so careful with money and so careless with our time?

The world measures wealth with money. Money buys visible things—cars, houses, clothes, jewelry.

Monetary wealth is a single number. A balance in an account, or an estimate of net worth.

Time is much more difficult.

We are all given time, and so money becomes the constraining factor in our lives.

The money constraint never seems to disappear—there is always more to buy.

We avoid talking about how much time we have left, because no one likes talking about death.

But that is exactly the antidote.

The Stoics were fond of a Latin saying: “Memento mori.”

It means “remember death.”

The point is to remember that we all die at some point. And that while money can be lost and gained at any time, we never get back tim

We use the same words for time and money.

But we must remember that we cannot earn time; the best we can do is spend it wisely.

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