The case for being a generalist

My case for the generalist life: many small bets, range as the product, and why I brought the table.

So here is a confession.
I work on too many things.
Lol. As if you didnt know.

Right now, in one folder on my Mac, thanks to Claude Max, there are forty-odd apps I have started. A posture app that nags me when I slouch. A tracker that pulls my Whoop data every night. A film-script writer. A room-rental thing. A quiz game ranking celebrities. A property manager built in an evening. A film script. My book 2.

And thanks to Claude, I can now shape my world to indeed be a museum of passion projects.

Some of these shipped.
Most did not.
All of them got a name, a logo, a weekend, and a burst of love before the next thing walked in.

And I didnt stop at that. My #parkedIdeas list is longer than ever and on each passing day, am cooking more passion projects. And I dont see myself stopping.

The world has a word for a man like me.
Scatterbrain.

The world also has a kinder word.
Generalist.

And here is my argument in favour of being one.

The plate

Picture yourself at a buffet. Not a fancy one. A regular spread at a regular hotel. You would probably do three laps before you touch a plate. Then you would build a plate of nine things that you’d probably not imagine together. A plate could have Granola next to egg-fried rice, next to some dry fruits, next to some yogurt. You want a taste of all of it.

And then there are people who order one dish. A paratha. A dosa. They eat it slow. They relish, savour it. They send it back if it is wrong and get a replacement. They know what they came for. And they will do whatever it takes to get it.

I love such people.
I admire them.
But I am not that.

Oh, the buffet reminds me of Warren. Buffett. The guy who talks about saying no more than saying yes. The epitome of focus. Famously will not touch things he does not understand. In an alternate universe I would like to be him: capital allocator, taking long-term bets, inspiration to many.

But today, at 43, I think I like how I am – a generalist, a scatterbrain, a Jack of all trades. And I am about to double down on that.

The identity

If I look back at my notes and public posts, on Blogger and elsewhere, I am not surprised to see that I have been wanting to be a Generalist, a Multipotentialite, a Polymath, a Jack of all trades for a long long time.

In 2007 I saved an essay by Einstein, The World As I See It. And I saved a note alongside that the guy may be known for physics but he was as good with the violin, political discourse, and of course writing letters.

And funnily, no one calls Einstein unfocused.
They call him curious.

Brings me to identity conversation. Deep down, all of us are identities. We think, behave, act, operate and make decisions that are in coherence with our identities.

You are a doctor. That is your identity. And each thing you do stems from there. From the car your choose to people you hangout with to the kind of work you think you can do.

You are an actor. That’s your identity.

Walk into a room and ask for introductions. Most people would say, “Hi, I am Gaurav and I run marketing for Unilever” or a variant there of. Work supersedes anything else. And then all your actions are evaluated and judged by the others per that. And the worst part, your performance stems from that.

Do this as an experiment. When you meet someone next, ask them who they are. And notice if their intro includes the work they do and if you can “see” their lives as a direct outcome of that work.

Now, in my case, I’ve been aware of this identity induced myopia. And thus I have a hard time explaining what I do. Some years ago, one of my Twitter bios was: “I am 37, a marketer, a writer, a productivity-porn seeker, an aspiring multipotentialite, a Mumbai-dweller, a Delhi-product who wants to live to 120 and climb Everest.”

When I read it now, I realise there is no coherent identity thread in it. There is not one job title in it. But there’s a list of things that I am interested in. And if I were to extrapolate those into identity, I have a stack of identities that dont fit in together. And my mentors have begged me to cut to one or two.

I’ve had a hard time cutting these and I was often shy about my inability to do that. But at 43, I think I am ready to embrace that. And the fact that I will probably add more to it.

The fear. And the lust.

Also, I have this fear that if I choose one, I will miss the others.

Pick films, and I lose startups.
Pick startups, and I lose the book.
Pick books, and I miss conversations around brands.

The thing is, the buffet was never only greed. Part of it was a man who could not bear to send any plate back to the kitchen. The lust for others made me not want to commit to one.

Meru made me realise this. It was after a while that I committed to doing one thing. And I could see that while I was set for a great economic windfall and impact with work and a great team to get things done, I would miss many other things that keep me alive. And I just couldnt bear that.

The case against me.

The smartest people (friends, mentors etc) in my life have told me to pick one. Or two.
Never few.
And focus.
And they have used kind words. Here are some of those…

A friend once read my forty-year goal list.
He wrote back, and I am quoting him: “almost everything on this list is achievable. But things linger. Maybe drop everything and try doing just one thing for a considerable period, and you will get it. He was not wrong. He was describing the cost of my plate, and describing it with love.”

Pradeep recently told me that my entire setup is superfast and supergood with taking things from 0 to 0.1.

A mentor told me a harder thing.
You get to be exceptional at two, maybe three things in one life. For people like you, he said, the pain is not the work. The pain is the quitting. Killing the other thousand things you already know you are good at, so the two can grow.

And there are more.

These voices do not contradict each other.
They harmonise.
Pick. Focus. Quit the rest.
This is the best advice in the world for most people, and it is given to me by people who want me to win.

I have heard it for two decades. And I have not taken it. The one time I took it, I had to quit in like 18 months. I think this is a not a man failing to decide. This is a way of life and a decision. And with advantage of some hindsight (I can look back on how I made decisions) and maybe some age-imposed wisdom, here is the reasoning under it.

The small bets thinking

Lets start with the math of small bets.

A specialist makes one big bet. He puts the whole bankroll on one dish. If he is right, he eats like a king. If he is wrong, the meal is gone. The upside is real and the ruin is also real. Buffett is a great example of concentration and doubling-tripling-xxxing on his conviction with follow on investments. To a point that he starts to own a controlling stake.

I on the other hand like taking make small bets. And rather than listening to what the world tells me, I will double down on making many small bets.

Lets get back to the buffett thing. Assuming I pick up 19 things on my plate. By the law of numbers, a couple of those will be cold, one will be excellent and most will be just fine. And one, I do not know which one, will be the best thing I will talk about all year.

So, I dont really need everything on the plate to land. I need one. Or two. That is the entire trick, and to me, it is the opposite of scattered. It is a hedge with the lid left off the upside.

In fact, most VCs operate like that. Allocate capital. They have a theme. Take bets. And hope some of them would be 100X.

Most portfolio managers do that – pick a portfolio (they often tend to specialise into sectoral things) and then hope that not all go to ruin.

But we don’t see this wide, concentrated bets in post-industrialization worldly disciplines like medicine, engineering, teaching and all that. I wonder why. Maybe cos the time and generation they grew in, the world had started to reward one person dong one thing really well?

Plus, the thing is, each time I marry a lesson from one discipline to another, am often able to spot patterns and trends and lessons and wins that I would otherwise miss. I could create a screenwriting software because I knew of the frustration of writers with Final Draft and then Claude enabled me to build a prototype very fast! The podcast I started with Akshay, Founder Thesis, put me in rooms with founders I had no other way to reach. The Goa post (Ultimate Guide to Living in and Remote Working from Goa) I wrote on a whim brought me people, ideas, and work. I still get comments on the that post.

One dish, in each case, paid for the whole walk to the counter. When I was filling my plate, I didnt know which one would that be. That is the point. You cannot know. So you take the buffet.

What do you bring to the table?

For years I answered the what do you bring to the table question wrong.

I tried to fake depth depending on who I was meeting. If I was meeting a marketer, I would say, I have 20 years of brand experience. If I was meeting an investor, I would say I’ve worked with many founders. If I met a prospective date, I would say am an author. I would hope like hell that I sound like a specialist. I am probably good at those narratives cos more often than not, I would get the gig.

But deep down inside, I knew it was not me. I was merely living one version of the story that I didnt want to. Often reminded of the quote from Fight Club – “you buy things you dont need to impress people who dont care.”

But now, I will do things differently.

I will acknowledge that I love the idea of taking many bets, doing many things at the same time.

I will probably make writing my first port of call because, well, easy to explain. And then I would offer to people that I am a brand manager, marketer, strategy-er, sparring partner, podcaster, filmmaker, event manager, problem solver and all other things.

And I will talk about my super fast, 0 to 0.1 journey ability that allows me to run project pilots fast. I would then talk about Ready Fire Aim. I would then talk about Action. I would talk about Movement. And the whole schabang.

Thing is, the specialist sells depth in one room. They goes all the way down a particular Rabbit Hole. The generalist on the other hands knows how to connect those holes to make fabulous system of tunnels that you could use to navigate the neterworld. For me, the range is the product and the offering.

They often say that we ought to be T-shaped or I-shaped or comb-shaped. I say you need to be shapeless. You need to be like Red. You need to be the person who knows a person who can get things done. You must the person people call when the problem does not fit a department. This problem-solver life would only happen when you’re known as someone who’s able to spot lessons from one and apply to another.

I want to talk about a few archetypes here.

There is this guy, Julian Shapiro.
He goes deep into things that excite him, becomes a kind of master, and then condenses what he learned into guides better than the textbooks written by people who only did that one thing. That, I think, is the generalist move done right. Not shallow everywhere. Deep in bursts, wide across them, and then the wiring shared out loud. My friend Srijan (do read this by him) would be in the same boat.

I once sat in a session about a man I will not name here.
A lone genius who ran a team of other geniuses. He could write, direct, run a camera, sketch, design, paint, and doodle. When I met him, I wrote in my notes that night: if he is not a polymath, I do not know who is. I came home inspired and a little jealous. Not of any one skill. Of the permission he had given himself to hold all of them at once and call it a career instead of a confusion. That permission is the thing I am writing this to hand myself. And to others like me. The skills are learnable. The permission is the hard part.

Oh, depth is not the enemy here. The generalist who never goes deep on anything is just a tourist, and a tourist sells nothing. The right move I think, is depth in seasons.

Go all the way down on one plate until you can teach it, then surface, then go down on the next.

Over a life you stack five or six of those deep dives, and the wiring between them becomes a thing no single-room specialist can buy, hire, or fake.

But, to be honest, I do not know if I can be deep in anything. I do not think I have it in me to go deep even in seasons. Or even for a road. I will merely scratch the surface at best. And that too may not give me joy.

So even the life of Julian and the unknown person is not for me.

So, then what?

Many bets. One at a time

The reconciliation between my people (who ask me to focus) and me (who refuses to) is one word long. Sequence.

I will do multiple things but for particular amount of time, I will do one thing. Say, for the month of July, I will only work on my book. For the month of August, I will only work on a podcast. In September, I will not do anything. And so on and so forth.

In a month, I do three things for 80% of my time. And then all the potpourri in the balance 20%.

This is a simplistic explanation. Three things in a month. 80% of time. What I choose to do may not even end for a month. Or it may end in a few days. Maybe I will do a thing for 5 days. Or 3 chunks of a thing in 6 months.

The idea is be to take things to a point where I can transfer the project to someone else, you know, Build, Operate and Transfer. I will then find EIRs or someone who would actually run those. I dont know how but at least on paper, this sounds doable. I even did a version of this with TRS, P3 et al. But then, I failed to keep control and inspire my partners to think beyond.

I will thus hard focus on that thing for a certain amount of time. And then I will find someone to take it ahead. And unlike last time, keep control. And then. move on to the next thing.

I dont know the shape it would take. But I like the sound of it.

The devil is of course is details but I know that atleast my biggest driver, FOMO, would be at bay. I would get to see my projects and shauks on the shelf while I work on one bet at a time. It will probably give me the range. And for each thing that I ship, the validation that someone is taking care of it. Assuming I can find these people. And then, ofc, maybe AI could!

To be honest, I tried a version of this in the month of June. I told myself that my identity for the month of June is that of a writer and I will finish Book2. I almost did it. I need another mont to get it out of my system. May be in August. Cos July is the event manager month. Lol. For the month of July, I am an employee to my own Claude and a large thing is event management.

Oh, this is also what I want C4E to be. Not an agency that does one thing for clients. But a small team that builds many things. The way Tiny and Late Checkout and Bending Spoons do. A studio. A service setup. A product company. A portfolio of small bets under one roof, run by people who do many things and are done apologizing for it.

Back to the buffet. And onto the future.

So we are back at the buffet, you and me, have plates in hand.

Here is the reframe. I am not avoiding the main course by loading up small plates. For a man like me, the buffet is the main course. The variety is not the appetizer before the real meal. It is the meal. The range is not a delay on the way to focus. It is the thing itself.

You have been told to pick. You have been told your curiosity is a leak. You have been handed marshmallows and told to admire concentration. And maybe they are right. But then, you are human and you are allowed to want the other thing. You are allowed to want the buffet.

The bets are small. Deliberately. By design.

Let’s see how it goes.

Tweets vs Blogposts

Even when we are in 2020, why do I prefer blogging over tweets? As a creator, as a learner and as someone that wants to grow!

Hola! 

If you are a longtime reader of this blog (or blogs in general), you would know how blogging as a hobby has been sort of replaced by things like Instagram, tweets, and so on and so forth. Both in general and for me. And how blogging is now a lot more “content marketing” where companies pay peanuts to desk monkeys to churn out words that trap those search engine spiders logs. And how the “content” that is created does not really do anything good to any reader, even if they may want to read about that topic. And how there is so much content that it’s impossible to filter noise and signal; assuming you know what is signal for you! And how long-form writing by non-writers is dying a slow death? 

It’s sad that so many people sharing so many deeply personal anecdotes with so many strangers is all gone. I mean it’s now moved to Twitter and Instagram and all that. But I am not sure how many people are blessed with the talent to push their thoughts in mere 280 characters (or maybe 2200 for Insta). I, at least cant. Not that gifted. May be if I work hard on writing, I may learn the art of brevity? 

And this is why I have kept the blog alive. And this is why I love the idea of writing letters (come, be my pen pal?). And this is why I like the idea of journaling, diary entries, notes, etc. 

The thing is, a blog allows me to push my unfiltered thoughts, things I am thinking on, things I am working on, things I seek opinion on. And put those somewhere on the world wild web. For others to see and respond to and allow me to think better.

I miss those times when I’d be brimming with ideas about the blog posts that I’d want to write. I’d have a draft folder thicker than all the 7-8 Harry Potter books combined. And I’d look forward to publishing posts and wait with bated breath for that one rare comment that I would get once in a month or two. It was another level of exhilaration. Something that the Twitter generation would never know – after all, tweets are far faster to engage with 🙂

Anyhow. 

So, today, I am thinking about where do I want my content to go (this is what I’d do with my blog – write write write till I get tired; vomit out all my ideas, thoughts here; and since the blog is in the public domain, I’d try harder to put forth better arguments; and by the time I was done writing, I’d have some sort of clarity). Here is my attempt to think with my words. 

And, with that, here we go. In no order… 

1. Individual as a Media Company

In the times to come, unless you are a media company (even as an individual), you’d lose out. As a business, as an individual, as even a rock or a vegetable. Stories, media, content would help you stay relevant. 

You thus have to think like a media company and churn out content that is valuable and interesting and all that. 

2. 1000 True Fans

The entire idea of 1000 True Fans would be far far more relevant in the times to come. Creators (a word I used when I applied for Gumroad’s gig for customer service) would live lives that they want and will rely on patrons to support them with micro-transactions, micro-donations. And with time, you would see more and more people go down the creator route. We are already seeing the likes of Patreon, Onlyfans, etc allowing people to create economically sustainable lives. 

3. Writing

As someone who likes to straddle multiple things and at some point in time make an impact for a billion people, I need to be very very good with words. After all, words do move mountains. And these words will open doors for me, allow me to know more people, satiate my curiosity, and so on and so forth. 

In one word, my words will give me access. And thus I need to get more active and more aggressive with this! 

4. Text vs Pictures vs Video

If a picture is worth a thousand words, a video is worth a thousand pictures. So, to improve the output by a 1000×1000, I need to pivot to doing videos at some point. Not sure though when.

PS: Thanks, Annkur for the nudge. Do tell me what would you want to see on a video from me. 

5. One, single, unified home for content

Right now, my content is scattered at multiple places – my own website, medium, blog, Mailchimp, tiny letter, substack, and more. And with each passing day, these platforms are only going to grow and more platforms would come in. And thus the content will scatter even more. 

And as a result, my patrons (and the ones I want to get access to) would probably not find what they are looking for! 

So I need to find a solution to this. May be I will use the website to showcase the best work and one blog destination to dump these thoughts? I don’t know yet. 

6. Tracks that people want to read about

Continuing with the scatteredness, it is no secret that I am a scatterbrain. My writing, output, and other things are spread too thin. I talk about marketing, entertainment, content, podcasts, entrepreneurship, writing, habits, notes, poker, and a million other things. 

And thus there is no way I can give a consistent experience to readers that are interested in just one genre. I mean if you are a filmmaker, you may want to read what I had to write about The Trial of the Chicago 7 but why would you read about how I refuse to have a kitchen at my home? Or that walking barefoot is the thing you need to practice but living in a city like Mumbai, it’s literally impossible! 

So once I know what and how and where all I am writing, there has to be a way for people to identify “tracks” they want to consume and they must be able to go down that path easily. For example, when you are subscribing to newsletters on those large websites, you have an option of subscribing to certain sections (kind of content) and receive updates from only that section, that track. I will have to implement that! 

7. Twitter

Lemme talk about Twitter. The thing that got me down this path! 

The thing with the tweet is, even though there is a permalink of the tweet per se, to me, a tweet looks and feels ephemeral. It is something that’s hanging in the air. I’d love to change it and have a more solid, permanent, tangible link. Like a URL to a website. A website feels a lot more solid to me. Oh, by the way, the public URLs that I host on my own website on? They are tough to pull off – I keep trashing my website every now and then and I start from scratch! I need to fix this. 

Plus, while most of my greatest connections have come via Twitter, I still can’t wrap my head around the fact that it’s the primary destination where I create content. It can at best be a distribution platform. And heck, it’s a powerful destination! No? 

8. Writing to pay your bills

Making money and pivoting to being a writer! This is a big one. And this is what I am most conflicted about. 

The thing is, I’d love to be on substack or Patreon or something because I like the idea of monetizing my audience, my true fans. Even though I do NOT write with the intention of making money off my writing, I have been told by at least one person (thanks, Krishna!) that he is happy to pay me for what I write. Apparently, it adds value to his life. And that to me is music. 

For two reasons. A, I add value. The reason I even write in the first place. And B, people find it valuable enough to pay! 

So, if I can get 1000 people like Krishna, I’ll be free from the rigmarole of holding onto a steady job! And I can potentially take a step in the direction where I won’t have to work for others. And spend my life like a dog chasing cards – in random pursuits, where the chase itself is a reward! 

Of course, once I start seeking money for what I write, I need to not get sucked into this honeytrap and go down the desk-monkey route. 

The other thing that I am sure of is that I do not want to “profiteer” by sharing things I know. Whatever little I know, I know those because I have had generous people who were kind to me and shared things with me without expecting anything in return. And it is not right for me to profiteer when I myself haven’t paid for those! So that!

A big part of me thus does not want to charge at all. May be I’ll accept donations? I can ask people to donate whatever they deem is ok. But then, while I go with the pay what you go model, do I want to guilt-trip people into paying? Dunno. 

And if and when I do go the monetization path (in whatever shape or format), I need to decide how do I do it. With Patreon? Substack? Stripe? Ideally, I’d love to have a button or something (may be stripe connection to WordPress) on my own website. Let’s see. 

Sigh! You see the conflict? 

9. Accountability.

This is a big one. Right now, I write things as and when I feel like. There is no structure, no predictable cadence, no topic, no accountability. But once I decide that I want to be a writer for hire, I would have to be a lot more accountable. Someone said it right that a predictable routine is one of the secrets behind a free, wild, flowing, interesting life – the kind that gives you experiences that you long for. And the experiences that can shape you into a better man! 

So, I need to probably pull them socks up and get to a routine. For what I write, even if it’s across genres and all that. No?

***

So yeah, these things. 

What started as a rant, a comparison between tweets and blog posts has become a tome that I am not sure who would read. 

I will decide over the next few days and I will of course keep you guys posted. Till then, it’s over and out!