Let’s talk about something weird.

You’re playing a video game right now.
It’s called Your Life™. And whether you realize it or not, you’re deep into the main questline: Career Mode.

Wait… What Kind of Game Are We Playing?

If you’ve ever played a Role-Playing Game (RPG) — think Zelda, Skyrim, or even The Witcher — you know the drill.

You start as a weak, confused character. You choose a class (like wizard, warrior, or rogue). You complete quests. You level up. You unlock skills. You fight increasingly bizarre bosses. You collect weird loot (like an Amulet of Slightly Better Public Speaking™).

You also make decisions that shape your story. Sometimes you grind. Sometimes you explore. Sometimes you accidentally trigger a side quest that spirals into a whole new career.

Most importantly: there’s no one “right” way to play. And no one gives you a proper tutorial.

Real life? Suspiciously similar.

So even if you’ve never touched a PlayStation controller or built a Dungeons & Dragons character sheet, don’t worry — I’ll walk you through the metaphor as we go.

🧠 Tl,dr; You’re the main character. Your career is the quest. This essay is the unofficial walkthrough you never got.

—

Now, the awkward part is:
Most of us didn’t choose to play this game.
We kind of... spawned into it.

When you were around 16 or 17, you were handed a broken controller, a laggy user interface, and a bunch of vague instructions like:

“Pick a stream.”
“Get into a top college.”
“Don’t screw this up — this is your whole future.”

And the worst part?
No one told you what kind of game this was.
No tutorial. No manual. No ability to skip the cutscene where Uncle Raj explains why he regrets not doing an MBA.

So you picked something — maybe a safe bet, maybe what your marks allowed, maybe whatever felt least like failure — and the screen blinked:

🎯 MAIN QUEST ACTIVATED: Climb the Ladder

Objective: Study hard → Get job → Upgrade job → Get a spouse → Buy apartment → Buy bigger apartment → Retire or burn out

💀 Failure Condition: Not doing all this before age 35

The Problem

This game isn’t broken.
It’s just… auto-piloted by default.

And if you don’t bother reprogramming it, the system assigns you the generic questline most people are on — the “9-to-5 → promotion → 2 vacations per year → mysterious midlife crisis at level 42” route.

But here’s the thing.

Somewhere along the way — somewhere between meaningless calendar invites and corporate jargon like “bandwidth constraints” — you start to get this weird feeling:

Wait... who the hell designed this game?
And why am I playing it on nightmare mode with no healing potions?

Enter: The Career Anxiety Multiverse™

If you’re a millennial or Gen Z, you already know the anxiety I’m talking about.
You’ve probably had at least one of the following thoughts:

• “Am I behind?”

• “Should I switch industries?”

• “Why does everyone on LinkedIn sound like they’re running for Prime Minister?”

• “Why is that 25-year-old on Forbes 30 Under 30 while I’m still learning how tax works?”

• “Why do all startup founders look either suspiciously hydrated or deeply sleep-deprived?”

In the corporate world, we’re surrounded by the pressure to optimize.
In the startup world, it’s even more cutthroat — where being the youngest, fastest, most-well-funded burnout victim is treated like a badge of honor.

Everyone’s speedrunning.
Everyone’s tweeting advice.
Everyone’s silently panicking while pretending they’re absolutely crushing it.

The Truth

No one really knows what they’re doing.
But some people are just better at designing the game they’re playing.

Because here’s the actual plot twist:

Life is a video game. And you can change the rules.

You can customize your build.
You can design your own win condition.
You can fight a different boss or leave the dungeon altogether.

This essay is your unofficial walkthrough.
A cheat-sheet for Career Mode.
A user guide no one gave you - not your school, not your boss, not your favorite productivity bro on YouTube. And no, it is not going to tell you to “follow your passion”.

It’s for people who:

• Secretly feel like they picked the wrong class (Accountant) but really want to multiclass into Bard-Monk-Strategist

• Want to take big bets, but worry they’re too late or too weird

• Are tired of confusing job titles and want to find actual meaning

• Want to stop pretending their LinkedIn banner is their soul

We’re going to talk about:

• XP systems

• Boss levels

• Side quests

• Skill trees

• Regret monsters

• And how to level up without rage-quitting at 29

By the end, I hope you’ll stop thinking of your career as a ladder to climb
…and start seeing it as a level to beat.

Ready?
Press START.

Subscribe now

🧠 Level 1: The Tutorial (aka Your Early 20s)

Every game starts with a tutorial.

The problem is: in real life, the tutorial doesn’t come with a “Skip” button. Or a pop-up that says, “Relax, this is just practice.”

Instead, you get dumped into the opening level with:

• A set of “base stats” you didn’t choose

• Some blurry instructions from confused but well-meaning elders

• And a parade of overly confident NPCs (parents, relatives, job interviewers, Instagram influencers) acting like they’ve already finished the game

And you’re expected to just... go.

It is unfair. It is random. But that’s just how it is.

But the good part is, you CAN boost XP and plump up your stats. You unlock side-quests, hidden quests, quests you can reach only after completing certain other quests - but that’s just how the world building has been done for this game.

✨ The Default Main Quest

The system does assign you a quest. We saw an example of it above — the Climb the Ladder questline.

This is the default main quest. You didn’t design it. You just spawned into it.

And the thing about tutorials? They try to funnel you toward a certain playstyle. You’re handed the Sword of Stability, the Shield of Prestige, and the Cape of Corporate.

When you try to pick up another weapon—say, the Dagger of Creative Chaos or the Staff of Entrepreneurial Pain—an NPC will appear and gently shame or scare you.

“Hmm... but how will this look on your CV?”
“Are you sure you can do that? Only 0.01% of the people make it.”
“You’re wasting your degree.”

It’s literally their job to give you FOMO. They’re quest-line enforcers.

🎓 My Tutorial Build: A Hot Mess (That Aged Like Wine)

Here’s what my tutorial looked like. On paper, it might look chaotic. But in retrospect, I was building a wildly versatile character. And this is the part nobody tells you about.

Here’s a short, selective summary written as —

Quest / Side Quest ———> Duration ———> What I Got / XP Gained

Chess obsession ———> 7 months ———> Went from “how does the knight move?” to State Gold Medalist, Under-13 National level player. Got confidence that I probably learn well in non-academic setups too.

Studied Pharmacy ———> 4 years ———> A functional understanding of the human body, food, cosmetics, drugs, did neuro-drug design research which today informs my “biohacking” lifestyle

Taekwondo, Karate ———> 3 months ———> Trained 3-4 hours a day for 3 months. Walked out with a gold medal, a cracked toe, and the knowledge that the human body can do wonders when pushed to its limits. 15 hour work days? What, like, it’s hard?

Sri Lanka Paper (final year) ——> 6 months ———> Presented research on challenges for women founders in startups; Got mistaken for the professor. Got drunk on academic validation, while spending sleepless nights planning to tackle the eventual glass - or as my study called it - “lucite” ceiling

Corporate projects during MBA———> 3-6 months each ———> Did social work field studies, practiced primary research techniques, digitized crime data for cops, helped the largest Self help group of women farmers go organic - all before turning 23

Coffee snobbery ———> Casual hobby ———> Made friends at my job in Dubai with the then-World Coffee champion; Learnt to argue about pour-over techniques with white men in suspenders. Also helpful around condescending Whiskey bros.

Theatre actor ———> ~16 years on and off ———> Context / character switching became a force of habit. I became my own mindset coach by “slipping into character” at high stakes situations in CEO’s office, Sales

Poker ———> 1 month (with a trainer) ———> Picked up just enough to take money from VC tables. Hehe. Hehehe.

This wasn’t strategy, and for sure not planned from the get-go. It was instinct + boredom + saying yes to things that seemed fun. It was only in hindsight that this XP combo started making sense.

I was trying weapons. I was leveling up agility. I was collecting weird XP from side quests no one else cared about.

🧠 What the Tutorial Teaches You (If You’re Paying Attention)

Tutorials aren’t meant for winning.

They’re for:

• Learning how your character moves

• Discovering your risk tolerance

• Getting beaten up by the world and realizing you don’t die from embarrassment

• Building your internal User Interface: what lights you up, what bores you to death, what you’re secretly good at

Most people try to optimize during the tutorial. Big mistake.

Trying to “look sorted” at Level 1 is like trying to min-max stats before you even know what game you’re playing.

📉 What Most People Think They Should Do

A lot of people follow advice that they pick up from places, including movies. Some particularly not-great ones are:

❌ “Find my passion” ——> You haven’t touched enough buttons yet to know what lights you up

❌ “Pick a stable job” ——> Stability early on can calcify you into a class you didn’t choose

❌ “Follow the youngest - X (founder/ player/ whatever) - ever” ——> Life is not a speedrun. And no one cares if you “sold your first company before 30” — unless you’re also…not miserable

The early game is not about clout. It’s about taste. Knowing what makes your brain sing before you sell it to the highest bidder.

What do you want to feel more of?
What friction are you weirdly willing to tolerate?
Where does your brain get noisy with ideas?

💪 Better Tutorial Strategy: XP Over ROI

✅ Say yes to weird projects.

❌ Don’t over think how it fits in your 5-year plan

✅ Build stamina, not status.

❌ Don’t get trapped by early prestige.

✅ Take note of what energizes you.

❌ Don’t mistake success for fulfillment.

✅ Track your own XP bar.

❌ Don’t look at someone else’s loot and panic.

You’re building a kit. You’re discovering your class. You’re preparing for boss fights you can’t even see yet.

✅ Level 1 Complete: You’re Now a Level 2 Human

You made it through the fog.
You didn’t win. But you didn’t quit.
You touched the buttons. You saw behind the curtain. You got a glimpse of what playing your own game might feel like.

And that, honestly, puts you ahead of 90% of players.

🍫 Level 2: Designing Your Own Quest (Before It’s Too Late)

If Level 1 was the realization that the default quest is a lie, Section 2 is what you do next: panic briefly, then pull up your imaginary quest journal and start scribbling.

Because here’s the thing — once you realize you can play your own game, you’d think the next step is obvious.

But it’s not. It’s terrifying.

You’ve exited the tutorial zone, sure. But now you’re standing in the forest in your underpants, holding a wooden spoon. There are paths in every direction and absolutely no NPC telling you what to do. Just a faint internal voice whispering, uh… maybe go that way?

And that’s the moment most people get stuck. So they… go back. To the main quest. The one they didn’t choose. Because at least it came with a job description and dental.

But not you. You, dear reader, you are stubbornly holding that spoon and deciding to figure this thing out.

🎯 The 3 Types of Main Quests (Choose Your Fighter)

Let’s break this down using a classic RPG archetype model:

🏔️ Quest Type: The Mountain Climber

Description: Clear Destination. High ambition. Wants to be CEO, billionaire, or win a Nobel.

Danger level 🔴 : Burnout + Existential Crisis at Base Camp 3

🌊 Quest Type: The River Meanderer

Description: Wants richness of experience, not status. Flows around the rocks.

Danger level 🔴: May forget to build a savings account.

🧩 Quest Type: The Puzzle Solver

Description: Doesn’t care about the destination, just the next problem to solve. Often found starting companies or building odd things.

Danger level 🔴: Can become a hermit surrounded by half-built side projects.

Most people are a mix of the three. And that’s okay.

The trick is to consciously pick your primary quest type — and own it. Because if you don’t, you’ll end up measuring your life using someone else’s questline. (That’s how puzzle-solvers end up depressed on LinkedIn. Wrong scoreboard.)

While I didn’t formally sit down to write a life design manifesto in my early 20s, something instinctual kicked in. Every side quest I picked — chess, taekwondo, bike riding (oh yes, that too) theatre, MMA — was secretly running a simulation in the background. Testing my playstyle.

Turns out: I liked speed. I liked chaos. I liked building from scratch. And I liked beating the odds.

By the time I’d been through email-reads in bathtubs, chaotic 12-hour supply chain ops, and enterprise sales warfare, I realized I was playing what game designers would call a custom sandbox career.

There was no job title for it. No 5-year HR plan. But I felt alive.

⚔️ The Final Boss in this level: Guilt

The hardest part of designing your quest? Guilt.

Guilt that you’re not living up to your degrees. Guilt that you did not climb the mountain or meander with the river or solve enough problems.

Guilt that your parents can’t explain your job at weddings.

Guilt that you’re 31 and still don’t own property, unlike Tanya who just posted “#adulting” with a balcony view and an overpriced coffee machine.

And worst of all? The “youngest ever” cult.

🧠 “She became VP at 25.”
💰 “Forbes 30 Under 30.”
📉 “Now she’s taking a sabbatical to rest her nervous system.”

It’s an anxiety trap disguised as achievement porn.

Nobody tells you that the youngest-whatever is often followed by the fastest-burnout or the hardest-identity-crisis.

You’re not late. You’re not slow. You’re playing a different game. The only timer that matters is the one you chose to start.

If you know your quest, you’re already ahead.

So, design your quest. Don’t outsource it to society.

And once you’ve picked it, double down. Start grinding. Even if you’re still holding the wooden spoon you started with in the tutorial zone.

But now comes the hard part: deciding what kind of player you want to be.

Level 3: What’s Your Build? (Specialist vs Generalist)

In this MMORPG called Life, now that you’ve picked your quest… it’s time to choose your build.

Some go full Gandalf: Maxed-out wisdom tree, does 1 damage per hour, but can recite philosophy during code reviews and quietly judges your life choices on Reddit.

Others are rogue generalists: 17 browser tabs open, 3 side hustles, mild impostor syndrome. Allergic to form fields but can flirt, fundraise, and fire off a Notion doc — all before breakfast.

But here’s the catch:
The game doesn’t tell you what you are.

Worse, society often gaslights you into picking the wrong build.

🧙‍♂️ The Specialist Build: Deep, Sharp, Rare

If you love:

• Becoming the best at one thing

• Solving deep, technical puzzles

• Getting paid handsomely to do just that one thing

Congrats. You’re a Specialist.

Specialists are like enchanted weapons.
They do one thing. And they do it better than anyone.

The world needs them to:

• Build the rocket engine

• Diagnose the rare disease

• Write the compiler for the compiler

🛑 But they can get trapped.
Promoted to manager? Burnout.
Asked to lead cross-functional work? Anxiety attack.

They’re leveled up in a vertical. And the world moves sideways.

🧰 The Generalist Build: Broad, Fast, Patterned

If you:

• See connections no one else sees

• Learn fast, execute fast, context-switch faster

• Hate being bored

You might be a Generalist.

You’re not the sword — you’re the Swiss Army Knife. You’re not the legendary sword. You’re the absurdly useful Swiss Army Knife — not as shiny, but you save the team when the dragon’s chewing on the tank.

Generalists shine in:

• Early-stage startups

• Ambiguous roles (“figure it out” zone)

• Bringing humans, tech, and business together

🛑 But they risk looking “shiny object” or “not deep enough.”
People confuse curiosity with confusion.

🎮 Dual-Classing is OP (Overpowered)

The real cheat code?

Be a generalist across time, and a specialist in moments.

• Learn broadly.

• Specialize on demand.

• Stack up 2–3 specialist “modes” over a decade.

🎯 This gives you:

• The credibility of mastery

• The agility of range

• The surprise of multiplicity

Think:

• Engineer who can sell

• Marketer who can code

• CEO who started as a theatre kid with mild insomnia and a coffee addiction*

(*Also fun at parties. These side quests open more doors than you’d think.)

You don’t need to pick a side. You need to know your base stats — and then level up with intent.

Be unpigeonhole-able. But also, undeniably good at some sh*t.

Phew. Okay.

Now that we’ve got a perspective — and maybe a few existential XP points — it’s time to chart your path to “victory.”

After all, what’s the point of likening your career to a video game if you’re not planning to beat it?

🎮 Coming Up in Part 2 — this Sunday, 5th October.
Skill tree respecs, career as a series of “bets”, regret monsters, burnout dragons, XP multipliers, and how to escape the wrong dungeon, how to “win” the game, level the playing field with bad “base stats”, and more

Subscribe now to make sure you have this delivered to your inbox!

Subscribe now

Everyone wants to talk about the dopamine hit when a deal closes. Nobody talks about the entropy. The grind. The mental DOMS. The kind of repetition that breaks most people - or builds something cold and surgical inside the ones who stay.

This post isn’t about smiling your way through discovery calls. It’s about holding power. Building edge. Selling like a killer, albeit a charming one, not a puppy.

1. Stop Being Nice

I’m not sure how to tell you this without sounding like the Andrew Tate of Sales but: Nice gets you ghosted. Nice gets you looped in endless “just checking in” purgatory. Nice is weak.

Nice is not the same as kind. Nice is eager to please, quick to say yes, and allergic to discomfort. Kind knows the room, sets the tone, and doesn’t flinch when it’s time to steer.

Nice says, “Thanks for your time.” Strong says, “Let’s get aligned on next steps.”

The best sellers set boundaries, drive meetings, redirect noise, and treat time like capital. They show up with intent.

The best sellers hold boundaries. They set the agenda and stick to it. If something new comes up, they acknowledge it, then slot it separately. They lead calls, not follow energy.

You want to be liked? Go into brand marketing. You want to be remembered? Hold the room.

2. Trust > Likability

People don’t buy because they like you. They buy because they trust you. Being honest - saying “You don’t need this feature” - builds more credibility than a thousand follow-ups or fake enthusiasm. Charm fades. Truth sticks.

Let’s be real: salespeople already walk in with a reputation. Tech teams distrust you. Finance thinks you're fluff. If you're selling AI or ML infra today, your charm isn't getting you far.

What gets you in the room - and keeps you there - is consistency, clarity, and showing up when it counts.

Some of the best relationships I’ve had in sales started with friction. A CFO pushing hard on price. Me holding the line while advocating internally for early access, roadmap features, better SLAs. They saw I fought for my org—but also for them. I gave them honest views, even if it meant risking the deal.

They didn’t always like me. But they trusted me. And when the money moved, they knew I’d show up with integrity.

3. Always Have a Plan B

If you’ve ever banked on a “guaranteed” deal closing EOD, you already know how that story ends.

Hope is not a strategy.

A deal isn’t real until the money lands.

Most teams have deal hygiene frameworks - upside, probable, commit. But frameworks are worthless if you're not honest about what’s real. Take your closure probability seriously. Most of you treat your pipeline like wishful thinking. Stop it.

That "90%" you’ve been telling yourself? Treat it like 60% and plan accordingly.

You want to be confident in your number? Then hunt like a bloodhound and have more than one ace ready to play. And buy yourself the time to use them.

4. Act Like a Partner not a Vendor i.e. Control the Process

Sales is a jungle. Either you’re driving the process or someone else is driving you off a cliff.

If you're not actively managing the speed and structure of the evaluation, your competitor is. Letting the buyer run the show is the fastest path to losing control—and the deal. Doing what they ask, when they ask, without asserting your path makes you a vendor. A replaceable one.

If your product is strong, don’t flinch at evaluation. Propose an RFP. Set clear next steps. Lead the buyer through a decision, not a maze.

The best sellers define the success path and co-own it with the buyer. They educate, steer, push when needed, and call BS when the ask is lazy.

5. Protect Your Thinking Space

There’s always one more follow-up you could send, one more call you could book, one more thing to tweak in a deck. That doesn’t mean you should do it.

Execution without space to think is how you burn out, make bad calls, and lose your edge. Sales rewards sharp instincts - but you don’t sharpen a blade by slamming it against steel all day.

B2B sales is one of the few jobs where, if you deliver, you can tell your manager to back off - and they’ll listen. Use that leverage. Block off time. Guard it like hell.

This is when you plan. Plot. Sometimes it may mean building backup pipeline. Run deal rewinds in your head. Pull out the aces you saved. The best sellers aren’t just hustling - they’re cold, calculated, and two steps ahead.

6. Too Much Choice Kills Conversion

When you give a buyer too many paths, they freeze. Or worse - they pick the wrong one, churn later, and blame you.

This isn’t a buffet. You’re not here to entertain. You’re here to prescribe.

Narrow the choices. Own the recommendation. Frame the decision with confidence.

Most buyers want you to lead. The clarity of a strong POV is what they’re paying for. Freedom? That’s a trap. And it costs you deals.

7. Over-communicate and Rally the org

Great sellers don’t operate solo. They pull strings, stack the bench, and run plays with precision. They sell internally as hard as they sell externally, getting buy-ins from stakeholders - be them commitments from product or ownership from delivery teams.

Enterprise sales is a team sport: if you’re trying to win it alone, you’re toast.

Get marketing to create air cover and drive urgency. Loop in post-sales early to de-risk. Get your CEO to send that one-line nudge when it matters. Use the weight of the org to tilt the room. Over-communicate.

Yes, your pre-sales does not need the whole story, but knowing the whole story is what them invested.

After a certain point, sales often becomes about selling DESPITE the org and not because of it. If you think this is unreal, why do small companies sometimes beat the proverbial Goliaths? Because they are able to get buy-ins from all the stakeholders needed (“the delivery guy is also the pre-sales guy”, ring any bells?).

Big deals are battles, and the way to win them is with alliances. You win them by getting the room behind you.

Be the general. Build the momentum. Close with force.

Conclusion: Build Edge, Don't Beg

This isn’t theory. These lessons were earned the hard way - quota breathing down your neck, deals slipping at the last mile, internal chaos, and pressure that doesn’t care how hard you tried.

Sales isn’t for the likable. It’s for the clear-headed. The ones who lead, not follow. The ones who build systems, hold power, and stay sharp under fire.

Want to win? Stop being nice. Start being dangerous.

If this made you flinch or nod, send it to the rep, founder, or operator who needs to hear it.

📩 Know someone selling under pressure? Send this their way. Or steal it and look smarter in your next team huddle.

🧠 Subscribe for more execution notes from the field. No fluff. Just fire.