The Things I Stopped Worrying About (and the Potholes That Taught Me Why)
For most of my life, I worried about getting things right.
The right career.
The right decisions.
The right city.
The right relationships.
The right version of myself.
Like many ambitious people, I believed life was a complicated puzzle, and if I collected enough information, worked hard enough, and made enough intelligent choices, I could solve it.
I built frameworks.
I analyzed possibilities.
I tried to predict outcomes.
I was the kind of person who could spend hours thinking about a decision that would take five minutes to make.
Then life did what life does.
It introduced variables that weren’t in my spreadsheet.
A career I had invested years building changed overnight.
Plans I had carefully designed disappeared.
Things I thought would define me became irrelevant.
Things I never expected became the chapters I remember most.
Slowly, I stopped worrying about being right all the time.
I stopped worrying about whether my journey looked like everyone else’s.
I stopped worrying about falling behind.
Because I discovered something strange:
Most people aren’t actually moving on a straight road. They are simply better at hiding their potholes.
The person who looks successful may be quietly questioning everything.
The person who seems certain may be terrified.
The person who appears to have the perfect plan may be one unexpected turn away from starting over.
We spend so much energy comparing our behind-the-scenes struggles with someone else’s highlight reel that we forget something important:
Everyone has potholes.
The difference is what they do after they hit them.
Do they sit there and complain about the road?
Do they pretend the damage never happened?
Or do they get out, look at what broke, learn something, repair what they can, and continue driving?
That shift changed how I see life.
I still plan.
I still dream.
I still create frameworks and probably still have too many browser tabs open.
Some habits are beyond saving.
But I no longer believe that a perfect plan creates a perfect life.
The unexpected moments—the failures, detours, delays, and breakdowns—often become the moments that shape us the most.
That idea became the foundation of my memoir, About Life Choices & Potholes.
It is a book about the roads we choose, the roads chosen for us, and the unexpected bumps that quietly transform us into the people we were meant to become.
The biggest thing I stopped worrying about?
Whether my life was following the map.
Because I’ve learned that sometimes the best stories begin when you take a wrong turn.
Six Months Into This System, Here’s What I’d Tell Myself on Day One
I’ve been running this exact process for about 6 months now, long enough that it’s stopped feeling like a system I’m following and started feeling like just how I work, the way you stop noticing you’re driving a specific route once you’ve done it enough times. I wanted to go back and write to the version of me who started this, mostly because he was more worried than he needed to be, about several very specific things.
“This is going to take longer than just doing it the old way”
She believed this for the first couple weeks, and I understand why — building the habit of writing notes first, running them through research, editing properly, felt like more steps than just hitting record and hoping. It is more steps. It is not more time. The old way spent all its time on one disposable post. This spends slightly more time up front and gets paid back twenty times over by the end of the week. She’ll figure this out around week three, when she does the math and immediately regrets not doing it sooner.
“People are going to notice I’m reusing the same idea everywhere”
Nobody has ever once mentioned this to me. Not a single comment, not a single “didn’t you already post this.” I used to lie awake slightly anxious about being caught doing something I’d quietly convinced myself was a shortcut. Nobody’s watching closely enough to notice, and even if they were, one idea shown to them once, in one format, isn’t repetition from where they’re standing. That fear cost me more sleep than it deserved.
“The system will fall apart the first time I have a bad week”
This is the one I’m proudest of being wrong about. I’ve had actual bad weeks since starting this — sick, distracted, genuinely out of ideas on a Monday morning. The system didn’t care. There’s usually a backlog of decent notes sitting around from a better week, waiting their turn, completely unbothered by whatever mood I’m in on any given Tuesday. That was the entire point of building it this way, and I still find it slightly miraculous when it actually works exactly as designed during a week I didn’t have the energy to think about it at all.
“I’ll get bored of doing the same eight steps every week”
I expected the repetition itself to eventually wear on me, the way any routine eventually does. It hasn’t, and I think I finally understand why: the steps are repetitive, but the content isn’t. I’m not doing the same thing over and over. I’m running the same process over different raw material every week, which turns out to be a completely different experience than doing the same task on autopilot. The scaffolding repeats. The actual thinking never does.
What I’d actually say to my younger, unenlightened version, if I could
Stop worrying about whether this is going to work and just run it for four weeks before you judge it. You’re going to want to abandon it around week two, when it still feels like more effort than the old chaotic way and hasn’t paid off yet. Don’t. The payoff isn’t in week two. It’s in week six, when you realize you haven’t had a single Thursday where you didn’t know what to post, and you almost don’t notice that’s remarkable anymore, because it’s just how Thursdays work now.
She wouldn’t have believed me, probably. I’m telling you instead, in case that’s more useful coming from someone who isn’t currently panicking about whether Wednesday’s edit is going to take too long.
The truth is, I don’t really travel to collect countries anymore. I travel to collect questions.
Every city has given me one.
Some have asked who I wanted to become. Others quietly asked who I had been all along.
Looking back, the places that changed me the most weren’t necessarily the most beautiful. They were the ones that interrupted the story I was telling myself. They made me slower. Hungrier. More observant. Less certain.
If I had to choose ten destinations, these would be mine.
1. San Francisco, USA
Because no city has taught me more about ambition.
San Francisco smells of roasted coffee, eucalyptus after rain, salt carried inland by the Pacific, and impossible optimism. It is where startups become religions and productivity masquerades as personality.
I spent years there believing I was building a career.
In hindsight, I was also building an identity.
The city gave me friendships, opportunities, heartbreak, layoffs, immigration paperwork, impossible hills, dogs who believed every beach belonged to them, and sunsets that forgave almost everything.
It also taught me that Silicon Valley’s greatest export isn’t technology.
It’s hope.
2. Mumbai, India
Because nowhere celebrates chaos quite as beautifully.
Mumbai doesn’t ask for your attention.
It kidnaps it.
The city smells simultaneously of monsoon rain, frying vada pav, jasmine flowers, diesel, incense, fresh fish, sea salt and cardamom chai.
It is impossible to experience quietly.
Here, weddings become theatrical productions with enough food to feed entire neighborhoods. Local trains become sociology classrooms. Vegetable markets become negotiations worthy of diplomatic summits.
Mumbai reminded me that life was never meant to be optimized.
Only experienced.
3. Copenhagen, Denmark
Because simplicity is harder than complexity.
There is a stillness to Copenhagen that almost feels engineered.
Bicycles glide silently.
People trust one another.
Bread deserves its own religion.
Candles appear even when electricity works perfectly.
The city quietly dismantled my belief that success must always be loud.
Sometimes sophistication whispers.
4. London, England
Because history has exceptional storytelling skills.
London doesn’t feel like one city.
It feels like centuries having an ongoing conversation.
Every street carries an argument between empire and modernity.
Every pub contains at least three novels.
Every rainy afternoon somehow improves the architecture.
It taught me that civilizations, like people, are beautifully inconsistent.
5. Goa, India
Because joy requires less planning than we imagine.
Goa has an unusual relationship with time.
Lunch becomes dinner.
One conversation becomes an afternoon.
The sea edits priorities with remarkable efficiency.
The older I become, the more I appreciate places that encourage lingering over arriving.
6. Lonavala
Because some journeys are measured in conversations rather than kilometers.
The drive out of Mumbai has become almost ceremonial.
Fog rolling over the hills.
Roadside chai.
Corn roasted over charcoal.
Unexpected waterfalls appearing after generous monsoons.
Sometimes you travel hundreds of miles to escape.
Sometimes eighty kilometers is enough.
7. Pune
Because cities, like people, can mature gracefully.
Pune possesses an intellectual rhythm that has always appealed to me.
Bookshops.
Old cafés.
Students convinced they’ll change the world.
Retirees convinced the world was better before everyone else tried.
They’re probably both right.
8. New York City, USA
Because nowhere performs confidence quite like Manhattan.
New York moves with astonishing certainty.
Everyone appears late for something important.
The city celebrates ambition without apology.
Yet beneath its velocity are tiny moments of astonishing humanity—a jazz musician in the subway, strangers recommending bagel shops with religious conviction, Central Park reminding millions that nature occasionally wins.
9. The Airports Between Places
An unusual choice.
But airports have become some of the most defining places in my life.
They’re where identities change.
Visas expire.
Suitcases disappear.
Goodbyes become routine.
Airports are the geography of transition.
No one dreams of them.
Everyone remembers them.
10. Home
Whichever version of it exists today.
Home stopped being a location somewhere between immigration queues, corporate layoffs, return flights, family dinners, wedding seasons, and walking Sauli through unfamiliar neighborhoods.
I’ve discovered that belonging has very little to do with geography.
Sometimes it sounds like your parents arguing over tea.
Sometimes it’s the smell of biryani drifting through an apartment window.
Sometimes it’s watching fog roll over the Golden Gate Bridge.
Sometimes it’s simply knowing which grocery store sells the good mangoes.
Perhaps that’s why I struggle with lists like these.
The best destinations don’t give us photographs.
They quietly rearrange us.
Many of these places appear throughout About Life Choices & Potholes, not as tourist destinations, but as characters. They host careers and heartbreaks, immigration interviews and Indian weddings, lost luggage and found friendships, extraordinary meals and ordinary Tuesdays. Looking back, I don’t think I was travelling to discover the world.
I was travelling to discover that life, much like a good city, is best explored on foot—with curiosity, a healthy appetite, and enough humility to accept that the scenic route is usually the memorable one.
My favorite quote isn’t from a philosopher or a CEO. It’s one I’ve slowly arrived at myself:
“Life doesn’t change at crossroads. It changes in potholes and fallen trees.”
We spend so much of our lives waiting for dramatic moments—the perfect opportunity, the big decision, the career change, the wedding, the move. We imagine life as a series of intersections where we consciously choose left or right.
But when I look back, the moments that shaped me weren’t crossroads at all.
They were potholes.
The layoff I never planned for.
The relationship that ended.
The illness that slowed me down.
The wrong turn that introduced me to the right people.
The idea that failed.
The one that unexpectedly worked.
Potholes don’t ask for permission. They shake you, damage your plans, force you to stop, repair, rethink, and sometimes take a completely different road.
Ironically, those detours become the story.
That’s the idea behind my memoir, About Life Choices & Potholes. It’s a reminder that while we celebrate our choices, we’re often quietly shaped by everything life chose for us.
Looking back, I don’t remember every decision I made.
The Best Dish I Ever Ate Was Never Just About Food
People often ask me, “What’s the best local dish you’ve ever eaten while traveling?”
It sounds like a question about food. About flavors. About that one unforgettable meal that made you close your eyes and say, “Wow.”
But the older I get, the more I realize that the best dishes are rarely about the ingredients. They are about the people, the places, the memories, and the version of yourself that existed when you ate them.
I have eaten incredible food across the world — from the elegance of Copenhagen to the chaos and comfort of Mumbai, from the familiar streets of San Francisco to the hidden corners of cities that make you pause and wonder how many stories exist beyond your own.
But the meals I remember most are not necessarily the most expensive or the most famous.
They are the ones that carried a story.
A simple plate of food prepared by someone who had spent decades perfecting a recipe. A meal shared with strangers who became friends. A dish eaten while sitting somewhere unfamiliar, realizing that for a brief moment, you belonged there.
Travel has a strange way of doing that. It removes the labels we carry at home — our careers, our achievements, our failures, our identities. Suddenly, you are just another person sitting at a table, waiting for a plate of food to arrive.
And sometimes that plate teaches you more than any guidebook ever could.
One of my biggest realizations while writing About Life Choices & Potholes was that life itself is a journey of unexpected flavors. Some chapters are sweet. Some are bitter. Some leave a strange aftertaste that you only understand years later.
We spend so much of our lives searching for the perfect destination, the perfect career, the perfect relationship, the perfect version of ourselves.
But life is rarely a Michelin-starred experience.
It is street food.
Messy. Unpredictable. Sometimes confusing. Occasionally disappointing.
And yet, somehow, unforgettable.
The best dish I ever ate while traveling was not just a recipe. It was a reminder that every place has a story, every person has a history, and every moment has something to teach us.
Maybe that is why we travel.
Not just to see new places.
Not just to taste new food.
But to discover new versions of ourselves.
About Life Choices & Potholes is a collection of those discoveries — the unexpected turns, the wrong roads, the beautiful detours, and the lessons hidden inside the messiness of life.
Because eventually, we all realize the same thing:
The potholes were never interruptions in the journey.
Stop Burning Your Boats: Why the “Boring Quit” Wins Every Time
We’ve all heard the romanticized startup advice: burn the boats. Quit your job, leap into the unknown, and force your back against the wall so success is your only option.
But according to author Kay Jay in How to Start a Small Business That Actually Makes Money, this dramatic narrative is nothing more than a “survivorship bias machine.” While the rare stories of high-stakes gamblers who beat the odds make for compelling media, they conveniently ignore the massive graveyard of businesses that crashed under the weight of financial desperation.
If you are thinking about launching a business, Jay advocates for a “strategic exit” instead of a premature leap. Here is why keeping your day job might just be your biggest competitive advantage:
The 33% Advantage: Research published in the Academy of Management Journal shows that entrepreneurs who keep their day jobs while launching are 33% less likely to fail than those who quit immediately.
Time to Iterate: A steady paycheck acts as a safety net, granting you the breathing room to test your business model, validate assumptions, and survive early setbacks without the panic of immediate survival.
Reduced Sales Desperation: When your rent is covered, you don’t sound desperate on sales calls. That means you can hold firm on your pricing and walk away from “bad” clients instead of taking them just to make ends meet.
The Day Job as a “Funding Mechanism”: Shift your mindset. Your current job isn’t an obstacle—it’s the investor funding your runway, buying you the time to build a rock-solid foundation.
The Goal of a “Boring Quit”: The ultimate ideal is a “calculated step” rather than a gamble. A boring quit means you already did the hard work of validation and revenue generation before you needed the income, rather than betting your livelihood on work that hasn’t happened yet.
The “messy middle”—that transitional phase between a career ending and a new one taking off—demands the structural integrity of a financial runway. By refusing to burn your boats prematurely, you ensure your business is fueled by market demand rather than sheer panic.
If you want a step-by-step roadmap to building a sustainable, profitable venture without risking your livelihood, pick up a copy of How to Start a Small Business That Actually Makes Money today and learn how to master the art of the boring quit!
There’s a specific guilt that shows up right around the third time you post some version of the same idea in one week, a little voice that sounds suspiciously like a teacher checking for plagiarism, asking whether you’re actually being lazy right now, dressed up as a system. I felt that voice constantly when I started multiplying instead of creating from scratch every time. I want to talk about it, because I don’t think I’m the only one who’s felt vaguely fraudulent doing this.
Where the guilt actually comes from
I think it comes from a rule nobody stated out loud but everyone absorbed anyway: new content is virtuous, and reused content is a shortcut, and shortcuts are for people who aren’t willing to put in the real work. I believed some version of that for a long time, which is strange in hindsight, because I don’t apply that standard to literally anything else. Nobody thinks a chef is cheating for cooking the same excellent dish twice. Nobody thinks a musician is cheating for playing the same song at two different shows. But post the same idea on two platforms, in two formats, and some part of your brain quietly files it under “getting away with something.”
I did the actual audit on this feeling and it did not survive contact with logic, but it survived contact with logic for a surprisingly long time regardless, because guilt doesn’t require evidence, just a comfortable, familiar shape.
The reframe that actually worked
Here’s what finally moved the needle for me: nobody experiences my content the way I do. I see the same idea nine times because I’m the one making all nine versions. My actual audience sees, at most, one or two of those nine — a clip here, an article there, a newsletter they happened to open. To them, it isn’t repetition. It’s just the one piece of content they encountered, doing its job, once, the way any single post is supposed to.
The guilt was a symptom of being the only person in the room who’d seen behind the curtain. Everyone else just sees the show.
What I had to actually admit to myself
The uncomfortable truth is that “new content every time” was never actually a virtue. It was a constraint I’d mistaken for a value, and a genuinely exhausting one. Making something new from scratch isn’t more honest than multiplying a good idea properly — it’s just more expensive, and I’d confused the expense for integrity, the way you might mistake a harder workout for a better one even when it’s just worse programming.
A good idea, treated with real care and turned into several honest, distinct pieces of work, isn’t a shortcut. Writing an actual standalone article instead of just slapping a transcript online, cutting a clip that stands on its own instead of just trimming for length — that’s still work, real work, just not work I have to invent fresh raw material for every single time.
Where I landed
I still get a flicker of the old guilt occasionally, usually late at night, usually right before I post the fifth thing that traces back to Monday’s notes. I let it pass through without acting on it now, the way you’d let a familiar, slightly annoying song play out instead of turning it off. It’s not information. It’s just an old habit of thought that hasn’t caught up to how I actually work anymore.
The chef doesn’t feel guilty about the second plate. I’m working on it.
Ready to stop treating good ideas like single-use plastics?
When I first started, I fell straight into the trap that every new creator and entrepreneur is fed. I thought success meant building a flawless digital storefront before I was ever allowed to ask someone for money.
I spent weeks agonizing over color palettes, commissioning custom logos, and meticulously planning an Instagram grid that looked like it belonged to a million-dollar brand. It felt like hard work. It felt like progress.
But looking back through the lens of what I now know about building a Minimum Viable Business, all that time spent obsessing over “safe” digital marketing wasn’t productive at all. It was a defense mechanism—a deadly trap designed to protect my ego while quietly starving my bank account.
The Comfort of “Productive Procrastination”
When you are navigating the chaotic, unpredictable middle of a career transition or launching something new, the human instinct is to frantically grasp for control.
Building a website or curating social media feeds gives you an immediate dopamine hit. It lets you feel like you’re steering the ship, even when you’re standing still.
The Shield Behind the Screen: Designing a slick social media profile allows you to hide. It insulates you from the terrifying vulnerability of looking a real human in the eye and asking them to hand over their hard-earned money.
The Illusion of Feedback: If you post a reel and it gets zero engagement, it feels like background noise. It doesn’t sting the way a direct, face-to-face rejection does.
The Reality Check: If you cannot convince a single person in your immediate circle or neighborhood to buy your basic offer, a prettier font or a higher follower count isn’t going to magically create demand.
Why “Safe” Channels Fail in Month One
The foundational flaw with relying on organic social media growth or SEO when you’re trying to launch a venture comes down to a brutal constraint: time.
Algorithms Take Months: Building organic search traffic or a viral social media presence takes months—sometimes years—of consistent effort. If your timeline is a 30-day launch to secure your first paying customer or pay your rent, you simply don’t have the luxury of waiting for an algorithm to favor you.
Extreme Noise: Millions of creators are fighting a brutal war for fractions of a second of attention in overflowing digital spaces. In the online world, trying to play it safe makes you entirely invisible.
Vanity vs. Revenue: Likes, saves, and follower counts are comforting metrics, but they don’t pay the bills. A real business is built on a simple equation: an offer, a price, and a contact method. Everything else is just a distraction.
Breaking the Trap: Embracing the Friction
Escaping this trap requires a radical mindset shift. Instead of treating your business like an art project to be showcased online, you have to treat it like a clinical systems problem.
Embrace Direct Outreach: True validation happens in real-time interactions. Whether it is reaching out to your immediate network with low-pressure questions (“Do you know anyone who might need this?”) or utilizing local community channels, you have to go where the noise isn’t.
Risk the Immediate “No”: The discomfort you feel during direct outreach—whether messaging strangers or talking to neighbors—is simply the price you pay for speed.
Safe social media marketing feels cozy because it protects your pride. But if you want a business that actually makes money, you have to stop playing business. Step away from the endless tweaking of your digital footprint, embrace the friction of real-world conversations, and start chasing paying customers instead of likes.
Watch the full episode here:
Ready to Stop Playing Business?
If you are tired of hiding behind the comfort of a polished website, endless social media tweaking, and digital busywork, it is time to do what actually matters.
In my book, How to Start a Small Business That Actually Makes Money, I break down the exact 30-day framework to ditch the startup fantasies, price your offers with confidence, and secure your first paying customer in real time.
If I had to give one life-changing tip, it would be this:
Stop preparing to live your life. Start inconveniencing yourself by actually living it.
There is a particular species of human—and I know because I belong to it—that mistakes preparation for progress.
We don’t have ideas. We have systems for managing ideas.
We don’t write books. We build Notion dashboards about writing books.
We don’t start businesses. We spend six months choosing a logo because, obviously, investors care deeply about kerning.
Our browser has 427 tabs open. Every one of them is titled “I’ll definitely read this later.” We own more frameworks than functioning revenue streams. We can diagnose capitalism, AI, democracy, and the dating market before breakfast, yet still spend forty-five minutes deciding where to have lunch.
For years, I thought the missing ingredient was one more insight.
One more course.
One more spreadsheet.
One more perfect plan.
It turns out life is deeply unfair to people who love planning. It rewards people who are willing to look slightly foolish.
The first draft teaches more than the fiftieth outline.
The awkward sales call beats the perfect pitch deck.
The article you publish changes you more than the masterpiece you keep editing.
Most breakthroughs arrive embarrassingly underprepared.
I’ve realized that intelligent people have a peculiar curse. We can simulate success so convincingly in our heads that we confuse the simulation with the experience. We optimize routes we haven’t walked, solve problems we don’t yet have, and build second brains while occasionally forgetting to use the first one.
So if I could offer one piece of advice, it would be this:
Trade one hour of preparation for one hour of embarrassment every day.
Ship the imperfect thing.
Make the awkward phone call.
Publish the clumsy essay.
Ask the stupid question.
Start before your framework is finished.
Because eventually you discover that life isn’t changed by your best ideas.
It’s changed by the handful you were brave—or impatient—enough to put into the world.
