Life As An Entrepreneur: The Good, The Bad, And The Ugly

The city is alive. The offices are empty. I find myself alone in this big city.

I walk through the street, passing strangers from all walks of life.

It’s a Friday night. And I’m late.

I’m supposed to be meeting up with friends at the local bar. I would have been on time, but I had calls to make, and meetings to arrange.

I stumble into the bar, send one last email for the night, and find my friends. They’re seated around the table with a half drunk pitcher of beer. It looks like it’s going to be one of those nights. The type of night that start off innocent, but ends at four in the morning with a blazing headache. And feet that can’t walk straight.

I don’t know if I can afford a night like that. I have to be up at 5 am.

I ignore the thought, brush it away, and shake hands with my friends seated around the table.

It’s been awhile since I’ve seen them. But their faces look the same. And the jokes that ensue remind me that not much has changed.

I pour a glass of beer. And with each sip I take, I forget about the disasters from the week gone by – the failed opportunities and the blown sales. Or at least, I try to forget. But it’s damn near impossible. I’m getting drunk and numb, but my mind is still alive and racing. I can never turn it off. I can never stop thinking about business. It’s a gift and a curse.

I order honey garlic wings, and in between bites – I shoot the shit.

We crack jokes, reminisce, and dream our little dreams.

A new pitcher of beer arrives. The conversation becomes more serious. And we begin talking about career and jobs.

It’s funny…

Some people get drunk with their friends to forget about their career or job. I’m the opposite. After a couple of rounds, come my realest of convos. I live for this shit. You can see the ambition in my pores.

They tell me about their jobs and promotions and what happened at the water cooler last week.

I tell them about my grind and hustle and what happened with the client I was pitching last week.

They nod and follow along. But I know they don’t understand. I know they don’t get it.

The rift between us two is apparent. And it’s growing larger by the day.

“Damn…what you’re doing seems pretty risky. It’s crazy. What if it doesn’t work out? Then what are you going to do?” A friend asks.

The words leave his mouth, reach my heart, and cut it. Blood pours out.

The rest of the table looks on with eyes full of agreement – they watch me bleed. Their judgmental glare punches a hole through my stomach. And it hurts.

It hurts because it’s true.

To them what I do seems risky. But to me – what they do seems risky. We’re not cut from the same cloth.

They see a person hustling and bustling trying to reach the top of the world, and it inspires thoughts of fear and struggle.

I see people putting their life in the hands of one employer, and it inspires thoughts of false security and sheep like behaviour.  Yet I don’t acknowledge it. I never acknowledge it. I don’t have the heart to acknowledge it. Who the fuck am I to acknowledge it?

Instead, I say what I always say…

“Yeah…I guess.”

The conversation changes topic. I sip my beer. Crack more jokes. Pay my bill. And walk home.

I’m walking upstream, and the currents are overpowering me. I can’t stop the thoughts from causing havoc in my brain.

Soon, the realization becomes clear to me.

If I’m going to make it – I need to surround myself with people who are like me. I need to find those people. And build my army. Because if I keep spending time with people who are playing a different game than me…

Sooner or later one of us will fall because this way of living doesn’t work.

At least, it didn’t for me.

I fell.

Because you see…

I tried to teach my friends how to be bosses. But all they ever wanted to be was employees.

So now the love is gone.

Because we no longer wear the same uniform.

It sucks but it’s true.

Sometimes you have to let go of the friends around you, so you can grow into the person you want to become.

The life of an entrepreneur isn’t all sunshine and unicorns. You have to make decisions like these every single day. And it fucking hurts. It can be a mean and horrible place, and you’ll go through shit every single day. You’ll eat a lot of shit. And you’ll have no choice but to swallow it. Maybe you’ll even come to like the taste. Who knows?

But right now everybody wants to be an entrepreneur – people want to pack up, move to Silicon Valley, and start the next big thing. It’s the cool thing to do. But there’s a lot of nuisances that come along with this life of hustle.

I want to use this article to share those with you. I’m no expert so take it for what it’s worth.

The Good 

a. You learn how to make money and can make it whenever you please 

I never understood them. I tried to relate, but I couldn’t.

They would bitch about money all day, about not having enough, there was never enough. And yet they wouldn’t do anything about it. They would just sit at home all day, complaining and fussing.

Then they got jobs, and the same thing happened. They complained about bills to pay and rent payments to make, and how they didn’t have enough, there was never enough, and how they had to sit and wait two weeks to get their paycheque.

It was strange to me.

It was like crying over spilled milk, but instead of getting up and finding a rag – you sit there and bitch and moan for two weeks, until someone comes and hands you a rag. I didn’t see the logic in that.

But then it started to become clearer to me…

I realized it wasn’t their fault. They were conditioned to wait.

Because you see…

Average people don’t think and act like entrepreneurs – they’re much too passive.

The good thing about being an entrepreneur is you learn how to make money.

If you don’t learn fast – you won’t be an entrepreneur for long.

What you ultimately learn about money is the amount of money you make is positively correlated to the amount of value you deliver. And this realization changes everything. It makes you take a step back from the maze the world put you through, and you start to question everything. And that’s when things start changing.

At least, that’s when things started changing for me.

I stopped waiting, dreaming, and hoping – instead I woke up each morning, picked up the damn rag, wiped the milk from the ground, and got paid.

b. You get to mold your world to match your inner reality

I wake up with nothing more than the ideas in my brain. Each day is a blank canvas. There’s no one telling me what to do, or when to work, or how to work – I simply have to wake up each morning, pick up the paint brush, and paint.

Each day is an adventure. No two days are alike.

Will I paint a masterpiece? Or will I paint something that makes me want to crawl up in a little ball, and wither away in embarrassment?

Shit. I can’t call it.

It’s like playing a video game. That’s how it feels. Somedays go well. Somedays end with me defeated, on the floor of some hotel. I don’t know what today is going to bring. But the vision inside my head is burning a flame and it’s my job to keep it alive.

Normal people take the world and try to find their place in it.

Entrepreneurs take their vision of the world and create it.

There’s something magical about this way of life. You become almost godlike because you know you can bring almost anything to life – all you have to do is pick up the brush and paint.

Once you start thinking on this level – the world begins to open up for you, and you go from just another human being that is going through the motions – to someone who is creating the motions.

c. You get to know yourself like never before 

I was scared to check my bank account. I was standing in front of the ATM. My heart was coming out of my chest. And I was sweating profusely.

I wiped the sweaty card on my jeans and pushed it through the machine. I took a deep breath, controlled the tremor in my fingers, and punched my four digit PIN number. Then, I almost dropped dead. I had $73 dollars.

If you’ve never had your back against the wall….

If you’ve never been stuck in a hole…

If you’ve never ran out of funds when you had campaigns to launch, bills due, suppliers to pay, and products to maintain…

You don’t really know who you are.

For you don’t know…

What you’re truly capable of doing.

Entrepreneurship forces you to find yourself.

In the early days…

Your back is up against the wall every single day, and you must confront parts of yourself that aren’t pretty.

Thoughts of not being good enough. Thoughts of doubt, and fear, and ridicule. Thoughts of being unworthy of success and happiness because of some shit that happened to you when you were six years old.

You must confront.

If you don’t – you fail.

Everyday you have to look at yourself in the mirror, accept yourself for who you are, and find a way.

And when you do, there’s no other feeling like it.

For when your back is against the wall and it’s time to sink or swim – you realize that the world is yours if you simply swim everyday like you could sink any minute.

I swam that month. And made just under $15,000.

It’s not the money that’s important here.

It’s the fact that entrepreneurship will rip you a part, take the skin off your bones, and the good feelings out of your heart…until…

All your left with is what you have on the inside.

Once you muster up the balls to take a look at who you are on the inside – you become free. And you truly start working and hustling like the world is your playground. And that’s when you win.

You win…

When you forget about who you want to be. And you accept who you are.

Most people never get to this point. And that’s why they struggle.

I used to be one of them.

Somedays I still am.

d. You build the skills you need to make it wherever you go

I got a job. And learned how to punch data into the same excel sheet every minute of every work day.

I got another job. And learned how to make balance sheets balance every minute of every work day.

Then I graduated high school.

I didn’t know anything. Then I started a business. It failed.

But I learned how to sell, market, create value, launch, fulfill orders, satisfy customers, leverage cashflow, and network.

It changed everything. It opened the doors to an alternative universe.

I couldn’t get enough. These skills became my drug.

I launched more businesses. I failed again. I kept learning.

I learned and relearned and kept learning these skills for years and years and years. They were the only skills that mattered to me because they were the only skills I could take with me wherever I went. Whether I started a blog or a carpet cleaning company – these skills were universal. And could be applied to whatever I desired.

Jobs teach you the skills you need to land a promotion. Entrepreneurship teaches you the skills you need to make it in life.

When you learn and master these entrepreneurial skills…

Nothing else matters.

Because you can make it wherever you go. You have the goods.

It’s like Jay Z said…

“Put me anywhere on God’s green earth. And I’ll triple my worth. I-Will-Not-Lose.”

e. You’ll be the poorest man in the cemetery 

I was young and naive. I didn’t know what to believe.

“You want to get rich?” He said.

“Yeah.” I replied.

“Go take a trip to the cemetery.” 

“The cemetery?” I replied with a face full of confusion.

“Yeah…the cemetery – it’s the richest place in the world.”

I ignored him. And went back to shooting people in the face. I was playing GTA.

If you didn’t understand the above – I don’t blame you.

I didn’t either.

But then I came across the following. And it all made sense.

“The graveyard is the richest place on earth, because it is here that you will find all the hopes and dreams that were never fulfilled, the books that were never written, the songs that were never sung, the inventions that were never shared, the cures that were never discovered, all because someone was too afraid to take that first step, keep with the problem, or determined to carry out their dream.” – Les Brown

Yes, I want to be filthy rich. Yes, I’m going to be filthy rich.

You can call me materialistic and greedy or whatever.

But the goal isn’t just to make money for the sake of making money.

The goal is to bring to life ideas, creations, and adventures – the goal is to live a life that enables me and my loved ones to die poor.

To die having lived a full life. To die having experienced all there was to experience.

And that’s exactly what entrepreneurship allows.

In fact, it’s the only thing it allows.

One way or another, depending on how you play it, and how much hustle you have running through your veins – you will die poor.

It could be figuratively.

Or it could be literally.

I hope you make it the first and not the second.

f. You get to live. 

I used to be scared to die.

I used to fear it.

It would keep me up at night.

It would burden me.

It created a black hole in my heart. And I felt its weight every minute while I silenced the dreamer inside me and conformed to the path society put on my plate.

Then I listened to the dreamer inside me. And I launched my first business.

And I lost the fear of death.

Because I actually started to live.

“The fear of death follows from the fear of life. A man who lives fully is prepared to die at any time.” – Mark Twain 

There are a bunch of other good things about entrepreneurship – you’ll meet great business people, possibly make a fortune, and can live life on your own terms. You can create a fantasy land. And live in it.

We all know this.

But let’s spend some time discussing the bad now…

The Bad 

a. People will constantly ask you, “When are you going to get a real job?”

I woke up at 5 am. And I hustled till 12 am. I went to sleep. I woke up. I did it again.

I developed bags under my eyes. And throbbing pain my back. I sat in front of the computer every day and grinded.

And whenever I took a break to attend family events, or dinners, or night out with friends…

I heard the same thing…

“Tej is XX years old….and he still doesn’t even have a job.”

As an entrepreneur you’ll do more work in one day than most people will achieve in an entire month.


If you don’t have a normal job that gives you a salary for clocking in and clocking out…

The people around you won’t understand.

And they won’t consider what you do as “work.”

If you think it gets better once you make money – it doesn’t.

Because once I started making a little bit of change – they stopped asking me when am I going to get a real job…and they started telling me…

“You punch letters on a keyword. You haven’t worked a hard day in your life.”

b.  If you fail – you’re considered a loser. If you make it – you’re considered a ruthless, scumbag businessman who doesn’t do a thing for humanity.

Society appreciates and respects careers such as lawyers, doctors, and firefighters – but businessmen? “Ugh…they’re just in it to win it for themselves.”

That’s what people think. And I don’t blame them. I used to think that too.

Businessmen do win it for themselves.

But in the process…

They also make the clothes on your back, grow the food on your plate, and build the homes you live in.

So think about that the next time you diss them.

d. Freedom is a lie.

I thought I could set my own hours. I thought I could take days off.

I thought entrepreneurship would save me. And afford me to do all the thing I wanted to do.

I could finally pick up a hobby, I could learn a language, and I could travel. And work from anywhere. Except that’s a lie. Because building businesses is like raising kids.

If you don’t commit, you don’t win.

Freedom is a lie.

You have to go all in.

I sunk every time I half assed something. I swam every time I dove in head first.

Entrepreneurs have less freedom than employees. In fact, they have absolutely zero freedom.

You want freedom?

Make money.

Entrepreneurship doesn’t equal freedom.

Money = Freedom.

If you have it, you can do with it whatever you please, and you’ll have to answer to no one. If you don’t have it, you’ll always be at the mercy of those who do.

And I’ll be damned if my family has to live a life answering to someone.

e. You’re not really your own boss

I read it over and over and over again. It burned a hole in my brain.

“Be your own boss.” 

Every self help book advertised it. Every motivational speaker preached it. They all lied. But I swallowed their lies.

And I started a business. I became my own boss.

Except I really wasn’t my own boss because…

Every customer ended up being my boss.

Every supplier ended up being my boss.

Every client ended up being my boss.

And they were ten times worst than a normal boss.

And that’s the truth…

The truth they’ll never tell you.

f. You’ll never get to turn it off

I envy the people who can work eight hours, come home, and forget about work.

Normal jobs are cool because they make that possible.

You get in, do your work, and get out. Now you’re free to do whatever you please after work/on the weekends.

Entrepreneurship isn’t like that.

It’s the opposite.

It’s always on. And running.

And you’re always thinking and plotting and strategizing.

Even when you’re not “working”…

You’re working.

Because the thoughts are in your brain, and they’re running wild, and they’re burning a hole in your chest, and if you’re not careful…

They might end up making you miss out on the world around you.

Think it doesn’t get worst?

Oh it does…

Let’s talk about the worst side to entrepreneurship…

The Ugly 

a. Your partner, best friend, and family members will probably give up on you and leave.

I’m seated across a table with the man who made millions, went broke, made millions, went broke, and made millions all over again. He opens his mouth and speaks…

“If you’re going to go down this road – I need you to remember one thing.” 

“What’s that?”

“Only eat with those you starved with.”

Most of your friends, partners, and family members won’t understand your lifestyle.

They’ll snicker under their breath, derail your dreams, and will tell you why you’re going to fail. And eventually either you will give up and conform to their ideals or you won’t. And they’ll give up on you and walk away.

It’ll hurt. And you’ll feel pain. Lots of it. You’ll sink to the bottom of the ocean. And you’ll wonder why.

But that’s the wrong thing to do.

Because it’s only when you get out with the bad that you make room for the good.

The good will come.

And when it does…

Never let it go.

For they are the people you want to eat with.

A wise man once told me the greatest business decision you ever make isn’t actually a business decision – it’s a life decision. It’s the decision of deciding who you want to date/marry.

He said (I’m paraphrasing):

“You, young guys make stupid ass decisions about who you should be dating. You go out with these chicks that hang out with different dudes popping bottles all weekend long, instead of picking up someone with a brain that can be a good partner in life. You base your entire decision off looks or status or some other bullshit superficial trait. You make emotional decisions, instead of logical ones. And not once do you think about anything else. Not once do you sit back and take time to figure out what type of partner you need to build a great life with. Not once do you acknowledge that. Not once do you think if everything goes to shit, and all you’ve got is each other – could you still be happy? Could you support one another, and climb up together? Instead, you buy into these bullshit Hollywood dreams, and you chase it. And you turn these people into your spouse. And then one day you decide to put your foot on the gas pedal, and do something with your life. You decide to start a business or pursue a passion. And you fail. You fall flat on your face. Because you lost before you even started. You lost the very moment you picked a partner without ever considering whether or not they would support your ambition.” 

I didn’t see it then, but I see it now.

Find someone who loves you, supports you, and has all the qualities you need to build a great life with. It will help you win a thousand times faster.

It’s true for normal people working a 9-5. But it’s even more truer for entrepreneurs.

You need a support circle around you. And it starts with the partner you choose.

You’re not going to find your ideal partner in bars.

You’re not going to find your ideal partner in clubs.

But you may just find her in the fifth aisle at Walmart.

b. You might go bankrupt, like a million times over.

Majority of the people on the Forbes list are entrepreneurs.

And majority have or have been close to declaring bankruptcy, numerous times.

It’s just the part of the game.

I’m not saying you’ll go bankrupt.

All I’m saying is there’s a lot more ups and downs to this lifestyle so you need to have the stomach for it.

c. You might end up blowing your brains out, literally.

No one wants to talk about this.

I don’t either.

But I can only use my paint brush to paint full truths, so I will..

Depression is higher for first time founders. And suicide is real.

Check the stats.

Well that’s all I got. I’m a deflated balloon. Everything inside me is gone.

So does the bad and the ugly side to entrepreneurship outweigh the good somedays?

Yes. It does.

But you know what gets me through?

I think to the future. I think to when I’m a daddy. A husband. An uncle.

And all I think about is…

How am I going to tell my kids to follow their dreams…

…if I never had the courage to follow mine?

I leave you with one simple thought…

Tupac once made a song called, “Shorty wants to be a thug.”

He then rapped about the struggles and pitfalls of being a thug. And he ended the song by saying, “Do you still wanna be a thug?” 

It was clear the answer was an overwhelming no. Anyone who thought different was crazy. For no was the logical decision.

I’ve laid out the good, the bad, and the ugly about entrepreneurship.

And all I have left in me is one question…

Do you still want to be an entrepreneur?

If the answer is no…

I applaud you.

If the answer is yes…

You’re one crazy motherfucker. And you have no idea what you’re getting yourself into.

But email me…

Because you’re exactly the type of friend I want.

Tej Dosa
5:03 pm
Vancouver, BC