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#57: The perils of being your own boss ⚠️

Published about 2 years ago • 4 min read

Hello, hot thing.

I just returned to my desk after a two-week break — the first long break I've taken since I started working for myself.

If you don't know: I'm a freelance writer for B2B SaaS companies. The translation? I get all the chores done before you because I'm procrastinating on writing.

No, that's a lie. I don't get those chores done either.

But in a sense, I'm living the life my younger version could only dream of: Writing for a living. Having my own schedule. Working when I want to.

Basically, being my own boss. Sounds dope, right? 😎

Most days, I won't lie, it has its swagger. But it's not as glorified and hunky-dory as the internet makes it seem either. Want to flip the grass-that-seems-greener?

Here are three cons of being your own boss:

#1: No one can keep you accountable, disciplined, and motivated...except yourself

Being your own boss means you have that No One Tells Me What To Do attitude.

But, read that again: No one will tell you what to do. Fuck.

If you want to sustain your business, you have to be your own whiny boss. Your own cheery colleague. Your own nitpicky manager. Sounds overwhelming? It is.

Lesson: Buy hats, baby, because you're going to have to wear many 🎩

#2: No one's there to notice your failures...or your accomplishments

When I worked for a company, me, an introvert, despised the unnecessary meetings. The office politics. The diplomacy required to say "bugger off" professionally. Ugh. Don't miss it at all.

But me, also an introvert, loved being part of a team. Celebrating each other's wins. Handling mistakes, rejections, and tough clients together. Sigh. Miss that a ton.

You're all alone until you grow into a team — in the party dance and in the silent sobs.

Lesson: Practice hugging yourself 👐

#3: No one's your boss...except literally everyone you work with

You might think no one's your boss. Except everyone you work with owns a slice of that Who's The Boss pie.

If you have clients like me, you're answerable to them. If you have customers, you're liable to attend to their requests. If you have vendors, employees, or communities — you have commitments to fulfill to each of them.

Sure, you can divide up the shareholding of Bossing You Around at your own choice. But the external boss is there. Always.

Lesson: Choose your bosses carefully 👩🏼‍💼

Are these cons definitive and unworkable? No.

  • I ask my mum to wake me early and scold me to sit to work on time.
  • I make my friends pop champagne with me on a victory or bring me ice cream when I fail.
  • I love the clients who have part-ownership in the Boss Rochi Around stocks.

Nevertheless, the disadvantages exist. Finding the perfect career is figuring out what your dealbreakers are and what stuff you don't mind compromising on.

Choose your poison, in essence.

If I had to make the choice again today? I'd still choose to work for myself. I mean, I run the wheel, ya know? (Even if I'm a terrible driver sometimes.)


Book: Act your age by Talia Hilbert

If you don't like romance stories, I bet this book will change your mind.

Meet: Eve Brown. A 26-year old with no solid grip on her life. Everyone's always telling her to stick to things, to be responsible, to...act her age.

She runs into her polar opposite, too-together-and-tightly-wound Jacob Wayne. Runs into — quite literally. She gives him an interview for a chef job and then accidentally hits him with her car. Accidentally.

What follows is the best romance trope of all time.

My favorite part? Hilbert writes in a way you feel like you're sitting inside the character's head. The dialogues — internal, in their head, and external, to each other — are so raw, so natural, it tugs to your heart.

The worst part? It's definitely ruined romance for me now.

It's delicious, soothing, and mostly funny. Light-read but will make you smile for weeks after.


Poetry: Wind-related ripple in the wheatfield by Mikko Harvey

I love the shape of our apartment

as I walk through it in near-total darkness. I love walking slowly through that

darkness with my arms out, trying not to bump

into furniture. How many apartments

have I done this in now? I loved

them all. Or possibly I just loved

how they held darkness, slivers of streetlight

sneaking into the fortress, amplified and lent

personality by the darkness surrounding them. Wherever you are

is a country. Touch it softly

to make it stand still. Your hair getting caught

in my mouth all the time, like a tiny piece

of you calling- like a tree trying

to speak to a rock

by dropping a pinecone on it. It is my intention to listen

but my hands keep giggling while reminding me

I don't get to be a human being

for very long, as if this were the punchline to a joke

whose first half I missed. I arrived too late.

I typically arrive about three years too late.

I wish I had been able to sit

in that white, aromatic kitchen and look you in the face

but I was not ready. I was still on my way.

I was lingering inside the perspective

of the spider I noticed crawling

along the baseboard. You fried

an egg. Is it possible to change

who we basically are? Thank you for serving me cups of lemon tea

with honey in it. Even though such copious amounts of liquid

would no doubt drown the insect

I imagined myself to be, that was kind

of you.


Question for you: The good, the bad, and the ugly

I'm always eager to bust some myths about career, passion, and work-life. So tell me:


Thank you for reading. I'll see you Apr 28.

-Rochi


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