I Didn’t Know Being Your Own Boss Meant Living Life Like This

The side of solopreneurial life you don’t see online.

I Didn’t Know Being Your Own Boss Meant Living Life Like This
Photo by Dip Devices on Unsplash

The side of solopreneurial life you don’t see online.

The freedom to work on your own terms is exhilarating. 

I learned this when I quit my job to become a full-time writer in 2021.

No more rigid schedules or restrictive policies. I could choose my projects, set my work hours, and make my own rules.

For the first few months, it felt as if I’d unlocked the secret to a happy life. I woke up every day with stars in my eyes, and when I went to sleep at night, all I had in my heart was gratitude. 

This brand new life felt almost too good to be true.

Turns out, it was.

Within a few months, I found myself working around the clock. Amidst building my personal brand, writing articles, and working on the client’s content, I was always exhausted.

Not having the stability of a regular paycheck often made me question if I was truly doing my best. As the initial excitement wore off, the isolation of working alone took a toll on my mental peace. 

That’s when I realized what it actually means to lead a self-employed life.

It’s not only about the curated life and aesthetic workspace with all the plants and natural light that everyone shares on social media. 

All that looks attractive from the outside. 

But only when you live it, you learn the pitfalls.

You’ve got to wear many hats and take on an overwhelming workload — with no one to share the burden.

If someone told me about all this when I was getting started, it would have saved me a lot of trouble.

After struggling with work anxiety and severe burnout, I’ve finally come to know what it takes to be your own boss. These first-hand lessons were learned the hard way, and I want to make it easier for you by sharing my insights.

I’ve compiled everything you need to know before starting your creative endeavour. It’ll help you understand if you’re yet ready to be your own boss while shedding light on the lesser-known aspects of being self-employed.

If you’re not prepared, you could develop an unhealthy relationship with work

The main reason behind quitting my job was to live life the way I wanted. Travel places, do things I love, and take time off whenever I want without asking for anyone’s permission.

After a few months of writing full-time, I got the chance to plan a vacation. I booked tickets to a country I’d never visited before. I was thrilled that solopreneurship made this international trip possible.

The best part? I had an exciting new project waiting for me as soon as I got back. What more could I have asked for?

I wasn’t prepared for what happened next, though.

Instead of enjoying the time off, I was constantly worrying about when I’d be able to publish the new articles my clients had assigned to me.

The topics were running on a loop in my head, and I couldn’t stop thinking about the content brief, the structure I’d follow while writing, and how the client would react.

This took away the joy of the vacation and made me dread the work.

A picture I clicked during the Bali vacation when I was hunting for cafes I could work from (Image provided by the author).

Bottom line: Work anxiety is real, and you constantly play the balancing game when you’re your own boss.

Here are a few tips that might help:

  • Learn how to detach from work
  • Set clear boundaries between work and personal time
  • Identify tasks you can delegate when you take time off
  • Develop routines to ease back into work mode once you return.

You won’t get results every time you work hard

After having a few successful digital products like my 90-Day Freelancing Guide and Project Medium, I planned another product launch in 2023.

I worked on building Cyber Aid: A discussion forum where people who suffered from cyber crimes could come together and share their stories.

I followed similar steps as I had in my previous launches and put in double the effort this time.

  • Invested about $500 to build it
  • Spent another $100 each month to run the forum for 6 months
  • Posted 2x/week on LinkedIn
  • Made 5–6 YouTube videos
  • Kept Tweeting multiple times a week.

I did everything that was supposed to make it a successful launch, but it didn’t pick up traction.

I gave up the business, even though the sunk cost fallacy made it extremely hard.

I had the plan, but the results didn’t match my expectations.

This made me understand the fickle nature of leading an entrepreneurial life. Your best efforts might get wasted. 

It’s important to know when to quit, pack all the lessons you learned, and stop putting efforts into a dead cause.

Bottom line: Anything can happen when you’re your own boss. One day, you can be earning thousands of dollars, and the other day, nothing.

One of the LinkedIn posts I made to promote Cyber Aid (Screenshot by the author).

Be prepared for the times when abandoning a few business plans is the only way out

I started Books Are Our Superpower in 2020. A few months later, I had the idea of starting a paid book club/subscription-style newsletter.

The idea was simple — get amazing writers to publish 2 stories each week, ask readers to pay, and share profits with the writers.

What I didn’t anticipate was how much work it’d take for me as the founder to promote, coordinate with writers and readers, schedule emails, etc. It got so overwhelming that in just two months, I was burnt out.

The business idea was great. I even had 10+ people who signed up for a year of the book club’s membership. 

But at that time, I didn’t have the tools to execute it. 

No matter how much I wanted my book club with amazing writers around the world to thrive, it wasn’t the right time to continue the plan.

Bottom line: As a business owner, you’ve to be prepared to make difficult decisions at any point in your life. Even if it’s hard, you have to do what’s best for you, which sometimes can mean quitting.

A glimpse of the Slack channel I’d made to coordinate with writers of the BAOS Book club — a project I’ve now abandoned (Screenshot by the author).


The reality of being your own boss is a far cry from the glossy social media feeds you see every day. It’s a journey filled with both ups and downs.

The freedom and flexibility to work on your terms are undoubtedly the best parts. But you’ll also confront some harsh truths.

There will be challenges, setbacks, self-doubt, and moments where the only sane choice would be to walk away and make peace with some failed plans. These are all parts of the process.

The path to success is rarely easy, but it’s always worth it in the end.

If you’re planning to take the leap into self-employment, be prepared for the rollercoaster ride ahead. 

When you do it with the right mindset and strategies, keeping the long-term vision in mind, the journey can be immensely rewarding.

The pride of building something from the ground up, the freedom to live and work on your own terms — these are the spoils that’ll keep pushing you forward, despite the pitfalls.

I just launched Freelance Superheroes: A training program for writers who want to earn from writing online without leaving their job, attract gigs outside Upwork/Fiverr, and become irreplaceable. Get it today!

If you found this story helpful, here are more you might enjoy — 

Things I Wish I Knew Before I Self-Published My First Book
Setting realistic expectations from book sales as an indie author.
What it Takes to Publish on the Internet For 10 Years Straight
Behind-the-scenes of building a full-time writing career.