Hi, I’m Skyler, and this is my story. 


Ever since I started working a 9-5 job, I knew that I didn’t belong and strived for something different.

I never fit in, couldn’t be my authentic self.

I felt like an alien (maybe that is why I got an alien tattoo).

Living the same 7 days over and over again didn’t feel like living at all. 

Instead, I was just existing.

A 2-hour daily commute only made things even more unbearable. 

I used to tell myself that ‘there has to be more to life than ‘this.’ 

I always fantasized about starting my own online business but was completely overwhelmed.

I had so much self-doubt.

I went through so much self-sabotage.

I have always struggled with confidence and self-esteem issues.

I’ve been told for most of my life that I wasn’t good enough, and I should just give up.

When battling depression, some days it was hard to even function, let alone try to start an online business.

I was my own worst critic, and hated myself for a very long time.

I failed every time I tried to start an online business. 

Skyler Benson

It’s Never Too Late To Be What You Might Have Been – George Elliot 

Before I wanted to start an online business, I had dreams of being a famous rockstar.

I spent many years trying to start bands in my home city of Melbourne, Australia. But it never quite worked.

So, I quit my job and moved to London in 2009 to try to make it a reality. 

I had no plan in place, except for just moving.

Six months later, I was back in Australia, completely broke and in debt 

I moved back with family again. I returned to working at a University again. 

I was miserable and felt like a loser, that I had failed and made the biggest mistake of my life.

This time I was working as a casual, and not a full-time worker any more.

Over the next couple of years, I would work for 6 months, save money, and go travel.

All while trying to still pursue music

Then when my money ran out, I would return, and work at a job that made me hate myself.

Insanity is doing the same thing over and over and expecting different results.” – Albert Einstein. 

Skyler Benson in 2012

2012 – A Glimpse of Hope


Then one day in 2012, something different happened.

I was asked to join a new band. 

We played our first concert, shot our debut film clip, and booked an international show at the world-famous Whisky-A-Go-Go Bar in West Hollywood, LA, all within weeks.

Flying from Australia to the US to play a concert felt like a dream come true, followed by two weeks of partying in LA and living the rockstar life.

It made me realize that anything was possible.

This time, I didn’t try to talk myself out of anything.

I just said yes to every opportunity which presented itself.

I made more progress with music in a month, than I had in the previous 5 years.

But then the band fell apart shortly after returning to Australia.

I was back to the drawing board. It felt like time to do something different. 

I then pursued trying to be a music producer and DJ instead. 

But, the idea of playing EDM bangers to sold-out festivals across the world became more of a fantasy than reality. 

I finally accepted that I didn’t have enough musical talent, but I was great at marketing and enjoyed it too.

I also slowly realized that what I loved was travel, and not so much playing music.

I had anxiety for every single concert I ever performed.

Previously, it seemed that besides being a pilot or flight attendant, one of the only career paths to travel the world while getting paid, was as a touring musician. 

Meanwhile, I continued working a corporate job that I despised. I kept getting promotions I never asked for or cared about. I had mentally checked out a long time ago.

I had lost all the passion in my life. I felt like I was never awake and never asleep.

Each day blended into the next. I was extremely depressed and burnt out.

2016 was the year that everything truly changed.

I decided I was going to backpack Europe for 3 months. I also bought tickets for
Tomorrowland in Belgium and Ultra Europe in Split, Croatia. 

Both were on my bucket list of festivals. 

I was beyond excited.

I tried to convince my job to give me 3 months of unpaid leave, which was no easy task. 

They even offered me a promotion instead of letting me take time off. I declined.

I was willing to quit if they wouldn’t grant me unpaid leave. But, after a month, they eventually gave in. 

Then a thought came over me. 

I could go to Europe for 3 months and have the time of my life. Sounds amazing!

But then I would return broke, in debt, and to a job, and life, which made me depressed, just like before.

That didn’t seem like a good option anymore.

Then I had a crazy idea. It was the ah-ha moment.

What if I could start an online business? 

Then I would be able to work from anywhere and travel indefinitely! 

There was only one problem. 

I couldn’t apply my corporate admin job skills to an online business.

Even though I had a data integrity and analytics background, it was all related to University data and reporting information to the Government to secure funding and grants. It was super-specific to the education industry. 

So I had no real digital skillset and no idea where to begin. 

I was always tech-savvy and ‘good at computers,’ but after getting into a slump, I fell behind as tech advanced and had to play catch up. 

So, I asked myself, “how can I start an online business?”

I didn’t know the answer, but I was determined to find out. 

At the time, I found it almost impossible to find information anywhere I looked.

Those who knew wanted to keep it a closely guarded secret, like crossing into a mystical Narnia-like world. 

This time, I wasn’t going to give up. I was determined.

I decided to cancel my dream trip to Europe, and instead, I used all my savings to stay home and up-skill myself.

I still wasn’t sure what I wanted to do, so I learned many different things. 

I spent over 10 hours each day developing digital skills that would allow me to work online. 

It was then that I became obsessed with learning about copywriting, digital marketing, and SEO. 

Meanwhile, my colleagues and manager thought I was in Europe. 

There was no easy step-by-step manual. 

I read hundreds of blog posts.

Then I hacked together my own learning plan and strategy. 

I did hundreds of online courses on Udemy, LinkedIn Learning (formerly Lynda.com), and Skillshare.

After 3 months had passed, I never returned to my job again. 

Instead, I continue to study online. 

I learned more in 6 months than I would in a 3-year degree at the university I worked at.

The total cost was also less than the price for just one subject from a degree. 

I finally had enough knowledge and skills to start working online. 

Then, in early 2017, I started looking for clients. 

I tried a few different freelancing platforms. But Airtasker was the one I found to be most successful.

After getting my first few clients, I decided to take a massive leap of faith.


All In. Ride or Die.

  • I sold everything I owned. 
  • I bought a one-way ticket to Chiang Mai, Thailand (after getting drunk to have the courage to book the flight!) 
  • I ended the lease on my apartment. 
  • I left Australia with just a carry-on backpack and my laptop. 
  • I finally achieved my goal of being location independent, working online, and traveling! 
  • I spent over 2.5 years traveling while working online (and only came back home because of Covid).
backpack, and packing list

I had no clue what I was doing. No experience. No network.

But if I can do it, you can do it too.

When I was in school, people always told me that I had a “way with words” and that I should become a writer or journalist. 

I have always enjoyed writing. But after I finished high school, I just told myself that I would pursue writing “one day.” 

Then I never thought anything about it again for a long time to come.

For the past 4 years, I’ve been working as a freelance copywriter and content writer. I’ve worked with many clients and Digital Marketing agencies and gained valuable experience and knowledge.

I spent years ghostwriting content for other companies. But now, I’ve decided to put myself out there and make this blog my main focus.

If I didn’t take a chance and just start, I’d most likely still be working at my old job, have given up on all my dreams, and be dead inside.

A lot has changed since 2017. It is now easier than ever to start an online business.

But with so much information available, it can be hard to know where to begin and what advice to take.

The problem with many other bloggers is they started their blog over 5 or 10 years ago

The internet has changed drastically since then. 

Content and marketing strategies that used to work 5 or 10 years ago no longer do.

Many digital marketing agencies I have worked with still use outdated SEO and content tactics too.

Overcoming Failure and Self Doubt

This blog was created in 2022 to help others get started, with a modern approach to blogging, and is the guide I wish I had when I first started freelancing online.

But getting started wasn’t easy.

While I was working as a freelance writer, I spent the entire 4 years also wanting to start my own blog.

I came up with many different names, for many different niches.

I registered at least 5-10 domain names over those years, and even started designing websites for some.

But I never even launched a single website.

I talked myself out of it every single time, and made hundreds of excuses.

Whether you’ve tried before, and failed, or you’re just starting out, if I can do it, you can do it too.

In the past 4 weeks, I have made more progress towards my blog, than I had in 4 years

I finally launched my blog as my name, Skyler Benson, as well as a Medium account.

It feels great to have stepped out of the shadows, instead of hiding behind a faceless brand, or ghostwriting for different agencies.

Overcoming doubt, and just starting is the hardest thing to do.

You don’t have to be great to start, but you have to start to be great – Zig Ziglar

I want to help you succeed with an online business, whether you are a freelancer, creator, or entrepreneur.

My blog is a place to learn the strategies, tactics, and tools you need to succeed online.

Nice to meet you and to be part of your journey.

If you’d like to contact me, click here.