What It's Like To Be
What It's Like To Be

Below Average 9 - 5er to $150k+/year Self Employed Boss

by Alex Tooby 4 months ago in how to

A Timeline & Guide

Below Average 9 - 5er to $150k+/year Self Employed Boss

Let me guess, you’re considering quitting your 9 to 5?

Great! I whole-heartedly support you.

I just want you to know it’s not going to be rainbows and butterflies.. Quitting your 9 to 5, FOR REAL, is no easy feat.

But it can be done with great success (insert your best borat impersonation here), and I’m living proof.

Here’s my story and a guide that will help you put the pieces in place to make the transition from employee to CEO as short, easy and successful as possible:


I was 22 years old, had just got a degree in Print & Graphic Design and landed a full time job at a local print shop - just as intended.

I had a couple positions here, working in the design department and laboring in the back as a printing press operator (yes.. For real. There’s such a thing as printers that are NOT digital!)

I didn’t mind the job. When I actually had work to do it was fun and all fell within my wheelhouse.. But half of those 5 days a week I showed up, there wouldn’t be enough work to keep me busy.

I’d spend half the day on my phone, going for longgg bathroom trips just to waste time, hanging out in the break room, and eventually hovering over the punch clock, waiting for 5pm to roll around so I could leave and collect my 8 hours.

The Side Hustle

Soon enough all that down time turned into my side hustle time. I spent hours working on projects that had absolutely nothing to do with my job.

I felt bad, but not that bad, you know?

It was a.. “I don’t want to get caught doing this” but I’m also “not going to stop” type of situation.

Now this wasn’t my first time having a job and spending all my downtime exploring different options.

That was my life - always looking for an exit plan. Trying to find that opportunity that was going to take me away from a 9 to 5 and lead me to 100%, full-time, self employment.

Over the years I had a few wins.

I remember selling some old baseball cards my dad had (with his permission of course) on ebay and making about $450.

Then I sold some other old shit we had in the house - a random violin, grow lamps, tools, etc.

From there I caught wind of a site called Clickbank, which at the time was a pretty sketchy looking site that allowed you to sell other people’s digital products for a commission (aka, affiliate marketing).

I would drop my link wherever possible - Pinterest, Tumblr, Facebook - hoping that whoever clicked, would eventually buy so I could make a couple bucks.

At the same time I was using services like adfly that literally gave you $0.2 for every 500 clicks on a link..

These all amounted to a few wins and at times I was making great money, only for Pinterest to block my link and my income would go back to $0 in a matter of days.

None of these methods were sustainable, but I was definitely learning very valuable skills along the way.

Then, the internet marketing world started to expand a bit. Instagram influencers were becoming more of a thing, affiliate marketing wasn’t so sketchy and I was becoming more and more savvy.

The Tipping Point

At this point I still had my 9 to 5. Was making a little money on the side and was becoming increasingly resentful of my job.

If felt like the appropriate time to take a vacation - so I booked a trip to visit my dad in Nepal.

He himself was a serial entrepreneur who never finished school and was always inventing things when we were growing up (hmm.. I wonder where I got it from!)

After my parents divorced for the second time (yep, they broke up and legally got back together when I was a teenager) my dad left for India to go explore.

His second day there he was invited to a party at the Taj Mahal but that’s a story for another day.

Somehow 7 years had passed and my dad moved from India to Nepal, got in a motorcycle accident, the nurse in the ambulance became his wife and they opened a restaurant, holding the top spot on trip advisor for over 3 years (again - a story for another time!)

At that point I had already visited him in India twice and now it was time to visit Nepal, but I knew that I was only allowed two weeks off PER YEAR at my job. (Can you tell how annoying that is by my use of capitals?)

From my home in Canada, getting to Nepal takes about 24 hours travel time if you have a decent connecting flight. Then there’s the 8 hour time difference, so going for two weeks is not really enough - you need to stay for more time when you’re making that big of a trip (in my opinion)

So I wanted to stay for a month - well knowing I wasn’t technically “allowed” to do that. And that my friends is exactly when my blood started to boil, when I KNEW that I could not continue doing this 9 to 5 shit, reporting to someone else, making money for someone else, AND not being able to do what I want, on my own time?????

Yeah. I was done.


So I marched into my bosses office and told him that I need four weeks off and if I didn’t get it, I was quitting.

By the end he offered me a job in sales since I was so convincing and ultimately gave me the go ahead to take the 4 weeks off.

Of course I was happy, but that anxiety and increased heart rate I felt just walking into that office to ask for time to go explore the world, was not something I should ever (or spoiler alert: would ever) feel again.

So I went on the trip - it was amazing of course - met some unreal people, had a couple epiphanies (Nepal will do that to you!) and came back to work a couple more months before quitting for real.

And I mean for real this time.

Jumping into The Deep End

I put in my notice and told my family I was moving to Vancouver.

The most expensive province in all of Canada.. Without a job…

Yep. Just as crazy as my dad.

(By the way, my mom is an absolute gem and while she took the path of long term employment with the same company for 20 years, she’s already retired with a hefty pension and is able to say yes to all the things she wants. So, an equally respectable path to take in life and an inspiration to me in her persistence. I just so happened to lean a little bit more to the left on my views of employment)

Deciding to move was a cumulation of few things but what really happened in this move is that I forced myself to take the risk of not having a job and thus making it absolutely imperative that I make this whole self-employment thing happen. Or risk having to move back home. Yikes.

To facilitate this I had a few months of rent saved up and gave myself a timeline. If I can’t start bringing in some half decent income by X date, I’ll look for a part time job (note: NOT A FULL TIME JOB). Just something that could help pay the bills while I tried to make things work.


A few months later your girl was printed in Cosmopolitan Magazine.

Wait, what? I know I know.. I jumped ahead - I just got excited.

The Real Hustle Begins

What really happened between the move and that Cosmo article was this:

I realized in order to make some real, consistent income, I’d need to get out of my introverted head, stop trying to make little wins on the depths of the internet and put myself out in the real world (note: you don’t have to do this and later in this story you’ll see why)

I started offering social media consulting services. At this point I was actually quite good at this and was confident in my offering. I literally posted on craigslist or responded to “social media help wanted” posts and was able to get my first few clients.

From here I learned an extremely valuable lesson that lead me to where I am today.

(Spoiler alert #126: a multi-6 figure a year, self employed, online course creator!)

And that lesson was that I should not focus on all of the things I’m really good at, but rather focus on the one thing I am best at, and at that time, it was Instagram.

Finding Your Niche

I started to offer services specific to that, like Instagram Audits and Custom Hashtag Research, and all of a sudden I had a lot more clients that wanted this, then the social media consulting I was previously offering.

That was a big sign.

Then my brother - who we haven’t talked about yet, but is also a self-employed, serial entrepreneur, encouraged me to create an info product.

Instead of selling services that took physical expenditure from me, I went on to create my very first online course: Infamous to Influential - an Instagram Marketing program.

Now we have to note that during this time I was working really hard. Spending all day and night building a following on Instagram, encouraging people to join my email list, and constantly proving my authority by giving out free advice whenever and wherever I could.

Then it was time to launch.

I shared my course, listed it at $247 and left the doors open for 5 days.

In that time frame, I made..

$15,000 USD.

Yep. Fuck me right? Where had this been all these years? The amount of work I put in to get those adfly clicks that literally made me $0.14 per week.. To this?

Yep - this was it.

Scaling Sustainably

And that was just the beginning. I have since gone on to create 4 more courses and amped up my production value each and every time.

Each new course took hours upon hours to complete but the launches that followed all continued to exceed my income expectations by miles.

Now each course is simply available for purchase with very minimal additional effort needed - meaning each new customer is profit and income that allows me to continue moving forward, investing in my business and creating even better offerings.

4 Years Later

So now, 4 years after this story began, I live in Squamish BC, I own my own condo, I have a full time employee and I’m making way more fucking money than I ever did at any of my 9 to 5 jobs, AND I get to say yes to every opportunity that comes my way.

Now I’m not saying this road was easy, or short, but if I knew what I know now, back then, it wouldn’t have taken me so long.

And it doesn’t have to take you long either.

If you have a skill (unique or NOT), you can make an online course and you CAN see the success that I’ve seen.

So while stomping into your bosses office tomorrow and saying you quit might not be exactly plausible, it’s time to start thinking about the alternative.

It’s time to start creating some content.

Start positioning yourself as the authority.

And eventually, launching that product.

Because I swear to you - if you have the perseverance, the want, and the drive, you CAN quit your job and create the best career you’ve ever had, for yourself.


What are you waiting for?

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Alex Tooby
Alex Tooby
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