5 Reasons I Quit My Job to Build Passive Income Businesses

My life felt like this jigsaw puzzle — something was missing.

After many months of soul-searching, I finally decided to quit my job to build passive income businesses and design my dream lifestyle.

I’d been working for almost 2 years in the investment industry at the largest pension plan in Canada. I was well paid, had ample job security, and enjoyed working with really great colleagues. I was quickly approaching a point where I could see the next few years of my career.

Along the way, however, a question popped into my head:

“Is this what I really want to do for the next 5 years?”

Or an even tougher one:

“Where will this path take me, longer term?”

To my surprise, I struggled to answer these seemingly simple questions.

And the more questions I asked, the more showed up! It was like digging up a treasure chest only to find more clues.

Fortunately, I had a secret weapon — self-reflection.

Self-Reflection: A Key Step to Personal Growth

I’m a big believer of self-reflection.

Whenever I can find the time, I’d clear off my desk, put the phone away, and just start writing in my journal. It was the only time that I could really step back and evaluate where I was in my life.

In today’s fast-paced, 140-character world, we rarely have the time or space to think deeply about the important things in life and ask ourselves those simple yet illuminating questions.

It was in the pages of my journals where I battled these tough questions. I had to be honest with myself and write down what I really wanted from life.

Now, let’s dive into the 5 reasons I left the safe harbor of a traditional career to sail into the uncharted waters of passive income entrepreneurship.

Lucky for Jack, his magical compass always points to what his heart desires.

Life is like sailing the high seas — if you don’t have a good compass, you’ll just drift to wherever the wind takes you.

Looking back on my life so far, I realize I’ve always been chasing the closest island on the horizon, whether that was finding a job in finance or getting into business school, without much thought of the direction that I was going in.

Along the way, amid the intense competition for jobs, grades, and achievements, I lost touch with my inner compass, sailing instead in whatever direction others were going.

I didn’t want to live my life merely drifting to wherever the wind took me.

So I kept asking the hard questions and reflecting on my responses until I could see where my own inner compass was pointing.

And I quickly realized that it was pointing in a different direction from where I was currently heading.

I started to understand that the things which truly mattered to me would be almost impossible to obtain while pursuing a traditional career path.

My dream lifestyle (which I plan to create, not just dream about) is to have a high degree of flexibility in how I choose to spend my time.

I’ll explain more in the section on “Flexibility Multipliers”, but for now think of it as being able to hop on a plane tomorrow, fly to a different country, and continue working remotely and autonomously on your job or business.

Exercise №1: What will you remember when you turn 70?

Here’s an exercise that helped me better understand what I wanted in life.

Imagine that tomorrow you wake up and you’re celebrating your 70th birthday. You’ve just put the finishing touches on your autobiography and you’re having a huge celebration with your family and close friends.

As you walk around and reminisce about the good old days, you start recounting some of the highlights of your life. What will be those moments that truly stand out? Conversely, what might be your biggest regrets?

For me, if I were to look back on my life at age 70 and see that I spent most of it working on my career, I’d certainly feel a deep sense of regret.

I’d ask myself why I didn’t take more risks or explore more avenues in life? I’d wonder why I didn’t travel more to see the beauty and wonders of this world?

This leads me to my second reason… the gift of time.

Life is like this hourglass, except you can’t turn it over and reset the time.

I’ve slowly come to appreciate that time is the true currency of life.

I used to believe that money was my greatest problem.

Once I make enough money, I’d be free to do whatever I wanted, right?

The reality, however, is that money is no good without the time to spend it.

If your dream is to achieve financial freedom (or early retirement for some), then the path to get there likely involves working many years in your job while saving a substantial portion of your income (I’ve included an exercise at the end of this section on how much you’ll make in a lifetime).

Let’s say you did really well and you’re now looking at potential retirement before you turn 50. Your life might have looked like this:

  • You’ve spent the best years of your life slaving away at your career and moving up the corporate ladder
  • Your relationship with your spouse could be on thin ice as you’ve been “absent” for the past 2 decades
  • You’ve had little time for your kids (if you had kids at all) as they grew up
  • Your health ain’t as great as it once was after years of neglect and 12-hour work days, not to mention the additional stress of taking on more responsibilities as you became increasingly senior in your career, and
  • Let’s face it — you’re probably not going to retire early when you’re at the peak of your career — the allure of more money, achievement, and power is simply too enticing to resist, so you might as well work a few extra years even if you don’t need to anymore…

To be clear, I don’t think it’s impossible to work hard in a traditional career and still build a great marriage, raise kids, and maintain your health — I just recognize that it’ll be extremely difficult when your time is monopolized by a demanding job. And it became very clear to me that I was heading down this path in my own career.

I soon began to understand the folly of accumulating wealth without having time for the most important things — family, friendship, love, travel, personal growth, community, and spirituality, among others.

As online entrepreneur Tiago Forte puts it in this podcast:

It’s like we were given lemonade, only to trade it for lemons, to make more lemonade.

Today, I’m much more conscious of how I spend my “time wealth” within the constraints of my financial wealth, and not the other way around.

A Quick Note on “Flexibility Multipliers”

One of the main reasons we aim for financial independence is because we assume we’ll need a fortune to live out our dream lifestyle.

But as Tim Ferris explains in his seminal work, “The 4-Hour Workweek”, our financial wealth can be amplified by the number of W’s that we control:

  • What we do,
  • Where we do it,
  • When we do it,
  • Who we do it with, and
  • How we do it (yes, I know it’s not a W)

I call these the “Flexibility Multipliers” as having control over each one enhances your ability to create your dream life (without a trust fund).

Here are some quick examples to illustrate the point:

  • If you could control where you worked, you could relocate to anywhere in the world. You could be experiencing new countries, living in low cost regions (think Thailand), or maybe move to Florida because you’re tired of 6 months of winter every year. You could also live outside the downtown core and save money on rent or mortgage payments. All these options allow you to create your dream lifestyle earlier without costing a fortune.
  • If you could control when you worked, you could take advantage of all the discounts that airlines, hotels, and other places offer during off-peak seasons. Planes fly every single day of the year but when do most people travel? During the busiest holiday seasons, when tickets are the most expensive. Even having some flexibility over what days of the week you work can provide convenience and savings. Rather than compete for dinner reservations and movie theatre seats on the weekend, do both on a weekday when it’s less crowded and possibly cheaper.

Exercise №2: How much is the next 30 years of your life worth?

This is a mind-blowing question that I got from a close friend.

In a traditional career, we’re always trading time for money. So how much is your time really worth? You might know how much you make per hour or per year, but what about the next 30 years?

Here’s a spreadsheet template that will help with this exercise (to edit, make a copy in Google Sheets or download and open in Excel).

Once you have the results, ask yourself this:

If someone offered to pay you the net present value (NPV) of your lifetime income today (assuming your future income was somehow known), would you trade them for the next 30 years of your life?

For me, I was shocked by how little I was getting in exchange for the next 30 years of my life — and this was working at a very well-paying job.

So the next question was, is there something I can do that might pay less but allows me to enjoy more of my time wealth?

And in that search, I stumbled into passive income businesses…

Passive income is like planting an apple tree — it takes a lot of upfront work that will eventually bear fruit.

First, What is Passive Income?

I define a passive income business as:

“a venture that requires high upfront effort (time and/or money) that once completed, produces recurring income with minimal maintenance.”

It’s like planting an apple tree — it takes a long time to bear fruit, but once it does, it’ll consistently produce apples every year.

I’d heard about passive income businesses before, but only in the context of real estate rental properties and dividend stock portfolios.

Both are relatively capital-intensive (you need a lot of money to start with) and real estate, in particular, requires taking on substantial debt.

Recently, I started learning about content-driven passive income businesses such as blogging and online courses, which in constrast, are capital-light and only require an entrepreneur’s time and perhaps a few freelancers.

These businesses offer products ranging from information, reviews, ebooks, online courses, templates, etc. that meet the needs of a particular audience.

Why Passive Income?

I was attracted to the idea of no longer actively trading my time for money.

Instead, I would trade my time upfront to create passive income streams that require minimal maintenance. Not only would I get to be my own boss, but it would allow me to pursue my dream lifestyle.

Content-driven passive income businesses make money through a variety of methods, from traditional advertising to affiliate marketing to product sales.

I won’t be able to cover these in detail but if you’re interested, I recommend this great introduction by Pat Flynn at Smart Passive Income.

The Key to Success: Serving Your Audience Really, Really Well

As I learned more about the people behind passive income businesses, I realized that you didn’t need to be a genius, a developer, or even an expert in your particular domain.

What really drives success is the ability to serve a particular audience really, really well, typically by solving a problem or serving a passion.

So I asked myself, are there ways that I can help other people, using the experience and knowledge that I currently have?

I began brainstorming lists of topics that I was interested in and could write at least 50 blog posts about. Then, I narrowed my focus in two ways:

  • Demand: I checked the level of demand for this topic using a free tool called Keywords Everywhere to pull search volume from Google
  • Competition: I checked the level of competition for this topic using tools like SEM Rush and KW Finder

Finally, I evaluated if there were any gaps in the space that I could fill.

By the end of this process, I decided to build a skincare site with a focus on acne scars. You can check it out at The Derm Detective.

In short, I believe there’s a gap in this niche for high quality, science-based information about scar treatments and products.

More importantly, I have personal experience with this problem, so I understand my audience’s pain points and situation.

Exercise №3: More Information on Passive Income Businesses

Here are some great resources on passive income businesses for beginners:

  • Passive Income 101 and 3 Passive Income Models (YouTube) by Pat Flynn — both are great introductions to understanding passive income.
  • Pat’s First Online Business — an in-depth look at Pat’s first online business, an exam prep website for professionals in the architecture industry. Be sure to read his follow-up posts on what worked well and what didn’t work well in his first business.
  • The 4 Hour Workweek by Tim Ferris — an excellent book that covers not just passive income but also introduces ideas about lifestyle design, automation, and how we can live a truly fulfilling life. I found this book very refreshing and candid — Tim does not shy from “tellin’ ya like it is”.
The fear of the unknown can paralyze us from making major decisions.

Just to recap, we’ve gone through how:

  • I was not going in the direction that my inner compass was pointing
  • I was trading almost all my time for money, which left little for the most important things in life, and
  • I was convinced that I could build a successful passive income business by serving my audience really, really well

So what did I do at this point? Did I jump straight into it?

Nope.

For a long time, I sat on my hands and thought wistfully about how great it might be to run my own online business… except I could never do that because, well, it’s very risky, my ideas aren’t exactly revolutionary, and besides, I don’t know anything about being an entrepreneur.

All these reasons, I’d later realize, were just excuses that I invented to keep myself following the status quo because I was afraid of the unknown.

It wasn’t until another friend of mine asked me:

“What’s the worst that could happen?”

that prompted me to think long and hard about the downside case.

I always assumed that entrepreneurship was high risk, high reward — but when I examined this more closely, I realized that it wasn’t quite the case.

Realistically, the worst thing that could happen is:

  • I spend 2–3 years experimenting with different passive income businesses that ultimately don’t make any money
  • At which time, I can either try to return to my old job, look for another corporate job in finance, or do an MBA to “reset” my career
  • When interviewers ask me what I’ve been doing during this time, I’ll have plenty of examples to highlight the experiences and skills that I learned while building and running my own business
  • And best of all, I’ll still travel for several months either way

In short, the worst case is returning more-or-less to where I am today.

And honestly, that’s really not so bad.

I know some people may feel this puts them behind a few years in their life but quite frankly, I don’t measure my life against a timetable, so it doesn’t bother me. I’ll be working the rest of my life anyways, so what’s the rush?

Our fear of the unknown and discomfort with uncertainty can cripple our ability to take action. But if we can define that uncertainty and set some boundaries around it, it will no longer serve as an excuse for inaction.

Regardless of what happens, I’m pretty confident that my life won’t be over, I’ll still have the support of my family and friends, and the Earth will continue to revolve around the Sun.

Exercise №4: Define the Worst Case Scenario

When making your next major decision, I challenge you to ask yourself, “what’s the worst that could happen?”

Be realistic — the world is not going to end. If things don’t work out, what are your alternatives? Could you go back to the status quo? Can you think of ways you could move on or pivot? What have other people done when faced with a similar situation?

You don’t need to visit any forests to find your intuition — it’s always been there, you just need to listen.

The final and most important reason — I listened to my intuition and trusted my instincts.

Intuition goes by many names: the 6th sense, a gut feeling, an inner voice, the dog whisperer (okay, that one I made up). And I think it’s an often overlooked aspect of our personal growth and decision-making process.

Napoleon Hill, in his wonderful book on success, “Think and Grow Rich”, speaks frequently about Infinite Intelligence, a phrase he used to describe how successful people from inventors to writers to political leaders were able to come up with their most brilliant ideas and act upon them.

Infinite intelligence, or intuition, is what guides us towards our dreams and desires, especially when we face great uncertainty about the future.

My whole life, I’d been taught to value logic and reason over my intuitive and emotional faculties (and this is coming from someone with a degree in Economics where the fundamental assumption is rational human behavior).

Don’t get me wrong — logic and reason are great tools in many situations, such as calculating the cost of a trip, finding where you left your socks, or making sure your financial model has no #REF errors.

But these tools are not well-suited for the truly important decisions in life.

Can logic prove whether you should marry someone? Can reason show that you need to change careers?

Not really.

We use logic and reason to provide frameworks for decision-making, but we ultimately make those decisions based on our intuition — that “gut feeling”.

So were reasons 1 through 4 just a waste of time? Absolutely not.

All of the self-reflection, critical thinking, research, and mental preparation were necessary steps that led me to my decision. These elements now form the ship that I sail upon, and intuition is my captain.

Exercise №5: Listen to Your Intuition

The next time you face a difficult decision, lay out the situation and assess what your first reaction is. Often, our gut feeling kicks in long before we’ve had the chance to process all the details.

Now imagine that you’ve already made the decision — check to see what your reaction is. Repeat as needed for all the alternatives that you’re considering.

Don’t overthink it when trying to listen to your intuition. Often, our intuition can be distorted by our paradigms, beliefs, and most of all, an over-zealous rational brain.

I want to thank you so much for reading my post! I really enjoyed putting this together and would love to hear from you.

Which section resonated the most with you? Do you have additional ideas or thoughts? If you’ve been thinking of starting a business, what’s stopping you?

You can follow my journey into passive income at Flexibility Is Freedom.

Passive Income Entrepreneur Building Niche Online Businesses