Keep your job or pursue your passion?

“I’d love to pursue one of my many business ideas but I can’t afford to quit my job!”

This is by far the most common obstacle people present when it comes to the notion of pursuing something to break free and carve out some freedom in an unfree world.

And the solution to this dilemma of quitting and jumping off a cliff vs. doing something on the side until you build up enough income to quit?

There’s no right answer. In this article, I’d like to lay out the advantages and disadvantages of both models.

First, my story. I was extremely lucky when I started my first freedom business. I was married and had a wife that worked full time, and our rent wasn’t too expensive.

So after I got laid off from my corporate job, I was working some part time jobs and teaching swim lessons. The swim lessons eventually led to me starting a website, that after some work, started bringing in a few bucks every month. At first, even $1 of this passive income was super exciting to me! (even though when my very first sale came in, I was traveling around Europe, hadn’t checked email in 3 days and logged in only to see 4 emails from a furious customer who wasn’t able to get what he purchased 3 days ago and was ready to sue my pants off!)

But my goal was to make more than I was at my part time jobs. Within a few months, I achieved that, and it made no sense for me to keep working for $13/hour when I could make that much or more online, in passive format. So my theory was (and is), I’d rather make a small amount of money “while I sleep” than a bigger amount that I have to be there to acquire.


Even though I got lucky with having a partner that was supporting me at the time through ups and downs financially, it still comes down to values when we’re discussing quitting vs. starting a side business.

My highest value is freedom. I always knew that I could live in a van “down by the river” if it meant I were free vs. being forced to punch a time clock or work in a cubicle for money!

So you have to ask yourself, what is most important to you? Maybe the temporary security a job can provide is much more appealing to you then the idea of potentially being forced to live in a van, down by the river.

Or maybe you like the idea of bootstrapping to get what you’re really after. Perhaps the message you want to bring to the world via your business is burning you up, and any time staying at your job is delaying you getting where you want to be.

If you listened to my last interview with Jozsef Kiss, it is definitely possible to do both, successfully. It may mean getting less sleep than what is optimal, and it may mean sacrificing some or all of your weekends for a while.

But the most important thing here is to understand what your most important values are, and if they are aligned with what you are doing.

Is motivational speaking in your future?

Types of income

I mentioned this, but it’s an important point to drive home: Get super clear on the amount of money you are making vs. the type of money your are making.

Of course, this is Rich Dad 101 stuff but I still hear people discussing their total income as being the most important thing, when that could have little or nothing to do with their freedom levels.

Would you rather make $100k a year at a job or $50k a year online with a freedom business?

Making twice as much money sure sounds tempting. But let’s compare:

100k a year at a job

-More take home pay
-You can buy more stuff
-You can have a nice car
-You get a consistent paycheck (unless you lose your job!)

-You must be there to make money. You leave your job, you leave your money
-You have to work for people (working for people sucks!)
-You don’t get to express your individuality often
-You could get fired
-Only 2-3 weeks of vacation per year

50k a year with a freedom business:

-You can make money whether you show up or not
-You can be your own boss
-You can pursue projects that you enjoy
-You can’t fire yourself
-You can make money while you travel the world (yes easily at 50k!)

-You will likely not drive the car of your dreams for a while
-You have to live with constant uncertainty for a while
-Nobody will understand what you do for work
-You can (and likely will) do work every day
-You will be overwhelmed with life possibilities

So it’s essential to break down the difference between the two types of income. $1 made online passively is worth many times more than $1 made at a job.


Whether you go with keeping your day job, or jumping off a cliff into the unknown, your success will depend on your motivation levels.

This is where picking an area of interest is absolutely crucial to you sticking with it and becoming successful with your business.

Are you excited about the actual business you are doing, or is it all for the money? If it’s for the money, you may be able to generate enough motivation to last for a while, but eventually…you will end up whining and depressed, just like you were with your job! Let’s take an example:

I was working at a corporate job in a cubicle, managing accounts and partners for a software company. This company was someone else’s life dream, and even at that, it was a basket case of an organization and eventually fell apart. But my motivation levels were only to do well enough to keep my job and collect a paycheck. It meant doing lots of things “just for the money”. Even if I was really excited about the products (I wasn’t), they were never my dream and therefore I lost interest (on top of that, my tolerance for office politics is probably a lot lower than most!)

Then I started a personal training business. Freedom! Right? No. Within a year of doing personal training and managing trainers, I HATED it. I lost all interest in the business and ran it into the ground. I had my own thing going but I was not even interested in training clients.

Motivation will be the key to your decision to stay or go. Without it, either decision may suck the life out of you. Wouldn’t you rather do what really matters to you?

So before losing yourself in analysis paralysis on the “to quit or not to quit” dilemma, just ask yourself:

1. What are my highest values?
2. What type of income am I after and how much do I need?
3. What motivates me?

Then just put one foot in front of the other and make it happen.

What about you? Are you struggling with this dilemma of quitting your job vs. building something on the side? Let’s hear your challenges in the comments below!

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Kevin Koskella

Kevin is a podcaster and writer on living free, despite the crazy world we live in. Kevin travels full time and explores the world and how to achieve and maximize freedom in life.

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