Why I Quit My High Paying Job to Work for Myself“Are you sure about this?” asked my boss.

“Yes,” I replied, “I am.”

I had just handed in my two weeks notice.

“Where are you moving to?” he asked, curious to know which company purchased my allegiance. 

“Nowhere,” I said smiling, “I’ll be working for myself.”

And in that moment, I traded a life of structure and stability for a whole lot of risk.



I Had the “Perfect” Job

In February 2016, I left my job at a large consulting company. It was the most comfortable and well-paid job that I ever had.

Accenture Digital Chicago Office | Why I Quit My High-Paying Job to Work for Myself

I had mulled over this difficult decision for months. I didn’t hate my job. In fact, there were lots of things that I liked.

  • My team was wonderful. I made great friends and liked all my colleagues.
  • I never had to worry about money. I made more than enough for myself and then some.
  • Our office was gorgeous, with open space, natural light, and modern equipment.
  • Work-life balance was respected. After 5pm, my managers would tell me to leave!
  • Best health and retirement benefits.
  • Amazing team culture. We’d have lunch together every day and spend time together outside of work.

Even I knew how lucky I was to be at my job.


But It Wasn’t What I Wanted

If you said that I had the perfect job, I wouldn’t disagree with you. It had everything: financial stability, career prospects, work-life balance, great people, and health benefits.

But there was just one problem: I didn’t feel fulfilled.

At first, I wondered myself:

Is there something wrong with me? Why can’t I just appreciate what I have? Maybe I’m delusional and overconfident?

Now that the dust has settled, I want to share why and how I came to my decision. And why I believe that this is the beginning of the most exciting chapter of my life.

It is my hope that this will encourage and inspire you to take the leap, wherever that may lead you.


My Vision for the Future Didn’t Match Up with My Present

When I dream about my life 10 years from now, these are the things I think about:

  • Running multiple companies
  • Traveling all over the world.
  • Working on meaningful projects that improve people’s lives. 
  • Having enough money to live a life based on my passions.

Here’s the problem.

My future didn’t match up with my present. By staying at my company and climbing the corporate ladder, I would not be moving toward that vision.

When I think of the common themes in my vision for the future, I see the following themes:

  • Entrepreneurship
  • Travel
  • Money

Below I’ll run through my thought process in going through each of these points.


Entrepreneurship and Being Passionate About Your Work

The buzzphrase for millennials is to find what you’re passionate about and do it.

I experienced that passion as an undergraduate at The University of Chicago, when I started two startups with my friends. Without getting too much into details, we found meaningful problems in the world that stood out to us and presented our own solutions.

Relief Watch Team | Why I Quit My High-Paying Job to Work for Myself

The Project SAM Team back in Spring 2013

Every moment working on these projects was filled with incredible passion and drive. We were creating solutions that made a difference to real people.

We felt the strong sense of passion because of two reasons:

  1. The work we did mattered. We were solving problems that made people’s lives better.
  2. We had full responsibility. It was up to us to make this happen and no one else was going to do this for us.

In larger organizations, passion becomes an afterthought. When you are just one person among a 300,000 person company, it is difficult to make any kind of impact.



Travel is a Form of Education

There is a Chinese saying that goes like this:


It is better to travel ten thousand miles than to read ten thousand books.

Travel represents an incomparable experience. It’s an opportunity to educate yourself and see the world, different peoples and cultures.

traveling | Why I Quit My High-Paying Job to Work for Myself



Growing up, I was fortunate because my parents loved to travel. Every opportunity we had, we would visit a new country and experience new cultures, peoples, and foods.

It’s difficult for me to say exactly how travel has changed me, but I know that I can’t imagine a life without it!


Having Enough Money To Do The Above

Entrepreneurship, doing meaningful work and traveling sound fun and all. But sooner or later, you are going to have to answer the question: how are you going to pay for it?

Like a wrecking ball | Why I Quit My High-Paying Job to Work for Myself

Reality comes in like a wrecking ball…

There are many people who are able to travel and work on passion projects without making lots of money. However, I don’t want to just get by.

Financial stability is important to me. I want to thrive and build an income stream that lasts.

So how do we do this?


Passive Income and Active Income

I read a book a few years ago called Rich Dad Poor Dad by Robert Kiyosaki and it completely changed my understanding of what being “rich” meant.

Rich Dad Poor Dad | Why I Quit My High-Paying Job to Work for Myself

In a nutshell, there are two types of income: active income and passive income. They can be represented by the chart below.

Active income is income generated by services that are performed. This includes salaries, wages, tips, and commissions. Long story short, you trade your time directly for money, so ff you stop working, the money stops flowing.

Passive income is money that you don’t have to actively work for. It includes rental income, dividend income, royalties, and selling a product. The point here is that you have a recurring revenue stream that does not require your day-to-day involvement.

Kiyosaki describes passive income as having your money work for you, instead of you working for your money. He defines being “rich” as the point in which your can support yourself on passive income, which removes your need to work for active income.

However, there is no such thing as truly passive income. You’ll always have to do some work to set things up or to keep an eye out for things.


Freelancing Could Be the Solution

I felt that I could map my entire life out if I continued working at a large corporation. Basically, if I kept at it, my life would look something like this:

  • Nine to five, five days a week, every week.
  • Two to three weeks paid vacation a year plus public holidays.
  • A promotion every two years or so.
  • A small pay increase every year.
  • Get more responsibility each year for little financial compensation.

But with my technical skills as a web developer, I could start working for myself as a contractor or freelancing. As a freelancer, I could:

  • Set my own hours
  • Be paid based on a project fee instead of a time-based hourly rate
  • Work fewer hours and make more money
  • Work on the projects I want to


Coffee Shop | Why I Quit My High-Paying Job to Work for Myself

I traded a corporate office for coffee shops

Based on everything I read, I realized that if I played my cards right, I could work less and make more money as a freelancer.


Moving From Active to Passive Income

Despite the fact that freelancing is a step up from working for someone else, it’s still active income (as you can see in the chart above).

Therefore, I started to approach freelancing from a business perspective. I asked myself:

What if I could take everything I’ve learned, document it into a set of processes, build it up into a business and take myself out of the equation? 

Around this point in time, my sister was about to finish an intensive four-month web design bootcamp. I saw an opportunity to work together.

A month later, my sister and I founded Tandem Designs, our very own creative agency.

Tandem Designs Logo | Why I Quit My High-Paying Job to Work for Myself


Why I Quit My Job

At this point, I had a plan, but was still not ready to quit my job. I had just paid a few thousand dollars to incorporate our legal entity, so I had to be careful.

The next step was to find projects for Tandem. I started reaching out through all my network and setting up meetings with potential clients.

A month later, I had secured enough projects to cover both me and my sister for the next two months.

That’s when I realized that it was time. I had no excuses to not act. The path was laid out and I took the leap.


Looking Ahead to the Future

When I quit my job, I was shocked by the amount of support I received from my family, friends, and colleagues.

I want to take this opportunity to thank everyone for their support and encouragement.

I’m also happy to announce that a few months in, we already have more clients and are supporting ourselves! I no longer work a 40 hour week and can work from wherever I want. 

Our goals for the rest of the year are:

  • To build up our client base so that we can rely on client referrals for continued business.
  • To establish and document tour own streamlined process so that we can bring others on board
  • To bring in one or two people to help us with the business.

In other words, we want to

  1. Automate parts of the business to reduce active oversight.
  2. Delegate work to others so that we reduce how hands-on we have to be.

I believe that moving toward this direction will allow me to fully transition to the remote lifestyle that I am eager to try for myself.

The purpose of this blog is to document my experiences and to serve as a reference to any of you who also want to pursue your goals, whether it’s to work remote or to start your own business.

Best of luck to all of us as we forge our own paths!