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

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Victor is a DESIGNATION instructor, as well as the founder of The Remote Lifestyle, a blog chronicling his transition from working a corporate 9-to-5 to running an online business and traveling the world.

“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?” asked my boss, curious to know which company purchased my allegiance.

“Nowhere,” I said with a smile, “I’ll be working on my own creative agency.”

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

I Had the Perfect Job

Three months ago, I left my role as a Frontend Developer at a consulting company. It was the most comfortable and well-paid job that I had the privilege to work in.

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It was an incredibly hard decision to make. One that I mulled over for months. To put it into perspective:

  • My team was wonderful. I made great friends and think so highly of my colleagues.
  • I never had to worry about money. Even at entry-level, I made more than enough for myself.
  • We had a gorgeous working environment with open space, natural light, and modern equipment. It was an awesome setup.
  • Work-life balance was valued. After 5pm, our managers would tell us to leave! They really cared that we had a fulfilling life outside of work.
  • Top of the line health and retirement benefits.
  • Great culture and regular team social events. We’d go out every few weeks as a team to unwind and know each other better outside of the office.


If you’re lucky enough to work at a company like that, you’ll be hard pressed to find reasons to quit.

But It Wasn’t What I Wanted

If you said that I had the perfect job, it would be hard to for me to disagree. It offered everything: financial stability, career prospects, work-life balance, great people, and benefits.

Many people dream of having the opportunity that I had. And many may not understand why I chose to quit.

At first, I wondered myself:

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

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

I 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 think of my life 10 years from now, this is what I see:

I see myself running multiple companies and traveling all over the world. I see myself working on meaningful projects that improve people’s lives. I see myself being able to live based on my passions, not based on monetary factors.

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Here’s the problem.

What I envisioned for my future didn’t match up with where I was. By staying at the company and climbing the corporate ladder, I would not be moving toward that vision.

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When I unpack the paragraph above, these are the main points:

  • Entrepreneurship and meaningful work
  • Travel
  • Having enough money to do the above

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

Entrepreneurship and Meaningful Work

Being Passionate About Your Work

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

For me, that passion manifested through working on my own startups as an undergrad at The University of Chicago. Together with my friends, we started two companies:

  • ReliefWatch, an inventory management system created for health organizations in the developing world to track medical supplies and disease occurrences.
  • UEvents, a campus event finder that aggregated all the events happening on and around your college campus.

We found meaningful problems in the world – problems that stood out to us – and presented our own solutions.

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The team back when ReliefWatch was still Project SAM – Spring 2013

Every moment working on these projects was filled with incredible passion and drive. We were creating things that made a difference to real people. And that’s what made it meaningful to me, no matter how tough things got.

Passion Stems from Ownership and Responsibility

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

  1. The work we did mattered. We were solving problems that lacked existing and competent solutions.
  2. We took full ownership. It was up to us to make this happen. No one else is going to do our jobs for us.

In larger organizations, passion becomes an afterthought. For example, in consulting, each project has dozens of stakeholders of all levels on both the client side and the consultant side.

This cause responsibility to be diffused among the layers of bureaucracy.

In my experiences, these projects start with good intentions from both sides to deliver the best results.

Then somewhere along the way, after numerous rounds of hot-potato and passing the buck, things change.

Instead, it becomes: how do we get this across the finish line as quickly and painlessly as possible?

Being Challenged By Your Work

With responsibility comes obstacles and challenges. The harder the challenges, the harder you fight back.

When you work for yourself it’s a constant struggle. You’re responsible for everything from business to product development to marketing and legal.

It’s incredibly challenging but rewarding knowing that you’re your own boss.

When you work for someone else, your responsibilities are often limited to a job description. As a result, I feel that it’s much easier working for someone else.

It can be nice to put your feet up every once in awhile. But if you’re anything like me, you relish a good challenge.


So ask yourself:

Do you want to be challenged or do you want to put your feet up at this stage of your life?

Travel is a Form of Education

There is a Chinese saying that goes like this:

讀萬卷書不如行萬里路

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.

Travel is also the only reason why Reliefwatch, the company we started in college, existed.

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Long story short, two members of the Reliefwatch team spent Summer 2012 abroad. One in rural Peru working with Health NGOs, and the other one traveling through the Middle East.

They saw problems with inventory management among health organizations in rural areas and small business vendors in cities.

Reliefwatch wouldn’t have existed if they hadn’t seen this issues firsthand.

Travel Opens Your Eyes to Problems You Don’t See

Most of the startup ideas I saw during my time at The University of Chicago was stupid.

How many people are trying to create the next Facebook, Snapchat or a better networking app to replace LinkedIn?

These ideas are garbage because they are students’ attempts to solve their own minor inconveniences.

I’ll admit it. I’m a hypocrite.

My own startup UEvents falls under this category. My friend and I created it because we wanted to know what events were happening on campus on the weekends.

But as ReliefWatch demonstrates, travel is an opportunity for us to really see the problems that are impacting other people. To step out of our bubbles to see the real issues out there.

I’m no longer involved, but am proud to say that the company is now helping health organizations all over the world track disease occurrences and medical inventory. They are helping health organizations saving money and providing higher quality services to their patients – saving lives in the process.

This is exactly the type of project I want to continue work on in the future. And I recognize that I need to educate myself through travel to do so.

Having Enough Money To Do The Above

Entrepreneurship, doing meaningful work and traveling sound fun and all. But this is where reality comes in. How are you going to pay for it?

Reality comes in like a wrecking ball…

I can lie and say that money doesn’t matter. But money matters to me.

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 I do this?

Passive versus 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.

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I won’t go too much into detail as this topic will be its own post in the future. But here’s the main point:

There are two types of income: active and passive income. They can be represented by the chart below.

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Active Income (left) and Passive Income (right)

Active income refers to income generated by services that are performed. These include salaries, wages, tips, and commissions. Long story short, you are trading your time directly for money. If 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 is More Lucrative Than Working for Someone Else

In order to live The Remote Lifestyle (as my blog is named), I realized that I had to start thinking about money.

What I realized is that with my technical proficiency in building websites, I had a unique opportunity to work for myself.

I did the research and found that if I continued working at a large company, I would:

  • Have to show up five days a week and eight hours a day.
  • Be looking at a promotion every two years or so.
  • Be looking at a meager pay increase every year
  • Get a ton more responsibility for relatively little financial compensation

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

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I traded a corporate office for coffee shops

Based on everything I read, I knew that I could work less and make more money as a freelancer.

In fact, I’ve been doing freelancing for almost 3 years in preparation for this transition.

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.

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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 towards 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!

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