Confessions of a Corporate Dropout Turned Boss

Confessions of a Corporate Dropout Turned Entrepreneur

When it comes to being a dropout, there’s one thing I know for sure. It’s not as easy or glamorous as it seems on the surface. Whether it’s dropping out of Corporate or college, there’s a lot of unknowns involved. They say fear of missing out (FOMO) is a real thing. Well fear of the unknown is also no joke.

Not too long ago, I quit Corporate America, sold my condo, and moved across the country. In that order. No job lined up. Not a single client on the horizon.

It was my third time quitting a career without a Plan B. I gave everything away and left all my furniture.

What about clothes? I left it all, my business suits and winter coats were still on hangers the day I gave the new owners the condo keys. I took my fav pair of heels though. Other than that, I shipped my car and gave away everything else.

It was time to start a new chapter. Being born and raised in Hawaii, I had enough of East Coast winters. So I picked Southern California as my new home.

Related Content:

Pinfinite Marketing: Our Story & What We're About

1:1 Strategy Sessions for Your Career Transition

5 Things You Must Do Before You Resign

Most of my life, that is how I operated. One foot in front of the other, rarely in “logical” order. And never in a “rational” way.

What about the previous career quits? Even more spontaneous than the last quit. As mentioned, I quit my corporate job three times without a Plan B. Things worked out each time but it was definitely scary times.

What made it even more tough? Not having support from family and some close friends.

So after each quit, I learned to inform them after the fact. Or sometimes I straight up lied. Sorry, not sorry, Mom and Dad!

It just made things a lot easier...emotionally.

Grab your FREE E-Book today!

E-Book: Corporate Dropout: How I Got My Finances In Order Before I Resigned

Lies I Told…

Throughout my quits, I told countless lies. Some white lies, other straight up lying.

I didn’t like it.

At the same time, I weighed all the alternatives. Carrying the emotional burden of lying to my parents and close friends outweighed the emotional burden of dealing with their projected fears.

Knowing my parents and how they reacted each time I hinted at an upcoming job interview, I knew deep down that it was not worth telling them the truth until after I had secured a Plan B.

It didn’t make things easy...just slightly easier.

Looking back, I wouldn’t have changed my decision. Telling white lies or using a fig leaf may not be the best route for everyone, but it was for my situation.

I got a Tiger Mom...heck, a Tiger Family!

Some of the lies included saying I was:

  • “Working from home”...when I was actually unemployed for 5 months

  • Using up my vacation days to visit home...when I already quit Corporate and was starting up my business

  • Making enough in my side hustle projects that I could comfortably leave Corporate...when I was making nothing

  • Transferred to the West Coast by Corporate...when I relocated on my own dime after having left Corporate

The list goes on...what can I say, I’m super creative.

While I’m being completely transparent, I’ll also add that growing up, my family lived paycheck to paycheck. It wasn’t until years after I graduated from college that my parents became middle class. I had a ton of student loan debt and was not good with money until my early 30s.

Grab your FREE E-Book today!

E-Book: Corporate Dropout: How I Got My Finances In Order Before I Resigned

Yet, in many ways, I grew up privileged.

I had parents who supported me unconditionally (outside of my career decisions). They did whatever it took to get me the best education and much much more. Putting things into context hopefully helps to shed light on the following “unconventional” decisions and risks I took in the past.

Here’s the reality of what happened after I quit each time…

Quit #1:

In February 2016, I quit on impulse. I couldn’t stand another day working for a micromanaging boss and passive aggressive coworker. So I walked into my boss’s boss office and resigned. Right then and there.

I didn’t even speak to my direct boss. I went above him to his boss. It had been seven years with the company and to this day, I don’t regret a day there. It was just time to go.

A senior manager advised me to take time off to think things over (and calm down).

After several months at home, I realized that I still had a mortgage to pay.

I went back to the same company but moved to a new department. This time, it was a part-time position. I knew it would only be temporary. Eventually, I resigned a year later...for good.

Quit #2:

Resigning the second time around was somewhat scarier. Everything in my life fell apart pretty quickly as soon as I started my first weeks of unemployment.

From an unexpected breakup to my dad getting into a car accident to ending up in the ER myself while traveling in Europe.

This all happened within a month.

I used the months after that to get my health, sanity and life back in alignment. And it sparked my interest in getting my finances in order too.

I realized that I did not want to rely solely on an employer for a paycheck and health insurance.

Nevertheless, the whole experience left a huge scar.

In my mind, I still equate being "jobless by choice" with the notion that the worst case scenario is going to happen in my personal life.

Five months later, I found myself working in Corporate America...but with a plan. The plan was to become financially independent and get the hell out.

Then I got “FIRE’d”.

Grab your FREE E-Book today!

E-Book: Corporate Dropout: How I Got My Finances In Order Before I Resigned

For the next year and a half, I worked hard on cleaning up my finances. Soon enough, I paid off my mortgage and I was able to reach financial independence at 35.

Yep, I got FIRE’d….financial independence retire early (FIRE) that is. So there was that unexpected benefit from taking time off after Quit #2 to reset.

The best thing that came out of Quit #2’s “Eat, Pray, Love” soul searching journey was the start of my path to FIRE. In mid-2019, I got the hell out of dodge and resigned from the 9-5 lifestyle for good.

Quit #3:

When I wanted to relocate across the country, I had to really think things through. Even being financially independent, I had huge mental blocks. I was fearful that the events following Quit #2 would repeat again.

Fortunately, none of the horrific events repeated. No health scares. No hospital visits. And no breakups. Then again, there was no guy to breakup with!

With 2020 hindsight, the following are some key lessons I learned from quitting my job three times without a Plan B…

Get creative with ideas in this gig economy.

The gig economy centers around the concept of creating an income from short-term tasks. This encompasses those who are full-time independent contractors to those who moonlight by driving for Uber/Lyft several hours a week.

Are there any part-time opportunities that you may consider taking on in order to explore a different industry? Any fun side hustles you’ve been thinking about trying?

Grab your FREE E-Book today!

E-Book: Corporate Dropout: How I Got My Finances In Order Before I Resigned

Build a solid support network.

Having a solid support network is probably the most important yet most overlooked key to the transition.

Each time I dropped out, I chose not to tell my parents and some of my closest friends. Telling them I was going to be “unemployed” would lead to unnecessary concern and nagging.

Instead, I told them after the fact.

In between all the white lies, it still wasn’t easy for them to hear and accept. But they eventually got it after seeing how much happier I was as an entrepreneur.

Assess the people you currently spend the most time with. Are they people who are going to support you along the journey to the next chapter in your career?

Your vibe attracts your tribe...and the other way around too!

The key to getting to where you want to go in life is to be in vibrational alignment with where you want to be.

Most times we focus on tackling our challenges on a physical, emotional, and mental level. Rarely do we approach challenges from an energetic angle.

Sometimes the people we love can be energetically depleting even if they have the best of intentions.

Is your tribe making your transition an uphill battle when it doesn’t have to be that way? Perhaps it’s time to set some energetic boundaries and start building a stronger support network.

Confessions of a Corporate Dropout Turned Boss

Time to get woo.

Each time before dropping out, I went all out on seeking guidance. This means I went full force woo-woo.

Oh yeah, we are totally going there. For whatever reason, I’m all about psychics, tarot, and all things metaphysical.

Before resigning, I consulted a few mediums. I had a past-life regression reading, talked to psychics, did tarot readings, practiced Reiki and other woo-woo stuff.

Over the years, I learned to take it with a grain of salt. Specifically, I became more mindful of the advice and feedback given.

Mentors, psychics, and career counselors can provide a ton of helpful insights. But at the end of the day, I took what advice felt right and chucked out what didn’t resonate.

Bottom line: Collect data. Then just do you.

About to take the leap? Already resigned?

The trend toward a gig economy is real. A study by Intuit predicted that by 2020, 40 percent of American workers would be independent contractors.

If you are reading this book in the future, you may already be like “duh, everyone I know is a #girlboss!”

Whether or not the study proves to be correct, the 9-5 lifestyle just might be a thing of the past for you.

If so, what would you do if you never had to step into the office for a full day ever again? How do you plan to replace your income in a gig economy?

Grab your FREE E-Book today!

E-Book: Corporate Dropout: How I Got My Finances In Order Before I Resigned