Corporate Dropout to Entrepreneur: How to Replace Your Income in a Gig Economy

Updated: Nov 23, 2020

Corporate Dropout to Entrepreneur: How to Replace Your Income in a Gig Economy

Thinking of leaving Corporate to become an entrepreneur? Not sure how to replace your Corporate income? No worries, you're not alone. Though it takes time and a lot of hard work, I'm living proof that it's possible to replace your income in a gig economy.

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.

Just shipped my car and gave away everything else. The entire process emotional and freeing at the same time.

It was time to start a new chapter. Why the move? Being born and raised in Hawaii, I had enough of East Coast winters.

So I picked Southern California as my new home.

Most of my life, that is how I operated. One foot in front of the other, rarely in a “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 told them after the fact.

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

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. I felt carrying the emotional burden of lying to my parents and some close friends outweighed the emotional burden of dealing with their projected fears.

Knowing my parents and how they reacted each time I hinted at a new 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.

It may not be the best route for everyone, but it was for my situation.

Access my FREE E-Book!

Corporate Dropout: How I Got My Finances in Order Before I Resigned

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 comfortable 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 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 part of the middle class.

I had a ton of student loan debt and was not good with money until my early 30's.

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 “unconventional” decisions and risks I took during my career quits.

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 or 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?

Make money on Pinterest.

Got a product or service? Then it's time to leverage Pinterest to create multiple income streams.

There are many ways you can create active and passive income with your current resources and skill sets?

Ideas for multiple income streams.

There are many ways to have a side hustle these days. You don’t even have to start a business to do so.

This includes freelance writing to renting out your car. Investing in rental properties is a great way to create cash flow too.

During my weekends, I taught yoga and wellness workshops at the local hospital. I also worked the front desk of a yoga studio at one point too.

How I Created Multiple Income Streams:

  • My 9-5 job

  • Guest write for wellness websites

  • Teach yoga

  • Rent out my condo on Air BnB

  • Rented out my car

  • Invest in index funds

  • Answer online surveys

  • Run a blog biz: NotABondGirl

There are a gazillion more ways to reach financial freedom. But you don’t have to do it all! Try out 1 or 2 that get you excited and go from there.

As with everything in life, the fun part is the journey, not the destination.

I got to experiment with different types of side hustles. I eventually got to get a feel of what I enjoyed doing and let go of the activities that were not as enjoyable.

Got great ideas and content to share?

Overwhelmed by how the online space is so saturated? No worries.

Not too long ago, I was struggling to find my voice in the saturated social media world. I hustled and slept VERY little. Then I burned out.

What was I not seeing? I didn't want to throw money on ads that only brought in "likes" but zero sales.

After much trial and error, I found that I was getting sales and clients through a counter-intuitive approach. No more trying to figure out algorithms or staying ahead of the hashtag trends!

Finally, I learned how to navigate the digital marketing space without having to spend hours and hours online. Yes, I have a normal sleep schedule now.

How to Replace Your Income in a Gig Economy

Create Passive + Active Income Streams:

Passive income requires minimal to no effort to maintain. There may be a lot of heavy lifting upfront and income can fluctuate greatly.

Nevertheless, it's a great way to make money on Pinterest with the right amount of time investment. Here are a few ways to passively make money on Pinterest…

Stock photos

Got an eye for photography? Consider selling your photos as stock photos on your site or

Leverage Pinterest as your portfolio and direct website traffic to your site or iStockPhoto listing.


Got a lot of great content? Consider putting together your blogs, videos, and other content into an online course. I've created 7 courses for free on Teachable!

Offer e-courses on your site. Then create pins and infographics to direct pinners to your online course.

Website ads

When it comes to banner ad displays, the quantity of website traffic matters. If you have a large amount of website traffic coming to your site on the daily, website ads may be the way to go.

Get paid to display ads on your website. Then drive traffic to those banner ads with pins. Not sure if your fav brand has a banner ad referral program?

Check out all the companies and brands on FlexOffers!


Love blogging? Consider creating an e-book from your most popular blog content. Then create pins and infographics to direct pinners to your offering.

Promote affiliates

Join affiliate networks to promote products and services. I currently use FlexOffers!

Affiliate Links Best Practices:

Although affiliate links are currently allowed on Pinterest, I recommend pins be linked directly to your claimed business website.

Build trust first.

It takes time to build the "know, like and trust" factor with an audience. People rarely open up their wallets upon first encounter. So give it some time for folks to get to know and trust you before selling to them.

Access my FREE E-Book!

Corporate Dropout: How I Got My Finances in Order Before I Resigned

In my mid-30s, I reached financial independence retire early (FIRE) by creating multiple income streams from investments and side hustles.

I was able to leave a career that was no longer a fit. More importantly, it was time to get away from East Coast winters!

So I quit my job, sold the condo and moved across country. I gave everything away and just shipped my car.

Corporate Dropout to Entrepreneur: How to Replace Your Income in a Gig Economy