When is the Best Time to Change Careers?

Updated: Aug 14


When's the Best Time to Change Careers?

Changing careers is a big decision. While there's no "right or wrong" time for a career change, there are many things to consider to determine an ideal time and date to resign.


Some factors also depend on whether you plan to resign without another job lined up and your financial runway. One thing I learned from my past resignations: Time your resignation based on what makes most financial sense.


Related Content:


3 Ways to Earn $1000/month in Passive Income

How I Live Off My Passive Income Streams

3 Steps to Start Making Passive Income with Affiliate Marketing


Watch the below video!


I tried leaving the 9-5 grind 3 times. The first time was ugly and messy. Second time was a little better. Third time was the charm.


Here are some important factors to consider when you determine your resignation date:



Which passive income strategy is the best for building wealth?


Ultimately, creating passive income can help you take off the golden handcuffs of working in the 9-5 cubicle life.


Multiple passive income streams can help free up your time and energy to do other activities that you enjoy but may not be income producing.


As business owners, creating passive income can help you serve a lot more people without burning out. ⁠


The best passive income strategy for building wealth is one that is aligned with your strengths and interests.


When's the Best Time to Change Careers?

Your passive income strategy should feel exciting to you.


You're more likely to stick with the passive income strategy that excites you. When you are intrinsically motivated, it is more sustainable in the long run.


For instance, I had the choice of renting out my condo before I moved across the country. If I did so, each month's rent payment from the renter would have been passive income.


But having been a homeowner for five years, I did not enjoy dealing with home maintenance and other responsibilities. I knew that I would not enjoy being a landlord as those same responsibilities would carry over.

So I prefer other passive income methods like index fund investing. Doing so is much more in alignment with my strengths and interests. For people who love being home owners, they are likely better off investing in rental properties.


Ready to create passive income?

There are so many ways to create passive income streams. It doesn't mean you have to do it all.

Start with one passive income strategy and see which works best for you! Which passive income idea best suits your personality?

Quiz: Best Passive Income Idea for Your Personality!


When's the Best Time to Change Careers?

How to Overcome Money Mindset Blocks to Create Passive Income


Sometimes, creating passive income can feel like it's "too easy" or "too obvious.⁠" You might think that no one would pay for your digital product or intellectual property, especially when everything can be found online for free.


Over the years, I've learned that people, including myself, will pay premium dollars to save time. Most are willing to pay money for products or services that offer faster solutions and quality results.


Ready to replace your salary with passive income?


In 2019, I quit Corporate America, sold my condo and moved across the country. In that order, within a month.

In my mid-30s, I reached financial independence retire early (FIRE) by replacing my salary with passive income.

I was finally able to leave a career that was no longer a good fit by creating multiple income streams from investments and side hustles.


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. ​


​I left all my furniture behind. I took my favorite 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.


Although, I didn't have another job lined and was just starting up my business, I was financially independent.


Prior to resigning, I had played around with different side hustles and invested consistently in stock market index funds.


We all know it's not an easy journey to financial freedom, let alone change careers.​ Join me along my new chapter in sunny California!

Here's my story...


5 Different Ways I Created Passive Income Streams:

The main reason I was able to resign from the 9-5 lifestyle was from passive index fund investing.


Create multiple passive income streams.


Whether it's passively or actively earned, millionaires have an average of seven income streams. After all, having multiple income streams is one of the great keys to wealth.


There are many ways to create passive income streams. You don’t even have to start a business to do so.


This includes drop-shipping other people's products, creating an online course, affiliate marketing, renting out your car, and so on. Investing in rental properties is a great way to create passive cash flow too.


Which passive income idea best suits your personality?

Quiz: Best Passive Income Idea for Your Personality!


When's the Best Time to Change Careers?

For years, I experimented with different types of side hustles. Eventually, I got to get a feel of what I enjoyed doing and let go of the activities that were not as enjoyable.


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


There are many different methods to create passive income streams. The possibilities are endless! Currently, I earn passive income mainly from index fund investing.


Interested in creating passive income through index fund investing too?


You probably already know that the path to financial wealth is to have your money work for you. Investing in index funds allows your money to compound over time so that you can earn money while you sleep.


Not interested in stock picking and day trading? Want to sleep soundly at night despite the volatility of the markets? Me too.


Here’s how I minimize risks:

  • Diversify across different asset classes

  • Diversify within asset classes

  • Diversify across markets, countries and currencies

  • Diversify across time


When's the Best Time to Change Careers?

About to take the leap? Already resigned?

When it comes to being a corporate dropout, there’s one thing I know for sure. It’s not as easy or glamorous as it seems on the surface.


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.


While I don't recommend resigning without a plan, sometimes you know when enough is enough.

Creating passive income helped me leave the 9-5 lifestyle once and for all. It wasn't easy leaving a steady paycheck and company benefits behind.


A Corporate Dropout's Guide to Passive Income:

For years, I tried different passive income side hustles, from creating digital products to index fund investing.

Eventually, I got to get a feel of what I enjoyed doing and let go of the activities that were not as enjoyable.

Here's one thing I learned: ​The best passive income strategy for you is one aligned with your strengths and interests.


Which passive income idea best suits your strengths and interests?

Quiz: Best Passive Income Idea for Your Personality!


When's the Best Time to Change Careers?