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Top 3 Questions from "Quitting Your 9–5 Job" at FinCon22

Updated: Sep 29, 2022


FinCon22 Roundtable — “Quitting Your 9–5 Job”


I recently had the opportunity to lead a roundtable discussion at this year’s FinCon in Orlando about thriving during the Great Resignation.

To give a background, FinCon is one of the largest conferences for creators, influencers, and thought leaders in the personal finance space.

Every year, bloggers, podcasters, YouTubers, and celebrities on Instagram, Twitter, TikTok, and other platforms descend upon the convention to network, share ideas, and collaborate together.

There are an abundance of educational sessions covering topics such as financial independence, early retirement, digital nomadism, saving money on taxes, starting your business, growing, scaling, and monetizing your personal brand through writing books, freelancing, blogging, social media, digital courses, consulting, coaching, hosting events.

There are also tons of opportunities to network through social events outside of the educational content.

If you’re new to this post, I wrote a post in late August ’22 about the “Top 5 Major Factors That You Need to Consider Before Ditching Your 9–5 Job in 2022”.

I had the opportunity to share my experiences and expertise as a consultant and executive coach in helping physicians transition from clinical to non-clinical work.

Many of the questions surrounded around the following:

  1. Savings and income — when you quit your 9–5 job, you will no longer have a “steady” income unless you have significant savings and investments built up over time. Depending upon your expenses such as spouse, kids, mortgage, auto, and insurance (more about this later), you need to have anywhere from 6–9 month to 3–5 years to be best positioned for leaving your full-time job. Additionally, income that is not tied to full-time work such as passive income from businesses, stocks, and real estate investments are some of the best sources of income to build up prior to leaving your full-time job.

  2. Health insurance — insurance is one of the biggest factors keeping individuals tied to their jobs. The modern healthcare system in the United States is tied to having adequate health insurance derived from working for an employer (ie health insurance tied to your job). Options for freelancers, solopreneurs, self employed, and small business owners can be be limited and oftentimes extremely expensive for individuals let alone if you have a family to support. Some of the options discussed included: COBRA coverage (usually 6 months or more) of employer sponsored coverage once you leave your job, signing on with your spouse’s employer sponsored coverage, going onto healthcare exchanges to look at more affordable options. Other participants mentioned that they have signed on with private concierge options (an affordable monthly option) and use it only when absolutely needed. In the end, health insurance is a huge factor and there are no right answers, and it is important to consider having adequate coverage by exploring the available options available in the current marketplace.

  3. The purpose of income — lastly the discussion centered around pursuing meaning and purpose in one’s life over hoarding income purely for the sake of an income number. Many of the participants would gladly make 100k per year or more doing what they were good at, passionate about, owning their time, spending time with their loved ones, ability to take care of their health, and making a difference, as opposed to selling their soul going to work for a corporation for 40–50 years, not being passionate about what they were doing for a living, and not being in control of their time or income. Interestingly, many of the participants in the latter were of the Millenial and GenZ cohort, and many stated that they would not work for a corporation that did not resonate with their social values regardless of the salary that they were getting paid. I anticipate that the younger generation wants to make a difference and is willing to sacrifice income in lieu of passion, meaning, and purpose.


I had the pleasure of meeting colleagues and friends made during the pandemic in real-life, and it was great to share experiences, and bond over drinks and dinner. Some of the notable brands included Physician on Fire (Leif Dahleen, MD-Anesthesiology), Darwinian Doctor (Daniel Shin, MD- Urology), and Financial Success MD (Corey S. Fawcett, MD-Surgery).

At the FinCon22 author booth promoting my bestseller, “How I Quit My Lucrative Medical Career and Achieved Financial Freedom”

Next year, FinCon23 will be in the “Big Easy” in New Orleans, Louisiana and will be looking forwards to sharing, connecting, collaborating, and creating.

See you next year in the “Big Easy”


About: Dr. Christopher Loo is a physician who became financially free at the age of 29, and retired early at the age of 38, as a result of making strategic investments after the 2008 financial crisis. A graduate of the MD-PhD program offered jointly through the Baylor College of Medicine and Department of Bioengineering at Rice University, he is the author of “How I Quit My Lucrative Career and Achieved Financial Freedom Using Real Estate”, and is the host of the Financial Freedom for Physicians Podcast. He is a regular contributor to KevinMD and has spoken about the importance of financial literacy for Passive Income MD, the White Coat Investor, Board Vitals, SEAK Non-Clinical Careers, SoMe Docs, Doximity, Medpage Today, FinCon, and other high-profile financial brands geared towards high-income professionals.


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