Wallet Hacks

How I Gained Enough Confidence to Quit My Job to Blog Full Time

(I don't usually write a ton about the business of blogging, even though I do write about side hustles and entrepreneurship. With the FinCon conference around the corner, I wanted to touch on something I often get asked about – how I quit my job to pursue blogging full-time. You may not be thinking about quitting your job to become a blogger but hearing what I did may help you leave your current situation for one you think is better.)

On January 2005, I wrote my first blog post for Bargaineering. It was one of those cheesy “Hello World!” type of posts where I shared my future plans for the nascent personal finance blog. I named it Bargaineering because I like finding bargains, I was (am?) an engineer, and I liked portmanteaus before I knew they were called portmanteaus.

(Unfortunately, Bargaineering no longer exists but here's the first post via the Wayback Machine)

It would make a few hundred dollars that first year. It was a sum that vastly exceeded my wildest expectations. I told my then girlfriend, now wife, that if Bargaineering paid for one vacation a year I'd be ecstatic. I didn't even picture a nice vacation, I was thinking a road trip to a bed and breakfast somewhere nearby!

Fast forward to early 2008, my lovely wife and I were married. We went on our honeymoon to Hawaii for two weeks.

And I quit my comfortable job at Booz Allen Hamilton the day I came back.

In the years since, having experience even greater successes beyond even wilder expectations, I've often been asked how I made The Leap, a phrase coined by Tess Vigeland, to self-employment.

It was emotionally difficult because the future is so unpredictable.

With the benefit of hindsight, here's how I remembered gaining the confidence to quit.

I Didn't Hernán Cortés My Ships

Hernán Cortés was the famed Spanish conquistador that, upon landing in Veracruz in 1519, was said to have ordered his men to burn their ships.

The reasoning was that if you kept a backup, how committed are you to the mission?

If you could retreat back to Europe, you had a way out.

Without ships — you succeed or you die.

People often point to that story and say “Wow, Cortes was smart!” (unless you lived in Veracruz already in 1519 but that's another topic for another day)

I take a different view. How many explorers did something similar and were never heard of again? Survivorship bias at work my friends.

I did not burn bridges, ships, or anything else because that's stupid. When I quit, I did it in a way where I could go back. I might have to start over at the bottom of the org chart but that's fine. I had the skills, had once been cleared to work in the defense industry, and “retreating” was still an option.

If things didn't work out, I'd go back. That's not to say it would've been easy to go back. There would've been quite a bit of pride swallowing but at least there was a way back.

You can push harder when you have a safety net.

I Built Up A Financial Runway

In Scott Trench's book Set for Life, he talks about a financial runway. “A Financial Runway is the amount of time you could survive without the need for wage-paying work or actively working to produce income.” (from his guest post)

I used a similar idea in 2008 – I took the income I earned on the side and calculated it as a multiple of my full-time job's salary. If my salary was $60,000 and I made $120,000 – I “bought” myself two years. My financial runway was two years because I “pre-earned” that income.

When I quit, I had amassed ~10 years of financial runway. I knew that even if this whole blogging thing flamed out, I'd be 10 years ahead of schedule and had that much time to figure out the next thing. (or go back and perhaps retire a little early)

I Knew I Wasn't a Corporate Highflier

When I quit my job in 2008, I'd been working in the defense industry for five years. That's long enough to know who is a high flier on the fast track and who isn't.

I wasn't.

This meant that my growth trajectory was going to be fairly mundane. I'd get my annual ~2-4% raises, mix in a few promotions that might get me a higher raise, then retire after 40 years. I could switch companies for a 15-20% raise every so often but do that enough and you run out of companies or develop a reputation (or so they say, I don't believe it).

The corporate life would've been good, comfortable, safe, predictable… and it would check off all the “life needs” boxes for me. If it weren't for the blog doing well, I know I'd still be there now. It's a great life, no doubt about it.

When my hard work and good fortune put a rocket ship in front of me, I decided safe and comfortable were great but a rocket ship is a freaking rocket ship. I got on and held tight.

I Had a Strong Emotional Support Structure

Speaking of safety nets, the real safety net was my lovely wife. It's no surprise I quit the day we came back from our honeymoon (though the decision was made long before).

There was the tangible safety net – she was employed, had a great salary and career arc, and had health insurance.

Then there was the intangible emotional safety net – the incessant cheerleading that, when it's happening, seems silly and pollyannaish. The reality is that there is something to be said about unwavering outside support when you're internally wavering.

I firmly believe that human beings make decisions emotionally and look for logic to support them. Her emotional support paved the way for the logical reasons.

She's the real rocketship.

There Was a Nascent Personal Finance Blogging Community

Nowadays, you have a huge personal finance blogging community and a variety of forums to visit if you want to talk to money bloggers.

Every year I go to FINCON, which is an annual conference attended by over a thousand bloggers and members of the media. It's put on Phil Taylor, founder of PT Money, and his fantastic team. Phil's been blogging for over ten years too. There are separate FINCON Masters events, smaller events held in other major cities throughout the year. There are casual meetups in various locations throughout the year.

If this all existed back in the mid-2000s, I may have quit my job even sooner. We had a smaller community, focused around forums, but even then it was a fun community to be a part of and share ideas. Facebook didn't go public outside of universities until 2006.

The community exists today is amazing and so incredibly supportive. It's also just a lot bigger, with people sharing their experiences, more vibrant and connected version of what existed when I quit.


Just kidding — I didn't quit because you only live once.

I quit because I had good models.

My grandparents (on both sides) did different but similar versions of escaping to Taiwan from China. My parents left Taiwan for the United States. Quitting a well-paying job for the lure of entrepreneurship, while not on the same level of risk and danger, was my version of leaving comfort in search of something more. They sought to level up and so did I.

So far, so good… but don't underestimate the power of models.

If you're on the verge of making a similar decision and want someone to talk to, email me or leave a comment.