Declining old media advertising

I was doing some financial housekeeping the other day and I realized my online company’s operating profit YTD finally outstripped my day job income from the very last full year. I was excited not so much by the amount, but because I had finally proved to myself that I could finally make something sustainable on my own. Creating something from nothing is a thrill.

Financial Samurai and the Yakezie Network started in the summer and winter of 2009. We’ve all heard that most businesses fail within 5 years, so getting over the 5 year hump is definitely something I’m pleased about. It’s been a fun and long road since then – lots of failures, lots of conflict, lots of stolen ideas, and lots of doubt. I’m not sure I’d be as appreciative of my situation now if it wasn’t for a lot of problems in the past.

It wasn’t until 2012 that I decided to focus more attention on making online revenue since that is when I left my job. Before then, I was just writing for the fun of it. I still write mostly for the joy of writing, but there’s a little more business strategy involved now. Writing for leisure and connecting with other people online is probably what saved me from quitting. I think most of us blog because it’s a rewarding experience unlike any other.


It’s taken me five years for my online income to surpass my day job income. I’ve always had the confidence that this crossover would one day occur, but I never knew when it would happen. I’m not sure whether I should be happy with the result, or displeased by how long it’s taken. Five years is a darn long time to work and wait. (Related: How Much Do I Have To Make As An Entrepreneur To Replace My Day Job Income?)

There are plenty of bloggers out there who surpass their day job income within a year or two. Perhaps it’s more a function of income? It’s much easier to surpass a $50,000 day job income than a $500,000 day job income, for example. Or perhaps it’s because their material is just so awesome and many more people can relate that they achieve quick success. Whatever the case may be, I think replicating any day job income is a respectable achievement because all our income and costs are relative.

Lots and lots of people want to make money online. But lots and lots of people aren’t willing to put in the commensurate effort to make it happen. Therefore, for all those who want to generate online income, my recommendation is to commit to thinking that you’ll make NO meaningful income for the first three years. If you can commit to this high probability, that means you truly love the field.

The first three years is all about building your brand. I’ve found that many people don’t fully trusts sites that haven’t been around for at least a year or two of because nobody wants to commit for fear of it shutting down. I don’t want to watch a new TV series live because networks cancel TV shows all the time – sometimes mid-season! Instead, I wait for at least a couple seasons to go by and watch the shows on Netflix.

In order to build your brand online, you’ve got to come up with a portfolio of consumption-worthy content. Once you develop your community base, then you can have advocates who will regularly share your content with the world.  They don’t want to share your stuff if they think you’re going to disappear on them before the year is out. It makes them look bad. Three years, and 300+ articles should be a good enough amount of time and effort to create a respectable brand.

Once the brand and community are built, then you can figure out a tactful way to monetize without losing your readership. Don’t be afraid to monetize your site at this point. Most of your loyal readers can’t wait to help you after you’ve given them so much for free all these years.


Only after two and a half years of writing did I finally somewhat believe I could make a livable income stream online. But even then, I was worried about leaving because my job was all I knew for 13 years. Change is stressful!

I’d like to provide some rough parameters for when quitting your day job to pursue online entrepreneurship is a good idea.

1) If you’re receiving at least 100,000 pageviews a month. I believe it’s possible to make 10 cents a pageview if the site is perfectly optimized in personal finance. Given nobody, or no site is perfect, let’s assign a 5 cents per pageview value. In other words, a site with 100,000 page views a month should be able to earn roughly $5,000 a month. Most single people should be able to live off this amount. If not, they should read our sites!

2) If your online income earns at least 50% of your day job income. Given your online efforts are part-time, there should be a strong correlation with income generation and effort. Most people looking to get out of a job to work online are saving aggressively. So if your online income is earning 50% of your day job income, and you are saving 50% of your day job income, then your lifestyle won’t change at all.

3) If you’ve got at least two years worth of living expenses saved. Two years is an important figure because if you’ve spent two years working on your business or blog and it’s not generating any meaningful income, you’ll probably want to find a day job again. Employers start to become skeptical of your day job gap after two years, even if you’ve been working like a dog to build something that has failed.

The above three points are the main guidelines I’d go with before quitting your job to become a full-time blogger. One point alone is probably good enough for you to take the leap, if you’ve got an idea or an already running venture. But if you can satisfy all three points, then all the better. The below are some other points that are worth mentioning before taking the leap.

* If you’re willing to still work for others by being a freelancer. Being a freelancer takes a lot of hustle because you need to find clients. Freelancing is the least removed occupation from a day job as it is another full-time job. At least you’re your own boss. But remember, there is a big difference between being a blogger and being a free-lancer. Don’t confuse the two!

* If you’re able to negotiate a severance. The larger your severance, the longer your runway for trial and error. My severance was a positive surprise, so I didn’t have too much fear after the check was deposited. In fact, all I wanted to do was slack off for six months and travel. But I decided to write my severance negotiation book instead.

* If other people are just throwing money at you to invest in your business. If a lot of people believe in you by putting their money where their mouths are, then you should probably quit your job and focus on your business full-time as well. The correlation with effort is huge with blogging and other online businesses.

* If you’re willing to suffer. If you’re willing to sleep on the streets, work crazy hours, eat sparsely, be consumed by stress, and successfully battle fits of insecurity then go for it. Living in America is relatively comfortable compared to many other places. If you’re willing to sacrifice your luxuries for a couple years, then go for glory.

I strongly discourage people to quit their jobs before moonlighting online for at least a year. No amount of words or instruction can truly prepare you for all the little things that happen once you’re your own boss.


I’m curious to know how long it will take you, or how long did it take you to replace your day job income with your site? For folks who make a lower income level, shouldn’t it be more motivating to give online entrepreneurship a go since the hurdle is easier to achieve? Do you think replicating your day job income with online income is feasible?

When do you think is the right time to quit your day job and become a full-time blogger? One of my dreams for the past 10 years is to be able to blog from home in San Francisco, blog from my vacation rental up in Lake Tahoe, and then blog at my parent’s house in Honolulu.

If you can develop multiple income streams online, you can potentially make a full-time living as a professional blogger. Many bloggers make more than bankers, techies, doctors, and lawyers! The key is to be patient, work on your site while working a full-time job. When there’s enough momentum, or a minimum income stream, you can take the chance to make a living blogging full-time.


I never thought I’d be able to quit my job in 2012 just three years after starting Financial Samurai. But by starting one financial crisis day in 2009, Financial Samurai actually makes more than my entire passive income total that took 15 years to build. If you enjoy writing, creating, connecting with people online, and enjoying more freedom, learn how you can set up a WordPress blog in 15 minutes like this one. 

Leverage the 3+ billion internet users and build your brand online. There are professional bloggers now who make way more than bankers, doctors, lawyers, and entrepreneurs while having much more fun, much more freedom, and doing less work. Get started. You never know where the journey will take you!

Updated for 2017 and beyond.