How to Increase Your Income: Deep Habits and Wide Randomness

4 min read

In my sophomore year of college, I applied for a three week study abroad program in Japan. I didn’t have a passport, I knew nothing about Japan, and I had never traveled internationally before. I just thought it sounded fun.

Fast forward one year. I went on the trip. It was a blast. I also became good friends with the professor who led our group. 

Fast forward two years. That same professor wrote the letter of recommendation that helped me land my first internship with a local company.

I had no idea that attending a study abroad trip would lead to a connection that would lead to an internship. It was a random series of events that I could not have predicted.


This is a beautiful example of doing something unconventional (applying for a study abroad program) that exposed me to randomness (meeting an influential professor), which led to a future income stream.

The more I think about it, though, the more I realize that most new income streams arise from exposure to randomness. 


Last year, one of my dad’s friends suggested that I offer statistics tutoring lessons. I threw some ads up on Craigslist and within a week I had my first client.

This client referred me to someone else they knew, and shortly afterwards I realized that I could tutor people across the country completely online. This helped me connect with countless students in statistics classes and earn a few thousand bucks in side hustle income.

I had no idea that exposing myself to the randomness of Craigslist would lead to a new income stream.



Late in 2016, I read an article on how to start a blog. That same day I decided to buy the domain name ‘’ and a hosting plan. Within a week I published my first article. Shortly afterwards, I wrote a post that went viral and I became hooked on blogging.

Fast forward one year and I find myself consistently earning hundreds of dollars through this site each month. It was never my intention to turn blogging into a side hustle, but through randomly starting a blog I eventually grew this income stream from the ground up.


The Two Paths to Higher Income

If you’re looking to increase your income, there are two paths you can take.

1. Go “wide” and develop new income streams through exposing yourself to randomness.

2. Go “deep” with your current income streams through daily habits. 

The first path is exactly what I have described in the three previous examples. It involves doing new things outside of your normal routine. For me, this meant applying for a study abroad program, offering tutoring services online, and randomly starting a blog.

All three of these actions were unusual for me, but they all exposed me to randomness that eventually led to new income streams.

For most of you reading this, you probably have one or two sources of income. Perhaps you have a day job and a side hustle.


The way to develop new income streams is through doing things you don’t normally do on a regular basis. 

For me, this year I plan on sending out cold emails to try and form freelance writing connections. This will be something new I haven’t tried before. I have no idea if it will lead to any writing gigs, but I’m at least exposing myself to the opportunity.

I also recently joined a new cryptocurrency meetup group I found through By joining this group, I’ll have an opportunity to be surrounded by people who are interested in money and technology.

There’s no guarantee that I’ll form any new connections or friendships, but I am at least exposing myself to a new environment full of like-minded people.

Through cold emails and new meetups, I am inviting more randomness into my life. This could lead to future income streams that I can’t predict right now.


Some other ideas for gaining exposure to randomness might be:

  • Listening to new podcasts
  • Reading genres you normally ignore
  • Starting your own site
  • Attending conferences

These are all viable ways to expose yourself to new ideas, new relationships, and potentially new income streams.

Go Deep

The other approach to increase your income is to “go deep” with your current income streams. This means focusing even more on your day job to get promoted or working to make your current side hustle / small business even more profitable.


The benefit to this approach is that you can have a narrow focus and concentrate most of your time and energy on increasing income streams you’re already familiar with.

Depending on how feasible it is to move up the ranks at your day job, you may be better off starting your own side hustle or small business. If you choose this route, I recommend developing some serious daily habits.

For me, this blog is my main side hustle. I set aside 2 – 3 hours each morning to work on it. This habit has helped me churn out posts on a regular basis and increase my income over time:


I’m effectively going “deep” with this side hustle in hopes that I can grow this income stream significantly over the coming months and years.

If you have a current side hustle – blogging, dog walking, babysitting, freelancing – the key to growing this income stream is through daily habits. If possible, set aside time every day to grow this stream just a little bit. Over time, your daily effort will likely lead to increased earnings.

Why Not Both?

If possible, choose to go both “deep” and “wide” to maximize your income.


Set aside time each day to grow your side hustle.

Work to move up the ladder at your day job.

Then use the weekends and evenings to occasionally expose yourself to random new opportunities for income. You could go out into the world to do this (conferences, meetups, etc.) or you could do it from the comfort of home (read new blogs, listen to new podcasts, send cold emails).

The decision to go wide, deep, or both is up to you.

If you keep doing what you’ve been doing in the past, you can expect your income to grow at the same rate it has been. But if you use habits to deepen your current income and randomness exposure to develop new income, you increase your chances of earning more in the future.

The more you earn, the more you can save. The more you save, the more freedom you gain.

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8 Replies to “How to Increase Your Income: Deep Habits and Wide Randomness”

  1. Wide and deep…I like it! I hope you find great connections through your emails and meetups. It’s all about planting seeds right and seeing which ones will sprout!

    1. I like that analogy…planting seeds and seeing which ones sprout. I have no idea if any of my new efforts will lead to different connections or income streams, but I’m at least putting myself out there to see what happens 🙂

  2. That’s great. It’s always nice to connect with people. I have learned that knowing someone is generally how most people get jobs. They say location x 3 but you also need to network x 10 in my book.


  3. lol@accidentally writing a viral post. I can relate because it did happen to me. I reluctantly wrote a post that was request by a reader, about how we increase our income to $400K. Interesting enough the post has outperformed all the other posts, and gets featured a lot by other bloggers!

    It’s also impressive how you are able to produce good content everyday! We only publish once a week 🙂

    1. I know, right? I was shocked when major brands started reaching out to me to repost something I wrote. I’m not too surprised that $400k post has done so well for you – that’s an abnormally high income that I’m sure many people are curious about. Thanks for the kind words, keep up your weekly posting as well – everyone has a writing schedule that works best for them 🙂

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