Nearing the end of my second sabbatical

I took my first sabbatical in 2021.

Then I went back to work in February 2022.

In March 2023, I was laid off (it was an early-stage tech startup; these things happen).

Since then, I’ve been on sabbatical again.

Except this time I told myself I would focus more on making money from my side businesses so that I can make this a permanent thing.

So I’ve been working a lot on that.

I made my first $1 of internet money by selling a course about how to get into tech sales (the course now has over 150 students).

I launched a new website called AI Writers Academy.

And I’m working on a few other websites that aren’t public yet: B2B Sales School, B2B Sales Strategy, and Feel Good Forum.

The general idea is to have a portfolio of content brands (website, YouTube, TikTok) that generate revenue via courses and affiliate marketing.

I’ve also been traveling (Cabo, New York, Puerto Rico, Kansas, Maui, Napa).

Taking long naps on the couch in the afternoon when the sun comes in through the window.

And working on another poetry book (coming soon).

It’s my ideal life.

Every morning I wake up with a blank slate.

Some days I work 14 hours because I’m genuinely excited about what I’m working on.

Other days I spend two hours at the gym, another two hours cooking breakfast, then take a nap and wake up for happy hour.

But I only have about three months of cash runway left.

The course is generating some revenue but not nearly enough to cover my expenses.

So, the way I see it, I have three options:

1. Generate more revenue from my side businesses (sell one of the brands, make more courses, build a new revenue stream)

2. Find contract, part-time, fractional work (this is the in-between option because it has elements of running my own business but I would be doing the same work as I would if I were to get a full-time role)

3. Get a full-time role (this is not a bad option because I could maximize my savings and get to the passive income lifestyle via traditional finance, e.g., stocks that pay dividends, but I’ll be sacrificing some of my freedom in the short term)

I want to manifest #1.

It’s the option that will allow me to continue living this free, traveling, creative, entrepreneurial lifestyle.

But I feel the pressure of three months of runway, and I'm wondering if that's enough time to get my entrepreneurial revenue to a level that matches my personal expenses.

If I do end up needing to get contract/full-time work, I probably need at least two months to do the search process, which gives me one month to focus on generating entrepreneurial revenue.