
A new side hustle…
one step at a time
Prelude to the side hustle journey
Greetings, folks. This page will detail my venture into side hustledom.
I won’t be alone, however. My guide will be Chris Guillebeau’s 2017 book, Side Hustle: From Idea to Income in 27 Days. Because I’m juggling other projects, I don’t expect to finish in 27 days, but this page is now out there, with arms folded, waiting for updates, forward steps, and the inevitable backward missteps.
In fact, I’m going to use this task tracker he generously allowed me to share beyond his community.
And before I go any further in this, I’m going to hearken back to Simon Sinek’s book: Start with Why. It’s a book about leadership, but to me, the title says it all, After all, shouldn’t we first be leaders of ourselves?
Okay, off the soapbox. What’s my ‘why’?
Here it is, thanks to an excerpt of an email I received from charitywater.org:
We’ve met young girls who walk in the 115ºF heat of the Sahel Desert to collect water from 1,000-year-old holes.
We’ve met women in Ethiopia who walk to the river before sunrise and don’t get back until after lunch.
We’ve even met mothers in Mali who sometimes sleep next to an open water source so they can be first in line when the water refills the next morning.
For hundreds of millions of people, being born female means that life revolves around collecting water.
It’s a burden that limits opportunities, jeopardizes safety, and steals time—approximately 200 million hours a day worldwide.
The good news is that this is a completely solvable problem.
So, my vision: Make money online and donate 20% of the proceeds to a charity–in this case, charitywater.org.

DAY 1: Predict the Future
A side hustle has many benefits and no downside. It all starts with your answer to an important question: Twenty-seven days from now, what will be different about your life?
❏ GOAL #1 - Make some extra cash for a specific purpose, whether to pay off a loan, buy a big-ticket item, take a vacation, or just build up your emergency fund.
❏ GOAL #2 - Create a sustainable and ongoing source of income that makes a real difference in your quality of life.
❏ GOAL #3 - Replace or exceed the income from your current job.
❏ OTHER - Choose your own goal! In my case, I want to complete my online course entitled ‘Goodwill Words’, share it via Teachable, and donate 20% of the proceeds to various charities.
DAY 2: Learn How Money Grows on Trees
Step 1 - Your potential side hustle is…
❏ Feasible (you can start it and earn money in a short amount of time)
‘Starting it’–It’s up to me to finish a mini-course and a lead page.
❏ Profitable (You’re not looking for an idea that merely sounds interesting, you’re looking for a profitable one.
I have to define ‘profit’. Certainly, bring in enough money so I have something to donate. I guess I would also add that I’ve covered the cost of WordPress.com site.
❏ Persuasive (It’s not enough to have a good idea—your idea has to arrive at the right time, and be so persuasive that it’s hard for customers to say no to.)
Re: my persuasion–The first five benefits of the course:
- Adds a positive purpose to our day.
- Offers chances to improve someone else’s day. [Do good to feel good.]
- Gives us a creative outlet.
- Provides an ‘authentic audience’ for writers.
- Affords writers opportunities to practice their skills.
More questions from Chris:
Step 2 - The High-Potential Idea Checklist:
❏ Can you describe how to turn your idea into action in one sentence?
❏ Is there an obvious way to make money with this idea?
❏ Does this idea solve a problem for someone?
❏ Can you figure out how to make this idea happen quickly?
❏ Is it relatively low maintenance?
❏ Can you get paid more than once for this idea?
DAY 3: Brainstorm, Borrow, or Steal Ideas
Okay, so Chris’s task tracker suggests that I narrow down to at least three ideas I conceive.
While I’m pretty sure which direction I’m going, I’ll follow the blueprint. I mean, really, who among side hustlers can limit themselves to just three ideas, much less one.
Idea #1: Develop a course for writers and good-doers to deliver ‘goodwill words’ to support others needing a little support.
Idea #2: Offer brainstorming services and ebooks of already brainstormed topics for writers, marketers, teachers, and students.
Idea #3: Rent myself out to complete ‘targeted and detailed curations’ of a website’s content.
DAY 4: Weigh the Obstacles and Opportunities of Each Idea
The task tracker categorizes them as ‘opportunities’ and ‘constraints’. I’m going to revisit this chapter in the Side Hustle book for a little clarification.
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