27 Days Of Side Hustle: Brainstorming Your Home Business Ideas

27 Days Of Side Hustle: Brainstorming Your Home Business Ideas

Book giveaway: Congratulations to Tara from Ontario for being the winner of our giveaway! A special thanks to everyone who participated. Happy saving!

Do you have an amazing home-based business idea that you haven’t yet made into a reality?

Or maybe you have some extra time on your hands and you’re looking for ways to make some money on the side?

Me too – for both of these things.

That’s why this month I’m working through a new book called Side Hustle: From Idea to Income in 27 Days by Chris Guillebeau. During the course of this series, I will keep a log as I work through the steps outlined in the book.

So, what is a side hustle?

Good question. It’s a small business or project that you create and run alongside your full-time job.

Even better, if you have enough profitable side hustles, or if you have one that grows enough, you may not need a full-time job at all.

What if the side hustle doesn’t work out? Well, that’s easy – start again.

Ideas fail all the time. Businesses do too. And in the end, it’s only 27 days.

During these first 6 days of my personal side hustle journey, I will:

Day 1: Set your goals

The first thing you need to figure out is what your goals are.

This was simple for me: My goal is to create a project that will earn a small amount of money, that I can use for investment capital.

And if all goes well, I hope to earn enough to fund my RRSP.

Next, we learn about high potential ideas – business plans that are feasible, profitable, and persuasive.

Guillebeau lists the following criteria:

  • Can you describe how to do it in a sentence?
  • Is there an obvious way to make money?
  • Does it solve a problem for someone?
  • Can you get paid more than once?
  • Can you start it quickly?
  • Is it low maintenance?

My first potential hustle - does it fit the bill?

As soon as I started this process, I was approached by a friend with a new blog idea – the first idea I wanted to commit to.

The blog would be called "Geeks With Gains" (his concept, not mine) and his pitch was good. A social media concept where we link video gaming to fitness and nutrition

Let’s revisit the criteria for "high potential ideas" to see how it actually stacks up as a side hustle:

  • Can you describe how to do it in a sentence? Yes: "Geeks With Gains" would be a niche blog for video gamers who like to stay fit, focusing on fitness tips and nutrition.
  • Is there an obvious way to make money? Sort of...
  • Does it solve a problem for someone? Yes! I think…
  • Can get paid more than once? YES!
  • Can you start it quickly? No, there is a lot of content generation and audience building.
  • Is it low maintenance? No, at the beginning it would be very high maintenance. Though it could become low maintenance over time.

Because it only fits some of the criteria, the plan is to keep it as a passion project for now and chip away at it over time.

Day 2: Brainstorm at least 3 side hustle ideas

With the blog pushed to the side for now, it’s back to brainstorming new ideas.

Idea 1: Sell my basement junk on online platforms, such as eBay, Kijiji, Facebook Marketplace, and any other format I could find.

My basement junk

Idea 2: Play in a band – Admittedly I already do this, so I am cheating a bit, but I wanted to see if I could improve the business side of playing in a band to increase revenue.

My band

Idea 3: Screen print custom-designed T-shirts.

Screen printed shirts

Day 3: What obstacles and opportunities do your ideas present?

On day 3, I need to review my ideas and decide which are even possible.

Some are only good as starter ideas because they take little effort to start, but aren’t sustainable.

Example: Selling the stuff in my basement isn’t sustainable because someday I will run out of stuff. It isn’t a great side hustle, but it will give me some cash in the short-term.

Related: Organizing A Profitable Yard Sale In 9 Easy Steps

On the other hand, although playing in a band and the t-shirt business are harder to get going, there could be potential for huge growth.

These would be considered Next-Level Ideas – ones that are reproducible and will grow over time.

When you look at your side hustle ideas, you need to look at the pros and cons. In other words, look at what opportunities they present and what obstacles they may place in front of you.

Be honest!

Let’s look at how my 3 ideas do when divided into their pros and cons:

Side hustle idea 1: (Starter) Sell the stuff in my basement

Obstacles Opportunities
  • Time needed to dig through boxes, catalogue, price, and actually post the items
  • Not repeatable, I will run out of stuff
  • Limited income, used items are not worth a lot
  • No startup cost
  • No creative process: simply post and sell
  • Clears out my basement to use for another project

Side hustle idea 2: (Next-Level) Play in a band

Obstacles Opportunities
  • Time needed to learn songs, write songs, practice material, play shows, book gigs, and promote gigs
  • Need to hold merchandise until it sells
  • Negotiating each gig is difficult and the pay varies
  • Breaking onto the scene is hard to do and it takes time to develop a following and find venues willing to hire you
  • Late nights playing shows and early mornings with the kids don’t mix
  • Repeatable process
  • Get paid to do what I love
  • Possibility for growth and increased pay
  • Multiple revenue streams from playing live shows, merchandise (t-shirts), and eventually music sales
  • Little-to-no startup cost

Side hustle idea 3: (Next-Level) Screen-print single colour T-shirts

Obstacles Opportunities
  • Growing a customer base
  • Getting a good price on shirts
  • Dealing with unsatisfied customers
  • Quality control
  • Waste due to printing errors
  • Simple process to print t-shirts
  • Growth potential is good. I can start small and buy better equipment as I earn
  • Repeatable process
  • Low startup cost. $100 or less for the kit
  • Variety of Places to Sell - Etsy, Facebook Marketplace, Kijiji, eBay, word of mouth referral

Day 4: Honestly re-evaluate your hustles

At this point, you have to admit something to yourself: Some hustles just aren’t possible for you!

Most of them will be out of your wheelhouse for any number of reasons. Maybe you don’t have the skills, or maybe you don’t have the money.

You won’t be able to make just any side hustle work. It depends on your situation and your talent.

If you can combine a passion with demand, then you have a hustle. Find something you love and find people who want to buy what you’re selling.

The last ingredient you need is the money or other resources to start the business – if you can’t afford to start, you don’t have a hustle.

This is where you need to be honest with yourself. Use the obstacles and opportunities you outlined yesterday and see which options are really best for you.

In my case:

  • Selling my basement junk is not a big enough project. It isn’t sustainable, and it would feel like I was taking a shortcut in this experiment. I need something more complex.
  • Playing in a band is something I’m already doing and it doesn’t pay well. It’s more of a passion project than a side hustle.
  • Honestly, screen printing t-shirts seems to have the most promise. Even if I don’t make many sales, the start-up cost is small and so is the time commitment.

Day 5: Figure out your projected profits

One idea seems to be in the lead!

Let’s see if the t-shirt side hustle is worthwhile by calculating the projected profits:

Expected Income - Expected Expenses = Projected Profits

Remember, a side hustle must be easy to start, it has to give repeatable results, and it has to be profitable.

You want your costs to be much less than the projected profits.

The first month of my t-shirt printing hustle will look something like this:

The T-Shirts - Month 1

Item Income or Expense
Projected Sales Income 20 Shirts @ $8/shirt + $25 setup fee = $185
Screen Printing Kit Expense $75 @ Michael’s w/ 40% off coupon, taxes in
T-Shirt Purchase Expense $3.99 x 20 Hanes at Walmart = $92 taxes in
Projected Profit: $18

This isn’t too great of a profit, but I am just starting out.

Let’s see if the next month will be any better...

The T-Shirts - Month 2

Item Income or Expense
Projected Sales Income 50 shirts @ $8/shirt + 2x$25 setup fees = $450
Screen Printing Kit Expense None
T-Shirt Purchase Expense $2.39 x 100 = $239 from wholesaler
Fabric Ink Expense None, with leftover supply from last month
Photo Emulsion Expense $42
Projected Profit: $169

This is a much better profit, and I’ll have 50 shirts left over to help with next month.

Overall, it seems pretty promising.

Day 6: Let’s pick a side hustle

Okay, enough thinking...It's time to choose an idea and stick to it.

To do this, I'll need to gather all the info I’ve learned about my hustle and see if it makes the cut.

To do so rationally and efficiently, I need to think about it in terms of:

  • Feasibility: Is it easy to do?
  • Profitability: Can I make money doing it?
  • Persuasion: Do people want it?
  • Efficiency: How quickly can I put it into action?
  • Motivation: How much do I want to do it?

In order to better answer these questions, it’s best to answer in list form like this:

Screen printing assessment

  • Feasibility: High
  • Profitability: High
  • Persuasion: Medium
  • Efficiency: High
  • Motivation: Medium

This step really helped me see that I made the right decision in choosing the t-shirt project.

With low start-up costs, and the fact that I could act quickly, it just made sense.

The first 6 days: A reflection

Frankly, I did this first section of the book in a couple of days – I wanted to dive in and I had some great ideas.

Now I’ve managed to whittle all my ideas down and I feel good about it.

That being said, it may take you longer to pick a side hustle. Everything kind of fell into place for me.

I might not make any money, but it’s worth a shot.

I keep telling myself it’s only 27 days. And if it fails, I can always sell the stuff in my basement until I come up with another idea.

Hey, I may do that anyway!

Your thoughts?

What about you? Are you working on a side hustle of your own?

Let me know in the comments how your own hustle is going, how a past hustle has gone, or if you have any ideas you’ve been meaning to get to.

Want more of the hustle?

Check out all my entries in this series as I work towards creating a profit from passion:

Disclosure: Some links in this article may be affiliate links. We're letting you know because it's the right thing to do. Here’s a more detailed disclosure on how HTS makes money.

Editorial Disclaimer: The content here reflects the author's opinion alone, and is not endorsed or sponsored by a bank, credit card issuer, rewards program or other entity.

Hot Credit Card Deals This Month:

  • COMING SOON: No foreign transaction fees + up to 5X reward multipliers
    • Coming August 1 to all cardholders:
    • 0% foreign transaction fees – a 2.5% savings.
    • 5X points on groceries, dining, and entertainment.
    • 3X points on gas, daily transit, and select streaming services.
    • Apply today to qualify for the lower $99 annual fee this year.
  • Pay Your Balance Faster with 0% Interest for 10 Months
    • Best introductory balance transfer offer in Canada right now.
    • Pay off pre-existing credit card debt with a 0% promotional balance transfer rate.
    • No annual fee and no minimum income requirements.
    • Offer not available to residents of Quebec.
  • Best credit card in Canada for 2 years in a row
    • Our top rated credit card in Canada in 2018 and 2019.
    • Earn up to 30,000 points as a welcome bonus in the first year.
    • 5 points per $1 spent on groceries and dining.
    • 2 points per $1 spent on travel, transit and gas purchases.
    • Monthly fee of $10 instead of an annual fee.
  • Rate Your Wallet in 3 minutes or less. Take the quiz


Michael's picture

I've been wanting to get a decent side hustle going for a while just to earn some extra cash for fun stuff like eating out or games or whatever. The part I'm stuck on is finding something I can sustainably do around work and three kids but also something I have the skills for. I might have to check this book out!

February 05, 2019 @ 12:13 pm
HowToSaveMoney Team
HowToSaveMoney Team's picture

Hey Michael,

One of the biggest challenges for creating your side hustle is definitely finding that balance. Best of luck to you!

February 07, 2019 @ 12:06 pm
CathyInCanada's picture

Love that you had this in checklist format, since my mind works that way! Wish you had a magic answer to keeping motivation high and action consistent.

February 07, 2019 @ 4:41 pm
HowToSaveMoney Team
HowToSaveMoney Team's picture

Motivation is the hardest part of this whole thing. Hopefully following along will help you keep it up :)

February 08, 2019 @ 10:24 am
Harry's picture

Nice little article, thanks for sharing.

February 07, 2019 @ 7:46 pm
Mary Axford
Mary Axford's picture

I tried selling Avon and Regal at different times in my life. I ended up spending more then i was making. Finding something that kept my interest and made money would be great. I love how you break everything down when explaining someones book. This book sounds like it would be interesting and helpful in finding a side hustle.

February 07, 2019 @ 8:30 pm
Cheryl's picture

I keep coming up with wanting to sell cookies. But where? Online sales seem expensive when you add up the cost of packaging and shipping. Farmer's markets in the summer months? In the area I live in most are very expensive to rent a spot to set up your table and most want you to commit to the whole season and pay in advance or half up front. Which kind of sucks if you don't know if there'll be an interest in the product. There's one market that's not too expensive at $35 for a spot (bring your own table, chair, tent) and no minimum on dates booked. It's every 2nd Sunday for 5 hours, though there'd be set up and take down, 7 or 8 committment. It's next to a dog park, so doggie cookies might be an idea. Hmmmm....

February 08, 2019 @ 2:00 am
HowToSaveMoney Team
HowToSaveMoney Team's picture

That last part seems very doable! You could offer both dog cookies and human cookies to double your audience, or do dog cookies one week and human the next and see which one does better.

Just make sure you don't mix up your batches ;)

February 08, 2019 @ 10:24 am
Charlene's picture

If one does start this little (hopefully lucrative) side business and is able to make some tidy profits, and it is done on a regular basis, does one have to declare the extra income and report it on income tax??? :(
Any tax implications???

February 08, 2019 @ 2:00 pm
Vik's picture

Good work, thank you.

February 08, 2019 @ 3:43 pm
LisaM's picture

I don't think I need a long-term side hustle BUT selling the random stuff we've accumulated over time would be great in a couple of ways - clear up our living space AND pay down some debt.

February 09, 2019 @ 2:33 pm
HowToSaveMoney Team
HowToSaveMoney Team's picture

Hey Lisa,

I think that sounds like a great idea. Get a head start on that spring cleaning!

February 11, 2019 @ 5:01 pm
Laurent L
Laurent L's picture

I do a bit of side hustle with dog walking. It's a good gig.

February 10, 2019 @ 2:57 pm
HowToSaveMoney Team
HowToSaveMoney Team's picture

That would be a great gig! Do you use Rover.com?

February 11, 2019 @ 5:01 pm
T's picture

Always looking for ways to make a little cash on the side.

Thanks for the motivation!

February 11, 2019 @ 11:27 am

Post new comment