Side Hustle Planning Checklist…

…What to Do Before You Start

So you’ve got the itch.

Maybe it hit during your commute while scrolling social media or that moment when your coworker said “I’m just living for Friday” for the 38th time this month.

Whatever sparked it, you’re here because you’re thinking about starting a side hustle. High five for that!

But before you sprint headfirst into logo design, domain names, and colour palettes (which is the entrepreneurial version of rearranging furniture in a house you haven’t built yet), let’s take a beat and lay the foundation.

This isn’t about killing your momentum. It’s about giving your hustle the best chance to actually, you know… work.

Let’s walk through your Side Hustle Planning Checklist—a fun, practical, no-fluff guide to getting your ducks in a row before you start.

1. Know Your “Why”

Nope, not just because money is cool. (Although, yes—it absolutely is.)

Before you dive in, get crystal clear on what you want your side hustle to do for you.

Do you want:

• Extra cash for vacations or bills?
• To slowly transition out of your 9–5?
• To finally use a skill that’s collecting dust?
• A creative outlet that actually pays?

Write it down. Tape it to your monitor. Because when you hit a wall (and you will), your “why” is the thing that keeps you showing up.

2. Pick Your Focus (Not ALL the Ideas)

This is where a lot of would-be hustlers get stuck: idea overload.

You’ve got five tabs open: print-on-demand mugs, coaching, flipping vintage books, a podcast about productivity, and maybe a digital planner side hustle?

Stop. Breathe. Pick one.
You’re not committing for life—you’re committing to one experiment at a time.

Ask:

• What am I good at or enjoy?
• What do people ask me for help with?
• What’s something I can test quickly?

You can always pivot later. But you can’t build momentum in five directions at once.

3. Do a Tiny Bit of Research

This is not your permission slip to fall into a YouTube rabbit hole for three days.

Just do a little market sniff test:

• Are people already buying what you want to offer?
• Who are your potential competitors or role models?
• What’s missing that you could do differently?

Tools like Google Trends, Reddit threads, and even Etsy searches can show you what’s hot (and what’s not).

Bonus tip: Look for pain points—those are gold mines for side hustlers.

4. Define Your Offer (Simple is Sexy)

What exactly are you offering? Like, specifically?

Instead of:

“I help people with productivity”

Try:

“I help overwhelmed solopreneurs organize their week using Notion dashboards.”

Boom! Specific, valuable, clear.

You want your offer to pass the “Would your grandma understand it?” test. The clearer it is, the easier it is to sell, post about, or pitch to potential clients.

5. Get to Know Your Ideal Customer

If you’re trying to serve “everyone,” you’ll attract… no one.

Your side hustle will take off faster if you talk directly to a specific type of person. Think about:

• What they struggle with
• What they’ve tried that didn’t work
• What they dream of solving

Give them a name. A vibe. A favourite snack. (Okay, maybe not the snack—but bonus points if you go that far.)

6. Decide How You’ll Make Money

Let’s talk revenue. Not hopes. Not vibes. Money.

How will this thing actually pay you?

Common side hustle monetization models:

• Selling a service (freelance, consulting)
• Selling a product (physical or digital)
• Affiliate marketing
• Advertising or sponsorships
• Teaching or coaching

Pick one. Keep it simple. If you try to monetize in five ways at once, you’ll dilute your results and probably your sanity.

7. Audit Your Time (Reality Check Time)

Be brutally honest with yourself here. How many hours do you really have each week for your hustle?

• 5?
• 10?
• 3 and a half if you bribe yourself with coffee?

There’s no shame in your number. The goal is to match your hustle plan with your actual life, not some fantasy where you magically become a productivity wizard overnight.

Create a “side hustle slot” in your weekly calendar and protect it like it’s your gym buddy or therapy appointment.

8. Gather Your Tools (but don’t overthink it)

You don’t need 17 subscriptions and a Notion dashboard with moving widgets. You just need the basics to get started.

Ask:

• Do I need a website? (Often no, at first.)
• Do I need an easy way to collect payments? (Stripe, PayPal, Gumroad, etc.)
• Do I need a portfolio or a landing page? (Carrd, Substack, Canva, etc.)

Pick tools that are:

• Free or low-cost
• Easy to learn
• Good enough to get going

Don’t let tech be the excuse you use to delay starting.

9. Set Up a Simple Way to Stay in Touch

If your hustle involves people (and most do), set up a basic email list. Even if it’s just friends and curious coworkers at first.

You don’t need a huge audience to make money. You need a small group of the right people who know what you offer and trust you.

Try:

• Substack (perfect for writers or creators)
• MailerLite or ConvertKit (for digital products or coaching)
• Gumroad (if you’re selling templates or mini-products)

10. Give Yourself a 30-Day Sprint Goal

Forget 6-month plans. Start with a 30-day mini-mission.

Examples:

• “I will send 3 cold outreach messages per week.”
• “I will publish 1 helpful post every Sunday.”
• “I will make $100 from my digital planner.”

Make it doable. Track progress. Learn from the results.

Remember: the goal isn’t perfection—it’s momentum.

Ready, Set… Start!

Look at you—planning like a pro before diving in. That already puts you ahead of 90% of people who stay stuck in the “someday” phase.

Now take that one idea. That one offer. That one hour a week.
And just begin.

✨ Action beats intention every time.
✨ Clarity comes from doing.
✨ Side hustles don’t have to be overwhelming—they just have to start.

So, grab your checklist. Pick your lane. And permit yourself to start messy but motivated.

What’s your side hustle idea?

Hit reply or leave a comment—I’d love to hear what you’re cooking up and where you’re at on your journey.