Learn how to start a side hustle after 40 when you’ve got life experience, a few gray hairs, and zero patience for the latest social media challenge.

Let me guess…

You’ve hit the magical age of 40, and suddenly life feels like a giant game of Choose Your Own Adventure—except half the pages are missing, and the stakes feel a whole lot higher.

You’ve got responsibilities—kids, bills, maybe a mortgage—and if you’re anything like me, you’ve also got this nagging voice in your head whispering…

Is this it? Is this my life now?

Don’t get me wrong, I’m grateful for everything I have. But when I turned 40, I realized two things:

1. Time is moving a h*ll of a lot faster than it did in my 20s.
2. I didn’t want to wake up at 60 and still be stuck in the same rut.

I was tired of the hamster wheel.

The endless cycle of working my 9 to 5 (or let’s be honest, 8 to 6), paying bills, and counting down the days until the weekend.

I wanted more.

More freedom, more fulfillment, and yes, more money that didn’t depend on me clocking in every day.

But you know what stood in my way?

Fear.

That sneaky little voice that said, “Who do you think you are? You can’t start something new now old lady!”

If you’ve heard that voice too, let’s try and tackle those fears together.

Learning how to start a side hustle after 40 isn’t just possible; it might be the best decision you ever make. (Sounds corny, but true nonetheless.)

This post may contain affiliate links. This means I could earn a commission if you purchase through my links, however, there is no cost to you. Rest assured, I only promote products that I use or think are great. Thanks for reading!!

Fear (and Why It’s Totally Normal)

Let’s talk about fear.

Yep, that tight, queasy feeling in your stomach when you even think about doing something outside your comfort zone.

Fear is like the overprotective friend who means well but keeps you from having any fun. It whispers things like:

What if you fail and look like a total idiot?

What will your friends and family think?

You don’t have the time, the skills, or the energy to pull this off.

And my personal favorite: You’re too old for this.

First of all, let me say that fear is normal and I have boatloads of it.

Everyone feels it. Even the people you see crushing it with their multimillion dollar side hustle empires started off terrified.

But here’s the thing about fear—it’s kind of like a bad roommate. It’s loud, annoying, and constantly in your face, but it only has as much power as you give it.

I get it, though. Fear feels real.

When I started my first side hustle, I had a million excuses lined up. What if I failed? What if it was a waste of time? What if I embarrassed myself?

None of those things happened.

Well, okay, I made some mistakes and I’m sure some people thought (and still think) I am crazy and should just get a job.  

But you know what? I survived, and I learned.

The truth is, fear doesn’t go away; you just get better at ignoring it. You take a deep breath, remind yourself why you’re doing this, and take one small step forward.

The biggest regret isn’t failing—it’s never trying in the first place.

Soooo…let’s quiet that fear, shall we? Because if you’re over 40, you’ve already survived a whole lot tougher stuff than starting a side hustle.

Shift Your Mindset From Why Me? to Yeah, Why Not Me?

Let me tell you a little secret…

Most of the people out there that are making money with their own side hustles or businesses aren’t geniuses or superhumans.

They’re just regular people who decided to start. That’s it. They didn’t wait for permission, the perfect time, or a magical burst of confidence. They stopped over analyzing and just went for it.

And guess what? You can, too.

Starting something new after 40 might feel daunting, but let’s flip the script a little bit. Think about all the advantages you have right now. You’ve got experience. You’ve weathered life’s storms. You know how to handle challenges without having a meltdown (well, most of the time).

You’ve probably got some skills or hobbies you’ve been perfecting for years that you could totally turn into a side hustle.

What you don’t need is to be an expert or have everything figured out before you start.

I promise you, the world doesn’t reward perfection—it rewards persistence. The people who win are the ones who are willing to take messy, imperfect action and learn along the way.

So instead of asking, Why would anyone buy from me? ask, Why wouldn’t they?

Instead of thinking, What if I fail? think, What if I succeed?

You’ve got everything you need to start right now—you just have to believe it.

Starting Without Overwhelm

If I’m being perfectly honest, learning how to start a side hustle after 40 when your schedule is already jam-packed with work, family, and laundry that seems to multiply overnight can feel impossible. I’m tired, you’re tired.

But here’s the good news—you don’t have to launch some grand empire on Day One. You just have to take one small step on Day One.

Step 1 – Pick a Hustle That Fits Your Life

Don’t overcomplicate this.

Choose a side hustle that aligns with your skills, interests, and lifestyle.

Love taking photos? Sell stock images online. Obsessed with organizing? Create printable planners. Love shopping? Start doing affiliate marketing. (Learn how here) Got a knack for writing? Start a blog. (Learn how here)

The key is finding something that excites you and doesn’t feel like another chore on your never-ending to-do list.

Step 2 – Start Small (Seriously, Tiny)

When I started my first side hustle, I didn’t try to do everything at once because, well, that’s the fastest way to burn out.

Instead, I broke it down into bite-sized steps. Want to sell printables? Start by creating one design and listing it on Etsy. Want to blog? Write one post and hit publish.

The trick is to focus on the next step, not the whole staircase.

Step 3 – Make Time Work for You

I’m sure time is not exactly in abundance when you’re juggling midlife responsibilities.

That’s why you have to get creative. Use the “found” time in your day, like your lunch break or the 15 minutes after the kids go to bed, or when you first get to work and really don’t feel like doing anything for anyone before 10:00am.

And don’t underestimate the power of consistency.

Even if you only spend 30 minutes a day on your side hustle, that adds up to over 3 hours a week—and trust me, a lot can happen in 3 hours.

The point is, you don’t need to overhaul your life or work 24/7 to make progress. Just take it one step at a time, and before you know it, you’ll look back and realize that you’ve actually got something tangible to work off of.

Learn as You Go and Pivot

The only way to really learn is by doing.

Then, you take what worked and do more of that. You take the other stuff that didn’t work and don’t do more of that. Doesn’t have to be any more complicated than that.

See what others out there are doing and build from there.

They learned what to do, and so can you. Can you do what they did just a little bit differently? Maybe a little more you?

Starting messy is better than not starting at all. Every expert was once a beginner who had no clue what they were doing. The secret is to embrace the learning process and be okay with not being perfect.

Pro Tip— You don’t have to do this alone.

There are so many resources out there to help you get started. Take an online course, watch YouTube tutorials, or join a Facebook group for side hustlers. Ask ChatGPT even.

I promise, the internet is full of kind strangers who will happily help you out. (Just avoid the ones who shout in ALL CAPS—they’re usually not helpful.)

Overcome the Judgment Trap

Let’s talk about that little voice in your head that says, What will people think?

You know, the one that pops up anytime you consider doing something bold or different.

If you’ve ever worried about your friends, family, or that random acquaintance from high school judging your side hustle, you’re not alone. It’s one of the biggest roadblocks for anyone starting something new.

This was a big one for me and still is.

The truth is people are going to have opinions no matter what you do.

Some might cheer you on (yay for supportive friends!), while others might raise an eyebrow or make a snarky comment.

But guess what? Those opinions don’t pay your bills, and they definitely don’t define your worth.

When I started my side hustle, I had people say things like, “Oh, so you’re doing that now? How…cute.” “Are you sure you don’t want to just go get a job?”

It stung at first, but then I realized their opinions didn’t matter. What mattered was how I felt about what I was building and where I wanted to go.

Here’s how to ditch the judgment trap:

• Focus on your “why.” Remember why you’re doing this—whether it’s for financial freedom, more time with your family, or just proving to yourself that you can.
• Find your people. Surround yourself with supportive friends, join online communities, or follow inspiring side hustlers on social media. Message me if you’d like, I’ll respond!
• Embrace the cringe. Yes, you might feel a little awkward when you first put yourself out there, but that’s just part of the process. Awkward today, awesome tomorrow.

The bottom line? You can’t let fear of judgment hold you back. The people who matter will support you, and the ones who don’t…well, they can stay stuck in their comfort zones while you go out and create something amazing.

The Midlife Hustle Advantage

I know I’ve mentioned this before, but let’s take a minute to celebrate the fact that you’re over 40 and thinking about starting a side hustle.

You, my friend, are bringing a secret weapon to the table: life experience.

Think about it. You’ve already survived awkward teenage years, early career fumbles, and probably at least one completely regrettable hairstyle (hello, chunky highlights of the 2000s).

You’ve learned how to problem-solve, manage your time, and keep going even when life throws you curveballs.

Those skills? They’re going to make you a side hustle superstar.

Starting something new at this stage in life isn’t a disadvantage—it’s your superpower. You’ve got wisdom, resilience, and a strong sense of what you want (and don’t want) in life.

And let’s not forget—you’ve also got a certain level of patience. You’re not looking for get-rich-quick schemes or chasing trends just to keep up. You’re building something real, sustainable, and meaningful.

That’s the midlife hustle advantage.

So, let’s drop the “I’m too old for this” nonsense right now. If anything, you’re perfectly primed for this moment.

What Success Looks Like in the Beginning

Okay, let’s talk about success.

It doesn’t have to look like a six-figure income right out of the gate. In fact, the most satisfying wins are often the small ones, especially when you’re just starting out.

Here’s what success might look like in the early days of your side hustle:

• You make your first sale (cue happy dance!).
• Someone leaves a glowing review or tells you they love what you’re doing.
• You finish a task you’ve been procrastinating on, like setting up a website or listing your first product.
• You hit a mini-milestone, like earning enough to cover a family dinner out or your monthly Netflix bill.

These “quick wins” are the fuel that will keep you going.

Celebrate every single one of them, no matter how small they seem. Trust me, each little victory adds up to something big over time.

Take the First Step Today

Alright, we’ve talked about fear, mindset, and even those sneaky little quick wins that keep you going.

But now it’s time to get real—you’re never going to feel 100% ready to start your side hustle. And that’s okay.

The key is to just start.

Here’s what I want you to do today—yes, today.

Pick one small, doable action that moves you closer to your goal.

Maybe it’s brainstorming ideas for your side hustle, creating a free account on Etsy or Shopify, posting something on social media, or watching a quick tutorial about something you’ve been curious about.

You don’t have to figure out your entire business plan or solve every potential problem upfront.

Just take one step, no matter how tiny, and let that momentum build. Trust me, it feels amazing to see progress, even if it’s just baby steps.

And remember, you’re not in this alone. I’m cheering you on, and so is a whole community of other midlife hustlers who know exactly how you feel.

So go ahead, take that first step—you’ve got nothing to lose and so much to gain.

Optional Resources to Kickstart Your Side Hustle

To make your first step even easier, here are some tools and resources that helped me when I started my own side hustles:

Website Hosting & Domain Name: I use and recommend Bluehost for setting up websites. It’s affordable and beginner-friendly.

Email Marketing: If you’re planning to grow your audience, check out ConvertKit for email campaigns.

Social Media Scheduling: I swear by Tailwind to save time and keep my social media game strong.

Courses to Learn More:

Affiliate Marketing: Making Sense of Affiliate Marketing.

Selling Printables: Gold City Ventures E-Printables Course.

Blogging: Check out my own post: Believe the Hype: How to Start a Blog and Make Money.

Freelance Help: Need a logo, product photos, or anything else? Fiverr has affordable options for hiring freelancers.

You don’t need every tool right away, but these can make your life so much easier as you grow.