I’ve Tried Almost Every Online Side Hustle. Here’s What I’d Tell a Dad Starting Today

August 9, 2026
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If you spend enough time looking for ways to make money online, something strange happens.

Every few days, you discover another opportunity that looks better than the one you were considering before.

One week it’s affiliate marketing.

Then you hear about selling printables on Etsy.

Then someone tells you Amazon KDP is the way to go.

A few days later, you’re watching a video about dropshipping, AI automation, freelancing, print-on-demand, YouTube, blogging, digital products or some new software that supposedly changes everything.

I know this cycle very well.

Because I’ve lived it.

Over the years, I’ve tried a long list of ways to make extra money online. Some worked better than others. Some made a little money. Some became meaningful sources of income. Some were interesting for a while and then lost my attention.

And after all those experiments, one of the biggest lessons I’ve learned is surprisingly simple:

Finding a side hustle that works is often easier than sticking with one long enough to make it work really well.

That’s especially true when you’re a dad.

You don’t have unlimited hours to experiment.

You have work, kids, responsibilities, errands, bills, interruptions and about seventeen other things competing for your attention.

So if I were starting again today, I would approach side hustles very differently.

Here’s what I’ve learned.

I’ve Been Making Money Online for More Than a Decade

My online journey didn’t start with a perfectly planned business.

It evolved through experimentation.

Around 2010, I started a personal-development Facebook page called How To Think Positive.

Over time, that page grew to more than 2 million followers.

I eventually expanded the brand to other platforms including Instagram, TikTok, Pinterest, YouTube and a website.

That project has become my most consistent online business and remains an important source of income for me through advertising and content monetization.

But I didn’t stop there.

Like many entrepreneurs, I kept wondering:

What else can I try?

So I tried a lot.

I’ve used Amazon Associates and other affiliate programs.

I’ve published four books through Amazon KDP.

I run an Etsy store selling designs.

I’ve created and sold ebooks.

I’ve created online courses.

I’ve experimented with dropshipping and ecommerce.

I’ve done freelance work.

I’ve designed websites for local businesses.

I’ve worked with SEO, Google Analytics and email marketing.

I’ve used more social media schedulers, design platforms, marketing applications and AI tools than I can probably remember.

I’ve also worked with things outside the typical online-business world, including 3D printing, UV printing, sublimation, graphic design and product creation.

I manage many of my own websites and VPS hosting as well.

I’m telling you this not because I think you should try all of those things.

Quite the opposite.

My Biggest Mistake Wasn’t Picking Bad Side Hustles

For a long time, I thought the challenge was finding the right opportunity.

I now think that was the wrong question.

A lot of things can make money.

That’s one of the confusing parts about entrepreneurship.

Affiliate marketing can work.

Etsy can work.

KDP can work.

Freelancing can work.

Blogging can work.

Digital products can work.

Ecommerce can work.

Content creation can work.

The problem is that when you see twenty things that can work, you start believing you need to figure out which one is perfect.

So you keep experimenting.

You make $50 doing something and wonder whether another business could make $500.

You make $500 and see someone online claiming they made $10,000 doing something completely different.

Suddenly the thing that was working for you doesn’t seem exciting anymore.

You jump.

Then you jump again.

I’ve done this more times than I’d like to admit.

And in many cases, the business wasn’t the problem.

My attention was the problem.

The Side Hustle Trap Nobody Talks About

There’s a concept commonly called shiny object syndrome.

Entrepreneurs are especially vulnerable to it because we like possibilities.

A new business feels exciting.

A new tool feels exciting.

A new strategy feels exciting.

Maintaining something that already works?

Not always as exciting.

But maintenance and repetition are often where the real money is.

Starting an Etsy shop might be exciting.

Uploading your 150th optimized listing probably isn’t.

Starting a blog is exciting.

Updating old articles, improving internal links and publishing consistently for years requires more discipline.

Publishing your first book is exciting.

Building a catalog and improving the marketing around it takes patience.

That’s where I think many aspiring solopreneurs get stuck.

And dads have an additional problem:

Our available time is already limited.

If you only have five hours a week to work on your side business and you divide those five hours between four business models, none of them gets enough attention.

That’s one of the reasons I created Dad Solopreneur.

I want to explore what happens when we stop asking:

“What else could I start?”

and begin asking:

“How far can I take the thing that’s already working?”

Your First Goal Shouldn’t Be $10,000 a Month

Internet business content can distort your expectations.

You constantly see giant numbers.

$10,000 months.

$30,000 launches.

Six-figure stores.

Million-dollar businesses.

Those numbers can be inspiring, but they can also distract beginners from the first milestone that actually matters:

Getting someone who is not your friend or family member to pay you.

Your first $1 matters.

Then your first $10.

Then your first $100.

Because once something makes money, you have proof.

Not proof that you’ll become rich.

Proof that the basic mechanism works.

If you make your first $100 selling digital products, for example, don’t immediately abandon digital products because someone told you AI consulting is hotter.

Ask better questions.

Why did those customers buy?

Where did they come from?

Which product sold best?

Could you create five related products?

Could you increase traffic?

Could you improve conversion?

Could you turn $100 into $300?

Then $300 into $1,000?

This sounds much less exciting than starting another business.

It is also how businesses grow.

The Best Side Hustle for a Busy Dad Is Usually the One You Can Sustain

I don’t think there is one universally best side hustle.

There is a best fit.

Before you start something, I’d consider five things.

1. How much time do you actually have?

Not how much time you wish you had.

How much time can you consistently give the business every week?

If the answer is five hours, build around five hours.

A business that requires you to answer customers all day probably isn’t ideal if you work a full-time job.

A business that allows you to create assets at night and sell them asynchronously may fit much better.

2. Do you enjoy the work enough to repeat it?

You don’t need to be passionate about every task.

But if you absolutely hate the core activity required to make the business work, consistency will be difficult.

For example, I did web design for local businesses.

I know how to build websites.

The money can be good.

But eventually I got tired of dealing with clients.

That matters.

I’d rather build online assets from my computer that can generate revenue without requiring me to constantly manage individual customer relationships.

That insight helps narrow my options.

Your preferences should narrow yours too.

3. Does the business create leverage?

I like businesses where work done once can continue producing results later.

An article can bring traffic for months or years.

An ebook can sell repeatedly.

A course can serve multiple customers.

A social media post can reach thousands of people.

A digital download can sell while you’re doing something else.

Affiliate content can continue earning commissions after it has been published.

That doesn’t mean these things are passive.

Most “passive income” requires a lot more active work than the phrase suggests.

But leverage matters.

Especially when your time is limited.

4. Can you reach the customer?

This is where many side-hustle ideas fall apart.

The product isn’t always the problem.

Traffic is.

You can create the greatest digital product in the world, but if nobody knows it exists, you don’t have much of a business.

That’s why I believe learning basic digital marketing is one of the best investments a solopreneur can make.

SEO.

Social media.

Email.

Content marketing.

Copywriting.

Analytics.

You don’t need to master all of them.

But you need some reliable way to get attention.

5. Is there a logical path from small income to larger income?

This is an important question.

Suppose you make your first $100.

What would getting to $1,000 require?

More traffic?

More listings?

Higher prices?

A better offer?

More content?

Automation?

A second product?

If you can see the path, you can improve the system.

If the only way to make twice as much money is to work twice as many hours, you may eventually hit a ceiling.

If I Were Starting From Zero Today

If I were a dad starting from scratch with five to ten hours per week, I would keep things simple.

I would choose one primary business model.

Then I would choose one primary traffic source.

That’s it.

For example:

Digital products + Pinterest.

Affiliate website + Google search.

Etsy store + Etsy search.

YouTube channel + affiliate marketing.

Newsletter + sponsorships.

TikTok content + a simple product.

The exact combination matters less than your ability to stay with it.

I would give the experiment enough time to produce real data before jumping to something else.

I’d track what I publish.

I’d track traffic.

I’d track clicks.

I’d track leads.

I’d track sales.

Then I’d improve whatever part of the system is weakest.

This is much more boring than constantly chasing new opportunities.

That’s probably a good sign.

What I’m Focusing on With Dad Solopreneur

Dad Solopreneur is partly my attempt to follow my own advice.

Instead of starting another dozen unrelated projects, I want to focus on building one useful resource for dads who want to create additional income online.

I’m going to share what I’ve learned from the things I’ve already tried.

I’ll also continue testing tools, software, AI platforms and side-hustle ideas.

But there’s an important difference.

The goal isn’t to jump from business to business.

The experiments become part of the business.

When I test something, I can document it.

When something works, I can explain why.

When something fails, I can explain that too.

When I discover a useful tool, I can show you how I’m using it.

You don’t need another person on the internet telling you that every opportunity is amazing.

You need someone willing to say:

This worked.

This didn’t.

This made money, but I hated doing it.

This probably works, but I don’t think it’s worth ten hours of your week.

This one deserves more attention.

That’s what I want Dad Solopreneur to become.

You Don’t Need More Ideas

If you’re a dad trying to build extra income, there is a good chance your problem isn’t a lack of ideas.

You probably already have too many.

The internet will happily give you another hundred.

Your next step may simply be choosing one.

Pick something that fits your time.

Pick something with a real customer.

Learn how to get traffic.

Get your first sale.

Then resist the urge to immediately start something new.

See what happens when you stay with it.

I’m trying to do the same thing.

And this time, I plan to document the journey.

Final Thought

Making money online is real.

But it usually looks a lot less dramatic than social media makes it seem.

It looks like publishing another article when nobody is paying attention yet.

Uploading another product.

Testing another headline.

Improving a landing page.

Recording another video after the kids go to bed.

Checking your numbers.

Learning.

Adjusting.

Repeating.

I’ve spent years proving to myself that many different side hustles can make money.

Now I’m more interested in a different question:

What happens when you stop chasing every opportunity and give one good opportunity the attention it deserves?

That’s the experiment.

And if you’re a dad trying to build something of your own with limited time, you’re invited to follow along.

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