How I Decide Whether a Side Hustle Is Worth My Time

There are more ways to make money today than there have probably ever been.

That sounds like a good thing.

Sometimes it is.

Sometimes it just means there are more ways to waste three weeks.

I’ve tried enough projects, platforms, tools, income ideas, and “opportunities” over the years to know that the question isn’t simply:

Can this make money?

Almost anything can make money if you throw enough time, effort, and stubbornness at it.

The question I’m much more interested in these days is:

Is it worth my time?

At 74, that question matters more to me than it did at 34.

Time matters more. Energy matters more. And I have considerably less enthusiasm for spending 40 hours figuring out how to make $17.

So when I look at a new side hustle, I put it through a few tests before I get too excited.

Does It Fit Something I Already Know?

This is usually where I start.

If an opportunity connects to something I already know, own, or do, that gets my attention.

That doesn’t mean I’m afraid to learn something new. Quite the opposite. I’m constantly learning new software, platforms, cameras, tools, and things I probably didn't know existed six months ago.

But there’s a difference between adding a new skill and starting completely from scratch.

Amazon Influencer is a good example.

I already knew how to make videos. I owned a lot of products. I was comfortable explaining how things worked. I had years of experience making YouTube content.

That gave me a head start.

Now suppose tomorrow I decide there’s good money in repairing Swiss watches.

I own a screwdriver.

That does not make this a sensible business decision.

I like side hustles where something I’ve already learned gives me an advantage.

After 50, you ought to get some credit for all those years of experience.

How Much Money Do I Have to Risk?

I get nervous when somebody calls something a “side hustle” and step one involves writing a $10,000 check.

That may be a perfectly legitimate business.

It’s just not the kind of side hustle I’m looking for.

I prefer opportunities I can test small.

Can I use equipment I already own?

Can I start with a basic version of the software?

Can I produce five of something before producing 500?

Can I find out whether customers actually exist before filling the garage with inventory?

I’ve learned that it’s considerably cheaper to discover an idea doesn’t work when you have $200 invested than when you have $20,000 invested.

Funny how that works.

How Long Before I Know Whether It Has Potential?

Some things take time.

YouTube takes time.

Publishing can take time.

Affiliate marketing can take time.

I don’t expect everything to make money by Friday afternoon.

But I do want some way to tell whether I’m moving in the right direction.

I like milestones.

What should I know after 30 days?

After 90 days?

After six months?

Maybe I'm not making much money yet, but am I getting views? Customers? Subscribers? Clicks? Inquiries? Some indication that a pulse exists?

If the only business plan is:

“Just keep doing this indefinitely and someday it will work,”

I start getting itchy.

Patience is important.

So is knowing when you’re digging a dry hole.

What Am I Really Making Per Hour?

This one can ruin a perfectly good success story.

Somebody says:

“I made $1,000 with this side hustle.”

Great.

How long did it take?

Ten hours?

Now you have my attention.

A hundred hours?

Still might be worthwhile, especially if you're building something that keeps producing income.

Five hundred hours?

We need to discuss what we're calling a business.

It’s easy to brag about revenue and forget about time.

I try not to do that.

Now, hourly income isn’t the whole story.

If I spend several hours creating a YouTube video and that video earns money for years, I can’t fairly judge it based only on what happened the first week.

The same is true of an article, a book, or certain affiliate content.

But eventually, the math needs to make sense.

My time has value even if nobody is punching a time clock for me.

Can Today’s Work Keep Paying Tomorrow?

This is one of my favorite characteristics in a side hustle.

I like work with a long tail.

If I mow somebody’s yard Tuesday, I get paid for mowing the yard Tuesday.

Nothing wrong with that.

But if I create a good YouTube video Tuesday, it might still earn something next year.

An article can continue bringing people to a website.

A book can continue selling.

An Amazon Influencer video may continue producing commissions.

Affiliate content can keep generating referrals.

I like doing work once and getting more than one bite at the apple.

People call that passive income.

I’m a little suspicious of that phrase.

There was usually an awful lot of active work before anything became passive.

Still, I like the idea that something I create today can keep working after I move on to something else.

Does It Depend Entirely on One Company?

This matters more to me now than it used to.

Amazon can change something.

YouTube can change something.

Facebook can change something.

A commission program can disappear.

An algorithm can suddenly decide it doesn’t love you anymore.

Anybody who has worked online long enough has received one of those emails that starts:

“We’re excited to announce some changes…”

Almost without exception, they’re considerably more excited than I am.

I still use platforms. They’ve been very good to me.

But I like side hustles that lead back to something I control too.

A website.

An email list.

A library of content.

Relationships with viewers and customers.

The more pieces I own, the better I sleep.

Do I Enjoy It Enough to Keep Doing It?

Notice I didn’t say:

“Do I love every minute of it?”

That’s unrealistic.

I enjoy gardening. I don’t enjoy every weed.

I enjoy YouTube. I don’t enjoy every part of editing and uploading.

I enjoy online income. I don’t enjoy discovering that some website changed its interface again just about the time I figured out where everything was.

Work is still work.

But there needs to be something about it that I enjoy.

If every part of a side hustle irritates me, then it had better pay extremely well.

I already spent plenty of years doing things because I had to.

At this stage of life, I’m not particularly interested in creating another job I hate.

Does It Fit the Life I Want?

This may be the most important question.

A side hustle is supposed to improve your life.

If it makes a little money but takes over every evening, every weekend, and every vacation, I'm not sure we've accomplished much.

I like flexibility.

I want time for the garden.

I want time to make videos.

I want time for other projects.

I want the ability to walk away from the computer when I've had enough computer for one day.

Maybe you want to travel.

Maybe you want to spend more time with grandkids.

Maybe you want to fish every Thursday.

Put that in the equation.

Money is not the only thing the side hustle costs.

Sometimes it costs freedom.

Can It Grow Without Requiring Twice as Much of Me?

I don't need every side hustle to turn into a corporation.

An extra $500 or $1,000 a month can be very worthwhile.

But I do like opportunities where income can grow without my workload growing at exactly the same rate.

Can software save time?

Can I automate part of it?

Can the same work be used more than once?

Can one piece of content support multiple income streams?

This is something I particularly like about creator work.

I might make a YouTube video about a product.

That can generate YouTube revenue.

The description can contain an affiliate link.

I may also create an Amazon Influencer video for that product.

The same subject might become an article on SeniorGig.

One piece of knowledge. Several possible uses.

That makes sense to me.

Am I Solving an Actual Problem?

This question eliminates a lot of bad ideas.

Why would somebody pay me?

What do they get?

Do I save them time?

Help them make a decision?

Teach them something?

Fix something?

Entertain them?

Make their life easier?

People spend money because they get something they value in return.

If I can't explain the value in a sentence or two, I probably don’t understand the opportunity well enough yet.

“Everybody will want this” is not an answer.

Usually when everybody is the customer, nobody is.

Would I Still Want to Do It If Success Takes Longer Than Expected?

This one is important because nearly everything takes longer than expected.

Especially online.

The fellow selling the course may tell you otherwise.

Funny thing about people selling courses. Their side hustle is frequently selling courses about side hustles.

Results can be slow.

Income can be inconsistent.

Something you thought would work may flop.

Something you almost didn't bother doing may become your best performer.

If a project is going to require six months before I know whether it has legs, I want to know whether I’m willing to give it six months.

Sometimes the answer is no.

That’s okay.

Not every good opportunity is a good opportunity for me.

My Five-Question Test

If I want to simplify the whole thing, I come back to five questions:

Do I understand it well enough to have an advantage?

Can I start without risking a bunch of money?

Is there a believable path to making a worthwhile return?

Does it fit the life I actually want to live?

Can the work I do today still have value tomorrow?

It doesn't have to get a perfect score.

But if four of those answers make me uncomfortable, I probably don’t need another spreadsheet.

I need to move on.

There will always be another opportunity.

That’s one thing the internet has no shortage of.

The trick is recognizing that opportunity and distraction can look an awful lot alike when they first walk through the door.

At this stage of my life, I’m not interested in doing everything.

I’m interested in doing the things that make sense.

And preferably making a little money while I’m at it.

SeniorGig.com