Practical Rules for Choosing Independent Projects After 50

One of the advantages of getting older is that you finally realize you don’t have to say yes to everything.

That sounds obvious.

It apparently took me a few decades to figure it out.

When you’re younger, it’s easy to chase opportunities because you’re trying to build something, prove something, earn more, move up, stay busy, or just avoid feeling like you’re standing still.

After 50, and especially after retirement age, I think the equation changes.

The question becomes less:

“Can I do this?”

and more:

“Do I want this taking up part of my life?”

That is a much better question.

Because every project costs something.

Time.

Attention.

Energy.

Money.

Patience.

Sometimes all five.

So before I take on a new project these days, I try to look at it from a few angles first.

Does It Fit the Life I Want?

This is probably the biggest one.

I don’t want to build a side hustle that turns into another job I can’t get away from.

That defeats the purpose.

I want flexibility.

I want time to work on things I enjoy.

I want time outside.

I want time for the garden.

I want time for YouTube, family, travel, or whatever else I’ve got going on.

If a project sounds profitable but requires me to be chained to a schedule I don’t want, that’s a problem.

Money matters.

So does freedom.

And at this stage of life, I’d argue freedom matters more than it used to.

Does It Use Something I Already Know?

I’m a big believer in using what you already have.

Experience counts.

Skills count.

Tools count.

Relationships count.

An audience counts.

Knowledge counts.

If I’m looking at a project that connects to something I already understand, I give it extra points.

That doesn’t mean I won’t learn something new.

I’m still learning new things all the time.

But there’s a difference between adding one new skill and deciding to become a completely different person by next Tuesday.

If you already know gardening, maybe that leads to content, consulting, local help, or products.

If you know tools, maybe that leads to reviews, YouTube, Amazon Influencer, or affiliate income.

If you spent 30 years in a trade, maybe that experience has value to people who are just starting out.

After 50, there ought to be some return on all the years you’ve already put in.

Is It Low Risk to Test?

I like projects I can try without betting the farm.

Literally or figuratively.

Can I test the idea with a few hundred dollars instead of several thousand?

Can I try one version before I commit to ten?

Can I use something I already own?

Can I validate interest before I buy inventory?

Can I create one article, one product, one video, or one service offer and see what happens?

That’s the kind of testing I like.

I’m not interested in putting a pile of money into something just because a fellow on the internet says the market is “exploding.”

The internet has been exploding with something every week for the last 25 years.

Most of it eventually stops exploding.

Is There a Clear Way It Makes Money?

This sounds simple, but you’d be surprised how many projects get started without a good answer.

You can have a beautiful website.

A nice logo.

A clever name.

Great business cards.

A fancy social-media account.

And still have no idea how money actually changes hands.

I want to know:

Who pays?

What are they paying for?

Why would they pay me?

What problem am I solving?

How many times can I reasonably expect that to happen?

If I can’t answer those questions without using words like “eventually,” “hopefully,” or “once it goes viral,” I’m probably not ready.

Does It Have a Chance to Keep Paying?

I like projects where the work can have some lasting value.

That doesn’t mean everything has to be passive income.

Most passive income is very active at the beginning.

But I like work that can keep doing something after I finish it.

A video can keep getting views.

An article can keep bringing traffic.

A book can keep selling.

A product review can keep earning commissions.

A digital resource can keep selling.

That is appealing.

If every dollar requires another hour of my time forever, that can still be worthwhile, but I want to know that going in.

Do I Enjoy Enough of It?

I don’t expect every task to be fun.

That would be a pretty high standard.

I like gardening.

I don’t like every part of gardening.

I like making videos.

I don’t like every part of making videos.

I like online business.

I could live quite happily without dealing with another login screen that asks me to verify my identity.

The point is, I need to enjoy enough of the project that I’ll actually stick with it.

If the whole thing feels like punishment, I’m probably going to find excuses not to do it.

And at this age, I have enough experience to come up with some very convincing excuses.

Is It Going to Own My Schedule?

This is different from whether I like the work.

A project can be enjoyable and still demand too much.

If it requires me to answer messages at all hours, be available every weekend, or constantly react to other people’s emergencies, I think hard about that.

Some people enjoy that pace.

I don’t.

I prefer work I can plan.

Batch.

Schedule.

Walk away from.

One of the best things about working for yourself is supposed to be control.

If the project removes all your control, it may not be as independent as it looked.

Am I Saying Yes Because I Want It or Because I Hate Saying No?

That one can sneak up on you.

Sometimes projects show up because somebody asks.

A friend needs help.

A company reaches out.

A customer wants one more thing.

A new opportunity appears.

And before you know it, you’ve said yes to five things you never actually wanted to do.

I’ve learned that “no” is sometimes a business strategy.

A pretty good one too.

Every time you say yes to something, you’re saying no to something else.

Maybe that’s time.

Maybe that’s rest.

Maybe that’s a better opportunity.

Maybe that’s sitting on the porch doing absolutely nothing for an hour.

That last one is underrated.

Does It Pass the Six-Month Test?

I like to imagine the project six months from now.

Am I still glad I started it?

Would I still be willing to do the work?

Does it still fit my life?

Is it making progress?

If the answer is probably yes, that’s encouraging.

If I already resent the thing in my imagination and I haven’t even started yet, that’s information too.

Your gut isn’t always right.

But it’s worth listening to.

Especially if your gut has survived 50 or 60 years of bad ideas.

Does It Have a Logical Stop Point?

This one is important.

Not every project deserves to live forever.

Some should be tested.

Some should be seasonal.

Some should be shut down if they don’t work.

I like having a point where I can evaluate:

Is this still worth doing?

Is it growing?

Is it profitable?

Do I still enjoy it?

Is there something better I should be doing instead?

Too many people keep bad projects alive because they’ve already spent time on them.

That’s called sunk cost.

I call it throwing good hours after bad ones.

If something isn’t working, sometimes the smartest move is to stop.

Is This Really a Project, or Just Another Distraction?

This may be my favorite test.

New ideas are fun.

Starting something is exciting.

Finishing is where the money usually lives.

I can always think of something else to try.

That doesn’t mean I should.

Sometimes a new “opportunity” is just a way to avoid doing the boring work on the project you already know you should finish.

I’ve been guilty of that.

Probably more than once.

So now I try to ask:

Is this better than what I’m already doing?

Or is it just newer?

Those are not the same thing.

My Rule These Days

If a project:

fits my life
uses skills I already have
can be tested without much risk
has a clear path to income
gives me some control over my schedule
and still sounds worthwhile after I’ve slept on it...

... then I’ll take a serious look.

If it fails most of those tests, I usually move on.

There are too many opportunities in the world to spend all your time rescuing bad ones.

That may be the biggest difference between choosing projects at 25 and choosing them at 75.

When you’re young, you think time is renewable.

Eventually you figure out it isn’t.

That doesn’t mean stop trying things.

Quite the opposite.

It means be a little pickier about which things get your time.

That’s not being cautious.

That’s finally understanding what the expensive part really is.

SeniorGig.com