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The Case For Dating Your Business Ideas

How to know which idea to go after?
Probably the most common question pertaining to ideas for young entrepreneurs.

If you are anything like me.
(For your sake, I hope you aren’t.)
(Yes, I am serious)
You have this nervous twitch.
Now, it’s not exactly a literal twitch.
But it works very much the same way.

You try to enjoy life.
You try to go out on dates.
You try to grab lunch with a friend.
You try to enjoy family get togethers.
You try to enjoy the Netflix movie.
You try to enjoy your morning workout.
Hell, you even try to enjoy vacations.

But you quickly find that the twitch can’t be turned on and off.
The twitch can’t be silenced.
The twitch can’t be controlled.
The twitch can’t be managed.

It’s there.
It’s real.
And it’s not going anywhere anytime soon.

The twitch that I am referring to is the idea twitch.

Now I know what you are thinking.
“Oh come on, you’re telling me you don’t like getting ideas all the time?”
Well.. No not particularly.

But that’s a topic for another time.

The real question at hand is simple.

How in the world do you decide which business to go after?
How do you pick?
I have 5 good ideas!
But I don’t know which one to go after!

I think business and relationships draw a very interesting parallel.

Now take this with a grain of salt because I am by no means a relationship guy.
I do not have tons of experience in long term committed relationships.
I am the pickiest person that I know and unfortunately that bleeds into all aspects of life.

But, literally, all my friends and family are in long term committed relationships.
And I observe.
I watch.
I listen.
And I get more than my fill of unsolicited relationship advice.
Usually coupled with uncomfortable examples and stories…

Thanks Mom and Dad.

I think when you are going through the idea stage, it’s a lot like dating.
It’s freaking awkward on your first date.
It just is.
You may tell yourself it’s not.
But it is.

It’s awkward.
You really don’t know much about each other.
Are you a good fit for each other?
It’s hard to say.

It’s the date where you could potentially forget your date’s first name.
Talk about awkward.

Most people go through a similar process.
With business ideas at least.

They start to entertain the idea of working for themselves.
(Woah, look at that girl)
They start asking themselves what they could do.
(Hm, is she single?)
Here’s where the ideas start.
I could mow lawns?
(What about her? She’s so tall!)
I could hang Christmas lights?
(Oh and her! Man she’s beautiful, look at that hair!)
I could cure cancer?
(Woah, she’s so athletic!)
I could make the Uber for toothpaste.
The Uber for diapers.
The Uber for coffee creamer.
The Uber for laundry.
The Uber for gym towels.
(I could seriously marry any woman in this movie and die a happy man.)

The idea stage is like dating because you’re just getting to know one another.

You’re unsure if you’re a good fit for your idea.
And you’re unsure if your idea is a good fit for you.

It’s pretty rare for entrepreneurs to have just one idea and go after it.
(Marry the first person they’ve ever dated)
They usually have a few and end up picking one to go after.
(Date for a while, then settle down with “The right one.”)

“This idea aligns with my background.”
“This idea is exciting.”
“This idea keeps me on my toes.”
“This idea challenges me.”
“This idea is ambitious.”

“This person aligns with my background.”
“This person is exciting.”
“This person keeps me on my toes.”
“This person challenges me.”
“This person is ambitious.”

Sure, it’s not perfect.
But give it a chance.
Give her a chance.
Wait, are we talking about people or ideas?
See what I did there?

How do I know what idea to go after?

Date them.
Find out what you like.
What you don’t like.
What do you have in common?
Spend time with them.
Meet their friends and family.
Learn about their backgrounds.
Their hopes for the future.
Their opportunity.

Wait, are we talking about people or ideas?

That’s my point.

If you never date people, how are you going to know if you’ve found the right person or not.

You don’t have to spend every waking moment thinking about your idea, but you should check in with it every so often.
Spend time with it.
Work on it.

Relationships are tough.
Entrepreneurship is tough.
Picking the wrong idea sucks.
Picking the wrong spouse sucks.

You lose a lot of money through divorce.
You lose a lot of money through a failed idea.

Do your homework on the front end and don’t rush into anything.

You remember dating?

You used to date people even though you knew you’d never marry or want to spend years with them?
It was just kinda fun.
All your friends were dating people.
So you decided to date people.

No one likes being a 3rd wheel.

Well it’s a good parallel with choosing a business to work on.

And since we are diving into this parallel between dating and vetting business ideas, I need to throw something out there.

Monogamy isn’t for everyone.
Regardless of whether you believe it’s morally right or wrong, people decide that it isn’t right for them sometimes.
So for goodness sake, please don’t think I am advocating for one or the other.
That’s not my mission here.

Go ask someone whether you should go all in on one idea or two.
You will get a few different answers.

Ask someone whether you should get married and spend the rest of your life with one person.
You will get a few different answers.

Date around and explore your ideas.
Play around with them.
Talk to people about them.
But for goodness sake don’t think you are limited to a monogamous relationship when you finally decide to settle down with an idea.

For many people, monogamy is right for them.
They pick one idea and go after it until it either succeeds or fails.
But for others, monogamy is really just not in their DNA.
They can’t help but look elsewhere.
Constantly look at new opportunities.
They just can’t turn it off.

Luckily for us creators, there isn’t anywhere near the same stigma around polygamy of businesses as there is around polygamy of human relationships.

And again, I am just using this as a parallel.
I am not advocating for one side or the other here.

How you decide to live your business relationship life is a completely open book.
People will likely accept you whether you’ve married 3 business ideas or you decided to settle down with just one.

So don’t sweat it.
Go try everything.

I’m going to end this post with a quote from my favorite author, Tim Ferriss.

This quote is from a blog post where Tim explains the pro’s of being a “Jack of All Trades”.

The jack of all trades maximizes his number of peak experiences in life and learns to enjoy the pursuit of excellence unrelated to material gain, all while finding the few things he is truly uniquely suited to dominate.

The specialist who imprisons himself in self-inflicted one-dimensionality — pursuing and impossible perfection — spends decades stagnant or making imperceptible incremental improvements while the curious generalist consistently measures improvement in quantum leaps. It is only the latter who enjoys the process of pursuing excellence.

Tim Ferriss

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