The Unknown Path

I had two choices.

Leave or stay.

What would I be leaving for?


To move to Chattanooga.

Where I’d be unemployed.

And I’d live with my grandfather.

What would I be leaving behind?

A job I liked.

I had an awesome boss.

$46,000 a year.

I had been there over two years.

I liked everyone I worked with.

The flexibility was great.

I got to take ski breaks.  No one with a “real job” gets ski breaks.

I did.

Hmmm… staying sounds better doesn’t it.

I didn’t.

I left.

People are faced with decisions like this all the time.

Typically they’ll choose the second option.

I think most people would say I should’ve chosen the second one.

After all it is the “safer” option.

People usually choose what they call the “safer” option.

What they really choose is the option with the most clear path, the option with known outcomes.



Since I chose option 1 above, people asked me a lot of questions.

“What are you gonna do?”

“Where are you gonna live?”

“What about money?”

I had the same answer for most of them.

“I don’t know.”

Sounds scary doesn’t it?

I was scared at times.

I still am.

Known Path Upside

Why did I choose to leave then?

It wasn’t easy, but it wasn’t complicated either.

Staying gives me one of about 3-5 different outcomes.

Known outcomes.

I wasn’t excited about those known outcomes.

Even the best case scenario for staying, wasn’t that appealing to me.

It probably included a low 6 figure salary 20 years down the road.

Working 50 hours a week with 2-3 weeks of vacation per year.

The work wouldn’t be that fulfilling to me.

The known path had low upside.

So I left.

I figured out the outcomes I didn’t want, and eliminated them.

What’s The Worst That Could Happen?

So we’ve decided we don’t like any of the known outcomes.  We’re not excited about them, they don’t seem fulfilling long term, or whatever other reason.

But we’re still scared.

When I’m scared about the unknown path, I ask myself “what’s the worst that could happen?”[1]

I actually think about it.

What is the worst possible outcome of the unknown path?

In this case, it was probably running out of money and moving home with my parents where I would take my old job in Memphis.

That’s not really that bad.

The unknown path has low downside

The Possibilities Are Endless

So what outcomes do we get with the unknown path?

Well, they’re unknown.

But there are virtually an infinite number of them.

What was the best outcome for me now?

I don’t know, but it’s a lot better than the best outcome for staying.

Maybe I meet someone starting a business that I’m excited about so I partner with them and we sell it 4 years later for millions.

Maybe it’s coaching a high school basketball team for two years until I get some connection into a college program that leads me to be an NBA assistant in 5 years.

Maybe it’s something else entirely.

It’s definitely better than the best outcome of the known path though.

The unknown path has high upside.


So what have we figured out so far?



  1. None of the known (orange) outcomes are that appealing to me.
  2. The worst unknown (blue) outcomes aren’t that scary.
  3. The best unknown (blue) outcomes are awesome.

Then the question is, how do we get to the best unknown (blue) outcomes?

Optimizing the Known Path

We’re trying to make the known outcomes better.  To do this, we can use the unknown path.

If we choose the unknown path we’ll reach other points where we’ll have decisions between unknown and new known paths.

New known outcomes will emerge that we never saw before.

If we keep choosing the unknown path, these outcomes, over time, get better and better, assuming we’re doing productive and interesting things.[2]

And after choosing the unknown path enough times, we’ll get far enough down the tree that we’ll reach a point where we see a known path that appeals to us.

One with outcomes way better than our original known outcomes.

So we just keep asking this question.

  • Would we be happy with the outcome of the known path?
    • Yes – Do it
    • No – Do something else

And after enough time, and decisions you’ll find yourself here.


Maybe it’s not a decision between $200 million and $1 Billion.

But following the unknown path enough times, will get you somewhere far better.

It may be this year, it may be in 5 years.

Until I see a known path that I want though, one that I’m truly excited about, I’ll keep choosing the unknown path.

  1. Tim Ferriss inspired
  2. This all requires actually DOING SOMETHING.  Choosing an unknown path and playing Xbox and eating chocolate cake 8 hours a day probably won’t end well.

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