Great Founders Must Manage Paradox: The Paradox Map

Great Founders Must Manage Paradox: The Paradox Map
"The test of a first-rate intelligence is the ability to hold two opposing ideas in mind at the same time and still retain the ability to function" - F Scott Fitzgerald

When I started my first company I didn’t realize that being a founder means facing an endless stream of challenges.

Being naive has advantages. If I knew I’m not sure I would have started.

But in facing those challenges, a founder needs to make a critical distinction each time. 

Am I facing a problem to solve, or a paradox to manage?

Here’s my favorite way to think about the difference:

A problem to be solved is something that can be done ONCE.

Think of it like catching a ball.

It might be a difficult catch, but once the ball is caught, the problem is solved.

A paradox to be managed is an ongoing challenge between two seemingly opposing concepts.

Paradox can’t be solved once and be over with.

Think of it like a juggler.

The motions required to work with paradox need to be ongoing.

Most of us get lots of training in school around how to solve problems. 

Managing a paradox, not so much. 

That’s bad because many of the most valuable challenges in work and life involve managing paradoxes.

So how do you manage a paradox?

A little-known tool to help manage a paradox: The Paradox Map

A good way to think about managing paradox is with a tool called a Paradox Map.

To learn how to use it, let’s think about two concepts in tension with one another: Stress and Tranquility.

Stress actually has POSITIVE aspects at times.

Tranquility has NEGATIVE qualities at times.

To work with a paradox map, list the positive and negative qualities of each idea.

Imagine you are in the negative quadrant of stress - distress, overwhelm, and irritation (bottom left on this Paradox Map). 

An effectively managed paradox moves from the negative quadrant of one side to the positive of the other.

In this case, moving from the negative aspects of Stress to the Positive aspects of Tranquility - Relaxation, Replenishing, Rejuvenating goodness!

But in a paradox, too much of a good thing becomes bad.

That’s how paradoxes work.

Eventually, that tranquility turns into the negative aspects of Tranquility - into boredom.

But then what?

Masters of paradox move to the opposite pole’s positive corner.

Boredom is proactively replaced with challenge (good stress).

Then as the challenge builds, more stress transitions into distress...

Until rest and rejuvenation begin the cycle again.

Mistaken identity. Mistaking a Problem for a Paradox

Many fail in designing a satisfying career because they are under the “stress as problem-to-solve” illusion.

You know the story. A guy kills himself during his career in the hopes of enjoying a relaxing retirement. 

This happens to founders all the time.

They design a post-founder retirement, imagining that multiple years (even decades) in the positive quadrant of tranquility will be enjoyable.

But after some initial period of relaxation, that person inevitably feels the negative aspects of tranquility.

Without the paradox lens, they don’t know they need to move on the map (to the positive side of stress).

They are in the negativity of tranquility.

This is the Tranquility Trap.

To avoid this trap, a master of paradox manages between these two opposing ideas DURING a career.

Sustained energy is sourced by managing the stress-to-tranquility paradox with ongoing rituals.

Well-designed practices move you through the Paradox Map in a shape that looks like an infinity symbol.

Try these reflection questions to move through the Stress AND Tranquility Paradox:

What helps you identify when you are experiencing the negative aspects of:

  • Stress
  • Tranquility

When you are in the negative corners of the Paradox Map, what helps you:

  • Restore
  • Bring you needed challenge

A great retirement will include relaxation AND thoughtful challenge.

The best work of your career will involve intense work AND cycles of needed rest.

You need to move through the infinity symbol on a paradox map.

Master jugglers don’t do it alone

Managing any paradox is a dynamic process. 

The world changes, your business changes and a well-managed paradox suddenly needs new attention. That’s the game.

I encourage founders to use your Board or an executive coach to help you stay on track flowing through a Paradox Map. 

It can be hard to see when and where you need to move when you are dealing with it alone. 

Working with paradox is not easy. But it can be more approachable with clear awareness, the right support and a good map.

To recap

  1. Determine if the challenge you face is like catching a ball once (Problem) or requires ongoing juggling (Paradox)
  2. If juggling is required, draw a Paradox Map
  3. Identify the processes and support you will need to move you through the map to effectively work with the paradox at hand.

Great Founders Must Manage Paradox: The Paradox Map

Frameworks and Tools
"The test of a first-rate intelligence is the ability to hold two opposing ideas in mind at the same time and still retain the ability to function" - F Scott Fitzgerald

When I started my first company I didn’t realize that being a founder means facing an endless stream of challenges.

Being naive has advantages. If I knew I’m not sure I would have started.

But in facing those challenges, a founder needs to make a critical distinction each time. 

Am I facing a problem to solve, or a paradox to manage?

Here’s my favorite way to think about the difference:

A problem to be solved is something that can be done ONCE.

Think of it like catching a ball.

It might be a difficult catch, but once the ball is caught, the problem is solved.

A paradox to be managed is an ongoing challenge between two seemingly opposing concepts.

Paradox can’t be solved once and be over with.

Think of it like a juggler.

The motions required to work with paradox need to be ongoing.

Most of us get lots of training in school around how to solve problems. 

Managing a paradox, not so much. 

That’s bad because many of the most valuable challenges in work and life involve managing paradoxes.

So how do you manage a paradox?

A little-known tool to help manage a paradox: The Paradox Map

A good way to think about managing paradox is with a tool called a Paradox Map.

To learn how to use it, let’s think about two concepts in tension with one another: Stress and Tranquility.

Stress actually has POSITIVE aspects at times.

Tranquility has NEGATIVE qualities at times.

To work with a paradox map, list the positive and negative qualities of each idea.

Imagine you are in the negative quadrant of stress - distress, overwhelm, and irritation (bottom left on this Paradox Map). 

An effectively managed paradox moves from the negative quadrant of one side to the positive of the other.

In this case, moving from the negative aspects of Stress to the Positive aspects of Tranquility - Relaxation, Replenishing, Rejuvenating goodness!

But in a paradox, too much of a good thing becomes bad.

That’s how paradoxes work.

Eventually, that tranquility turns into the negative aspects of Tranquility - into boredom.

But then what?

Masters of paradox move to the opposite pole’s positive corner.

Boredom is proactively replaced with challenge (good stress).

Then as the challenge builds, more stress transitions into distress...

Until rest and rejuvenation begin the cycle again.

Mistaken identity. Mistaking a Problem for a Paradox

Many fail in designing a satisfying career because they are under the “stress as problem-to-solve” illusion.

You know the story. A guy kills himself during his career in the hopes of enjoying a relaxing retirement. 

This happens to founders all the time.

They design a post-founder retirement, imagining that multiple years (even decades) in the positive quadrant of tranquility will be enjoyable.

But after some initial period of relaxation, that person inevitably feels the negative aspects of tranquility.

Without the paradox lens, they don’t know they need to move on the map (to the positive side of stress).

They are in the negativity of tranquility.

This is the Tranquility Trap.

To avoid this trap, a master of paradox manages between these two opposing ideas DURING a career.

Sustained energy is sourced by managing the stress-to-tranquility paradox with ongoing rituals.

Well-designed practices move you through the Paradox Map in a shape that looks like an infinity symbol.

Try these reflection questions to move through the Stress AND Tranquility Paradox:

What helps you identify when you are experiencing the negative aspects of:

  • Stress
  • Tranquility

When you are in the negative corners of the Paradox Map, what helps you:

  • Restore
  • Bring you needed challenge

A great retirement will include relaxation AND thoughtful challenge.

The best work of your career will involve intense work AND cycles of needed rest.

You need to move through the infinity symbol on a paradox map.

Master jugglers don’t do it alone

Managing any paradox is a dynamic process. 

The world changes, your business changes and a well-managed paradox suddenly needs new attention. That’s the game.

I encourage founders to use your Board or an executive coach to help you stay on track flowing through a Paradox Map. 

It can be hard to see when and where you need to move when you are dealing with it alone. 

Working with paradox is not easy. But it can be more approachable with clear awareness, the right support and a good map.

To recap

  1. Determine if the challenge you face is like catching a ball once (Problem) or requires ongoing juggling (Paradox)
  2. If juggling is required, draw a Paradox Map
  3. Identify the processes and support you will need to move you through the map to effectively work with the paradox at hand.

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Matt acquires or invests in cash-flowing digital businesses with $1-$5M in EBITDA.

Occasionally, he takes on advisory engagements for interesting projects. If this is of interest, feel free to share more.

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