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Define “Enough” Before It Defines You

February 28, 2026 / by Michael Redman

ISSUE #010| THE LEADERSHIP CONTRARIAN


Hand holding hourglass on open road

What Are You Actually Building Your Business For?

What’s the end goal?
And how will you know when you’ve reached the elusive finish line called “enough”?

Before we go any further, hear this:

I want the best for you. I want you to build a successful business and live a deeply satisfying life. I want you, when you’re old, to be able to say:

I lived well. I loved my family well. I built something meaningful. And the people who mattered most were still there at the end.

As a leadership and business coach working with startups all the way to seven- and eight-figure companies, I hear the stories behind the stories. The wins. The pressure. The quiet strain in marriages. The subtle drift with kids. The identity that gets wrapped tightly around performance.

Recently, someone close to one of my clients said to them, “You never stop. You’re always talking business. You’re always pushing. What are you pushing for?”

That question landed hard with my client.

Most entrepreneurs don’t feel stressed, we feel driven. Growth feels normal. Pressure feels normal. The pace becomes familiar. Even addictive.

But very few of us stop long enough to ask:

  • What is this business designed to produce in my life?
  • What is enough?
  • Am I building intentionally or just building because I’m wired to build?

Businessman thinking about future goals


The Numbers Are Brutal

Ninety-five percent of businesses fail within ten years.
Only a tiny fraction ever break $1 million in revenue.

And when it comes to families?

How many marriages fail?
How many just endure?
How many successful founders quietly drift from their children?

I’ve seen leaders hit financial success and lose relational wealth.
I’ve also seen entrepreneurs fail financially and have to start over — sometimes without enough time left to repair what really mattered.

Success in business without success at home is not success.
Too often, it's a trade you don’t realize you’re making until the bill comes due.


The Core Problem

Most business owners have revenue goals.

Very few have clearly defined life goals that their business is designed to serve.

If you want a healthy business and a healthy life, three things are non-negotiable.

1. A Clear Life Goal

Begin with the end in mind.

What do you want the most important people in your life to say about you at your funeral?

Your spouse.
Your children.
Your closest friends.

Yes, even your peers. Even your customers.

Have revenue goals. Have growth targets. That’s wise.

But also define:

  • What actually makes you happy?
  • Is it healthy?
  • Does it align with your values?
  • Does it align with what God says leads to a full and abundant life?

If you never define “enough,” you’ll always feel like it’s not enough, and eventually your identity will get wrapped around your performance.

2. A Reasonable Plan

Many entrepreneurs say, “I want it all and I want it now.”

That’s not vision; that’s impatience.

A reasonable plan doesn’t mean going slow. It means going wisely.

You cannot intelligently plan for a $10 million company if you’ve never navigated the complexity of $5 million. Each level brings pressures you don’t yet understand.

Are you building at a pace that protects your marriage?

Are you scaling in a way that strengthens your family?

Or are you pushing because slowing down would force you to confront deeper questions?

Wisdom builds steadily. Ego rushes.

Business journey concept

3. Ongoing Navigation and Adjustment

This is where most people drift.

Long before business, I learned this in the woods camping with my grandfather and later navigating trails in Boy Scouts:

You choose a destination.
You chart a path.
And then you regularly stop and check your bearings.

People don’t get lost because they lack a goal.
They get lost because they failed to check their position and adjust.

The unexpected happens.
Circumstances change.
You change.

That’s why you have to keep checking.

If you never pause to ask:

  • Are we still aligned?
  • Is this pace healthy?
  • Has the cost increased?
  • Are we drifting from what matters most?

Then small deviations compound into major consequences.

Ignore even one of these, and you risk losing both the business you’re building and the life you’re trying to build it for.


The Encouragement

A healthy, thriving life as a business owner is not a fantasy.

It is possible.

I’m not saying that casually.

My wife and I have been married 33 years. Our marriage is full of laughter and joy. We’re close with our 30-year-old daughter, and she chooses to work with us.

We’ve built two successful businesses, one 22 years old and the other 14, without sacrificing the relationships that matter most.

It hasn’t been easy. We’ve faced economic pressure, emotional strain, hard seasons, and moments that required real growth and humility.

But we didn’t build success on broken relationships.

We honored our faith and we honored people.
We used our gifts.
We paid our bills.
We built margin and gave generously.

And when I look back, I don’t carry deep regret.

If we can do it, so can you.

Michael & Kathryn Redman

But it doesn’t happen accidentally.

It requires clarity about what matters most.
It requires defining “enough.”
It requires wisdom instead of ego.
It requires regular course correction.
It requires saying no to growth that costs too much.

You are wired to build. That’s a gift.

Just make sure you’re building something that will still matter when the revenue numbers no longer do.

Build accordingly.
Your future self will thank you.


Your Turn

If any part of this resonated with you,
even a sentence,

Would you send me an email and tell me?

I really value your feedback and it tells me if I’m making a difference or if I need to course correct.

Until next time,
Keep learning.
Keep growing.
And God bless,

- Michael

Topics: The Leadership Contrarian Newsletter

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