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On Growing Up:
Acquiring the Executive Functioning Necessary to Survive the $1M - $10M "No Man's Land" of Business Growth & Development |
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TL;DR
Growth requires maturity, which can not be outsourced. It must be developed internally.
As businesses expand, success depends less on working harder, and more on developing executive function using metrics, documentation, and systems. Owners who avoid this transition get in their own way. Those who embrace it thrive. Metrics, documentation, and systems are my sweet spots. I can help. Kris Freeberg, Economist | [email protected] | (360) 224-4322 |
June 5, 2026
As of this writing, I've been in business for thirty-one years. I've helped owner-operators who've been in business for the same amount of time, or longer. I've been involved in business purchases and sales. I've seen the whole progression from launch to exit.
In particular, this web page is informed by more than 10,000 hours of recent intensive experience assisting owner-operators with all aspects of their businesses, particularly navigating hurdles, choke points, and transitions. Here is what I've seen:
Businesses are like people. They go through stages of development. They begin as babies, and proceed from there.
I write this also from the perspective of a father and grandfather who has raised his own child through trying circumstances, helped him launch, and who now enjoys watching the growth and development of grandchildren.
As we all know, the skills that are necessary to care for a baby are different than the skills that are necessary to care for a toddler, a teenager, or a young adult. To do the job, the parent must mature along with the child.
My observation has been, it's the same with a business. In the beginning it's your baby. It's all about you, your personality, your hustle, your style. The business is you, and you are it. The customer relationships are your direct relationships. You do the work and have direct control of quality and output. Your charisma, adrenaline, and dopamine are adequate to get things done.
Then you hire a handful of people and everybody's on a first name basis, like it was in Kindergarten. Knowhow is between people's ears, or "tribal." It isn't written down anywhere, and that's fine. Documents and systems are minimal. Everything is informal and laid back.
You already know where I'm going with this. Books have been written about it. The latest one that caught my attention is Doug Tatum's No Man's Land about the $1M - $10M revenue range, and that Greg Crabtree variously refers to as a "Death Zone", a "Black Hole", or "The Messy Middle." Tatum's signature quip is, “Too big to be small, too small to be big.” Here's an AI generated summary of the book:
As of this writing, I've been in business for thirty-one years. I've helped owner-operators who've been in business for the same amount of time, or longer. I've been involved in business purchases and sales. I've seen the whole progression from launch to exit.
In particular, this web page is informed by more than 10,000 hours of recent intensive experience assisting owner-operators with all aspects of their businesses, particularly navigating hurdles, choke points, and transitions. Here is what I've seen:
Businesses are like people. They go through stages of development. They begin as babies, and proceed from there.
I write this also from the perspective of a father and grandfather who has raised his own child through trying circumstances, helped him launch, and who now enjoys watching the growth and development of grandchildren.
As we all know, the skills that are necessary to care for a baby are different than the skills that are necessary to care for a toddler, a teenager, or a young adult. To do the job, the parent must mature along with the child.
My observation has been, it's the same with a business. In the beginning it's your baby. It's all about you, your personality, your hustle, your style. The business is you, and you are it. The customer relationships are your direct relationships. You do the work and have direct control of quality and output. Your charisma, adrenaline, and dopamine are adequate to get things done.
Then you hire a handful of people and everybody's on a first name basis, like it was in Kindergarten. Knowhow is between people's ears, or "tribal." It isn't written down anywhere, and that's fine. Documents and systems are minimal. Everything is informal and laid back.
You already know where I'm going with this. Books have been written about it. The latest one that caught my attention is Doug Tatum's No Man's Land about the $1M - $10M revenue range, and that Greg Crabtree variously refers to as a "Death Zone", a "Black Hole", or "The Messy Middle." Tatum's signature quip is, “Too big to be small, too small to be big.” Here's an AI generated summary of the book:
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No Man's Land by Doug Tatum argues that many growing businesses become trapped in a dangerous middle stage where they are too large to operate informally, but too small to comfortably support the management, systems, and infrastructure required for sustainable scale.
The book explains how founder-dependent companies enter this “No Man’s Land” when growth outpaces organizational maturity, and it advocates disciplined finance, metrics, systems, delegation, and operational development as the path through it. |
"We're building the airplane while we're flying it."
Have you ever heard someone say that? I have. It sounds pretty scary, desperate, and miserable, doesn't it?
Believe me: it is.
Do you want to be in that situation?
No?
Well, then what?
I will tell you.
I don't care where you look or whom you ask. Everybody agrees that the four things needed to function beyond the infant stage of business development are:
- Metrics,
- Documentation,
- Systems, and
- Executive Functioning: the maturity to appreciate and use them.
You can read a bunch of books. You can hire expensive coaches to hold your hand and spoon feed you. You can join Mastermind groups involving proprietary curricula and expensive trips to exotic locations and monthly virtual group brainstorms. You can attend conventions. You can do all of the above.
Regardless what you do, how you do it, whom you involve, or how much time or money you spend, it must be done.
Some do it well, some do it poorly, some don't do it at all. Most are reluctant. Owner-Operators are doers who are too busy doing to handle anything else.
*** The Fatal Mistake ***
*** DO NOT DO THIS!!! ***
*** DO NOT DO THIS!!! ***
As I stated, most are reluctant. They'll say things like,
What this all amounts to is abdication, or surrogation, of Executive Functioning; an outsourcing of maturity.
And it doesn't work. It results in managers who either quit or are fired, demoralized & exasperated by "Do as I say, not as I do" owner-operators who skirt their own systems and violate their own policies & procedures. It's a terrific waste of money and loss of opportunity, profoundly disruptive to the organization, all because, like Peter Pan, the owner-operator refuses to grow up. It's a road to ruin.
Don't go there! Banish Arrested Development! Lean in to the challenge of personal growth! Embrace life long learning!
- "Executive Functioning is not my gift."
- "Core = What I Like. Chore = What I Don't Like. Executive Functioning is a chore to me. I prefer to work my Core and hire out my Chores." (Actually, Core = important strategic work and Chore = trivial but necessary tactical drudgery.)
- "I'm not good at this stuff. I need to hire others to do it for me."
- "Adulting. Ugh."
What this all amounts to is abdication, or surrogation, of Executive Functioning; an outsourcing of maturity.
And it doesn't work. It results in managers who either quit or are fired, demoralized & exasperated by "Do as I say, not as I do" owner-operators who skirt their own systems and violate their own policies & procedures. It's a terrific waste of money and loss of opportunity, profoundly disruptive to the organization, all because, like Peter Pan, the owner-operator refuses to grow up. It's a road to ruin.
Don't go there! Banish Arrested Development! Lean in to the challenge of personal growth! Embrace life long learning!
When is the right time? The sooner the better. Now would be good.
How? How does anyone afford the time?
Time Blocking.
All the experts agree on this. You set regular appointments in the calendar to work on this stuff.
Except they're not appointments with other people. They're appointments with yourself.
But you keep them just as you would keep appointments with other people. You show as much respect for yourself as you would show for them.
A lot of people struggle to do this. I have seen it. An appointment with a customer is "real." An appointment with myself? "Nice to have." But all too often, it isn't taken seriously, it gets shoved aside and forgotten. It's a struggle.
But those who do it, win.
How? How does anyone afford the time?
Time Blocking.
All the experts agree on this. You set regular appointments in the calendar to work on this stuff.
Except they're not appointments with other people. They're appointments with yourself.
But you keep them just as you would keep appointments with other people. You show as much respect for yourself as you would show for them.
A lot of people struggle to do this. I have seen it. An appointment with a customer is "real." An appointment with myself? "Nice to have." But all too often, it isn't taken seriously, it gets shoved aside and forgotten. It's a struggle.
But those who do it, win.
Recently, I interviewed a prospective client whose revenues are nearing $1M and who aspires to grow to $5M.
Why?
Where did he get that number?
I will tell you: he pulled it out of thin air because it's larger than where he is, and it's nice and round and sounds impressive.
According to Tatum and Crabtree, he aspires to be smack dab in the middle of what they call No Man's Land or The Black Hole. I don't reckon he has read the books, so he doesn't see the challenges ahead. He only sees an abstract number.
Be careful what you wish for!
Then I asked him how long he sees himself doing this line of work. His answer: "It depends on if I'm enjoying it."
Aha, so there's the key: managing such that work is enjoyable.
What? How?
I will tell you: those four things that doers say they have no time to do.
Everybody agrees:
Imagine!
Why?
Where did he get that number?
I will tell you: he pulled it out of thin air because it's larger than where he is, and it's nice and round and sounds impressive.
According to Tatum and Crabtree, he aspires to be smack dab in the middle of what they call No Man's Land or The Black Hole. I don't reckon he has read the books, so he doesn't see the challenges ahead. He only sees an abstract number.
Be careful what you wish for!
Then I asked him how long he sees himself doing this line of work. His answer: "It depends on if I'm enjoying it."
Aha, so there's the key: managing such that work is enjoyable.
What? How?
I will tell you: those four things that doers say they have no time to do.
Everybody agrees:
- Do those things, and you'll be able to disappear for a month and have your business run without you.
- Do those things, and you'll have a real business, not a glorified job.
- Do those things, and you'll have a turn-key asset that you can sell at a premium price, keep as a passive source of retirement income, or bequeath to your heirs.
- Do those things, and work will be fun.
Imagine!
How to be a Rock Star Salesperson. As an Economist, contemplating demand, recently I did some deep thinking about buying motives, and I arrived at this conclusion. When you really think about it, there are six motives for buying anything:
If you can demonstrate how the product or service you're offering checks all five boxes, people will be like, "Shut up and take my money!" and you will be a rock star salesperson. That's just how it works.
So what if you buckled down, blocked the time, and got your metrics, documentation, and systems together?
So what are you waiting for? I have expertise and experience in all of these areas. They're my Sweet Spot. I can help.
Reach out, and let's get to work.
- Excitement,
- Prestige,
- Belonging,
- Relief,
- Wisdom (defined as what's good for everybody in the long run), and
- Greed.
If you can demonstrate how the product or service you're offering checks all five boxes, people will be like, "Shut up and take my money!" and you will be a rock star salesperson. That's just how it works.
So what if you buckled down, blocked the time, and got your metrics, documentation, and systems together?
- Would it be exciting? Yes, because then you'd be free to do whatever fun stuff you want.
- Would you gain prestige? Yes, because having your act together is awesome.
- Would you gain belonging? Yes, because this is what the cool people do.
- Would you enjoy relief? Absolutely. You could actually delegate, take a break, and disappear for a while with no worries. And with a thriving, smoothly operating business, you'd be relieved of financial stress, with bills paid and money in the bank.
- Would it be the wise thing to do? Of course. It's what's good for everybody in the long run.
So what are you waiting for? I have expertise and experience in all of these areas. They're my Sweet Spot. I can help.
Reach out, and let's get to work.
