When business growth turns the owner into the operating system, working harder won’t create freedom. Sometimes you need enough distance to see what needs to change.
There is a strange moment in business ownership when you realize the company you worked so hard to build is actually working, but you can’t keep working inside it the same way.
Revenue may be growing. The team may be growing. Clients are coming in. From the outside, things can look pretty damn good. Inside the business, though, you may still be solving too many problems with the same tool you have always used: yourself.
You step in when something gets dropped because it’s faster. You answer the question. You rescue the client relationship. You make the decision. You fill the staffing gap. You keep the schedule moving while carrying the concern about payroll, sales, quality, culture and whether everyone is doing what they are supposed to be doing.
Because you are capable, it works.
At least for a while.
Eventually the business gets big enough that your capability is no longer enough to carry the structure underneath it. That does not necessarily mean the business is failing. It may mean the business has outgrown the way you have been running it.
Most founders begin as both visionary and operator. You imagine something that does not exist yet, and then you do whatever is necessary to bring it into the world. In the beginning, that is often exactly how a small business gets built.
The trouble comes when the business grows but the founder’s job does not.
A million-dollar company cannot indefinitely run with the same systems, owner involvement and decision-making structure that worked at $500,000. A $3 million business cannot simply be a busier version of the $1 million business. Eventually, growth asks something different of you.
Yet when you are standing right in the middle of the daily operation, the solutions that look most available are usually linear. You need more clients, another employee, another truck, more marketing, a bigger service area or a stronger sales push. You do more of what has worked before and hope that increased volume will create the future you want.
Sometimes it does. Sometimes it just creates more to carry.
That is the part of business growth we do not talk about enough. A successful business can outgrow the way its owner runs it long before the owner realizes that is what has happened.
I feel this especially strongly after the last several years.
In my landscape company, we never really stopped working during the pandemic. If anything, we worked harder. People were home looking at their properties, investing in outdoor spaces and spending money very differently than they had before.
Then the world opened back up. Kids went back to camp. Families started traveling again. Money shifted toward other priorities, and the people working inside our companies had been changed by the experience too.
Expectations around work, flexibility, compensation, time and quality of life shifted. Clients changed. Employees changed. Sales changed. Hiring changed.
I don’t think we simply returned to the way business worked before 2020, and I don’t think trying to recreate the old model is necessarily the answer.
When the terrain changes, the business has to adapt. The harder part is recognizing that sometimes the owner has to adapt too.
You may be working incredibly hard to solve a new problem with an old operating model. If that is true, pushing harder will not necessarily get you where you want to go. It may simply wear the groove deeper.
This is where I think the founder’s greatest strength can turn against her.
We know how to make things happen. If something isn’t working, we add effort. If somebody drops something, we pick it up. If we need more money, we sell more. If the employee isn’t ready, we do it ourselves. If the business needs another ten hours, somehow we find them.
That resourcefulness is part of why the company exists in the first place.
But there is a point where solving every structural problem with personal effort stops being impressive and starts becoming expensive. It costs attention, creativity and energy, and eventually it can cost your relationship with the business you once loved building.
When too much of your brain is occupied with tactical work, strategy gets squeezed out. Stay there long enough and imagination becomes harder too. Instead of asking, What else could this become? you find yourself asking, How am I going to get through Thursday?
Those are very different questions.
This is where the idea of getting away becomes interesting to me.
Not because leaving your business magically fixes it, and certainly not because sitting beside a river in Costa Rica is somehow a replacement for financial management, better systems, clearer roles or difficult leadership decisions.
Distance has another purpose. It changes what you can see.
When you are inside the operation every day, you are continuously responding to the business as it currently exists. Your environment keeps reminding you who needs you, what is urgent, what is behind and how things have always been done.
Get far enough away, and some of that grip loosens. You can begin looking at the company rather than simply reacting from inside it.
That is one of the reasons I travel. I am curious by nature, and changing my physical environment changes the way I think. New places interrupt familiar patterns. They remind me that there are other ways to live, work, organize, create and spend my time.
I have also spent years intentionally building enough owner freedom in The Garden Continuum that I can leave.
In September 2025, right at the beginning of our busy fall season, I traveled to Vienna for a week when my son began his Fulbright year. I then spent another week in Switzerland because seeing Rudolf Steiner’s Goetheanum had been on my bucket list for years. I returned to Europe again for his graduation this past June.
My business did not magically become easy enough for me to travel. I built structures, people and systems that made travel possible.
The freedom is imperfect. There are still difficult seasons, stressful days and problems that require me. I am still working on creating more freedom because the business keeps changing and I keep changing too.
But I know the difference between owning a business and giving the business every available piece of yourself.
The woman I want to work with wants some version of that distinction too.
This brings me to ReRooted.
If your business is genuinely in crisis, Costa Rica is probably not the answer right now. If you are panicked about next week’s payroll or believe the company could collapse if you step away for six days, the first work may need to happen much closer to home.
ReRooted is for the woman whose business is working, but who quietly knows she does not want to keep succeeding this way.
She may not know exactly what needs to change. She may only know that she wants more freedom, more strategic work, more creativity, better support or simply more life outside the company she created.
She is also someone who wants to travel. Costa Rica should create a little spark. The idea of waking up in a cloud forest, being surrounded by extraordinary plant life, having someone else cook your meals, sitting beside a river and spending time with women who understand what it means to make decisions all day should sound exciting.
If the thought of travel feels like another burden, this probably isn’t your retreat.
But if part of you thinks, God, I would love to get out of here long enough to think, then we may be onto something.
I am calling ReRooted a retreat because we are leaving our normal environments and creating room to breathe, but this is absolutely not six days of checking out.
We are going to work on our businesses.
Our midday sessions will give us time to get inside what we think we know and start challenging it. We’ll look at what still belongs, what needs to go, what needs to be delegated or systematized, where we have been solving structural problems with personal effort and where something that is already working deserves to be amplified.
We’ll ask whether the business you currently operate has the structure to support what you say you want next.
And yes, we are going to throw some serious spaghetti against the wall. That is part of imagination. You have to loosen your attachment to the answer you already know long enough for another possibility to emerge.
The difference is that you won’t be doing this alone at seven o’clock on Sunday night at your kitchen table while half your brain is already worrying about Monday morning.
You will have other owners around you. Someone may ask the question you haven’t considered, challenge an assumption you stopped noticing or recognize something you thought only you were experiencing.
That kind of proximity matters to me.
I am increasingly tired of expecting every meaningful connection to happen through a screen.
I love Zoom. It makes my coaching practice possible, and I am grateful for it. But Zoom does not replace spending enough time beside another human being for the polished conversation to end and the interesting one to begin.
That happens differently in person.
You eat together. You walk somewhere. Somebody says something over coffee that opens a completely different conversation. You laugh. You hear how another owner solved something. You realize someone else is carrying the same question. An idea gets built between three people that none of them would have arrived at alone.
That is part of why I am creating ReRooted.
Frankly, I am building what I crave too.
One of the most important things I have clarified while building this retreat is that I do not expect you to turn your phone off for six days and pretend your company no longer exists.
For some business owners, that would create more stress than restoration.
We will have protected time each day, likely after breakfast, when you can check in with your office, answer something important, make a client call or handle whatever genuinely requires you.
That is different from waking up and immediately surrendering your attention to email, text and Slack before you have even registered where you are.
I want some discipline around the edges of the day because I want your mind to have a chance to settle. I don’t want your phone to be the first thing entering your brain every morning and the last thing your nervous system processes before sleep.
There is a very real difference between staying appropriately connected to your business and allowing it to occupy every available inch of your attention. Practicing that difference may itself teach you something.
The other half of this matters just as much.
There will be movement, but you do not need to be a yogi. You do not need to be flexible, athletic or free of cranky body parts. The point is to move, breathe and get back into a body that probably spends an enormous amount of time carrying your brain around from problem to problem.
There will be beautiful meals that none of us needs to plan, shop for, prepare or clean up after. There is a river, extraordinary flora and fauna, and a hot pool heated by a wood fire.
There will be conversation and laughter, but there will also be quiet. We are not filling the week with excursions so you return home needing a vacation from your retreat. We are staying put long enough for another rhythm to take hold.
That slower rhythm is not separate from the business work. It is part of what makes the business work possible.
Creativity rarely arrives because we glare harder at a spreadsheet. Sometimes your mind needs to wander. Sometimes you need to walk. Sometimes you need to sleep. Sometimes you need a conversation that has absolutely nothing to do with the problem you were trying to solve before the connection appears.
I want to create the conditions where the imaginative founder part of you gets to come back online.
The woman who once looked at nothing and saw possibility is probably still in there. She may simply be buried under operations.
I don’t think every business owner begins with some cinematic moment of passion and purpose. Sometimes starting a company was simply the next logical move. You were good at something, people were willing to pay you, and a business gradually formed around you.
But somewhere along the way, there was imagination.
You believed you could make something happen that didn’t exist yet. That creative energy is very different from spending your days putting out fires.
When I think about what I want ReRooted to offer, it is not an escape from responsibility. I want it to help rekindle that imaginative, entrepreneurial energy that gets buried when responsibility becomes the dominant experience of ownership.
I want us to remember that building can actually be fun.
We may have serious questions to answer. We may make difficult decisions. Something may need to end. Something else may need to be funded, hired, sold, delegated or completely redesigned.
But there is enormous energy in possibility, and that energy matters.
ReRooted is part of a transition for me too.
After four decades in the landscape industry, I am thinking deeply about what I want the next chapter of my work and life to look like. I know that I want more time freedom. I want to travel. I want to write. I want to spend time with my grown children and my friends. I want to build community and continue doing work that feels meaningful without allowing work to consume every part of my life.
And I do not want to build what comes next alone.
I want women around me who have built things, carried responsibility, taken risks, changed their minds, gotten things wrong, figured things out and are still curious about what else is possible.
I want to sit in real rooms with those women, and I want business building to feel creative again, for me too.
That is another reason ReRooted exists.
I also know that a beautiful week away is not enough.
If you want change, you need support around the change.
That is why ReRooted includes two individual coaching sessions and two group coaching sessions surrounding our six days together. The retreat is not an isolated experience that begins when you land and disappears when you fly home.
We prepare before we go so you arrive with questions worth working on. Then we spend six days thinking, working, moving, resting, talking and allowing ourselves to imagine beyond what was visible from inside our normal operating environment.
Afterward, we work on translating what you discovered into decisions and action.
That is where a retreat becomes more than respite.
ReRooted takes place December 6–12, 2026, at Verdesana by Imiloa in the cloud forest of Costa Rica. The group is intentionally small, and the experience includes accommodations, meals, retreat programming and the coaching that surrounds our time together.
If somewhere while reading this you thought, Gosh, I wish I could do that, I would pay attention to that thought before immediately explaining to yourself why you can’t.
You do not need to know yet whether you can come, and you do not need to solve every logistical question before you talk to me.
I am not going to convince someone to spend six days in Costa Rica when she does not actually want to be there. I am much more interested in helping you look honestly at what is pulling you toward it and what is pushing you away.
Some constraints are real. Some resistance is the very business pattern you are trying to change. Knowing the difference is useful.
You probably will not build the next version of your business by doing exactly what you did to build this one. If you already know that, and the thought of six days in Costa Rica gives you even a little spark of possibility, I think we should talk.