Someone barely seen in rows and rows of productive crops

What’s Your Relationship with your Business?


You’re in a relationship with your business, and like any relationship, this one has dynamics.

So, what’s your relationship like? Do you have loving boundaries in place that allow you freedom to live outside of your business? Or are you obsessed and enmeshed in a codependent nightmare, in which your work and business define your life? Or perhaps somewhere in between?

I’m asking this question, because it’s often overlooked despite its importance. Our relationships with our businesses define the tenor of our lives, as well as our behavior. Entrepreneurs and leaders often feel that we can’t relax until we have our businesses in order (which never happens). Or that everything else in our lives has a lower priority than our businesses, including our families or our own health. Our obsessive behavior doesn’t ultimately serve the business, either. We can’t make great decisions when we’re exhausted and we certainly can’t see our vision clearly, if we never allow ourselves the time and distance we need to think creatively. How and why we make these important decisions about our priorities is based on our relationships with our businesses.


The nature of your relationship with your business depends on:

  • Who you think you are
  • What your role in the business is
  • What you think your business is


Who are you?

This is a big question, of course, and we won’t settle any age-long debates here. But, the relevant question here is how you are defining yourself. A lot of us fall into the trap of defining ourselves or our worth by our productivity, what we do, or our relationships. If our value is defined by how much we get done, we reduce ourselves from a complete and complex person to simply a “do-er of things.”

In this mindset, not only do we feel compelled to stay busy, we may not allow ourselves time to think, wonder, be curious, and ask difficult questions because these things will interrupt our flow of productivity. We may not want to say this is true, but check this against your own behavior and judgments. Do you feel obligated to justify down time? Is it hard to walk away from a to-do list full of ripe, achievable goals to take care of yourself? For myself, this is a hard thing to do. I love a good to-do list with lots of things crossed off. I feel like I’ve earned my dinner when I do lot of things. It’s a sticky trap.


Who are you really?

You exist independently of your business, relationships, and all the obligations you feel in life. These external realities do not define who you are. You have needs, wants, ideas, feelings, and inspirations that are unique to you and may have very little to do with your external circumstances and relationships. Only you can know these things about yourself and ultimately what you choose to do about your own personal reality.

When we’re too close to our businesses, as well as other relationships and obligations, we can lose sight of our own independence; that we do have an internal reality that is personal, distinct, and important. Our individuality is indeed our gift to the world. As leaders and entrepreneurs, we need access to our vision and personal clarity that is distinct from the external world. This is where our strength is. Slavish devotion to a to-do list or problem solving may not allow the space needed to see our own clarity.



What’s your role in the business? What are you to be doing?

As a founder, entrepreneur, or leader, what do you expect of yourself? What is your role to fulfill? Many entrepreneurs are absolutely committed to trying to fulfill the myth of the entrepreneur. Simply said, the myth of the entrepreneur is that you should always know what to do, be clear about your vision, never get tired, be awesome at everything, and only fail gracefully.

Since we expect perfection from ourselves while doing an insanely hard thing, our daily experience of entrepreneurship is loaded. It’s impossible to live up to our own expectations, and yet we feel like failures when we don’t. The situation then gets extra loaded if we define ourselves by our productivity and our own perceived success. So, what do we do? We work harder and stay busier in order to maybe achieve some sense of OKness. Are we doing it for the sake of the business? Perhaps. But it may also be that we work harder and prioritize work so that we feel we’re good people who are worthy of inclusion, love, and compassion.



What is your business?

How do you expect your business to operate? What is it to do? What’s its function? Most of us think of our businesses with profit as the primary outcome of interest and that the business functions like a fancy machine. The gold standard of entrepreneurship wisdom is to work on your business, not in your business. Which is to say, your job as the entrepreneur or leader is to be the primary machinist, setting up your cogs in concert with each other to create consistent, profitable outcomes. You succeed if the machine does the work its supposed to do; you fail if the machine creates unprofitable, inconsistent, unpredictable outcomes. This is true, of course.

However, the experience of the entrepreneur in this view is very lonely and stressful. In this scenario, their job is to attempt to make humans to behave like cogs, including themselves, and people are not cogs. People won’t be cogs for long without wanting to change things, leave, or disengage. Again, the entrepreneur is set up for a horrible time since their job is essentially impossible; imposing control on life. Systems are necessary, but are also insufficient for complex environments. A system may work one day and fail the next because our lives and markets continue to change so rapidly. The machine metaphor for business is not up to the challenge of creating thriving organizations in our current reality.



The Relationship – Enmeshment

Given these elements, we’re set up for a destructive relationship with our businesses. We don’t feel OK unless we’re endlessly productive in our role as a great entrepreneur who has set up perfect and durable systems in place that don’t fail in our wonderful business. So, when this isn’t true, what do we do? We work harder to be more perfect or at least more OK. And there is no end to the continual flow of more things to do and fix. In this common scenario, there is no rest.


Enmeshment is Enmeshment

Looking at human relationship dynamics can give us insight into our relationships with our businesses. In human relationships, an enmeshed relationship means we need another person to behave a certain way to fulfill our own personal needs for health and well-being. “People in enmeshed relationships are defined more by the relationship than by their individuality,” says Ross Rosenberg PhD, expert on enmeshed relationships (The Human Magnet Syndrome: Why We Love People Who Hurt Us).

A person who is enmeshed requires another person to “make them feed good, whole or healthy.” This is what people talk about when they say they lost themselves in another person. We have the ability to lose sight of what we know, want, need, and feel ourselves. Our sense of individuality is not defined internally, but by the other person (or in our case, business).



Here’s some signs of enmeshed relationships:

  1. You neglect other relationships because you are focused with maintaining your relationship.
  2. Your happiness or sense of OKness relies on your relationship.
  3. Your self-esteem depends on that relationship.
  4. When there’s a conflict in your relationship, you feel an extreme need to fix the problem.
  5. When you’re not around this person or can’t talk to them, “a feeling of loneliness pervades [your] psyche. Without that connection, the loneliness will increase to the point of creating irrational desires to reconnect.”
  6. There’s a “symbiotic emotional connection.” If they’re angry, anxious or depressed, you’re also angry, anxious or depressed. “You absorb those feelings and are drawn to remediate them.”
  7. This is what enmeshed relationships in life can look like; we feel we can’t live without our other special someone, we’re tortured when there’s discord, and our personal emotional realities don’t exist outside of that relationship.



Applying it to your business

What happens if we apply these criteria to our relationships with our businesses?

Starting with the first point, do you neglect other relationships because of a preoccupation with work? We’ll just go with yes on this one, since so many entrepreneurs are full on obsessed with their work. Sometimes the work demands complete and total attention, but is it really true all of the time?

The second point – is your happiness being dependent on how the business is going? I don’t know that I’ve met an entrepreneur that this isn’t true for. People who are obsessed with their businesses tend to not be able to be content when their business is struggling

The third point – is your self-esteem dependent on your business? Does your current Profit and Loss statement determine how you feel about yourself today? It’s OK if it does, especially since it does for almost every entrepreneur or leader.

The last three points can be considered together. Do you feel compelled to fix the issues and problems plaguing your business so that you can feel OK? Can you relax when there’s a pile of work to do? Can you comfortably delegate and schedule work for the following day, week, or year? Does your frame of mind ebb and flow with your perception of how the business is doing?

Given these criteria, where would you place yourself on an enmeshment scale with your business 0 – 10? We’re all on it, so you’re in good company. However, it is having implications in your life and business.



What’s the impact of that?

The impact of being enmeshed with your business is actually quite huge. Not only does it impact our abilities to take care of ourselves, live sane lives and have healthy relationships, it impacts our ability to lead and make clear decisions. We’ll talk about the personal impact, as well as the impact on the business.


Personal Impact

When I owned Hi Point, I had a deeply enmeshed relationship with my business. My business had to be my priority, because my sense of OKness in the world depended on how my business was doing. When you’re in business for yourself, there is a tremendous amount of work to be done. I’m not saying that if you’re not enmeshed, you’ll be able to work an easy 40 hours a week and have plenty of free time. That’s likely unrealistic. What is possible, though, is to have a space between yourself and your work so that there can be greater perspective, support, and self care without guilt.

My experience was that I took care of the basics for myself (when I was on my game), but my deep needs for physical health, a strong spiritual life, financial security, rest, and loving relationships were not being met. Not only did I not take the time to meet these deeper needs, I barely experienced them as needs at all. My actual needs didn’t make sense or fit in the context of my life. And since I saw the business’ health as my health, I didn’t really see the problem as serious as it was.


Business Impact

Our businesses are also being harmed, as well as us, because we are burned out without great perspective. When we are enmeshed in our businesses, we end up sleep deprived, with marginal nutrition, not exercising, not meditating regularly, and stressed relationships at home. Our immune and nervous systems are on edge, ready to pop at the slightest provocation. We have undiagnosed, untreated health issues that are likely tied to stress. We are depressed and isolated. We don’t sleep through the night. These are not good things.

When we are compromised like this, we can’t see the big picture, much less respond with courage and great leadership. When we’re pushed to the edge, we can’t respond to our employees with consideration, jump on a great opportunity with optimal insight, or problem solve as quickly. When we are enmeshed, anything we are called to do will be less effective than if we had perspective and the strength that comes with met personal needs.

When we reject our own needs, we reject the smartest, most competent, and compassionate parts of ourselves, because those are the parts that would make demands that our own needs are met. When we decide this is impossible or unwanted, we reject the sane parts of ourselves that would know that adequate sleep and exercise are not luxuries.



If the business is me…

If I am the business and the business is me, my worth as a human being gets tangled in the performance and value of the business. If my business is struggling, I am struggling personally. If my business fails, I am a failure. This is the shame of the entrepreneur and it is so painful and isolating.

Shame is an incredibly powerful and painful emotion that most of us would do just about anything to relieve. So, we can end up playing the short game. What can I do today to feel better becomes the question and the path forward? Doing what makes you feel immediately better is likely not the real work that needs to be done to secure a floundering company or guide a hugely successful company. This reaction is why we choose to rearrange the deck furniture on the sinking Titanic. It feels good to be busy, even if we are essentially doing nothing significant.

When we are enmeshed with our businesses, our anxieties and fears cloud our accurate judgment. In fact, our businesses have needs that are independent of us, that may not even include us. We may not be the solution to the problem at all, but while we are enmeshed, we would not be able to see that. When we are caught up in shame, we can’t ask for the help we need or the business needs. We don’t want others to see what’s really happening. We don’t even really want to see what’s happening.

It is very empowering for us as individuals and as leaders to realize that the business can be struggling without us struggling. We can stand on solid ground, and be able to see what needs to be done when we see the flaws of the business or the situation aren’t necessarily our flaws.

As I was getting ready to sell Hi Point, I was was slowly unwinding myself from this entwined identity. That space allowed me to take a more objective view and I saw that my business was, in fact, stronger than I had understood it to be. I saw that it had more value than I had realized and that the company had achieved greater results than what I was feeling. This was ultimately important for being able to negotiate a good selling price. With this perspective, I was also able to celebrate what I and others had created together. Without this perspective, I would have been a less competent negotiator and I wouldn’t have been as able to be as grateful for the people and the community that had meant so much to me.



Questions to consider:


  1. Are you enmeshed in your business? On a scale from 0-10 (ten being the most enmeshed), where would you place yourself?
  2. How would you describe your relationship with your business? Is it like a mother and a newborn? Are you like the boyfriend who doesn’t know how to say no to his crazy girlfriend?
  3. Is this enmeshment interfering with your personal life and needs? How? What needs are not getting met?
  4. Is this enmeshment interfering with your business’ needs? How? What needs are not getting met?
  5. Your relationship is defined by who are think you are, what role you play, and what your business is. Where do you see yourself being stuck? In one? In all three?
  6. What can you do to begin to shift where you are stuck?