Entrepreneurial Enmeshment

By Lauren Gaggioli

One trend I’ve noticed in my decade as a digital entrepreneur is what I have started to call Entrepreneurial Enmeshment.

I initially noticed it in myself. 

How It Started...

When I launched my first online business - a solopreneur venture that was primarily built through course creation and a niche podcast - I was, shall we say, zealous. 

Obsessed would also be appropriate. Possessed might also make the cut. 

It felt like my hair was on fire and the only way to put it out was to spend hours on end at my desk generating all the collateral required to build my tiny digital empire. I did this by heavily leveraging my existing teaching skills to develop my core curriculum and acquiring new skills including but not limited to video and podcast editing, conversion copywriting, SEO know-how, and website and email systems maintenance at a rapid rate in order to be able to manage the majority of the technical requirements too.

After all, I was committed to bootstrapping it. Outside of a professionally built website, I handled it all. And that meant learning it all. From scratch. All at the same time.

In those heady early days, it was not uncommon for me to wake up at 5am, down a couple of shots of espresso, and sit down at the computer by 5:15. My husband would kiss me goodbye as he headed off to work around 7:30. 

More often than not he would walk through the door at 6:00 that evening and find me glassy-eyed in the exact same spot he’d left me, frantically editing a podcast or crafting copy for a sales page, blog post, or email. Or - for a delightful change of pace - I’d be sweating it out under hot lights on a gruelingly overambitious filming day in our snug, poorly-ventilated guest room. 

I usually would’ve only taken a few five-minute breaks throughout the entire day. I’d snag a few turkey slices. (Who has time to make a proper sandwich? Not me!) A couple more espressos. (Sweet nectar of the gods!)  A pee break, possibly. (It’s widely known among entrepreneurs that bladders are the most inconvenient organ.) A shower, rarely. (I wouldn’t be leaving the house any time soon anyway! PJs all day!)

My husband would quickly notice that dinner was, in fact, not started. Nor had I gone on the grocery run we desperately needed. So we’d scrounge up take out (he’d pick it up so I could work a little longer, bless him), scarf it down while watching a single episode of a show, and I’d get back to it. Until midnight or later. Rinse and repeat.

Thinking about it now makes me really tired. Frankly, I need a nap having typed that all out, let alone having lived it. 

But the thing that kept me going through it all was the sense that it would end. 

That, on the other side of the hustle and grind, I would find respite. And, maybe, a well-made sandwich or something.

But that’s not what happened.

How It Kept Going...

What happened was that I kept the grind going. I fell into the after-I-complete-this-next-task trap. 

As Oliver Burkeman explains in 4,000 Weeks: Time Management For Mortals, one of my all-time favorite books for entrepreneurs... 

“Becoming more efficient just makes you more rushed, and trying to clear the decks simply makes them fill up again faster.”

I felt a strange sinking feeling in the pit of my stomach when I first read this sentence. I knew it intimately. 

By the time I had tackled the next task and the next task and the next, I was also supporting my new clients. Because I had so painstakingly crafted these courses for them and they had paid handsomely to participate, I felt duty-bound to reply to their each and every request as quickly as possible. 

Which led to checking my email and social media approximately every four seconds. All day. Every day.

And I kept on going - creating more courses, supporting more clients, engaging in ever more elaborate marketing campaigns.

Back to Burkeman…

“Rendering yourself more efficient — either by implementing various productivity techniques or by driving yourself harder—won’t generally result in the feeling of having ‘enough time,’ because, all else being equal, the demands will increase to offset any benefits. Far from getting things done, you’ll be creating new things to do.”

Oliver Burkeman

What began as a self-inflicted requirement to drink from the firehose of online business learning in order to get the lion’s share of the work done and bring a viable product to market in a reasonable amount of time as a solopreneur became a debilitating, compulsive need to create ever more things and to keep on top of everything I had already created. 

The paradox is that, by building online businesses that should (and do by some measures) afford us tremendous flexibility and freedom, we solo entrepreneurs can end up feeling trapped by them too. 

It’s a self-determined trap. We chose its parameters and set the snare ourselves. But it is a trap nonetheless.

And I’m not the only entrepreneur who has fallen into it. 

I have many friends who have built amazing enterprises in the digital space who have fallen victim to the same downward spiral, what I now call Entrepreneurial Enmeshment.

What Is Entrepreneurial Enmeshment?

To begin, let’s look at what enmeshment within family systems looks like.

“Enmeshment is a psychological term that describes a blurring of boundaries between people, typically family members. Enmeshment often contributes to dysfunction in families and may lead to a lack of autonomy and independence that can become problematic.” - GoodTherapy 

In a weird way, this definition puts me in mind of Kahlil Gibran’s On Marriage in which he cautions…

     Love one another, but make not a bond of love:

     Let it rather be a moving sea between the shores of your souls.

     Fill each other’s cup but drink not from one cup.

     Give one another of your bread but eat not from the same loaf.

     Sing and dance together and be joyous, but let each one of you be alone,

     Even as the strings of a lute are alonethough they quiver with the same music.

Essentially, if you can’t sturdily stand to the side of your parent, partner, or other family member, you’re in an enmeshed relationship.

The same holds true with your business. If you can’t stand sturdily to the side of your company and view it as something outside yourself, you’re in an enmeshed relationship with it.

And that is not helpful or healthy for you or your business.

Signs Of Entrepreneurial Enmeshment

According to PsychCentral, you might be in an enmeshed relationship if…

  • you don’t feel in touch with your feelings because you’re concentrating on another person’s needs
  • you believe it’s your responsibility to save, protect, or serve another person — or someone is treating you that way
  • you’re giving up hobbies or interests to adapt to the lifestyle or expectations of another
  • your relationship determines your happiness, self-esteem, or sense of self
  • you’re replacing other relationships with your partner’s or family’s
  • you feel anxious or scared if there’s conflict and do whatever you can to resolve it
  • you can’t make a decision without your partner or family’s approval, or when you make an independent decision, you face backlash, guilt, or shame
  • you feel uncomfortable spending time away from your partner or family

Now consider it through the lens of the entrepreneur. 

Try these rewritten symptoms of entrepreneurial enmeshment on for size…

  • you don’t feel in touch with your feelings because you’re concentrating on the business’s needs
  • you believe it’s your responsibility to save, protect, or serve your clients above and beyond the services they have paid you for
  • you’re giving up hobbies or interests to serve your perceived needs of the business
  • your numbers (monthly revenue, email list subscribers, podcast downloads, followers on social) determine your happiness, self-esteem, or sense of self
  • you’re replacing other relationships with time spent working on your business
  • you feel anxious or scared if there’s conflict with a client and do whatever you can to resolve it - even when that client is clearly being unreasonable 
  • you can’t make a decision without considering its impact on your business
  • you feel uncomfortable spending time away from your business, even when you have systems in place that support you doing so - or you’re resistant to setting up those systems in the first place

What To Do About Entrepreneurial Enmeshment

If this sounds like you, I have two bits of good news.

1. You’re not alone.

There are plenty of folks in this same spot with you. It’s a common way to be in the world of online entrepreneurship. 

Heck, it’s one of the reasons I used to host a podcast called The Unsexy Side. 

For all the talk in the digital world about how shiny and bright we all are hustling our little buns off, there’s an ugly underbelly. There are hard things to face. 

It’s a fun ride, but the ride has both peaks and valleys. All of us need to be more honest about the valleys, otherwise we’re going to entice those who are not in it for the long haul to pour too much of themselves into ventures they won’t stick with when things get tough.

2. You can choose a different path.

There is a way to break free of entrepreneurial enmeshment. In fact, I believe the antidote to entrepreneurial enmeshment is surprisingly simple.

The antidote to entrepreneurial enmeshment is to state your life’s purpose.

But, simple though it may be, it is not easy. You have to name your purpose in a very strategic way by giving yourself a life mission statement that is not too narrow or too broad and that is a true reflection of your Zone of Genius is pure magic when it comes to helping you disentangle yourself from your business.  

This is exactly what I teach in my course on purpose called Big Why Life.

The course is designed to help you see yourself from a multitude of angles. We examine evidence from the past and present that will help you peel off the layers of limiting beliefs you hold or have inherited and point you inward towards your most authentic, passionate self.

And then, with that full picture of yourself  in mind, we craft a personal mission statement that allows you to see how you can fulfill your purpose in myriad ways throughout your life. 

The course is designed to help you reset the needle of your internal compass. And the statement of purpose that you walk away with is the touchstone you can keep with you always, to help you recenter and reset whenever life inevitably blows you off course.

By helping you tease out all the ways you can fulfill your purpose - in business, yes, but also in your romantic relationships, your family life, your friendships, your community, your free time, etc. - you will feel more balanced and grounded in all respects. 

You can learn more about the program below.

If you’re feeling lost or at the end of your tether when it comes to the control your business has over your life, I am here to help. 

I hope you’ll consider joining me in the Big Why Life course because clarity of purpose is one of the greatest gifts we can give ourselves, our families, our clients, and our world.