Hope vs. Despair: Keeping Your Entrepreneurial Dream Alive in a Toxic 9-5

Updated: Dec 31, 2021

I am consistently amazed at how often I hear people’s workplaces described with eerie similarity to abusive relationships. Every workplace has its less-shiny points. Perhaps that token jerk or hot mess who makes everyone else’s work life a little bit harder. But that’s not quite what I mean. I’m talking about what it really looks like when workplaces are toxic because of an abuse of power. And I’m thinking long and hard about the impact of this on entrepreneurs-to-be who are still in the trenches.

Our work, like our intimate relationships, is a huge swath of our lives. It is what we spend the majority of our wakeful time doing, love or hate, to make the mortgage, pay the bills, finance some fun if we’re lucky and to make life work. Ideally, we enjoy whatever this is for us, or at least we don’t hate it. But too often, we don’t enjoy it for reasons beyond our control. Sometimes, sadly, we love the work itself but hate the kind of environment we must do it in.

For those of us of the entrepreneurial mindset if we have not launched our dream-business, or if its still a side hustle, the toll of a toxic work environment is compounded. (The same is true of abusive relationships, which we’ll explore in an upcoming post). In essence, abuses of power in any context are like kryptonite to your business aspirations. Why? Because growth requires nourishment, and abuses of power are not just unhealthy, they are the opposite of nourishing; they are inhibiting. Abuses of power take more than they give, they deplete our energy reserves and create conditions in which other negative things take root and thrive.

Entrepreneurial pursuits take a lot of Self-energy and a toxic workplace can leave you without any of this energetic gold left to fuel your dream. So often in my therapy practice, working with both domestic violence survivors and women in toxic workplaces, I hear the same things: “Getting through this is so exhausting, I don’t have the strength left to leave”. I’ll pause here to say that while there’s overlap between an abusive relationship and a toxic workplace, they’re not parallel. An abusive relationship is likely to be much harder to leave, more directly damaging and more impactful to other people (such as children). Still, our work is a place where our survival needs (money) are met and therefore, when the surroundings are toxic, we’re taking in some poison to keep our survival needs met. This, by the way, is “why she doesn’t just leave”.

There’s a big common thread here: the depleting nature of the situation works against the solution. Like trying to fill a bucket with a hole in the bottom, no matter how much we add, it’s never full. If we were just finding another job, or finding another partner, that would be hard enough. But building your own brand-new business not only requires numerous kinds of investment, including financial, logistical and energetic resources, it is also often an extension of who you are. So when you’re already depleted by what you’re surviving, building another whole branch of who you are in the world becomes a new kind of daunting.

Often, we “hit a wall” in moments of despair, feeling that our efforts to leave – to the better life we know we want – is impossible. If you’re still reading this post, chances are you know what I mean.


These moments of ‘hitting the wall’ can be absolutely arresting for the entrepreneur within us. When we hit that wall of despair and cannot visualize the way from here to there, parts of us which hold negative beliefs can rise up, take over or just shut us down. Whatever it takes to get us away from the wall. These moments will come and when they do, we have two choices to make:

The first choice is whether to turn toward or away from the discomfort. As humans we tend to dislike looking our discomfort in the eye. It’s not pretty. We don’t like it. It gets under our skin and causes that inner sense of ‘noise’. The doubt, worthlessness, shame, hopelessness, frustration, exhaustion, anger and more. Hitting the wall of despair drives us away from what we want. But have you ever wondered why? What if I told you that there’s an answer? That this isn’t a rhetorical question?

If you turn away, there isn’t a second choice. You’ve exited the opportunity loop early and missed the train to change-town. So I urge you, please, to turn toward your discomfort in these moments of entrepreneurial despair. How? The answer is in the second choice.

The second choice is how we choose to see the wall. Take a moment with this thought. How do we meet that wall when we find it in our path? What commonly happens inside us when we hit the wall is a lightning-fast response that we’re not even aware of. Before we know it, a domino effect ensues. Discomfort > doubt > retreat. But the best thing we can bring to the wall, if we can manage to turn toward the discomfort we find there is curiosity.

We often feel the wall is impossible to get past. We feel it’s there for a reason, that what’s on the other side must not be for us, or that we don’t have what it takes. We numb or retreat into social media or other soothers like food, alcohol, spending, or some readily available distraction. This can lead us on a downward spiral, deepening into despair because not only have we hit this wall, we turn back toward the less-good life, maybe feeling worse about the situation or – damage alert! – worse about ourselves. The wall drives us away from our growth, joy, abundance and health. Away from our aspirations and back toward our status quo.

But here are a few fundamental truths about the wall we hit within, and some questions to think on, so that you might meet this experience differently:

· The wall is often a response to someone else’s junk, rather than our own. This is where your toxic boss comes in. Toxic leaders inspire fear and self-doubt in their employees and like all bullies, they do this to bolster themselves. Are you hitting a wall because it serves someone else that you do so?

· The wall is there for a good reason. It might not feel this way, but that wall is most likely trying to protect you. What from and how? In subconscious ways we often fear success, or the risks involved with getting there. I’ve never met an entrepreneur who didn’t have some fear. When we work with that fear from Self (the work I specialize in) we can transform it. When we turn away from it or let it drive, the outcome is often that we remain stuck.

· The wall is more changeable than it may appear. When we hit the wall, it can feel colossal and impenetrable. But as we’ve established, they’re sometimes inspired by outside manipulation, and sometimes by our fears or self-doubt. When we do our inner work to become Self-led in entrepreneurship, that wall? It just doesn’t look the same anymore.

As I am fond of saying, we cannot change other people, but we can change ourselves, and when we do, it changes everything. And by ‘everything’, I mean how we meet, see and respond to all the fear, the doubt, the setbacks, and yes, even your toxic boss.


Abuses of power in your world (like a toxic boss or intimate partner) can lead to imbalanced power inside us. In other words, what’s happening inside reflects what’s happening outside. In most toxic workplaces, an abusive boss causes us to question ourselves and our abilities. And the next thing we know, we hit that wall inside that inspires the same thoughts.

I won’t go so far as to say that getting away from a toxic boss will solve all your inner resistance, but it will solve some. It’s also not always possible to escape a toxic boss when they look squeaky clean to the public (or higher management) or when you have to keep paying those bills. So then what?

Below is a list of things to remember to help you shift from DESPAIR to HOPE when dealing with a toxic boss, and to keep your entrepreneurial dream alive in your 9-5 (until you make it your reality).

· The despair your toxic boss makes you feel is not yours. Like a lot of bullies, your toxic boss is actively projecting their shame, insecurity and other junk onto you by figuring out where your vulnerabilities are and exploiting your feelings.

Knowing this can help you to re-examine the negative self-talk you encounter when you ‘hit the wall’. You can energetically ‘return to sender’ and hand that burden back to your nasty boss. Hey, look who’s hands are suddenly freed up to build her business and exit strategy?

· Empathy for your toxic boss is a waste you can’t afford. Listen, I’m a fan of compassion and empathy for those who are suffering. Indeed, I do recall that I’m a therapist. But feeling bad for your boss isn’t your job and I insist that you not work for free, especially not to your own detriment.

Not only is this working for no pay, but it is also spending where there will be no return. Better understanding how not to spend your energy means that you have more for you and your entrepreneurial dream. Freeing yourself of this habit is like getting a matched-savings account for your entrepreneurial juice. When you check the balance, you’ll have more than you thought. Outstanding! Bankroll it, sister. You’re gonna need it.

You can learn more about why feeling sorry for your toxic boss (or any bully) is dangerous in this excellent article by Mary Lamia, PhD.

· Throw them from the train. No, not literally, through these fantasies can have a healthy role in coping. What I mean here is create a ritual whereby you leave your boss at work. I can’t count how often I’ve been told that toxic bosses end up at home with my clients, energetically. We have all done it at some point – found ourselves thinking about work in bed at night, while having dinner with our kids, even during intimacy.

Toxic stuff sneaks home with us. The parts of us that try to resolve it never really clock out. You can create a ritual to evict your toxic boss from your psyche. This can be as simple as choosing a point on your commute home past which no thoughts of your boss are permitted, not allowing work talk in your bedroom, or asking the parts inside that worry about it to stay in an (imagined) safe space and let YOU (at your Self level) be with your invigorating, exciting entrepreneurial process.

If you're interested in knowing more about this from the 'parts', or Internal Family Systems angle, the work I do is built on this theory. Learn more here.

Your boss might pay you a salary but they don’t pay rent in your head. Exercise your right to throw them out. And yes, you can imagine it vividly.


One of my favorite old sayings, and one I bring up often in therapy sessions is, ‘The best fertilizer is the gardener’s shadow’. The meaning here is that our continued presence, and consistency, is the most important thing that we bring to our garden. The relevance in getting through a toxic 9-5 with your dream intact is that your toxic boss can’t keep you from going home and gardening.

I’m a gardener, and I hail from a long line of them. I know how slowly the progress reveals itself sometimes, and the aching pain of waiting, anticipation and the unknown when we’re nurturing something and fielding challenges.

In growing your own business, some things will be true fertilizer. The support of the people who love you. The resources you develop to help along the way. Financing, social exposure, speaking opportunities. But the best fertilizer is your shadow, your presence, your continued belief toward what you know in your heart to be right, and your determination to work through all that which gets in your way.

Stay the course, friends. The dream is within reach and nothing in your way is insurmountable. Not your toxic boss, not your negative self-talk, no lack of resources. It all begins somewhere, and you don't have to do it alone.

Interested in working with me on your entrepreneurial mindset and readiness? Contact me to discuss 1:1 sessions today. Also join my mailing list to get updates on this blog, offerings for entrepreneurs and free resources for developing - in Self-leadership - into your business!

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