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10 Reasons Entrepreneurs Rationalize Staying in Misery

As entrepreneurs, it's easy to fall into the trap of staying in a stressful, unhealthy business situation simply because it's generating money. The reasons for rationalizing and staying in a losing venture are probably familiar to all of us, but I would argue that it isn't worth clinging to anything that feels like it's killing you.

To be clear, I am not advocating shutting down your business if you're struggling. Sometimes pivoting is about changing one aspect of your business so you can shed the dead weight and open up to opportunities for new life. 

If you're feeling the weight of something in your business and you're craving change, maybe it's time to evaluate what's keeping you stuck. I've talked to many entrepreneurs about this, and I'm sharing what I've learned.

See if any of these resonate with you, or if you've had these same thoughts when thinking about pivoting in your business, but unable to move forward with a decision:

1. Fear of failure if you quit. You don't want to "give up."

We may cling to a dysfunctional business out of a fear of being seen as a failure or quitter if we walk away. Admitting defeat can feel devastating, even if moving on would lead to greater success and fulfillment.

2. You're worried about making ends meet without the income. You feel trapped financially. 

It's tempting to stick with a steady income stream from an existing business rather than face financial unknowns. As entrepreneurs, we may ignore the extreme toll on our physical and mental health and relationships to avoid potential money struggles.

I think the energy here is the problem because often it's when we release ourselves from something that the opportunities begin to flow again. The proverbial door closing so another can open. I know I've experienced this more times than I can count... and I bet you have too.

3. You don't want to waste the time already invested. 

After pouring months or years of long hours into building a business, it's hard to acknowledge that time as "sunk cost." I think this is a big one for a lot of us. Many entrepreneurs falsely believe if they just keep at it a little longer, they'll gain a return on their investment. Can something change and the ROI suddenly happen? Sure. But the odds are against it if you've been at it for a while and you've "tried everything"... sometimes it's just time to call it, and pivot.

4. You doubt you can succeed again. You lack confidence in starting fresh.

If you're an entrepreneur, that means you're someone who has poured everything into your business. But when something isn't working and you need to shut it down and pivot, it's not uncommon to feel that you lack the confidence to start over. Lots of us feel like we simply can't summon the energy to start fresh.

It doesn't take long before imposter syndrome creeps in, which makes taking a risk on a new endeavor seem scary... and sometimes even scarier than it would normally be because now we're in a state of fear which creates outsized monsters in our minds.

5. You're comfortable with the known pain. Change provokes anxiety. 

As awful as a toxic business situation can be for us as entrepreneurs, the truth is that we often normalize it until it becomes familiar. The certainty of known misery feels safer than the ambiguity of change. Fear of the unknown keeps entrepreneurs stuck! (Ask me how I know.)

6. You feel obligations to employees or investors. You don't want to let people down.

If you have a team, or you work with a team of contractors, walking away from a business or a part of your business means people losing jobs. If you're being supported by VC, pivoting means investors lose money. Many entrepreneurs wrestle with feelings of guilt and perceived responsibility to those who counted on the venture succeeding. We all go into business with the expectation and the hope of success, but that doesn't always materialize in the ways we hope. A healthy relationship with our business requires that we take an objective look at the situation and apply strategic thinking to moving forward, and sometimes that means scrapping plans and changing the strategy.

7. You're addicted to the adrenaline rush of chaos. You thrive on drama and intensity. 

Ah... the rush of doing it all and being all in! For some entrepreneurs, there's a pride that comes with being the captain of the ship of nonstop intensity. We've all been there, and I think it takes a special kind of person to be an entrepreneur because it requires a little of this, especially at the beginning. But when something is not working, the busyness of business becomes a blinder. We think that because it's all-consuming and we can't take a break for even a moment, that it means we're doing the right thing. The drama of that rush is the hit that makes us feel alive despite the toll on our wellbeing.

8. You don't realize toll on physical and mental health, or you're in denial about the damage.

This is a big one, and am always surprised at how pervasive it is. So many of us, as entrepreneurs immersed in the day-to-day chaos of a struggling business, often don't recognize just how much damage it's inflicting on our health and relationships until it's too late. And too late looks like burnout, a health crisis, or a lost relationship. It's vital that we take the time to assess our wellbeing on a regular basis and check in. Make sure we're feeling good about the path we're on. We often forget that we get to choose. 

9. You're overwhelmed by thought of uprooting everything. You're literally exhausted at prospect of shifting anything. 

Shutting down or leaving a dysfunctional business means massive upheaval in an entrepreneur's life. The monumental change seems exhausting, so we postpone a decision, when the act of making that decision will actually bring in new energy.

10. You hope situation will improve, and believe you can turn things around.

When we face adversity as entrepreneurs, we often cling to the irrational hope that things will turn around if we just hang on a little longer. We falsely believe we can single-handedly save a failing situation through sheer will. But this simply isn't sustainable. The cost comes in every department of our lives, our minds, our bodies, and our relationships. 

Yet despite all the reasons for staying, remaining in a bad entrepreneurial situation only leads to more misery and closes doors to better opportunities. By freeing our from what's not working, we entrepreneurs can experience powerful benefits.

Leaving a bad situation, closing down a failing project, or pivoting in your business to follow the things that light you up, give you energy, serve your heart, and feed your soul has many, many (many) benefits. But before we get to the benefits of pivoting, I want to encourage you to ask yourself this question:


"Why did you get into business for yourself? Why did you choose this specific thing as your business? Entrepreneurship is hard work, and I am willing to bet there are very big reasons you chose this for yourself and those reasons have nothing at all to do with money."


Leaving opens doors. The comfort of the familiar is seductive. But sometimes ripping off the bandaid is the only way for entrepreneurs to grow. Having the courage to walk away from a bad situation can lead entrepreneurs down entirely new, wildly fulfilling paths. The surest way to keep opportunities closed is clinging to what's not working.


Making Wellbeing the Goal: Why Entrepreneurs Should Shift Priorities

Many entrepreneurs launch businesses for the freedom it brings, and also with goals of making the most money and capturing the largest market share possible. Yet chasing money and dominance alone rarely leads to sustainable, fulfilling success. The never-ending drive for more, especially when something isn't working can easily lead us down an unhealthy path of stress and burnout.

That's why at a certain point, it becomes essential for entrepreneurs to shift priorities and make wellbeing the primary goal. Here are some key reasons why focusing on holistic well-being trumps money and growth goals alone:

  • Making wellbeing the goal improves creativity and decision making. Excessive stress stifles imagination and leads to reactive thinking. A well-being focus fosters creative solutions.
  • When you prioritize well-being, it increases productivity. People who feel healthy and energized work more efficiently with greater satisfaction.
  • A focus on wellbeing strengthens company culture. Balanced, happy leaders build positive, resilient company cultures.
  • Wellbeing at the top of the list boosts customer satisfaction. When employees feel cared for, they pass that care on to customers.
  • Making wellbeing the goal enhances resilience. Putting wellbeing first helps entrepreneurs better handle the inevitable ups and downs.
  • When wellbeing is the #1 thing, it drives sustainable growth. Companies focused solely on expansion often crash quickly. A balanced approach leads to steadier, long-term success.
  • When wellbeing is the priority, it lengthens founder career. Entrepreneurs who neglect self-care burn out fast. A wellbeing priority allows founders to thrive for decades.
  • Prioritizing well being sets a positive example. Leaders dedicated to wellbeing demonstrate the importance of an integrated work and life, which is ends that need to chase that figment of work/life balance.


Embrace it all. Do it all. And love your life. 


The benefits of taking a wellbeing-focused approach over profit-first thinking are clear. To make this shift, we need to put in place non-negotiable personal guideposts that reinforce balanced priorities. 

Join our BE*INWARD Community on Circle

BE*INWARD is a community where we continue to ask ourselves the question: What if we made well-being the goal? Now in Founding Member status. Lock in the exclusive, limited-time Founding Member pricing tier for as long as you maintain your subscription! 

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