1. Emotional Attachment to the Business
For many entrepreneurs, their business is more than just a financial investment—it’s a part of their identity. You’ve poured your heart and soul into building something meaningful, and it’s only natural to form a strong emotional connection. Psychologist John Bowlby’s attachment theory (1982) suggests that we can become emotionally attached to things that are deeply intertwined with our sense of self.
It’s okay to feel attached to your business—it’s a reflection of your hard work and achievements. But it’s important to remember that letting go doesn’t diminish your accomplishments. Sometimes, stepping away from the business can free you up to pursue new passions, opportunities, and a renewed sense of purpose.
2. Fear of the Unknown and Change
The fear of uncertainty is a deeply human experience. Change, even when it’s for the better, can feel unsettling. This is known as ambiguity aversion (Hogarth, 1987), where we tend to avoid situations that make us feel uncertain. The thought of life after selling your business might seem daunting, especially if you’re unsure about what the future holds.
It’s okay to feel nervous about the unknown. Transitioning from being a business owner to exploring new possibilities can be a challenge, but it also opens the door to new adventures. Embracing change doesn’t mean losing what you’ve built; it means making space for the next chapter in your life, one that could bring you more joy, freedom, and fulfilment.
3. The Sunk Cost Fallacy
Many business owners face a dilemma when it comes to letting go: the sunk cost fallacy (Arkes & Blumer, 1985). This is when you feel like you should keep going because of all the time, money, and energy you’ve already invested. You’ve worked so hard to get to this point that it feels wrong to walk away.
It’s okay to acknowledge the effort you’ve invested. But it’s also important to remember that continuing to pour resources into something that’s no longer working for you may not be the best choice. Letting go can be a brave decision—one that allows you to reclaim your energy and move toward something that will bring greater returns, both personally and professionally.
4. Your Business Doesn’t Define You
A business can become such a big part of your life that it’s hard to imagine yourself without it. According to Erikson’s psychosocial development stages (1959), we go through phases in life where our sense of identity evolves. For many, their business represents more than just income; it’s a reflection of their values, their creativity, and their purpose.
It’s okay to feel like your business is a part of who you are. But remember, your worth isn’t tied to what you do or own. You are much more than your business, and selling it opens the door to rediscovering new parts of yourself that you may not have had time to explore. Life after selling your business can be an exciting time of self-discovery and personal growth.
5. Perceived Lack of Alternatives
Some business owners feel that selling is the only option left when things aren’t going well. This feeling of being stuck is linked to the concept of learned helplessness (Seligman, 1975), where past experiences have made you believe that no matter what you do, nothing will change.
It’s okay to feel unsure about the alternatives. Selling your business doesn’t mean giving up—it means making a conscious decision to take control of your future. Whether you decide to retire, start something new, or even take a well-deserved break, selling your business can provide you with the freedom to explore other options and create a life that aligns more with your current needs and desires.
6. Overvaluation of the Business
Sometimes, business owners overestimate the value of their business due to their emotional investment. This is a common cognitive bias known as anchoring (Tversky & Kahneman, 1974). It’s easy to see the business through a personal lens and believe it’s worth more than it might actually be on the market.
It’s okay to feel proud of your business, but it’s important to stay open to feedback. While your business may hold great value to you, it’s also essential to listen to the market and understand what it can realistically sell for. By accepting a fair offer, you can move forward without being stuck in the past and embrace the opportunities that await.
7. Fear of Regret
Making any big decision—especially one as significant as selling a business—can bring with it the fear of regret. Regret theory (Loomes & Sugden, 1982) suggests that the fear of looking back and wishing you had made a different choice can paralyse your decision-making process.
It’s okay to worry about regret. But remember, regret often comes from staying in a situation that doesn’t serve you anymore. By selling your business, you’re giving yourself permission to explore new paths, reduce stress, and focus on what truly makes you happy. There’s a world of opportunities waiting for you, and you won’t know what they are unless you take that first step forward.
Selling a business is a deeply personal decision, and it’s okay to have reservations. The emotional attachment, fear of change, and other concerns you’re feeling are natural—and many business owners share them. But it’s also important to recognise that selling your business could be the key to unlocking a new, fulfilling chapter in your life. It’s not the end of something, but the beginning of something even better. With the right mindset and support, selling your business could very well be the best decision you ever make.
Written by Jason Litherland
Get in touch with us here for more information on selling your business.
