Is Being an Entrepreneur Destroying Your Self-Esteem? - Part 1

Is Being an Entrepreneur Destroying Your Self-Esteem?  - Part 1

Anxiety and mental health issues are skyrocketing amongst entrepreneurs. An often overlooked issue is the impact being an entrepreneur has on self-esteem.

Let’s face it, being an entrepreneur is tough. You face a variety of challenges, delays, and setbacks on a daily basis —not to mention the common issue of unstable cash flow. In fact, anxiety and mental health issues are skyrocketing amongst entrepreneurs. The constant uncertainty and feeling of being on a rollercoaster ride could be impacting your physical and mental health in a variety of ways. More and more articles are being release on what has been deemed “the entrepreneurial terror”. However, a commonly overlooked issue is the impact that being an entrepreneur can have on your self-esteem.

Factors That Impact Self-Esteem

While this is in no way an exhaustive list, there are several factors that are well known to impact self-esteem:

1. Success of your same sex parent

2. Success of your peers

3. The type of love you received as a child

4. How authentic you are (The gap between what you believe and what you do)

Is Being an Entrepreneur Destroying Your Self-Esteem?  - Part 1

Success of Your Same Sex Parent

Research has shown that your ability to surpass the accomplishments of your parents—especially your same sex parent—plays a significant role in your self-esteem. If the list of accomplishments of your parents, by the time they were your age is longer than yours, you might feel like you aren’t living up to their expectations. For example, if your parent made a senior level salary and you make a middle level salary, you are more likely to feel inadequate in comparison. Similarly, if your parent has a very successful business and you are struggling to make it, you might feel like there is something wrong with you. If, by age 30, your parents had surpassed major benchmarks like owning a house, becoming a manager, climbing Mount Everest, or solving world hunger, you could feel like a slacker if you are still trying to figure out what you want to do when you grow up, or if you are struggling to get your start-up off the ground.

Second generation entrepreneurs who take over the family business can feel the same way. Always living in the shadow of your parent is difficult. When your parent built the business to a thriving success, and you are losing money, your self-esteem is at risk. Most entrepreneurs need to borrow money from financial institutions or family members during certain times in their business. If you add borrowing money from your parents to the list, you could feel like you are not able to stand on your own feet.

Is Being an Entrepreneur Destroying Your Self-Esteem?  - Part 1

Success of Your Peers

The success of your peer group can directly impact your self-esteem. As an entrepreneur, there are three peer groups in particular that can be the cause for self-belittlement:

• Those you were educated with

• Entrepreneurs you network with and see regularly (especially those who started their businesses around the same time as you)

• “Your competition” (those who have similar businesses to yours)

Is Being an Entrepreneur Destroying Your Self-Esteem?  - Part 1

Peers you Were Educated With

Let’s start with the first group. If those you went to high school, college, or university with are more successful than you, it is likely to leave you feeling like an underachiever. The impact is similar to coming in last during gym class, or getting the lowest grade in the class. That old, unconscious competition, or feelings like you’ll never be as good as everyone else, can raise their ugly heads even in adulthood. It is amazing how easy it is to feel like you are at the bottom of your class and you’ll never be “one of the popular kids”.

Peers with Different Businesses

The second group is those who you network with and see on a regular basis at functions or networking events, but whose businesses are different from yours. It can be challenging to listen to your peers talk about how business is booming and they are struggling to implement expansion plans while you are riding a financial low. Constant reminders of how much better everyone else seems to be doing, can be a harsh blow to your self-esteem. It is easy to lose sight of the fact that they have different types of businesses, and therefore different challenges.

Is Being an Entrepreneur Destroying Your Self-Esteem?  - Part 1

Peers with Similar Businesses

The third group, your competition - those in the same field as you and possibly even your mentors - can be especially vexing, especially if your customer base has drifted over to them. When your competition, fellow accountants, coaches, chiropractors, energy workers, and house painters all seem to be so much farther ahead of you, it can be easy to start questioning as to what is wrong with you. It can be challenging to exude happiness for your peer when she is squealing over the new project she signed when you previously made the same pitch to the same group and were turned down. When the accomplishments of those in the same career as you seem to extend far beyond your own, your self-esteem can take a beating.

Is Being an Entrepreneur Destroying Your Self-Esteem?  - Part 1

Conditional versus Unconditional Love

Yep. Lots has been said about the impacts of your upbringing and your family of origin. Your family and early life experiences shape you, consciously and unconsciously, in more ways than you will ever know. One key factor is whether the love you received was conditional or unconditional. With conditional love, you had to do something (perform a specific action), be something (behave a certain way), or achieve something (like sports or high grades) that was deemed as “good” in order to receive love, approval and acceptance. In these situations, you may have learned that love was contractual. When you hit certain benchmarks, you will be loved.

As you grew up and became an adult, these benchmarks could have easily shifted to include family, house, career choices and income levels. As a result, many people who grew up in conditional love environments, can feel like they are not loveable if they haven’t reached those targets and goals. As an entrepreneur constantly struggling to reach your goals, you might feel like you are always second rate.

Moreover, many people who grew up in conditional love families, enter romantic relationships with people of the same mindset. If your parents or spouse feel you should “get a real job”, or keep pressuring you around how much money you make, your self-esteem can be eroded over time. It is already difficult to start a business when you have emotional support; it is a horrendous undertaking without emotional support.

In contrast, if you grew up with unconditional love, you most likely learned that you are a good and loveable person just because you are you. In these cases, what you achieve is great, but it is not the source of love, acceptance and approval others hold for you. Often, unconditional love parents will help you navigate setbacks, come to terms with them, and reorient yourself to either try again or change directions. They often focus on what you learned from the experience, and the fact that you took a risk and went for what makes you happy. Their gage of your success is your level of happiness. And, they love you regardless of your income level or career choice. (Please note, this does not mean that your loved ones don’t have boundaries. Having a boundary is not that same as withholding love. Boundaries are the way they have love for themselves).

People raised in unconditional love are more likely to marry or find romantic partners and friends who are unconditional love people. If you came from a background of unconditional love, and are currently surrounded by it, it is easier to recover from the setbacks that come with life and business. Your self-esteem will be strengthened by, and even upheld by, those around you.

Is Being an Entrepreneur Destroying Your Self-Esteem?  - Part 1

Authenticity or “You Can’t Out Run Yourself”

In his book The Six Pillars of Self-Esteem, Nathaniel Brandon describes self-esteem as a ticking time bomb. If you don’t disarm it by increasing it, sooner or later it will go off and destroy your life. Have you ever done something you knew was wrong, or went along with something you didn’t agree with? How did it make you feel? Did you feel guilty? Did it eat at you? Have you ever forgiven yourself? Did you have to come clean? How long did/have you carried it?

If you are like most people, going against your integrity can have a significantly negative impact on your self-esteem. The same thing can be true when you do things, or behave in ways that are not true to yourself. When you run your business in a way that feels or seems “wrong” somehow, you are going against your own truth. Our truth is one of the cornerstones of who we are.

One of the challenges with being an entrepreneur, is that often “good business advice” or “effective business practices” can feel at odds with who you are. Business gurus and coaches are always relating the do’s and don’ts of success. And, you want to be successful, don’t you? How often have you followed business practices that made you uncomfortable, you disliked or dreaded, or just simply didn’t represent who you are, what you believe in, and what you want for your business? After months and years of following advice that feels wrong to you only because it is considered “good business”, it is easy to look back and wonder how you got so far off-track. It can also result in falling out of love with your business and disliking the very thing you worked so hard to create.

Is Being an Entrepreneur Destroying Your Self-Esteem?  - Part 1

All that well-meaning advice can completely change the business away from your original dream. It takes huge fortitude to remain true to your original vision in the face off all the “do this and you’ll be successful” pressure. Yet, when you are not being authentic in who you are and what your business is, you are out of integrity. You are “faking it” and potentially at risk of imposter syndrome. When you are out of integrity, you have Nathaniel Brandon’s self-esteem time-bomb in play. And it is only a matter of time before it goes off.

Never fear! There is a lot you can do to restore self-esteem damaged by starting your own business, and maintain your business success. Please join me for Part 2 and learn more.


Renate Donnovan is passionate about the topics of self-esteem, resilience and possibility thinking – three things the business gurus tell her don’t go together well in marketing campaigns. She has dedicated her life to helping her clients and students (and herself) strengthen all three. She believes, “Self-esteem is a way of being, resilience is a skill, and possibility is a thought process. All three can be learned and developed.” Oh yes, she is also a counselling hypnotist, NLP Practitioner, transformational coach, educator, speaker and writer. You can visit her website at: Please check-out the “Free Stuff” tab for lots of free stuff and join her FREE 30 Day Self-Esteem Challenge starting Feb 1st.