I am a HUGE believer in sharing things like this, as it can help others by sharing.

December 9, 2025 by Sheryl J. Moore

I have made a lot of mistakes in my business over the past 20+ years.

A lot.

Here’s just a few that come to mind:

1. Choosing the wrong accountants, and not finding a CPA that is worth every penny I pay them;

2. Developing imposter syndrome after the CMO of one of the biggest insurance companies in the world said he “had pimples on his @$$ that are older than me;

3. Cheating my business out of hundreds of thousands of revenue because I undervalued my abilities;

4. Berating my first employee if she was five minutes late for work;

5. Assuming that everyone else is like me, and getting burned by (former) “dear friends” in this business;

6. Hiring people with experience in life/annuities, but no ability to assimilate with the culture of Wink, Inc.;

7. Not being engaged in my business for seven years following the death of my son;

8. Paying hundreds of thousands a year to a subpar web developer just because I was stuck in my routine;

9. Making a decision that alienated several mutual par whole life companies from my business; and

10. Letting my ego get in the way.

*****That said, I have had even more successes than mistakes.*****

1. Trying to help everyone that I meet;

2. Listening;

3. Deliberately developing friendships with influential people in life/annuities, who could help my other connections;

4. Paying-it-forward when I was blessed financially;

5. Being kind, even when it was not reciprocated;

6. Hiring people that I like, and investing in their education of annuities/life;

7. Carefully nurturing a culture in my company that encourages employee relationships, engagement and satisfaction for all;

8. Being smart about how to grow my business;

9. Getting a degree in pre-law (attending classes all day long) just four years into my business;

10. Advancing through the Goldman Sachs 10,000 Small Businesses program (the equivalent of an MBA in a couple of months);

11. Naming one of my top employees as President of my company, so that I can focus on strategy and business development; and

12. Harnessing the power of social media, when my company was still young.

I realize that I wouldn’t have the successes, were it not for the mistakes. I am grateful for powering through them, so that I can be a better entrepreneur and a better person.

What is one mistake that you’ve made in your business? How about a success as well? I am a HUGE believer in sharing things like this, as it can help others by sharing.

Go!  Join in the LinkedIn conversation here. -sjm