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What Would I Tell My 40-Year-Old Self?

Written by: Simon T. Bailey, Executive Contributor

Executive Contributors at Brainz Magazine are handpicked and invited to contribute because of their knowledge and valuable insight within their area of expertise.


Thank goodness I’ve been able to experience another year around the sun. As a result, I’ve been reflecting on what I would tell my 40-year-old self about life, based on failure, successes, sadness, and joy.

1. Take a risk and never play it safe.

When I was contemplating leaving Disney, all of the key people in my life said to stay in a secure job with benefits and future promotions. What they told me was great advice for themselves. Remember, people don’t see you the way that you are; they see you the way that they are. In my gut, I knew that it was time to find my happiness elsewhere. Be divergent and go in the opposite direction. You will find your voice in the process

2. When you don’t know, don’t go.

I know this will contradict everything that I previously said. However, here’s the gist. There will be times in life when you are unsure and don’t have peace. There’s an internal wrestling match in your soul. Yes, you want to jump from the ropes of life onto the mat of opportunity. But somewhere deep in your psyche, there’s a still, small voice that says, “wait.” It’s in that moment that our soul senses the divine timing of the universe. When you decide to go for it, everything will line up.

3. Love with no regrets.

When a man meets a woman, there’s a sense of knowingness that you’ve chosen this partner to have and to hold until death. However, what do you do when life happens, aka divorce? As you look back through the rearview mirror of time, celebrate what you learned and how you grew as an individual in that relationship. Take ownership of your areas of failure, forgive your spouse, and move on. It will be healthy for you and for your children if you are fortunate enough to be parents. By the way, there is one more thing: Seek professional help through a licensed therapist. I did, as I discussed in my latest book – Ignite the Power of Women in Your Life – A Guide for Men.

4. Situational awareness is your BFF.

There have been several instances when I was in the right place at the right time, but I wasn’t aware of how to show up because I didn’t see it or understand it. I was stuck in my limited worldview and didn’t use the tools of words to work through problems by asking questions. My analytical skills were in their infancy, and no one taught me the power of being uber responsive. Nevertheless, in every situation that I encounter now, at the conclusion, I say to my wife, Jodi, “What just happened?” and we dissect every word, tone, and exchange at the moment. We simply start with what is seen, heard, and felt.

5. Find a bigger room.

There will be times in life when you outgrow situations. I love this quote by British author Aidan Chambers: “Rooms are fixed size, which can’t be altered without pulling down walls and building new ones. They should be unchanging in shape and proportions. But sometimes they do change depending on who’s in them.” It is time for you to find a bigger room for whom you will become in the process. I found a bigger room when I joined the Kyle Wilson Inner Circle Mastermind group. I’ve never looked back and have been so tremendously blessed.

These are just a few suggestions that I wanted to share as I was mentally flossing. Your best days are in front of you, and how to do you begin to mentor by imparting your wisdom to those who are 10 years behind you.

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Simon T. Bailey, Executive Contributor Brainz Magazine

SUCCESS magazine calls Simon T. Bailey one of the top 25 people who will help you reach your business and life goals. He joins a list that includes Oprah Winfrey, Brene Brown, and Tony Robbins. Washington Speakers Bureau recognized him as one of the 12 business speakers who emboldened audiences to think big and lead with purpose. Simon was the first Black American sales director for the Disney Institute based at Walt Disney World Resort. Since leaving Disney, he has served more than 2,100 organizations in 50 countries. His three LinkedIn Learning courses have been viewed by 250,000 individuals in 100 countries. He’s also written 10 books and has one of the 100 most-read motivational and successful blogs.



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