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6 Things I Would Tell Myself If I Were 25 Years Old

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.


The next generation of leaders are entering the workforce in droves. As I think about them, I wished someone would pulled my ear, cut open my head and pour it in, or at least grab me by the collar and told me how to think about my personal brand in business. Maybe they did and I was too headstrong or a totally goof ball to listen.

Happy smiling handsome man with crossed arms looking to camera over beige background.

If you are seeking a profession, job, or next step in life, then please consider the following things that I’ve learned in 28 years, while working for 6 different companies and having 10 different jobs. Here is a list that will help you in your career and life.

Pursue Significance and Success will follow – People are emerging from the fog of the pandemic to realize that success is empty but the significance is fulfilling. Success is a fleeting moment and significance is lasting. Success is empty after the applause stops and the dust collects on the award plague, however, significance is a constant companion that reminds us to serve all, love everyone, and never take anyone for granted. Success may come as the result of a position, acquisition, or fulfillment of an unmet need, however significance works diligently when no one is looking and understands that it’s better to give than to receive.

Seek Out Stretch Assignments – When I worked at the Walt Disney World Resort, I took on my first leadership role overseeing a sales team. Word on the street was that no one wanted the assignment, but I believed that I had an understanding of people and wanted a shot.

The job required interacting with other strategic company partners as well as international travel. I had never left the comfort of the U.S. and certainly didn’t have a passport. The new role stretched me, expanded my thinking and exposed me to the global landscape. Part of developing is being uncomfortable being comfortable. I had to be willing to stretch beyond my immediate grasp.

Speak up and Make Something Happen – A woman sent me this e-mail after hearing me at a conference. She said “before I came to the conference I was ready to resign my position because of job dissatisfaction. The communication is poor between the departments, positions are left undefined, and expectations are unclear. I recognized that I needed to initiate open communication to have my needs met as a team member, but I had just been “going with the flow” and waiting for it to happen to me, not for me.

The meeting with my manager went well. I have a little bit more direction, some goals to meet, and I have given myself a deadline of 90 days (living in QUARTERS!) to determine if I should stay or if I should “get out of the way.”

Men, get over it if she makes more money – Celebrate your woman’s success. Some men feel threatened if their women are the breadwinners or make more money than they do. If you’re one of these men, get over it! Women want men who believe in them and will be happy for them instead of tearing them down because the male ego can’t take it. (At the same time, don’t expect her to take care of you. Make sure you get off your blessed assurance and do something to contribute to the economic stability of the family.

Everything you do tells a Story. Simply put, how you work and live tells a story and that’s what makes your personal brand unforgettable. People who leave an unforgettable imprint on hearts and minds seek for ways to go above and beyond.

What do I mean? After checking into a hotel in New Orleans recently, the room service attendant delivered a nice assortment of cheeses and some wine. Lovely, right? The problem is, anyone who knows me knows I’d much rather have milk and cookies – snack food. Well, I declined the nice gesture and told the attendant that he could take it back. He ask if I wanted something different. I mumbled a few things and didn’t think anything of it. I later returned to my room and found a wonderful assortment of Zapp’s potato chips and soft drinks. I have to admit, I savored every single bag of those amazing chips and thought about how great the service at that hotel was the whole time. The point is, what started out as nice gesture became more – it became unforgettable moment.

Expand your mind – You are the sum total of the 60,000 thoughts per day that have passed through your mind since you were a child. Begin to expand your thinking capacity by intentionally writing down what is right about you and the difference your life will make. Then meditate and review it on a daily basis. Then start saying it out loud and affirming who you are becoming. This shift will positively impact your self-image (how you see yourself).

Follow me on Facebook, LinkedIn, and visit my website for more info!


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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