What I’ve Learned About Success: You Have to Keep Starting Over

UPDATED: March 21, 2018
PUBLISHED: March 20, 2018

I have made a career out of helping people. I push them to understand the unique imprint they’re supposed to leave here on Earth. As for me, I just reached the half-century mark on this planet.

In those 50 years, I’ve moved from humble beginnings to a fast-tracked corporate career and to building my own successful business. I’ve worked with more than 500 leaders at 1,000 organizations in 45 countries. I’m a best-selling author and a sought-after speaker. Most important, I’m a father to two teenagers.

As I prepare to watch my son graduate from high school and head to college, I have reflected on my own life and career. What I realized is this: Success is not a path—it’s a cycle. At every stage and in every phase, when I let go of failure, paid attention to what my spirit was telling me, and focused intentionally about opening up to what wanted to emerge, I moved to the next level.

The core of my life’s work could be encapsulated into a single sentence by John Mason in An Enemy Called Average: “People are born as originals. But most die as copies.” I’ve learned and experienced firsthand that we all have the power to change that. Everyone has the potential to release the brilliance that was instilled in them at birth and to achieve incredible things in their lives. Many people are eager to join the next generation of human performance, and I’m blessed to guide people to do just that every single day. I couldn’t do it without first going through it myself.

Related: 7 Ways to Take Control of Your Life Today​

Humble Beginnings

My first year of high school was bad. I failed all of the trade classes. My parents thought that since my dad could build anything with his hands, I would follow in his footsteps, but it seemed the genes for constructing were recessive. As if flunking these classes wasn’t enough, I went out for the football team and was cut. I tried out for the basketball team and was also dismissed. I think the coaches felt sorry for me. I felt sorry for me.

I was suffering from a severe case of misfitism, a word I coined to describe the emotional baggage people carry when they think and feel out of place, out of sync, and disconnected personally and professionally. Misfitism is a chronic mental state that resides internally in a person’s psyche when he or she feels stuck in a tenured position or a dead-end relationship, or unfulfilled in his or her overall life.

What I’ve Learned About Success: You Have to Keep Starting Over

To combat misfitism, you must say yes to new possibilities and directions, even if at first you think they are beyond your reach. Luckily, after that first year of high school, my parents decided to shift me away from that environment, where I was underachieving and seemingly unenthused about education. They enrolled me in a new high school where my talents—like running my mouth—could be nurtured and appreciated. It was there that I met my saving grace in the form of an English teacher who encouraged my love of language and helped me embrace my strengths, skills and talents. By the time I graduated, I was the senior class president.

In my first school, I had been telling myself everything I was not. “I’m not athletic. I’m not creative.” When you tell yourself you’re not something, you train your brain to think that the potential for success does not exist. I learned at a young age that once I stopped focusing on what I was not and began to open up to what was working, success would rapidly follow.

Getting Intentional

After studying hospitality in college, I moved from Atlanta, a place I loved, to Chapel Hill, North Carolina. I took a job there just for the money, and the entire time I was in North Carolina I felt out of place. Something was off, and it wasn’t clicking for me—something I couldn’t put my finger on. I was going through the motions, sensing that I was spiritually impoverished, just existing.

I knew I had to let go of the flawed decision to move into a job for the wrong reasons. So I moved back to Atlanta, taking a reduction in salary. But I didn’t care. I needed to listen to what was in my spirit.

As I moved forward in my career, I learned the power and need for action with intention. Opening yourself up to what wants to emerge sometimes looks like taking chances, but more often it has to do with preparation and consistency. I would often compare myself with everyone else in my age group. Why didn’t I get the plum job assignment or start a business like many of the people I met? Where was my fancy car, designer clothes or house in the best ZIP code? Why did I run up my credit cards trying to fit in and keep up with everyone else?


As I moved forward in my career, I learned the power and need for action with intention.


Was it because I was dumb, slow or inferior in some other way? No. It was because up to that point, I failed to form the intentional, mind-shaping habits that would prime my mental canvas for success. Some habits—like pouring a cup of coffee in the morning before your eyes are even open—are small and do not change the way you think. But mind-shaping habits change the way you make decisions. They’re proactive and create the space you need to become the type of person who can accomplish everything you want to achieve.

One of the hardest lessons I learned about being intentional was when I received my first bonus check of $1,000. That was a big deal. Some friends called me the day I got my check and said they had received theirs as well. They were planning to buy some stock in a startup company in Atlanta called Home Depot and asked me if I wanted to join them.

I said no. I didn’t want to be intentional with that check; I wanted to celebrate and spend it! I don’t even know what I did with the money, but about a decade later I ran into one of the two friends and asked her if she had made the investment. She said yes with a big smile on her face. I missed a chance for a big return because I prioritized the short-term satisfaction of spending that money over the long-term gain on an investment.

In that case, I was lacking not only some basic financial planning habits, but the habit to be constantly forward thinking, keeping my eyes on the horizon for what was to come. Creating the habit ahead of time means you’ll do the right thing even in the face of distraction. When you do something over and over again, it becomes ingrained in your subconscious as a permanent behavior. Do you really have to think about driving or riding home? No, you just do it. Building mind-shaping habits into your workflow takes the brain power out of making the right decision in the moment. That way, when that lump sum of money drops in your lap, you’ll automatically know what to do.

Through time, trial and error, I did begin developing mind-shaping habits and building relationships, and I saw results. My career began to accelerate. I got a job with the best company in the hospitality industry, Disney, where I quickly moved into several roles before being promoted to sales director. But no matter how far I advanced in my career, I always came back to the same three principles: Let go, listen to your spirit and remain open.

Looking Inward

Fifteen years ago, at the urging of my spirit, I left Disney. Professionally, I was content but not happy. I was successful on the outside, but insignificant on the inside. I was going through the motions because I had settled for a chair, a check and a cup of coffee in a cubicle farm. It was time to start the cycle over again.

What I’ve Learned About Success: You Have to Keep Starting Over

I decided to cash out my entire retirement plan with significant Disney stock, and took out a line of credit on our house. I had three years of savings to make a new venture work. I could sense a new truth was beginning to emerge. I gave myself permission to focus on helping the least, the last and the lost in society. This was the best decision of my life.

I took all of the experience, wisdom and insights I learned up to that point and started a business that allowed me to pour my learning back into others. I began consulting, speaking and writing. Each door I opened revealed more and more doors. With each new chapter, I had more to learn, more chances to fail and more opportunities to share. That business continues to thrive today.

In pursuing my own venture, I’ve learned that being intentional about your choices and your message is vital to achieving success and reaching people’s hearts. People size you up in three seconds. Before you open your mouth, they’ve already made a mental assessment about whether you are someone they could know, like and trust. I’ve learned to be a walking, talking representation of what I stand for at all times. For me, that means to smile. Be nice. Say hello to the person who can do nothing for you. Greet the receptionist of the business with a warm hello. Introduce yourself confidently. Listen more and talk less. Speak clearly and thoughtfully.


As long as you are letting go of your failures and remaining open to what wants to emerge, there will always be something else waiting for you.


I even carry this message out through my physical appearance. I am very intentional about the message I am going to convey and dress to complement that message so that clothing becomes an attraction and not a distraction. This is so important to me because it can be the difference between whether someone truly hears what I am saying, which is why I do what I do.

It’s so rewarding when all of this intention pays off. Recently, a woman sent me an email after hearing me speak at a conference. She wrote, “Before I came to this conference, I was ready to resign my position because of job dissatisfaction. The communication is poor between the departments and expectations are unclear. However, after listening to you, 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, waiting for it to happen to me, not for me. I asked for a meeting with my manager, and it went well. I have a little bit more direction, some goals to meet, and I have given myself a deadline of 90 days to determine if I should stay.”

That is one of many emails that make all of the attention to messaging worth the effort. Everything I do and say is for the person on the other end of the speech, book, article, video or social media post. To serve my audience, I have to be able to cut through all of the other noise.

And it’s harder than ever to shut out the noise—even for myself. The more success you find, the more you are in danger of letting busyness obstruct your view of where you are in the cycle.

When you’re starting out or you’re not in a good place, the need for change and growth is obvious. When you’re realizing the success of your efforts, you must carve out time to really examine what is needed. I know firsthand that is easier said than done, and you have to find what works for you.

What I’ve Learned About Success: You Have to Keep Starting Over

This past year has been another quite significant period for me in my life and career. I’ve made another shift. I returned to my own lessons that I first shared years ago. I realized everything that I did to launch my new journey 15 years ago worked. Have I been successful? Yes. Am I generating enough revenue to pay the bills and live a comfortable lifestyle? Of course. But something again stopped clicking, and I sensed I was in a holding pattern similar to an airplane circling the airport waiting to hear, “You’re now cleared for landing.”

And I started the whole cycle over again—letting go, listening to my spirit and dedicating myself to being open.

That’s what I’ve learned most about success: You have to keep starting over. You can never let yourself remain on cruise control. If you feel like you’ve made it, that’s your cue. If you keep the wheel turning, success never runs out. It is infinitely abundant. As long as you are letting go of your failures and remaining open to what wants to emerge, there will always be something else waiting for you.

Related: 17 Inspiring Quotes About Reinventing Yourself


This article originally appeared in the March 2018 issue of SUCCESS magazine.

Simon T. Bailey is an international speaker, writer and personal transformation strategist. He is the author of Shift Your Brilliance: Harness the Power of You, Inc., and Be the SPARK: Five Platinum Service Principles for Creating Customers for Life. When he’s not working, he enjoys rooting for the Buffalo Bills (his hometown team).