Lofty Adventurer

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Rita Bailey served in key leadership roles during her 25-year career with Southwest Airlines, including Customer Service, Sales/Marketing, HR and heading SWA University for People. Rita knows what it takes to inspire, develop and lead people to perform because they want to, not because they have to. She served as past Chair for ASTD, now ATD (Association for Talent Development) and has been on advisory boards and committees for various profit and non-profit organizations.


From Corporate Executive to Entrepreneur

For several years, I met monthly with a group of 10 friends for the sole purpose of supporting each other in whatever we were “up to” (personally and professionally) We would rotate the gathering each month to one of our homes and spend three hours sharing what was happening in our lives. The beautiful thing about this group is that there was no agenda and no judgment. One day the person who originally started the group turned to me and asked if I'd be interested in a partnership to share this concept with the world. That was a lofty goal, and without hesitation, I said, “Yes.”

We started by defining what being “Up to Something” meant. The profiles of the person who fit our definition were those whose intentions were to make a difference in whatever they were “Up To”. We interviewed people from different industries, countries, professions, and walks of life and there were consistent characteristics among them all. They are focused, passionate, humble, bold and they all were making a difference in the lives of others. We wanted to get their message out to a greater audience as a way to inspire others who were ready to follow their dreams. We conducted presentations, workshops, launched other Up to Something groups and started writing a book about all the people we had interviewed. When my partner's husband was diagnosed with Alzheimer's, she decided to become his full-time caretaker, and I became sole owner of the trademarked name and business. Like other entrepreneurs, I had to determine the purpose, audience and message for the Up To Something brand. Up To Something is now a consultancy that helps people get clear about what they want and how to develop the best strategy and resources necessary to achieve their goals.

Brand Identity

I consider myself a Visionary. I imagine bigger possibilities that help others stretch beyond their comfort zones. I also take the big picture and chunk it into bite-size pieces that others can digest. My ability to connect with people at the heart and head level makes them feel comfortable sharing their most private thoughts and feelings. I seek the positives in every situation and look for solutions rather than walk away from challenges. My adventurous nature and curious mind drive me to be more courageous and take more risks. I have been blessed to experience many beautiful things in my life. My deepest joy comes from seeing others achieve their dreams and goals.

Overcoming an Obstacle

One of the worst days I have had since starting the journey is when a client told me that he felt I did not care enough about his success and didn't think that he had received the value for what he spent. It stirred lots of emotional feelings because I did care about his success. It was also a turning point for me because I realized that I shouldn't care more about a client's business and success than they care. 

I then started to dig deeper to identify their motivation and commitment to do the work. I also had to look inwardly and determine what I was doing or not doing that contributed to these feelings of failure. I concluded that some people want everything done for them and take no responsibility when they haven't done the work. Overall the experience helped me get better at assessing the situation and communicating in a way that could not be misunderstood. I am now more confident, focused and deliberate in my approaches.

Being an entrepreneur is not for the faint of heart. Do what makes you happy! Others can't steal your dreams if you have a strong enough WHY.

Joy in the Journey

I travel worldwide, sharing relevant principles for organizations and individuals who want to transition or transform personally or organizationally.  Using immersive processes provide the “what” but also the “how to” for people-profit results. I dream about creating documentary legacy stories of ordinary people who have lived their lives doing extraordinary things.

I am most proud of writing a book and launching three successful businesses. I have spread a message of hope and encouragement to thousands. I maintain excellent relationships with family, friends and colleagues.

In my spare time, I enjoy yoga, walking and hanging out with my Grands. In the second half of our lives (yes that means 100+) I intend to be healthy, vibrant and have fun as Henry and I travel the world.

I have three favorite quotes:

 “People don't care how much you know, until they know how much you care.”
“Those who say it can't be done, should get out of the way of those doing it!”
“I can find a rainbow in a shit storm!”

Visit Up to Something.