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Dr. Benjamin Ritter: “Selling, marketing, everything is just answering questions”

Selling, marketing, everything is just answering questions. I thought selling and marketing was just post it/build it and people will come. You can’t sell to someone that isn’t ready to buy. You need to take the time and nurture the process in order to sell. As a part of our series about entrepreneurs who transformed something […]


Selling, marketing, everything is just answering questions. I thought selling and marketing was just post it/build it and people will come. You can’t sell to someone that isn’t ready to buy. You need to take the time and nurture the process in order to sell.


As a part of our series about entrepreneurs who transformed something they did for fun into a full-time career, I had the pleasure of interviewing Dr. Benjamin Ritter, founder of Live for Yourself (LFY) Consulting. Dr. Ritter is a Chicago-based leadership and empowerment coach. He spends his work days coaching and guiding intrapreneurs, entrepreneurs, and senior leaders toward greater meaning at work and in life. His graduate educational pursuits earned him an EdD in Organizational Leadership from Pepperdine University, an MBA in Entrepreneurial Management and an MPH in Health Policy Administration from the University of Illinois at Chicago. During his time as a healthcare executive and side hustling entrepreneur he was over worked and under-utilized, and despite his professional success didn’t feel successful. After much introspection he pivoted professionally, founded LFY Consulting and started crafting a more effective, efficient, and aligned life. He is the curator of The Three C’s of Self-Leadership© and The LIVE System©.


Thank you so much for doing this with us! Can you tell us a bit about your “childhood backstory”?

My dad was a hard working entrepreneur. He did what he needed to do to get things done and make money. He used to take me on side handyman jobs when I was younger and to his real estate office. I became used to the idea that you took value from your work, and that you were responsible for the money and life you created for yourself. Work wasn’t a desk job to me, nor was it just one thing.

What was the catalyst from transforming your hobby or something you love into a business? Can you share the story of your “ah ha” moment with us?

I spent years side-hustling for extra money and to launch a business but nothing took off nor did it really feel right to me. I had a lot of false starts when it came to launching my own business. Then at my day job I sorta hit a breaking point of not being happy, I was overworked and under-utilized, and kept moving up in the organization but didn’t feel successful. Plus, in my recent promotion I felt that there were issues with leadership development which aligned perfectly with my interest and experience in coaching. At that point I spent some time reviewing the career I wanted and how I could get there. The quickest and best path looked to be getting my doctorate and launching a new company in the field of coaching. Since I was already a coach in a different industry, I thought it would be a smooth transition.

There are no shortage of good ideas out there, but people seem to struggle in taking a good idea and translating it into an actual business. How did you overcome this challenge?

Taking an idea and making it reality takes clarity, confidence, and control. You need to put in the effort to understand your why, what, and how, specific goals, milestones, and indicators of success. Plus you need to build the skills that will help you succeed, and then also believe that you can achieve what you’re setting your heart on. Then, you also need set processes and consistency in your efforts, and emotional resilience for when times are tough. I’ve spent a lot of time coaching myself, adapting, and staying consistent in my efforts and mindset.

What advice would you give someone who has a hobby or pastime that they absolutely love but is reluctant to do it for a living?

I’d take the time to really understand the core reason that is holding you back from doing it for a living. If you love something, then it’s important to you, and it connects to your values, which implies it’d be a pretty fulfilling job and career. If your core reluctance stems from a lack of confidence in yourself, then find ways to build confidence. But if your core reluctance is that you don’t want to make your hobby a job then I would avoid trying to make it a career.

Any job or career takes work and can be stressful. There is a chance that you might start disliking your hobby or pastime if you try to make it a career. You need to be ready and willing to put up with the stress that comes with being an entrepreneur.

It’s said that the quickest way to take the fun out of doing something is to do it for a living. How do you keep from changing something you love into something you dread? How do you keep it fresh and enjoyable?

The trick is to do the things you love to do, or find ways to make the things you dislike doing fun. Or just hire someone to do the things you don’t like doing. You also have to keep the meaning of your work and job front of mind. How can you remind yourself on a daily basis how much you love your work?

What is it that you enjoy most about running your own business? What are the downsides of running your own business? Can you share what you did to overcome these drawbacks?

I enjoy the freedom of choice and the opportunity for more at any moment. There’s no set path, only the one that you create.

The downsides are the pressures that come from problem solving, wondering if “this” is the right career path, and of course, always working toward getting new business.

To deal with these drawbacks I’ve basically coached myself through the process I use with clients. I create clarity, through understanding my why and goals/processes, focus on confidence through skill building and internal belief systems, and create control, through emotional awareness and curiosity, and boundaries.

Can you share what was the most striking difference between your actual job and how you thought the job would be?

The greatest difference would be the level of enjoyment I thought might accompany running my own company and coaching full time. A job is a job either way. There’s going to be that aspect from any career you choose. You just need to focus on the aspects you love more than anything that are created from doing a job that holds the most meaning compared to others.

Has there ever been a moment when you thought to yourself “I can’t take it anymore, I’m going to get a “real” job? If so how did you overcome it?

YES! 100% and a lot of the clients I work with are battling that same inner voice. It’s super important to review the source of that voice. Is it doubt? Or is it really your calling? Doubt will continuously rear its ugly head and that’s why you need to ensure that you have systems in place to provide evidence to the contrary.

Now, to be fair there are “real” jobs out there that could probably fit your values and create fulfillment for you and your life. So there’s no right or wrong answer here. So as long as giving up isn’t giving up on your calling and true self, you should take the path that will lead you to the life you want.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I would say the “copy paste” mistake is pretty funny. You send SO many emails all the time and sometimes they are similar in content or requests. Sending the wrong brand name in an email to a competing brand was pretty funny.

The lesson I learned. Slow down. Seriously. But not too much.

Who has inspired or continues to inspire you to be a great leader? Why?

I have to inspire myself. I teach self-leadership. No matter what happens in your life, you always have the ability to lead yourself. Your choices are your power.

How have you used your success to make the world a better place?

I do hope to become more successful over the years, and only so that I can impact more people. My goal is to create a level of empowerment in others so that they realize that their life is their own. They get to live for themselves. They get to choose the life they want. They can create the life they want. We all deserve that.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. Think bigger. You are only limited by your own experiences. I held back from the spotlight and thinking about the life I could be living in the past.
  2. Connect with your values. Fulfillment and motivation are directly tied in with your values.
  3. Strengthen your relationships in your field of interest. I spent too much time learning and not connecting. Your first opportunities will develop from your current relationships.
  4. Broaden your relationships/partnerships. Expand your network and develop win-win partnerships. Once again, the global most valuable currency is relationships.
  5. Selling, marketing, everything is just answering questions. I thought selling and marketing was just post it/build it and people will come. You can’t sell to someone that isn’t ready to buy. You need to take the time and nurture the process in order to sell.

What person wouldn’t want to work doing something they absolutely love. You are an incredible inspiration to a great many people. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

I would love to inspire people to live more for themselves. To realize that life doesn’t have to be impacted by the judgment of others, a lack of confidence, or fears. Life is meant to be lived in a way that is true to each individual. What do you value? How can you live your life in alignment with yourself? How can you realize that success is progress, and that failure is progress, and thus the journey of life itself is progress. Be accountable for yourself. No one else will be, and live for yourself.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Not only can water float a boat, but it can sink it also.” This quote reminds me that you can either cause destruction or support, and that it all depends on how you want to utilize your skills. Do you want to help others drown or float? No matter how I feel at any given moment, I always want to help others float.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

Esther Perel. Her thoughts on human sexuality, desire, and connection are so intriguing and have changed my life.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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