Recently, I made a visit to see a relative who lives in a retirement home here in Madison. Most would expect a retirement home to be sort of depressing and the last place to go for inspiration, but I found the experience to be quite the opposite.

I enjoyed hearing the stories and experience of the seniors. I listened, laughed more than I had in a while, and soaked up the tremendous life wisdom they shared with me.

As I walked down the halls on my way out, I started to reflect on my own life. I began to envision myself as an 80-year-old resident there. What would I be thinking about?

I was reminded of a recent article I read about a palliative nurse who recorded the most common regrets of her dying patients.

Click here for full article

.  She put all of her findings into a book called “The Top 5 Regrets Of The Dying.”  In the book, she shared that the most common regret was Wishing I would have had the courage to live a life true to myself, not the life others expected of me.

Click here to check out The Top 5 Regrets Of The Dying book

She further explained that when people realize that their life is almost over and look back on it, it’s easy to see how many dreams have gone unfulfilled. Another interesting finding was that the biggest reason for not fulfilling life dreams was not making poor choices, but failing to have the courage to step out and go for opportunities to live our dreams.

I began to ask myself, “What dream opportunities am I am not stepping out and going for?”

Right away, my heart starting thumping and I was reminded of a big dream I’ve had for some time now. You know, the kind you put back on the shelf for later, the one you will pursue when you have more knowledge, more experience, and more money.

My big dream combines 3 things I absolutely love; helping people grow businesses that they love, facilitating small groups, and escaping the harsh, Midwest winters for the white sand and blue waters of the Caribbean.

Yes, my big dream is putting on a small group, business-building retreat in the Caribbean. I knew it right away, this was my opportunity. I had to step out and do this. If I didn’t, I would be sitting around the cribbage table at the retirement home at age 80 and totally regret it.

Now the next thing that happened will surprise you, even after this powerful, “aha” moment, I didn’t do it. But I did start to talk about “doing it” (which was at least a step in the right direction).

The very next day, I was in a conversation with my friend, Darin, and he asked me what new business ideas I was working on, so I shared my big dream with him. Of course, at the very end, I said that this big dream was what I eventually wanted to do, but that I would do a less risky, scaled-down version here in Madison, first, and then build toward my big dream. Darin went on to ask me a very simple and life changing question, “Why start start small? Why don’t you just go big and do the Caribbean one?” I thought to myself for a minute and then responded, “You know, you’re right, why not?”

Even after the really powerful “aha” moment in the retirement home, it still took the encouragement of others around me to muster up the courage to step out and go for it.

So today, I am living my big dream. I recently launched a one-of-a-kind small group business retreat for life coaches, business coaches, fitness coaches, and service-based consultants. I call it the “Small Groups, Big Profits” Retreat and it takes place in sunny Punta Cana, Dominican Republic this February 4-9.

For more info on the retreat, click here

So I have two final questions for you…

#1 “What big dream do you have?

#2 And what dream opportunity is right in front of your face that you would regret not going for today?”

I’m saying NO to fear, NO to “maybe someday” and saying YES to going for it!

Wanna join me?


Chris Rudolph is a husband, father of 3, and a Freedom Business Coach for Digital Marketers. He specializes in working with those who are underpaid, hustling around the clock or missing out on valuable family time build their own Freedom Agency. He helps them grow their income, scale with a team and enjoy more time with their family.


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Chris Rudolph