Climbing the Ladder of Success...But Is It the Right Wall? (Monday Moment ep. 861)
Live Inspired Podcast with John O'Leary
John O'Leary
4.8 • 695 Ratings
🗓️ 9 March 2026
⏱️ 5 minutes
🧾️ Download transcript
Summary
Years ago, I spoke with 40 business owners. The goal of the event was to bring together some of the highest achievers, connect them with one another, and expand their businesses and their lives.
Wondering what success even meant to them, I kicked off the session by asking what they would do professionally if they could achieve anything and knew they could not fail.
After a moment of reflection, a brave gentleman stood and proudly announced, "I'd make it big. I mean, like really, really big!"
He wanted to increase sales, expand personal accomplishments and significantly achieve more success than any of his friends or former classmates.
This conversation was eerily similar to one I was part of almost a decade earlier with another gentleman. He, too, had strived to "make it big. Really, really big." The difference was that the conversation with him wasn't taking place in a boardroom with a lifetime of possibility in front of him. No, this conversation took place in a hospital room with a lifetime of regrets staring back at him. Let me explain.
Transcript
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| 0:00.0 | Hello, my friends and welcome to the Live Inspired podcast Monday Morning Moments with John O'Leary. |
| 0:19.3 | There's an old quote. Many of you remember it. |
| 0:21.1 | It goes like this. |
| 0:21.9 | If you do not change your direction, you may end up exactly where you are heading. |
| 0:28.0 | Well, years ago, I spoke with about 40 business owners in one room. |
| 0:32.8 | The goal of the event was to bring together some of the highest achievers, connect them with |
| 0:36.7 | one another, and then expand their businesses, and then hopefully, their lives. That was the goal. |
| 0:42.3 | Wondering what success even meant to these leaders, I kicked off the session by asking |
| 0:47.3 | what they would do professionally if they could achieve anything. They were thinking big, |
| 0:53.3 | and they knew they would not fail. |
| 0:55.8 | After a moment of reflection, a brave gentleman stood and proudly announced, |
| 1:00.6 | well, I'd make it big. |
| 1:03.0 | I mean, like, really, really big. |
| 1:07.6 | He wanted to increase sales. |
| 1:09.7 | He wanted to expand personal accomplishment and significantly wanted to achieve more success, he said, than any of his friends or former classmates. |
| 1:17.7 | That was a stated goal. |
| 1:20.0 | This conversation was eerily similar to me, one that I had just a couple decades earlier with a different gentleman. |
| 1:29.7 | He, too, had strived to, |
| 1:37.1 | and I use the finger quotes right now, make it big, make it really, really big. The difference was the conversation with that gentleman a couple decades earlier was not taking place in a boardroom |
| 1:42.0 | with a lifetime of possibility in front of him. No, this conversation was taking place in a boardroom with a lifetime of possibility in front of him. |
| 1:45.1 | No, this conversation was taking place in a hospital room with a lifetime of regret staring back at him. |
| 1:53.7 | Let me tell you more about it. |
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