Most people can point to the significant moments in their lives—those times when a piece of advice or a pearl of wisdom put you on your path to the future. My turning point came when my boss at Association X made me an irresistible offer. It was, like so many propositions that tempted my youthful enthusiasm and challenged my entrepreneurial instincts, an opportunity I couldn’t refuse. With a sly gleam in his eye that looked like he had spotted a fish about to bite the hook, he said, “Do you want my IT headache.”

Of course, I thought he was exaggerating. How much harder could his IT stuff be than what I was already doing? I had just given birth to my daughter Ashley. In addition, I had been given the responsibility of “birthing” a new for-profit subsidiary for Association X. In a short period of time, with few resources beyond my trusty rolodex and phone, I had discovered clients and brought them into the fold of Association X’s new website management company. I was already crushing it. Hadn’t I survived Y2K? Wasn’t I making my clients’ online dreams come true? I was pretty sure I had IT superpowers.

The vision of myself as one of the Avengers imploded when I discovered that the phrase “IT headache” was not hyperbole. It was a derailed AMS implementation and an incredible understatement. Association X was the lucky recipient of our vendor’s upgraded software package. We were the FIRST to use this new version of the product. There are lots of synonyms for “first.” One of them is “guinea pig.”

During the count-down to launch, I was as stressed as a newbie astronaut in the capsule. But after the critical key strokes were made, the data seemed to glide into place with the precision of a successful shuttle landing. I breathed a deep sigh of relief. As you might have guessed, it wasn’t long before things began to unravel.

Of the many glitches, the fact that Association X was not able to process payments for two months was the worst. The membership director, with whom I once shared fun lunches, was no longer speaking to me. Our AMS was so full of bugs that even a case of Raid wasn’t going to fix it. The resources were located in Hyderabad or some equally far-flung location. Patching the code was out of the question. Instead of calling the exterminators, we called the lawyers.

While this drama was playing out, I was struggling to keep the successful part of my career, the for-profit business, growing. Association X had problems that were more fundamental to its existence. An ongoing game of musical chairs in the corner office had brought Bob into the hot seat. Because Bob was semi-retired and temping at the top job, the staff initially dismissed him as a non-entity. This turned out to be a serious miscalculation.

Bob would not settle for the status quo. Hundreds of Bob’s probing questions kept everyone running scared and on their toes. At first, I was certain that Bob was part of a malevolent staff cleansing. I imagined that he had been hired as the executioner to give a new permanent CEO a blank slate.

Over time, I grew to understand that Bob’s compulsive curiosity, his detailed approach and his expectation that we think creatively was part of a commitment to excellence. I respected his tireless vigilance in a situation where he could have been coasting. He became a friend and a mentor.

Being the type of person who leaves no stone unturned, when Bob finally transitioned to full retirement, he provided a detailed report to his successor. This document outlined the senior staff’s performance, warts and all. There was stuff in there you wouldn’t want your best friend to know.

Unfortunately, Bob used the wrong email distribution list. Instead of sending this highly confidential information to the new CEO, he sent it to the very people who already were acutely aware of their own shortcomings. When I got home from work, the letter was in my inbox. I immediately called Bob. I could hear the hope in his voice when he asked about a magical retrieve button. I delivered the bad news as gently as possible. My last act of friendship for Bob was a late-night trip to the office to delete the email from each person’s inbox.

Time has not taken the edge off these experiences. Some of my early misadventures still make my skin crawl. The upside is that putting my feet to the fire helped me develop attitudes I would need to succeed later in my career. I learned this:

• Question everything
• Keep a stiff upper lip
• Don’t rush to judgement
• Take baby steps before you make a leap
• Apply the Golden Rule to all relationships
• Don’t rely on a magical retrieve button

Yes, what doesn’t kill you makes you stronger. But watch out, if you’re not careful—it can also make you a consultant.