Misstep 1: The Name Game
I was 23 and just off my first consulting project, feeling confident. I had taught Sears technicians how to use their customer relationship management (CRM) system. My not so secret trick was bringing donuts to each session. The next project was for Best Buy, they were also implementing new systems for their technicians.
With a bunch of colleagues, I headed to Minneapolis to learn the new system. I was so excited to have coworkers. The first project had been lonely—I would fly to a destination with a few other colleagues, but then we would all go our separate ways for the week. Sitting in a room full of people was energizing. We would learn a new detail about the system and then one of us would teach it back to the rest of the staff. It was only slightly terrifying because the project manager from my company had fired several of my coworkers in front of Best Buy employees. I know, savage!
I knew at some point I would be called to the front to present. My friend and colleague had started on this project before me and was explaining how a process plays out. He used a fake name, "Ms. Hornblower comes in and hands a tech her DVD player...." If you've never used a DVD player, trust me, they were popular.
I was then called on to present to the group. They wanted to make sure that I understood the process and could explain it. Welcoming the challenge, I smiled and went for it. Except instead of calling her Ms. Hornblower—which is also an awful name—I had to one-up him accidentally. "Ok, Ms. Hardblower." And then the room exploded in laughter. It took me a second to realize what I said. In that same second, I thought, I'm getting fired right now, in front of everyone. However, I noticed the client lead and my boss laughing uncontrollably. I thought, maybe, I still have a job when I finish this.
The group eventually stopped laughing, and I explained the rest of the process without any inappropriate mistakes. Trying to wipe away the sweat and discomfort, I listened to the Best Buy lead talk: "That was amazing. I've made a decision. At the end of every class, Ron presents."
And with that, I kept my job, most of my dignity, and learned an important lesson: humor is a powerful tool, but always choose your words wisely—especially names that can be easily twisted into something inappropriate.
Misstep 2: The Opportunity That Got Away
The second consulting firm I worked for was betting big on technology. We were project managers first, but our future was CRM implementations. My initial project was with SBC Ameritech, which was later purchased by AT&T. Per usual, I was working on a training project.
Things were going so well that a contact at SBC wanted to hire me. The salary he mentioned was more than double what I was making before bonus. And although I hated the commute, this would have been a huge step for my career.
Since I had a nice relationship with my boss, I mentioned that the client was trying to poach me. He was unbelievably honest and only a little too optimistic. I remember him telling me, "If that's what you want to do, go for it. They'll have to buy you out, but you should know, if we have a big year, your bonus could be double that salary."
I saw dollar signs and decided to stick around. Less than a year later the tech bubble burst. My company shut down, and the SBC offer had long vanished.
Lesson learned: do your homework. Explore every opportunity in detail and use that knowledge for leverage. Even if you decide to stay, knowing your worth leads to better career decisions.
Misstep 3: The Promotion That Fizzled
After college, I worked as a promoter, organizing parties and events around Chicago. One of my favorite projects was a dating game night at Joy Blue. The owner was a bit skeptical of the concept but went with it.
Running around town, I lined up gift certificates at fancy restaurants for the winners, set up a schedule for guest bartenders (basically twisting the arms of a few of my friends), and started promoting the event.
Since I love almost any chance to be in front of a microphone, I hosted the dating game portion of the event. I also found friends to be contestants, prepared questions, and felt ready to go.
As the promotion went on, the Sun Times and Chicago Tribune covered the event, and the bar was busy! You can still find this article: https://www.chicagotribune.com/2002/01/09/dating-life-a-game-or-a-science/
As the press grew, another bar poached me to bring the event to their establishment. With more money and the promise of a permanent gig, I took the offer.
But I made a rookie mistake: I didn't consider the audience. The new bar, Gin Mill, was a college hangout. The students didn't care about prizes, relationships, or my attempts at humor.
The Bigger Picture
Looking back, I'm grateful for these missteps. Each one taught me something invaluable about preparation, self-awareness, and resilience.
The true measure of success isn't avoiding mistakes, but how we learn, adapt, and transform them into opportunities for growth.
What moments have shaped your path? How have your missteps become stepping stones to something greater?
Failures aren't the opposite of success—they're part of the process. Look back with kindness, laugh at the awkward moments, and keep moving forward.
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