My 3 Worst Business Mistakes

We all make mistakes, and I’ve probably made more than most in my career. Being vulnerable I’m going to share my worst 3 mistakes and what I learned from them.

Story 1: Taking a Job without Considering My Values

I once took a job at R&R Partners, the firm behind What Happens Here, Stays Here. They also do marketing for MGM Resorts and other casinos. I was young and was excited to rub shoulders with some really creative and bright minds.

And to be clear before judging my career choice, I fully acknowledge that there’s plenty of questionable industries (gambling, narcotics, MLMs, etc.) and most people don’t have the luxury of being picky. In my case I knew moving to Las Vegas nearly every job was tied with the gaming industry (they call gambling the ‘gaming industry’ in Vegas).

I started my job working on government and nonprofit clients, which was fantastic for me. But management soon decided that my skillset could be used for MGM Resorts, so I was moved to that account as a promotion.

Quickly I learned I was in over my head. I was doing the marketing for three major casinos, which included their shows. One of the casinos had a topless show. I remember them giving me tickets to go with my wife (which was a major head scratcher, as I wonder how many men take their wives to topless shows). I didn’t go.

It was already a strange situation for me morally, and one day I was on a call with a major airline and they weren’t allowing me to run an ad with scantily clad women in their inflight magazine. I was literally on that call having to negotiate the amount of cleavage allowed in their magazine. And that’s when I knew I had to quit. And I did.

Mistake Made: Not understanding the real business that my company was in.

Mistake Remedied: Leaving the job, despite having to pay back my relocation fee and find a new job. It was the right decision and my life has been better for it.

Story 2: Sending an Angry Email

Early in my career I was working on a major project with a few coworkers, and one of them just wasn’t getting his portion done. I was trading notes with him on his portion, and it looked something like this:

Me: When are you going to get these numbers?

Him: I’m working on it, but it’s just not all coming together.

Me: You’ve got to get this in, otherwise we’re all going to have to stay late.

Him: It’s just not happening. Sorry.

Me: Unacceptable.

Later, his boss pulled me aside and showed me that he had forwarded the message chain to her. At first I was grateful; in my mind it was clear he just wasn’t pulling his weight.

But as we talked about it she taught me a valuable lesson. She acknowledged he wasn’t pulling his weight, and that I was probably right. BUT I sat about 30 feet away from him. Rather than trade messages I should have gone over and talked with him.

Mistake Made: Sending a message instead of talking about it.

Mistake Remedied: I now swing by coworkers desks to discuss things. Literally every sensitive situation since then I have talked it through and it has led to me generally getting reviews of being collaborative.

Story 3: Not Prioritizing People

I once started teaching a large 120-student university class on a whim. You can read the full crazy story here, but in a nutshell I only had a few days to prepare a curriculum and to start teaching.

That whole semester I felt like I was just one class ahead of my students. I was spending all my time prepping material, creating assignments, and grading exams. I was trying my best to teach these young, budding students about marketing.

When I got my course review at the end of the semester I was surprised to see how many students mentioned that they didn’t get any individual time with me.

“Was this part of being a professor?” I thought.

And then it hit me – this is the MOST IMPORTANT PART of being a professor! Class isn’t just about what you learn. Arguably the more you feel noticed, valued, and that your opinion matters you’re going to learn more as a result. Class is better when you’re called on my name and where the professor knows you.

In management it’s the same way. You’re managing individuals. Real people. They all need to feel noticed, valued, and that their opinion matters. The business is important, but the people are essential. (If you want to learn more about this, read 13 Principles of Becoming the Boss People Want to Work For).

Mistake Made: Not prioritizing people, in my case not meeting with students and letting them feel known.

Mistake Remedied: After that I scheduled meetings with each student at the beginning of the semester. It was amazing. I could call on them by name, understand their situation if something happened (e.g., were getting married, having visa problems, etc.), and help them feel valued.

Conclusion

To be clear, these are only 3 of the many mistakes I have made in my career. The major lessons I have learned have been to consider my values, don’t send a note when you should talk, and to prioritize people above all else have been invaluable in my career progression.