My Shoes Don’t Match!

It was 10 minutes before I was about to walk into my prospective client’s office and ask for a signature on the largest contract my company had ever received – $1 million dollars! Until that day, the largest project we had ever done was $200K. This project was 5 times that size which made me half ecstatic and half terrified! I was dressed to the nines in my best navy blue business suit. It screamed “I’m successful!”. As I was waiting outside the office of the man who would hopefully sign the contract, I looked down at my shoes. My tasteful, knee-length skirt couldn’t hide what I saw in horror. I was wearing two shoes that were completely different colors – one black and one brown! Neither one of them matched my suit. OMG!

Setting the Stage

I once heard that unsuccessful entrepreneurs spend time to save money while successful entrepreneurs spend money to save time. When I started my company, I didn’t have a choice. I started my company with a few hundred dollars in the bank and I was bootstrapping it without investors or partners. So I had to spend time to save money. I would work around the clock to avoid spending an extra penny!

Two years in, I was definitely on the fast track, working 80 hours a week, always chasing new business, often feeling like an imposter. “When is someone going to figure out that I have no idea what I’m doing!?”, I wondered. Thankfully, nobody did and I kept going, learning as I went along. I was having the time of my life and I was grateful for our growth trajectory. For the first time in my life, I reached the point where I could start making decisions based on factors other than money. As a busy entrepreneur, time was my most precious commodity so I started learning ways to protect my time even if it costs a few more dollars.

I discovered that shopping was one area where I could save time. When I found something I liked – a blouse, a suit, a pair of pants, a purse, shoes – I wouldn’t just by one of them. I’d by multiples in different colors. Don’t worry about the price tag. Buy a bunch of them and I wouldn’t have to spend time shopping around for more stuff. And that’s how I ended up with three identical pairs of shoes in my closet – one pair was black, one navy blue and one brown.

The Big Event

On the morning of my million-dollar client meeting, I was in my usual frantic hurry. It was early morning and I remember running into my closet to put on my shoes. The lights were off and I just slipped on a pair of what I thought were my navy blue shoes in the dim light. Then, I ran off to the office to gather some final papers before heading to my client’s office.

Amazingly, nobody at my office noticed the mismatched shoes and neither did I. At 10:30am, I headed downtown, driving my usual 10 mph over the speed limit. I still hadn’t looked down at my feet, I was more worried about the how I was going to convince my client that he should entrust a services contract for one million dollars to my small business.

Standing outside his office, I finally glanced down and realized that neither one of my shoes matched my business suit or each other! I looked at my watch – it would take me two hours to drive home in Chicago traffic, change shoes and drive back. I only had 10 minutes! It was hopeless.  

It was a moment that I’ll never forget. I shrugged my shoulders and decided to ignore it, and I shifted my thoughts to my speech, rehearsing the words I had practiced numerous times. I was going to hope the client didn’t notice my shoes and if he did, well, we’d have a good laugh!

The meeting only lasted 30 minutes, my client never noticed my shoes, and he signed the contract! I left his office on cloud 9. I decided to go back to the office with my mismatched shoes, rather than going home to correct my fashion faux pas. My employees found the whole thing hilarious and that began a tradition at my company that continues to this day.

Anytime I have an important closing meeting with a client, I always wear mismatched shoes! It gives me a funny story to tell. (One client even insisted on taking a picture of their signed contract next to my mismatched shoes!) It also enables me to talk about the million-dollar contract which established credibility for my company. I managed to turn an embarrassing mistake into a gift that keeps on giving. And best of all, I get to laugh at the situation in retrospect and I get to laugh at myself!

Lessons Learned

• Make lemonade out of lemons. I could have flipped out over something as silly as a pair of mismatched shoes and blown the chance at a million-dollar contract. But I held myself together and focused on the things that I still had control over. As they say, accept the things you cannot change, change the things you can and be sure you know the difference.
• Make fun of yourself! A mistake can be a challenge or a strength. I found a way to turn my mistake into a strength by laughing at myself. Others may be laughing AT me, but I think most of them are laughing WITH me.
• Don’t dress in the dark in your closet. Nuff said.

Submitted by: Carolyn J., Chicago, IL

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