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The Failure That Changed Everything

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Yesterday I ran into an old colleague from my first job in Chicago. He immediately grilled me, asking what I am doing these days and even wanted to know the cross streets of my home. It was clear that he was trying to determine how successful I am today… and probably the value of my home.

I worked with this guy for three short months in 2008. I had just arrived in Chicago with a fresh Master’s degree in American Fine and Decorative Art from Sotheby’s Institute of Art. My goal was to work in art sales, and I thought that this job at the auction house would lead to a long career in the arts.

I was wrong. The job wasn’t as described, and the work environment was toxic. I was expected to work at least 10 hours a day on weekdays, and I was usually scheduled to work on weekends. My colleagues were anything but nice. I remember how pretentious and condescending they were when I told them that I lived in Lakeview. Even my Upper East Side grad school classmates were kinder when I said I lived in West Harlem. (And Lakeview is lovely – it is a top Chicago neighborhood).

The company’s owner and namesake provided everyone with a true Devil Wears Prada experience although she preferred to carry both Hermes and Chanel to show that she prioritized displaying her wealth over organization.

My first day at the company was in September 2008. I had inconveniently timed my arrival with the start of the recession. Layoffs were immediate, and since I was one of the last people in, I was one of the first people out. I was one of four people laid off on December 16, 2008. The company still held a holiday party the next day… proving that the wealthy can still be tacky and tactless.

I failed at the career that I had thought I was destined for. It was a tough blow to my ego, and months of being laid off were an even bigger blow to my finances. The course of my life was changed completely, and for the better.

When the former colleague from the auction house asked what I do now, I explained that I started a blog eleven years ago and that I blog casually while earning a nice passive income. If you asked me at 24 years old what success would look like for me, I am sure that I would have said that I wanted to be head of a fine art department at an auction house. Today, I look at success very differently.

For me, success is getting to spend my time in the ways that I want, while not having to worry about money.

I am sure that everyone has their own idea of success. But this is the only one that matters to me. This personal definition of success is shaped by my life experiences. There were times when I could barely afford rent. For years, I felt like I was drowning in student loan and credit card debt. I spent years working miserable jobs just to make ends meet. It was years of hard work and blogging on the side that allowed me to earn the freedom and flexibility that I enjoy today. The fact that I earned it myself makes it mean so much more.

The colleague? He is back at the same auction house. I am guessing that his career went just the way he wanted. He might have heard my story and thought that I failed at what I set out to do.

My success is spending days with my daughter. Not having a set number of vacation days. Getting to turn down projects that don’t interest me. Being able to afford everything that I need and most things that I want. It is having the knowledge that I am happier now than I ever was before.

And shouldn’t happiness be more important than success?

Kit Wong

Monday 19th of September 2022

Love your post. We share the same interests - cooking, travelling and even our name. I cannot agree with you more about happiness vs success. I am 61 years old, raised 3 children and they are all in their late 20 now. I was struggling with work and caring for my kids for years. I could not decide whether to quit working to be a stay-at-home mom, or continue to juggle between work and family. The company layoff took care of that decision making for me. Raising children is very rewarding. Enjoy your journey. We are empty nesters now, looking forward to have grandchildren to take along to vacations.

Paige Westley

Tuesday 30th of August 2022

I can relate to this so much! After coming back from school my first year and taking a year off, everyone was set on the fact that I was going to be the failure and less successful than anyone. Today, my version of success is very different. and I am the happiest I've ever been. I am one of the only people I know from classmates that already owns a home, about to get married and have an amazing job that I absolutely love! I have everything I need and am still working towards being able to have everything I want, but I've never been happier!

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