From Fashion Editor to Business School Grad: What I Learned About Being an Entrepreneur

Well, I’ve graduated from business school. Call me a master of business administration! I wanted to spend a few minutes looking back on my two years at MIT Sloan and pulling out some takeaways for any of you considering applying to business school or matriculating this fall. I wrote my first Business Casual column in August 2011. I said that, “I wanted to write this column because some fashion friends have expressed an interest in swallowing the grad school pill themselves and tumbling down this crazy rabbit hole.” Now on the other side of the rabbit hole, here’s what I would tell future students...
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Well, I’ve graduated from business school. Call me a master of business administration! I wanted to spend a few minutes looking back on my two years at MIT Sloan and pulling out some takeaways for any of you considering applying to business school or matriculating this fall. I wrote my first Business Casual column in August 2011. I said that, “I wanted to write this column because some fashion friends have expressed an interest in swallowing the grad school pill themselves and tumbling down this crazy rabbit hole.” Now on the other side of the rabbit hole, here’s what I would tell future students...
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Well, I’ve graduated from business school. Call me a master of business administration! I wanted to spend a few minutes looking back on my two years at MIT Sloan and pulling out some takeaways for any of you considering applying to business school or matriculating this fall. I wrote my first Business Casual column in August 2011. I said that, “I wanted to write this column because some fashion friends have expressed an interest in swallowing the grad school pill themselves and tumbling down this crazy rabbit hole.” Now on the other side of the rabbit hole, here’s what I would tell future students...

1. Get ready to feel weird. My first month at school was a strange time. I was 27 and back in a classroom taking notes, terrified that I would be called on to answer a question I didn’t know the answer to. It was a particularly odd transition for me as a “nontraditional candidate” because I was coming from being a fashion editor writing about florals, denim and floral denim all day. Now, rather than browse fashion blogs first thing in the morning, I was rushing to finish problem sets. Plus, I was really intimidated by my peers. The good news is that a lot of other people feel the same way, and this uncomfortable phase passes.

2. You are the average of your five closest friends. I borrowed that notion from Dropbox founder Drew Houston who gave MIT’s commencement speech this spring. Keep it in mind as you are encircled by tons of new people when school starts. Who will push you forward? Who will open you up to new opportunities? Who will support you after you’ve just turned bright red during your public speaking impromptu? It was super helpful for me to see friends starting companies while at school. If they could, I could too. And now I have with StyleUp. Hanging around amazing people makes it easier to aim for amazing yourself.

3. Let your “failures” move you along. Going into MIT Sloan, I was playing around with a startup idea that dealt with ecommerce in China—I was way in over my head and ditched the plans in the first month. Then I decided I was going to work at Amazon for my summer internship. Amazon was expanding its fashion vertical, and I could bring a fashion insider perspective to their teams. Then I applied to interview... and got rejected. I didn’t even get the chance to interview for the job. Instead, I spent my summer days with the awesome team at Altuzarra and spent my nights laying the foundation for StyleUp. It was fantastic. Likewise, many of my classmates went into school certain that they wanted to do this job or work at that company. Sometimes it works out, sometimes it doesn’t. It’s hard to know when to keep fighting and when to re-direct. As long as you work hard, you’ll end up where you are supposed to be.

4. Focus is powerful. Many people see business school as a career re-boot, a productive step you can take even when you don’t know exactly where you want to step to. If you’re not sure what you want to do post-MBA, join a lot of clubs, talk to a lot of people. The sooner you make that concrete plan, the sooner you can focus your quickly passing two years to achieving your goals and leverage the school’s resources.

5. Go somewhere crazy. A lot of my peers got swept up in travel mania, checking Kayak for flight deals anytime they had a Friday off. I did not go to that extreme, but I did go on three big trips: China, Israel, and Silicon Valley. Only in bizarro business school world is that considered being pretty conservative with travel. Nonetheless, swallow the extra debt and leave school with memories of something crazy you’d never experience otherwise. After all, travel is a great way to strengthen friendships, get distance from your “failures,” and discover some perspective and focus.

All in all, business school is really expensive (often upwards of $120K), and it is a huge gamble in both time and money. It’s not for everyone. Am I glad I did it? Hell yeah. Moving forward, I’m happy to talk to anyone who is interested in this road. Hit me up @kendall_to_go. Plus, try my startup StyleUp—if you’ve got a closet full of clothes but nothing to wear, I think you’ll love it!