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You wear the same dress shoes to work every day for five years, despite the fact they are all scraped up and look horrible

You might be an entrepreneur if…you wear the same dress shoes to work every day for five years, despite the fact they are all scraped up and look horrible.

The funny thing about writing these posts is how many of them have improved during the last year. Case in point, I just got new dress shoes after wearing the same ones for 7-8 years. In fact, I splurged and got two pairs (yes, two!) of dress shoes.


Right before, or maybe right after, I got married I went and got me some Doc Martin shoes. Doc Martins became popular in the early 90s, although they had been around for a hundred years. During the 70s and 80s they were widely used by punk rockers and became something of a symbol of the punk rock movement until they started being sold at Nordstrom. For the record, I would just like to say that I was one of those who wore Doc Martins before they became popular. Off the record, I’ll say that sometimes I wore them with army surplus cargo pants cut off into shorts with argyle socks. Just a tiny detail of my sordid past.

But back to my more recent Docs. I got them soon after getting married, and within two years they had passed the point of being in style. However, by this time I had spent all my business funding as if it was going out of style and wasn’t taking a paycheck. Getting a new pair of shoes seemed like a luxury rather than a need. So I basically had two pairs of shoes in my life–those Docs and a pair of skate shoes, for skateboarding. That meant that I wore my Docs to work pretty much every day unless I was dressing like a skater because no clients were coming in.

About two years ago the Docs started wearing out, and I mean visibly wearing out. The leather around the toes started cracking until I could see my socks through the sides. But they still worked, and I figured people probably wouldn’t notice, so I just kept wearing them.

But finally, about a month ago, I decided enough was enough and I should probably make the investment in some new shoes. I was expecting to pay around $120 for a decent pair, but then I discovered Ross and Nordstrom Rack. For those of you who don’t know, Nordstrom Rack is Nordstrom’s outlet or overstock shop or whatever you want to call it. Basically it’s packed with all the stuff they don’t want in their main stores any more. And they have some really nice shoes from major brands for 50-70% off the retail price.

I had never been to a Ross before and thought they were like Fred Meyer or something. Just some cheap, ailing department store. But as I discovered they also sell overstock or aging items, and they have a lot of good stuff. They even sell i-Path shoes there.

So at Ross I got a pair of nice dress shoes for $30. And we’re not talking generic stuff, this is name brand stuff, for less! Then I found a pair of business casual shoes for $50 at Nordstrom Rack. So now I’ve got enough shoes to last me for the next 14 years.

One bit of advice to aspiring entrepreneurs–get loafers. You don’t have time for laces when you’re running a business.

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