Time sure flies when you’re having fun, and that’s exactly what we at Windward have found to be true over the past two years. As most of you know, Windward has been sitting in the same spot, on Clark Street in Lakeview, since it opened it’s doors back in 1982. In September of 2010, the original owners passed the torch on to three young entrepreneurs who were determined to turn the store into the best boardshop in Chicago – and beyond.

We would re-brand the store, dropping the old name of Windward “Sports” and using a more direct name of Windward Boardshop. We would launch an awesome website that would be user friendly and not only showcase our products but also be a place where our customers could get tech information, read about current industry news, stay up to date with shop events and more. We would hire a staff that would live and love everything about being involved with a shop like ours and in turn offer the best shopping experience possible. And the biggest project of all, we would completely overhaul the look and feel of the store from the inside out. We would tear down part of a wall, rip up the carpet, move the fitting rooms, add a lounge area and completely change the look and feel of the shop. Sounds pretty simple, right? That’s what we thought too…

It’s easy to imagine something epic, and completely different to actually make it happen. Much less making it happen in 3 weeks. I don’t think any of us realized what the next couple weeks of our lives were going to be like. Actually, I know for a fact, we had no idea how crazy it would be, how hard we would work and how proud we would be when it was all said and done. 

Recently, I was digging thru some old photos and started sorting out all the pictures that were taken during those crazy weeks in between taking over the store and re-opening as the new and improved Windward Boardshop. I laughed as I remembered the first couple days of moving EVERY product in the store, to the basement. (literally, everything in the entire store was moved down there.) We had all hands on deck – family, friends, employees – anyone that had two hands and was willing to help. And then the real construction set in – tearing up the flooring, tearing down a wall, re-wiring all the electricity and painting, lots and lots of painting. We had a dedicated construction crew that became part of our family by the time the whole ordeal was over. There were long days, long nights and a lot of hard work in between. 

I thought it would be fun to share some candid photos that I took during this whole crazy process. So many of our customers have been faithful to Windward since way before we were part of the shop. It was so important that during this “makeover” we wouldn’t lose any old customers – and that we would also be able to gain new ones. I hope that all of our customers, old and new, enjoy some of these photos and appreciate what we went thru, in an effort to keep Windward going strong – today, tomorrow and another 30 years from now. 

First, we began with the ladies section (or “side room’), blocking it off and starting the construction a couple days early. We thought getting a head start sounded like a good idea. We tore down part of a wall to make 2 new fitting rooms, painted the walls and tore up the floors, replacing it with a gorgeous dark wood laminate. The most exciting part of gutting the small room was what the construction guys found under the old flooring – a chunk of cement laced with empty cans of Hamm’s beer and American Spirit Cigarette packs. Apparently, whoever re-did the store before us liked to party. 

Then came the big job. The main room. Looking back, we had no idea how big the store really was – until we had to completely clear the entire place out. We officially closed down, covered the windows, and got to work. Everything off the walls, all the merch in the basement, what to keep, what to toss – it was an intense couple of days to say the least. It was time to start knocking walls down and make things happen. The clock was ticking and the grand re-opening date was already set.

And now, we reach the part of the remodel that we like to refer to as “crunch time.” In the beginning, 3 weeks seemed like a lot of time, in reality, 3 weeks is not a lot of time. During the construction, we set up an office (3 people, lots of catalogs, 3 computers, 1 small room) at Chris’ house where we feverishly filled out dealer apps, made orders and planned our grand re-opening execution. Needless to say, this was quite a bonding experience. 

Before we knew it, we were back in the store, bringing everything up from the basement and starting to set the merchandise. This time had flown by, and even though we were running on less than adequate sleep, we were more excited than ever, ready to complete this chapter and reopen the store. Pictures went up on the walls, merchandise was arriving, everything was starting to settle into it’s place. 

Then, on Saturday, November 13th, the window coverings came down and we were open for business. Friends, family and customers (new and old) poured in to see what we had accomplished. At this point, the last 3 weeks were a total blur. But we knew one thing – it was all totally worth it. 

Fast forward to today. It’s been just over 2 years since we opened the doors back up as the new and improved Windward. In that time we’ve grown, made mistakes, learned from those mistakes, laughed and genuinely love everything that we do. We’ve got a killer team that is our family and made great memories with this crazy crew. I hope you’ve all enjoyed this little memoir, I’ve certainly enjoyed reflecting on those crazy couple weeks. 

Here’s to the next 30!