Launching The City Lane Chicago, Behind The Scenes

CHICAGO | Those of you who have been following The City Lane (“TCL”) over the past few months will have noticed that there’s been some Chicago focused content going up on the website. I’ve been testing things out with the Chicago team and using the time to get it all working nicely. Now the time has come to announce the official launch of The City Lane Chicago!

It’s an exciting time, and I thought I’d use this post to give you a bit of an idea of what’s been happening behind the scenes to make this a reality.

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Why Chicago?

One Day At The Pub…

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The first international expansion of TCL was The City Lane London, which launched in the middle of 2015, although in a way there has always been a TCL London as that’s where I was personally based from 2009-2011. The generation of London content was split between myself, and my contributors Genevieve Waldron and Paul Mete. Genevieve hails from Chicago and Paul M from Wollongong, and when the decision to ‘move back home’ was made by them, Chicago won out over Sydney. They still wanted to be involved with TCL, and so the seeds for TCL Chicago were planted. It all happened over a pint and shared slice of brown butter tart at Marksman.

Having An Idea Is One Thing. How Do You Execute?

The first step might sound obvious, but it was to come up with a plan. TCL London never really got off the ground until it had been around for a year, and that’s because it was never its own thing. Sure there was a London portal where people could easily access all of the London content, but that was it. Sitting down with Genevieve and Paul M, we were able to brainstorm what had and hadn’t worked with TCL London over the past year, and apply this to TCL Chicago (and TCL London for that matter).

A Localised View

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TCL’s audience is a diverse one – there’s a big Melbourne follower base of those who are interested in Melbourne content, and a large global readership who are primarily interested in TCL’s travel content.

When TCL London launched it had no dedicated social media presence, with anything relevant to it going up on the regular TCL social media channels. The primary TCL social media accounts, like the website, have a global following and a large Melbourne and Australian audience. London or Chicago content isn’t that relevant to them unless its something travel related, or they’re going to visit. For TCL Chicago, it was clear that a dedicated e-mail address and social media accounts were going to be required from day one. If you’re in Chicago, you can get what’s relevant to you and not be bothered by “irrelevant” Melbourne and London content. TCL Chicago is very much a part of TCL as a whole, but has its own thing going on too. Dedicated city-based newsletters for e-mail subscribers will be coming soon too.

You Can’t Do It All

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Everything TCL London related came through to me during its first year. Working 30 hours a week at a day job, being located on the other side of the world, and dealing with a rapidly growing TCL as a whole meant that there wasn’t enough time for me to give London the attention it deserved. The result was that things stalled. TCL Chicago needed to have someone on the ground, managing things from over there. Genevieve agreed to take on this role, and she’s the first port of call for anything Chicago related.

I keep an eye on the e-mails, take care of the administration side of things, am always available to provide guidance, and have the ultimate say over what happens with Chicago content, but generally until photos and text reach my desk for editing, I stay one step removed. Many people fail to realise just how much administrative work there is when running a website like this – you’re basically running a small company, with all the administration that comes with that. I’m the accountant, the lawyer, the IT guy, the creative director, the editor-in-chief, the receptionist. Having someone in Chicago in what is essentially a management role means that TCL Chicago gets the attention it deserves, and allows me to allocate my time more efficiently.

Finding Contributors

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If you want a proper presence in a city, you need to have contributors there. An obvious point perhaps, but as long as you can find the right people, a bigger team is better – not too big that it’s unmanageable though. Genevieve knew a few people through her contacts which got things off to a good start, and from that we were able to get conversations going over e-mail. Me sharing my vision and making myself available to my team to answer any questions, and everyone sharing ideas.

We had a few people who were initially interested who dropped off the radar as they realised that this wasn’t for them, but we found new people too. Over time we all got a better idea of what worked and what didn’t, and developed a good work flow that’s made my life, and my contributor’s lives, easier.

Developing A Work Flow

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The work flow that we use today is simple – it helps me stay on top of things, and lets my contributors know how to go about their work. There’s a Dropbox folder for TCL Chicago, with a sub-folder for each contributor, and an Instagram folder. If a contributor takes a photo that might be good for the TCL Chicago Instagram account, they can pop it in there and name the file with any relevant info. Whenever I want to post something I’ve got a selection of photos waiting for me.

There’s also a tracking sheet in the Dropbox folder, which contains 6 columns – Article Title, Author, WordPress Status, Photo Status, Text Status, and Comments. The team edit this as appropriate, updating the various status columns with the relevant options from a set drop down list. I can open the tracker at any point in time and know exactly where everything stands. When the text and photo status columns say “In Dropbox”, I know that I can go into that contributor’s folder, grab the files and start my editing. Simple, and a world away from the mashup of e-mails and lost text threads that used to cause much confusion.

We also have two WhatsApp message groups – one for “management” and one for all contributors, which makes real time communication with everyone simple no matter where they are in the world.

A New Way Of Dealing With E-mail and Direct Messages

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There are many people who say that e-mail shouldn’t be used as a to-do-list, but that’s exactly how I use it. Perhaps this will change in the future but at the moment it works well. If you’re sending through Direct Messages on social media I’ll probably get around to it at some stage, but if it’s important, send me an e-mail and in most cases it’ll be responded to within a week. There’s simply no time to constantly check every possible avenue of communication. I used to be the kind of person who would respond to every e-mail or message that came my way within 24 hours, and it is something that I do in my day job, but for TCL, I’ve long done away with that rule.

For TCL Chicago (and London) I only ever glance at the e-mails and, unless its really important and requires my intervention, I leave it to my team to sort out. If you send through an unsolicited e-mail, a press release or “opportunity” that’s just not relevant you’re probably not getting a response. It felt a bit rude at first to not be responding at all, but at one point I was spending that much time responding to e-mails and social media messages that I wasn’t actually getting any work done. I’ve personally taken a loss of income by dropping my day job from full time down to to part time, so I need to use those unpaid hours wisely.

Nothing Beats First Hand Experience

Flying To Chicago

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Regular TCL readers will be aware that Cathay Pacific have been awesome with their support of TCL over the past year. My trip to London, where the idea of TCL Chicago first came into being, was made possible with Cathay Pacific’s support, and for my flights to and from Chicago they provided me with lounge access and Business Class upgrades. Flying to Chicago via Hong Kong is a different route than most would expect and does take an extra two hours versus the East Coast of Australia via Los Angeles route but it’s a great option for several reasons.

Firstly the times sync up well. You get the red eye from Melbourne/Sydney up to Hong Kong, nab a few hours sleep on the plane, and arrive in Hong Kong at 7:00am. You can use your four hour layover to freshen up, get a feed and get some work done (even if you don’t have lounge access the food options at Hong Kong International Airport are great at free WiFi is available). You leave Hong Kong at 11:50am and can do some more work or relax on the plane before getting a few more hours sleep at a time that syncs up to Chicago. By the time you land in Chicago, at 12:55pm, you have an entire half day available to you, and are synced up with local time, helping to avoid jetlag. Of course this option also means you avoid having to transit through LAX!

Another reason to take this route is that Cathay is simply a great airline to fly. Even before I started collaborating with Cathay I flew with them quite a lot and when I’m paying for flights out of my own pocket (which I did in this case), I try to fly Cathay where possible. To me they strike a good balance between the casualness of say, Virgin and the textbook efficiency of an airline like Singapore Airlines.

Finally, if you want to break up a long flight like this with a short break, Hong Kong is one of the best places in which to do it. Several times I’ve arrived at Hong Kong in the morning and had an evening flight, and have used the half day to hop onto the Airport Express train into Central and explore, taking in the atmosphere of the city, and getting in some shopping and great eats.

Get To Know The City

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I had never been to Chicago before, and if I was going to do something as big as this, it was important to me that I experienced Chicago for myself. As you approach Downtown Chicago from the Kennedy Expressway, you really appreciate how big Chicago is and why it is considered one of the world’s great skyscraper cities. Walking through downtown, admiring the art deco architecture and more modern styles, and seeing the elevated rail lines above you all helps to create a distinctly Chicago feel.

After a few days of exploring downtown and several of Chicago’s neighbourhoods, hanging out in public spaces, checking out bars and eateries and chatting to locals, I had a much greater sense of the place. It all means that I have a much better perspective from which to edit the content that my contributors submit.

I also fell in love with the city, and seeing the people of the Chicago mobilise for several worthy causes during the current political climate has further encouraged me that Chicago is the right city for TCL to be expanding to. I only scratched the surface with my first visit, and hopefully the TCL Chicago is successful and I’m afforded the opportunity to visit several times again.

Meet The Team

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We live in a connected, global world, and there’s no way that TCL Chicago could have existed if this wasn’t the case. So much of what you’ve read above is only possible because we’re all connected and always online. Having said that, there’s still something very important about meeting people face-to-face; something that online messaging and video calling can’t replace. I hadn’t met any of my Chicago contributors other than Genevieve and Paul M in person, and it was important to me that I changed this.

Hanging out with my Chicago contributors and enjoying dinner and conversation was lots of fun, and we all learned a lot about each other. I was able to really lay out my vision for The City Lane in a way that just wasn’t possible without face-to-face contact. I left Chicago feeling energised and full of ideas about where TCL Chicago could head.

The Future

Redesign The Website

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The final piece of the puzzle, that will really bring everything together, is the new TCL website which will be launching soon. Over the years the TCL website has been through several changes, all designed to put the focus on the content, and make it easy for people to find what’s relevant to them. Historically I’ve done all of the website work by myself, but with over 1,200 pieces of content already on the site, an average of two pieces of content going live each day, and dedicated teams in London and Chicago, it’s time for a big upgrade.

To that end, I’ve engaged a web developer to bring my vision to life in a way that looks less “blog like”, and in a way that lets the content shine. I’ve really thought about how people want to use the website, and soon you’ll be able to visit dedicated city portals, and do things like view lists and guides on maps, and find the best articles we’ve written about a city with ease. It’s just about there, and I can’t wait to reveal it to you all.

…and Then What?

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The Japanese word Kaizen literally translates as ‘change for better’, and in a business/workplace context it refers to activities that continuously improve all functions and involve all those involved from top to bottom. This idea of small-step, continual improvement is something that I try to apply to TCL. We’re still learning as we go, and my team and I are always trying to find ways to improve things, to make sure we get the content that you want to read, and that we like to write, up on the website and social media channels.

I’m open to trying new things, and am constantly tweaking bits and pieces of TCL. I see TCL from a certain perspective, my contributors have a similar, but different view of things, and you, the reader, have your own perspective. No matter how hard we try, we’re never going to be able to see things exactly as you do but I can assure you that when I’m editing, I try to see each piece of content from the point of view of the reader. To that point, I want you to know that I’m always open to comments, positive or negative, as long as they’re constructive. If we’re doing something you like, let us know. If we start doing something that you’re not convinced works, let us know. There’s no point in TCL becoming bigger if it’s not also becoming better.

Bring on 2017 and, officially, hello Chicago.



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