Project 365: Lessons Learned

I’m one month into Project 365, where I take a picture every single day this year. At the bottom of this post are the pics from all 31 pictures taken in January 2010. Most I like, some I hate, a few I love. But I’ve learned a few lessons learned thus far in Project 365, and here they are…

  1. Taking a picture every day is hard. No shocker there. It can lead to mundain photos of just daily life, things that are quite boring. And when I’m inconvenienced by something that takes my attention away from taking a photo, or keeping my eyes peeled for something photo worthy, I find myself struggling at the end of the day to take a photo and that usually leads to something really lame or boring. Lesson learned: No matter how hard it is, I must strive to take a photo either earlier in the day or if I can’t I must take a photo that is not as boring as convenience might lend.
  2. It’s hard to be creative when you’re not feelin’ it. Forcing creativity usually results in really lame pictures, forced. However, I do find myself spotting moments of humanity’s sadness in daily life, in the world around me, moments of humanity that I want to capture, someone pushing a shopping cart of cans up a hill, and I want to take a photo of that, but there are so many reasons why I don’t, mainly that it seems degrading to the subject. Lesson learned: Find something beautiful, no matter my own definition of beauty. What I think is beautiful could be something quite sad, quite cold, but yet beautiful. Like that stupid plastic bag dancing in the breeze in American Beauty. Sorry for the lame example, but it makes the point.
  3. The iPhone camera is simply not good enough for this project, not even close. I’ve been using the free Adobe Photoshop app to tweak the photos, but the original photo leaves much to be desired. Lesson learned: bring my point-and-shoot with me wherever I go, at the minimum. If I can, bring my Canon EOS 40D.
  4. I’ve been doing Project 365 with Ali and that helps a lot. Doing it together really helps each of us remember, and it’s a lot fun too. We’re experimenting a bit, and challenging each other and having a lot of fun. I’m helping her learn her Nikon D40 and learn more about digital photography, and doing this project together everyday helps both of learn from each other and inspire each other.
  5. Be spontaneous. I’m just getting the grasp on this now. Wednesday evening I got home from a doctor appointment around 8pm and there was a possum in my driveway. Most people would say “big deal.” But I immediately reached for the camera. Why? Well it’s a quick pic for my daily quota, but also it’s something different and unique – something I don’t experience every day. Taking pictures of my dog Elmer, while he’s cute and all that, is just kinda routine, expected. A possum in my driveway, a little different. Lesson: have a camera with me and be ready to take a picture of those moments that pass as quickly as the come. Be quick, be spontaneous, be confident.
  6. Raise the bar. Over the last few days of January I’ve been trying to take pictures that I’ve always wanted to take. A picture of a droplet, intervals of the moon (or sun), star trails. There are many more pictures I just want to take to cut notches in my belt, if you will, and to prove to myself that I can do it. It’s easier to take these kinds of photos that take a lot of time when, well, when I have the time. But the more I cut my teeth on these kinds of challenging pictures, the easier it becomes to take them. Key lesson here to just keep raising the bar for myself, don’t be afraid to take pictures I may think I’m not good enough for; I just may surprise myself.

So far what I’m really enjoying about this project is how it demands my attention and a commitment. I love that I must dedicate a little time every day to being creative, and taking a break from everything else. I love that the pictures also show me where I’ve been, or what was on my mind, or a mood I may been in, or a circumstance, the weather and seasons, or even a new idea I’m toying with. I’m using a variety of lenses, from my Canon EF-S 70-200 f/2.8 to my 60mm macro lens or 15mm Tokina fisheye. I’m using them to help guide me as much as I’m choosing them for certain subjects. That’s a cool record of daily life that I can look back on. Also, the pictures that I’m choosing for Project 365 each day are just one photo among many others. I am taking other photos of other things, or of the same subject. So I have a record of that in Adobe Lightroom too, and all tagged properly so I can look back at my library. Very cool indeed.

I’m looking forward to more! I think getting through the first month was the toughest, making it a habit and routine is the hardest part. Now it’s part of my daily routine.

OK, onto February!

[flickr-gallery mode=”tag” tags=”project365,january,2010″ tag_mode=”all”]

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Entrepreneurial Lessons in 2009

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2009, you sucked! Good riddance to you! That was a horrible year that I just get sick thinking about. As it pertains business matters, it all started in late 2008, the second half of September to be precise, when the economy tanked. The entire country panicked, and the global economy didn’t respond any better. It really was the Global Economic Crisis, and as NPR is now reporting apparently it’s been “abated” but the effects are to linger for quite some time. One thing is certain, CitySquares was affected greatly and quite immediately. I won’t go into the details and the describe the punches we took, those we handed out, and the battle scars we have to show for it, but I will highlight some of the challenges and battles that really stand out in my mind:

  • As soon as the hard times hit I saw an immediate response by the staff at CitySquares. For the most part, the team held together and today we’re tighter and stronger for it. Like a tribe, we stuck together and hunkered down while battles and storms happened all around us. We were not well fortified but we survived and now we’re about to thrive! On the other side of the coin, a couple of our tribesmen demonstrated an inability to persevere and overcome these challenges, and some weaknesses were exposed and ultimately eliminated. Thankfully that ended rather quickly and the tribe was/is better for it.
  • Small businesses, specifically brick and mortars and mom-and-pops, got their asses kicked much like we did. Those who hadn’t yet learned to fly unfortunately fell from the nest and met their demise in ways that were hard to watch. Balances went unpaid, phones disconnected, and personal stories of financial tragedy were common. It was truly heartbreaking to see. Yet many also survived and are resurfacing with tougher skins and stronger businesses!
  • Beyond the staff at CitySquares I also experienced something completely new and foreign to me – board members and shareholders reacting in different ways. The vast majority of them demonstrated a wisdom and calmness that really impressed me and taught me a whole lot about pragmatism and experience. That, however, was not always the case. In a couple of isolated incidents I witnessed naked panic, fear, and fright and this came from the worst places possible in the corporate structure. I will not divulge the details not for lack of transparency but for reasons of respect and professionalism – that is a fine balance you know! As a result of these panicked and frightened reactions it was apparent to me that something had to change and change immediately or the company was destined to collapse for unacceptable reasons. It’s one thing to fail because a business model fails, or because of timing or market and/or economic reasons, but its another to fail because of human emotions, poor judgement, and failure to communicate and work as a team. At the end of the day, however, our shareholders demonstrated their commitments to the company but continuing to support us financially and through other supportive means. Again, we are now better for it!
  • As a leader I learned so many lessons in the past 12+ months, but two in particular that I will not ever forget. For the sake of brevity there were a few incidents in the first half of 2009 when I lost control of my emotions and let anger and fear win. These incidents are not something I care to revisit in detail and am embarrassed to detail. I have made amends in both instances. These two cases taught me some huge lessons, lessons that took me months to truly understand and apply to life and work.
  • In a tribal organization like ours, loyalty, communication, and teamwork are absolutely vital. What became incredibly apparent to me was how strong the tribe is when communication is at its best, when leadership is performing in the right ways, and when the tribesmen are truly committed to each other and to the tribe’s visions and beliefs. There is something almost dogmatic about a small company! I saw people step up to the plate in the most amazing ways. It’s still happening today. People are not willing to settle for less, nor willing to sit back and be OK with the way things are or may be heading, they expect more from themselves, from the others, and from the tribe as a whole. There is much of this happening right now, as it should always be! A sort of shuffling is happening internally, and its happening in a way that is uniting the tribe only more and making the company better and more focused and determined than ever before.

These points are the major ones that stand out for me, as an entrepreneur and as the chief of the tribe. There’s lots of business related stuff too, like how we got through the last 15 months, and what changes we made to our business/model/execution, etc. And those things are continuing to happen, but the reality is this: CitySquares is stronger, more successful, and closer to our goals than ever before! Its because of the above points, among lots of others, that we are here today.

A few of my entrepreneurial goals for 2010 are as follows, and I will soon be blogging about these things:

  1. Continue to grow and mature as an entrepreneur, as a CEO, and a tribal chief. How? Continue to identify and improve those leadership traits where I am weakest, and harness and cultivate those where I am strongest. I cannot do this alone either, I need my tribe to help me, I need to read and learn more, talk less, say more, listen more.
  2. Blog here more often, with transparency, and with purpose.
  3. Create and participate more in entrepreneurial circles, networks, and communities (e.g., The Founder’s Quandary)

I am still working on these ideas and a couple others. I will be blogging again here very shortly. Stay tuned for more!

2010 is going to be an extremely good year for CitySquares. No doubt we still have lots of lessons to learn and battles to fight, that’s par for the course. But if we can survive and unite the way we did in 2009, than 2010 is really going to be something else!

Happy new year to you all, may your 2010 be filled with new found freedom, with health, and prosperity.

Evolution in the Startup

As CitySquares has grown over the past 9 months or so, from 3 people in my basement to 14 people in a South End office space, we’ve all had to grow and evolve. I believe the expression is, “A rising tide lifts all boats.” Unfortunately I don’t think that’s 100% true in a startup company. Just because the company is growing and is achieving measurable success doesn’t mean that everyone is going to be able to grow and adapt to the changes. And in a startup things can change daily. It’s survival of the fittest and that includes me.

Much of my job as the founder and CEO, among other things, is to make sure that we, as a company, are adapting to change, learning lessons, and applying today’s lessons to tomorrow. But that applies to me, individually, too – I must adapt to change. I must learn lessons. I must apply those lessons to tomorrow.

I could give many examples, from changes in the market place, to changes in the economy, to changes in the company. I’ll use morale as a specific example though. It’s a constant issue, always needing monitoring and attention – like a delicate plant that needs just the right combination of water and sunlight. If you overwater it, you’ll drown it. Too much sunlight and you’ll dry it out. Too much attention to morale in a company and you set a precident and shit doesn’t get done. Too little attention to morale and you risk a coup! Morale doesn’t just mean fun either. Morale is many things, and first and foremost it’s spirit. It’s like being an athlete and not being what you wear. If you’re a Boston Red Sox player – you’re part of something bigger – you represent the Red Sox. You better believe in it. You better buy-in to it. And that’s a challenge – getting your teammates to also buy-in. Without buy-in, you don’t have spirit. Without spirit, you don’t have people that care. And it’s all downhill from there. So before you can have fun, you gotta generate buy-in.

If evolving isn’t simply adapting to change, for the better, than I don’t know what it is. The only way to know is to wait and see the results. Evolution is a slow process, but the results can be seen quite clearly. I can confidently say that everyone is evolving and therefore, CitySquares is evolving.