Transitioning My Career

Last June, I left my full time employment designing software. It was a bit rough, but I’ve been running Oaktree Media part time since 2009 so I had a lot of work to fall back on. With my departure from the 9 – 5 job, I thought it would be a good opportunity to put a bit more effort into Music Lives. Since then, we have launched a magazine (now newspaper) and opened a space-sharing office with 6 other people. It’s been quite a ride.

Along with the increased focus on Music Lives, I also started picking up a few volunteer based or “pro-bono” jobs to help get my name out there. While working for free when freelancing is your only source of income may seem like a crazy decision, a few of the projects have led to more paying gigs, so I’d consider that a good business move. Beyond that, though, volunteering my time and skill set meant that I had the opportunity to work with some organizations who’s goals and ideals align very much with my own. One of these organizations was Transition Guelph. If you haven’t heard of the Transition Movement, I highly recommend watching the video below. It’s a bit long, but eye-opening.

After my experience with 52 to green, I’ve become passionate about learning more about environmental movements, and the motivation behind the Transition Movement is something that excites me and fills me with hope. Over the last year, I’ve had the chance to work with some amazing individuals who share my passion for positive environmental change, and the new Transition Guelph website is one that I’m really passionate about. Since meeting the TG crew, I’ve also done work with eMerge Guelph, The Guelph-Wellington Task Force for Poverty Elimination (new site coming soon!), and Minga Skill Building Hub. I also worked with a New York based not-for-profit through Catchafire called Folk Arts Rajasthan. All the projects have done more than put money in my pocket – they have been incredibly rewarding and work that I am truly proud to be a part of.

Coming soon, I may have the opportunity to work with one of these organizations on a more full time basis. The position isn’t 100% aligned with my work history, but I’ve never been more excited about an opportunity. I have realized over the last six months that there are certain ideals that I strive to maintain, and working with organizations and in industries that support my ideals makes the work more fun, more passion filled, and more rewarding. I believe that this realization has marked a transition for my own career. No longer will I be satisfied to simply earn a paycheque. I choose to hold out to find work that I enjoy doing on a personal level, and I believe that quality of my websites will improve.

I am also beginning to really understand how the work I can do building websites and sharing messages fits into a broader picture through communication strategy. This understanding now opens up a number of doors for me to work with awesome people to help the right message reach the right audience. Being passionate about what I’m creating allows me to see the broader picture, and how all the pieces fit together.

While I might not be making as much money, I know that I’m putting my skill set to use to help solve some very important issues, help some very amazing people, and feel more morally aligned with the work that I’m doing. 

Design Thinking

Design thinking is a pretty broad term that refers to the approach that problem-solvers use to troubleshoot complex problems, collect information, and find solutions. Traditionally, design thinking has been employed to tackle design issues, namely how to build a new product or solution to solve a problem that exists. If that feels like a really general definition, it should. Design thinking approaches can be applied to almost any problem that exists in the world. It’s a problem-solving approach that breaks away from traditional analysis, and employs empathetic, creative, and (hold on to your hats) emotional strategies for getting to the root of the problem.

Design ThinkingFor those of us who have worked in the creative field, design thinking is a nice way to label what I consider good brainstorming techniques. One element of design thinking is the solution-based approach that it uses to look at problems. What that really means to me is the design thinking approach to problem solving is inherently productive. It seeks to find a solution to the problem while taking time to define the root issues of the complex problem.

While there are many techniques and approaches which fall under the design thinking umbrella, there is an article published on FAST Company that does an excellent job of breaking down the basics and I’ll use that as a template:

Define the real problem

The really appealing part of design thinking for me is the way that you define a problem. Often, problems present themselves wrapped in layers of subjective, confusing details. Getting to the root of the problem can often be difficult for people who are emotionally invested in the issue being addressed. The design thinking approach for getting to the root of the problem is primarily concerned with one question: WHY?

Remember when you were a kid and you realized that statement could be countered with the question “why?”. I’m sure we all have conversations with teachers, parents, and friends that went something like this:

boy and cooked vegetablesKid: Why do I have to eat my vegetables?
Parent: Because you do.
Kid: Why?
Parent: Because they are good for you.
Kid: Why?
Parent: Because they help your body work properly.
Kid: Why?
Continue on to parent giving up…

Despite how annoying this pattern can be, it’s so important in understanding why we behave in certain ways, and forces us to question regular behaviour. Design thinking looks to find NEW solutions, and that process really requires diving into the everyday behaviours that we assume to be true. The a-ha moment in design thinking often comes when you realize half way in to the problem definition phase that there is a habit or behaviour that is actually contributing to the root problem. Once you make that discovery, you can switch gears and start thinking about how to change that behaviour.

Create and consider all options

I think one of my favourite things about the design thinking approach is that it is brainstorming in the truest sense of the term. There are no bad ideas. There are no dumb questions. Everything should be taken into consideration when building a solution to a complex problem.

You can’t solve every problem with the same solution. Too many organizations fall into bad habits and patterns of using the same tools, people, and ideas to solve different problems. Design thinking prescribes this brainstorming activity to try and break the mold to find new and different ways to approach problem solving. While 95% of the ideas may not work, 5% will be more efficient, longer lasting, and simply better solutions than what you’re already using.

Sometimes it might feel like you’re moving in a silly direction with a troubleshooting exercise, but it’s only when you reach the end that the thought pattern informs you and gives you greater insight into the complex problem you are trying to solve. If we didn’t give ourselves to explore all the possibilities, that insight would be lost.

Reframing the problem

One great way of brainstorming to look for new ideas is to reframe the problem. I took a design process class last year, and we were tasks with a generic problem that each student was expected to explore on their own. The biggest problem I had (along with many of the other students) was coming to a solution to early in the process. Most of us saw the problem laid before us and instantly wanted to start developing a solution. Instead, we should have taken time to do research, explore different options, and develop prototypes.

BrainstormingIt wasn’t until we came to the “reframe your problem” week of the course that this approach truly took hold. Trying to work backwards from a solution to actually re-define the problem is exceptionally challenging, but often extremely rewarding as well. Reframing the problem really comes from asking the design problem question in a different light.

Recently I was working on navigation restructuring in TribeHR. I wanted to create a simpler navigation system that was going to grow with the app. I decided to approach the problem by listing out all the different actions that can be taken in the app and look at the navigation from that approach. It was a really successful process, and I was happy with the solution that I had developed. But rather than going to town, I figured I would try reframing the problem as I had recently in my course. I asked a new question: “What KIND of actions are users looking to complete?” I started listing all the tasks that people do in the app, and what triggers them. I ended up coming up with two categories 1) app-driven behaviour (actions that people do in response to something that happens in the app) and 2) real world driven behaviour (something happens in day to day life that requires you to log in and complete a task in the app). While this understanding didn’t pan out with the navigation restructuring, I realized that if we could maximize the app-driven behaviour, in the form of notification, we would have a better chance of drawing the user back in to the app. Now as I design out more features, I look for smart uses of notifications to engage the user!


Stuck in the SieveAt this point in the process, you should have a ton of awesome ideas on how to approach your complex problem. It is now time to take those ideas and refine them into an action plan. Sometimes multiple ideas from the brainstorming session can be combined to form a solution. Sometimes one idea will stand out in the forefront. Taking those ideas and forming actionable items that can be tracked and measured is a great way to move forward.

This is also a great time to break down the big picture ideas into smaller tasks. Smaller, actionable items are not only less daunting, they are more likely to get accomplished.


As I’ve mentioned before, it’s okay to fail. Failing just means that you’ve crossed one possibility off your list of solutions. Head on back over to your pile of ideas and try again.

Execute and Learn

One of the great qualities of design thinking that has been adopted by so many start up companies is that methods which they use to execute, and in turn, learn from mistakes. While the whole process is focused around creating many ideas, filtering down to a few, and then discovering a solution, the true value is the way in which you execute, sometimes fail, and then start over.

If you have used this process, failed, and iterated, sometimes you’ll find that the problem that was defined early on is actually a problem that isn’t best solved by you, your team, or even your company. Some designers will claim that you should have a solid solution by the time you’ve made your way through the design thinking process, but I will argue that you can never stop learning and never stop making mistakes.

Keep Learning!

Looking for more resources on design thinking? Look no further:

Learning to design

I thought a good first post would be something that was easy for me to talk about – learning the art of web design. I often have people asking me where and how I got started in designing websites and software. I’m pretty much self taught, so my stock answer is always “play”. But what does that mean exactly?

Play in Photoshop

There are a ton of good tutorials out there that will teach you how to move around Photoshop, which is the best tool out there for designing websites. Most of the tutorials, however, will walk you through specific actions required to create a specific design or element of a design. If you’re trying to learn new techniques, these tutorials can be really advantageous. My recommendation for “learning the ropes”, however, is to copy. Pick 5 websites that you really like and try to recreate them pixel for pixel. Quite often you will find yourself stuck because there is a specific technique that is used in the design of the site that you don’t know how to replicate. That’s where good old Google and the aforementioned tutorials will help you along the way.

Amateur Web Designer Night

Play with code

HTML, CSS and JQuery are amazing tools for any web designer. Knowing what’s possible when a client asks you for specific features can make or break a project. Again, there are ton of tutorials out there that will help you learn. Try and find some functionality in a website that you like, such as CSS sprites, a javascript image slider, or true table-less design, and practice until you get them just perfect. A great way to learn is to deconstruct other people’s code line by line to see what everything does. That’s how I built my first website when I was 14.

Play with personal projects

Building up a portfolio can sometimes be a daunting task. Try picking a topic and building a website around it. Maybe a fan site for your favourite band, or a database of recipes of your favourite foods. Learning to design and build within a theme is great practice for learning about target market, UI design and social media tools. At Oaktree, Aaron and I decided to build a website that would feature local live music events. It’s been a great learning experience!

Dive right in

When I used to start a new project, I procrastinate because I don’t know where to start. I’ve learned over years of practice that the best approach is to dive right in. If you’re starting with a website design, look for inspiration through gallery sites. Pick a style that you like and try to recreate some of the element (not pixel for pixel, mind you – just the general concept). As you move forward with the design, you’ll find that it changes and evolves as you pick up on specific elements of the design that you fall in love with – an oversized header, or an awesome font in the navigation.

After you’ve found that inspiration, the sky is the limit. Create two or three designs for every project you’re working on. Then take a break and revisit them the next day. You’ll see what sticks and what doesn’t, and ideally the end result is a beautiful, sleek site that you’re proud to include in your portfolio!

For more of my work, visit Oaktree Media. You can always get in touch with me if you have any questions!