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:

Humility and the art of revision

As a designer and an idea person, I often get carried away with new ideas and designs. I’m a brainstormer, and when I hit something that I like, I have a habit of latching on … hard. Most of time, however, my ideas are just that: ideas. They tend to be really big picture at the beginning, and rarely based on customer or user feedback. As a result, when I start diving into the details, ideas that seemed awesome at the start fall apart quickly and leave me feeling a bit disappointed.

I am not alone in this behaviour. I am fortunate to know a lot of people who love big thinking and design. One of my best friends used to have a blog titled

So the question becomes, how do we take these great ideas and turn them into great solutions?

squareLogoWhitespaceRecently, I’ve been working with a number of friends on a new project called Eleven Media. The goal is to provide up and coming bands with little or no money with a solid online presence. This means a professional website, photoshoots, maybe video or recording depending how far along they are. The initial idea came because Aaron and I noticed that so many bands are using services that take a cut of the record sales, and don’t actually have a home on the web. Since we planned on offering the service for free (taking kickback from any online sales in the future) we thought bands would be all over it.

They weren’t. 

In fact, most musicians and bands Aaron spoke with flat out turned down the service saying it wasn’t something they thought y could make use of. We were obviously confused. Most people pay money to have systems like this custom built for them. We were obviously missing something.

Do customer research

Rather than giving up altogether (which has been tempting) I set about trying to understand where the problems were in the system we had developed. I spent some time talking to promoters, bands, and musicians to figure out where our idea was flawed. The issue finally surfaced after a few pints with a friend who is part of the two piece electronic band:

Me: So would you be interested in a custom designed website?
Him: No. If I really need a better site, I’d rather learn how to do it on my own.
Me: What if you could manage all the content, add pictures, songs, and connect it with all your other social networks?
Him: That sounds like a lot of work.
Me: What if I could give you the ability to sell your own music and merch without having to pay another website a cut?
Him: *Eyes instantly brighten* YES. That sounds good.

In that quick conversation, I learned where the problems were with our proposed idea, and what actually had traction that we weren’t paying enough attention to.

Listening to customers is not a new concept, but often user experience designers will tell you to get something in front of your customer in order to get feedback. Prototyping is a great way to get feedback on workflow, design ideas, and general user interface elements, but when you’re working with the initial concepts, and nothing tangible, it’s hard to find the right questions to ask.

User interviews are not a new concept. People have been using formal interviews to help establish market research for decades. In many cases, however, the early stage development of an idea can be hindered by structured interviews because you’re not always going to get all the information you need. By asking specific questions, you may be missing out on an important answer to a question you haven’t asked! So I say go unstructured and let the interviewee lead the conversation.

Being wrong is hard, but it’s also important

Our initial idea with Eleven Media was built around the assumption that bands wanted awesome websites, but just didn’t have the resources (read: money) to obtain them. When people started turning us down, we were genuinely confused. And it stung a little bit. Essentially people were telling us that we were wrong, and that never feels good.

But as they say in the entrepreneurial world, failure is an important part of building success.

If you feel confident that your initial idea still has merit, don’t give us. Regroup, refocus, and relaunch. Every time you’re wrong about something, it gives you the chance the learn, grow, and then be right about it next time!

Revising big picture ideas

When we learn that our initial awesome amazing idea was wrong, it’s sometimes hard to bounce back. The natural reaction is to throw out the idea and maybe, or maybe not, start over again. Maybe I’ve been working in an agile workplace for too long, or maybe it’s just starting to have positive effect on my design outlook, but I think a better approach to trashing a project is to simply revise and move forward. Just because you weren’t right the first time, it doesn’t mean that you have to be wrong forever.

If you have the chance to talk with potential customers, running elevator pitches past them is great way to gauge if you’re on the right track. Brainstorming with like minded people is also a great way to get feedback on changes that you want to make to big picture ideas. If you’re lucky enough to have entrepreneur meetups in your area, make use of that resource (I’m totally guilty here…) and see what other professionals think.

Last but not least, translate your ideas into marketable materials and see how they are received. Eleven will be launching a new website next week with the changes and ideas that I’ve heard from other people. I’m feeling more confident in my ideas now based on the revisions that we’ve made. Ultimately I know that we are providing a better service because I knew when to give up on an idea, and how to recover by revising rather than discarding!