Journey of Discovery, Part One: Testing the Waters with My Business Idea

This is part one of a long-form “check-in” post that I’ve broken up into a couple of chewable chunks for Medium. I will post the full version at togetherworking.com when I’m done posting the two parts here.

This is me, journaling my “Journey of Discovery” with developing an online business on the side, while working full-time. A business I’ve called, for better or worse, Working Together, and which is currently nothing more than a blog (and therefore just a hobby).

Yes, for the few Working Together regulars (whoever you may be) there is more to Working Together than just the writing! For one, there are bigger plans for an eCourse on design thinking tools and methodologies, as well as plans for a podcast and YouTube channel to share content faster and more “off-the-cuff” than the writing allows (I love to write and edit, but oh… is it ever so painfully slow). Hopefully there will be some honest insights in here that will help others in a similar situation.

Let’s begin with a bit of background colour: I am trying to establish Working Together while also working a full-time, professional job and being a loving husband and father who is committed to quality family time. As a result, Working Together is pushed to the margins of my day. Basically, I have early mornings if I manage to go to bed early, or evenings if I manage to resist the exhaustion that washes over me while I rock snuggly babies to sleep next to our white noise machine. Sometimes, I also have lunch hour, but it’s not a guarantee. And that’s it!

It feels like everyone in the world has an unfair advantage over me, but I follow my intuition which tells me to channel my inner tortoise: slow and steady wins the race.

Because of my limited time, from the start, I’ve believed that my business model for Working Together should be simple and effective. My tendency is to gravitate towards the opposite… and then to overthink things… into oblivion. So, as soon as I started to turn my mind towards business, I knew I would have to constrain myself with a few founding principles. Here are a few that this post has forced me to articulate:

Simple and effective, as opposed to complicated and clunky.

Small, yet scalable online, as opposed to ornate and overly dependent on a bricks and mortar space.

Oriented towards creating value for a defined customer, as opposed to working in generalities.

Geared towards the intuitive and spontaneous, the messy and the experimental, AKA the authentic… as opposed to the intentional and planned, the overwrought and strategized, AKA the perfect.

Some of these come from having an idea about who I am, what my strengths and weaknesses are, etc. When things are simple, I find that I act. When things are complicated, I find that I theorize.

So, I’ve made a commitment to spend at least one hour per day on Working Together, and so far, I’ve done pretty good since I started in earnest five months ago. On my worst days I put in less than an hour. On my best days I get a few uninterrupted chunks of time to do the work, and I come out the other end with some real progress. But since I’ve started, I never spend no time on Working Together. Everyday there’s always something small that can be done, and there’s always lots of thinking and planning to do while in transit.

So, what have I been doing (aside from writing blog posts)? Well, over the past two months, I’ve been:

…interviewing potential customers and drafting some early value proposition designs;

…working to create a loose team of friends and family around me to act as a bit of a sounding board, to give my ideas the oxygen they need to survive and become actions;

…pivoting the online course concept to other audiences;

…slowly building and practicing a media production strategy that is appropriate to my needs: one that allows both flexibility and creativity.

On top of all this, I’ve also been: purchasing the necessary supplies for my podcasting rig and lining up the first five interviews; drafting some early concepts for an eCourse and an eBook; exploring cheap lighting options for video; taking online courses on personal branding and eCourse creation; researching and reading-up on all manner of business development literature, plus all sorts of other logistical things. I am endlessly surprised by how exciting business can be, and am fascinated by how the internet has changed the game.

“…interviewing potential customers and drafting some early value proposition designs.”

I had started the Working Together blog with a broad and expansive notion of what I was interested in: social innovation and how groups of people can be brought together to make some magic happen. Knowing my tendency to gravitate towards generality, I niched down into a group that I had a little bit of experience working with through my wife’s business Connect-The-Dots: home learning families. This was a group of folks that I would one day join (since our plan has always been to “road school” our children). They were inspiring to me, and I wanted to learn more from them. Most importantly, they were a group of people I wanted to serve: I wanted to build awesome online learning experiences for home learning families. In particular, I wanted to work with teens in those communities.

So, pushing myself in the direction of action as opposed to theory, I had a few meetings with home learning families I had worked with in the past to ask them some questions. Before the meetings, I did my homework and read the first few chapters of Value Proposition Design, by Alex Osterwalder and others, and came armed with some good questions to ask. After three meetings, I organized my interview notes into a Value Proposition Canvas, and started thinking about ways that I could offer something of value to these families.

I couldn’t believe how productive the Value Proposition Design (VPD) process was! From three short meetings I had a fountain of ideas about potential products and services that I could provide this group of folks. However, a lot of these weren’t online courses… BUT I wasn’t getting validation for my original idea of creating an online learning experience for my target audience.

I also learned of a few significant difficulties that I needed to consider. For one, my potential market was motivated towards a do-it-yourself (DIY) approach to education. They were also committed to providing immersive, face-to-face experiences for their children. This was what attracted Heather and I to home learning too: creating a learning atmosphere more akin to a field trip than a classroom. Providing an online course to these families would be a challenge, as it seemed that many home learners were being actively directed away from screens and towards face-to-face interactions with fellow learners and teachers.

In addition, because of the fact that these families were usually single income (with one parent staying at home to facilitate DIY learning experiences), my ability to charge premium rates would be limited… unless I wanted to pivot to kids enrolled in private school, and present the course as an extra-curricular prep-school that would give kids a competitive edge…but I felt that this group of kids didn’t need what I could offer. And besides, this wasn’t my original intent.

Finally, I realized I would be marketing on two fronts: on one, the parents; on the other, the teens. Two entirely different conversations, two entirely different social media marketing strategies. I needed to be competent with one group, and cool with another. Trust would be tough to build. A classic “war on two fronts” quagmire. Cue sweat.

“…working to create a loose team of friends and family around me to act as a bit of a sounding board to give my ideas the oxygen they need to survive and become actions.”

Another thing that I’ve been up to is creating coaching and accountability networks around me — something that I get a lot of value from in my day-job (for more on that see here). So, along with my friends Matthew Lehner and Chris Naismith, we started a small mastermind group with a really simple structure: meet every two weeks for one hour, each give a ten-minute update on what we’ve accomplished and what are challenges are, then for the last thirty minutes, one of us gets to benefit from group coaching on one of our key challenges. Matthew and I have met a number of times already, and Chris will join us when he returns from his stay in Greece. We will be running full barrel by September, and possibly also have a fourth member by then too.

My wife, Heather, has also been a sounding board for ideas, learnings, frustrations, and so on. When we get the opportunity to talk one-on-one (usually when the kids are asleep or being babysat), I manage to squeeze some Working Together into the conversation, and benefit from her incredibly sage advice. She knows my strengths and weaknesses best, and helps me see the ways in which I might be hiding something from myself. Alas, the advice of a spouse is never disinterested! The history of our relationship gets woven into the history of Working Together. Things become loaded. Things have to be talked through. Ongoing conversation is a requirement.

To take a quote from a Metropolis screenshot:

I think that this quote captures a big part of the business development narrative that is often missed: the relationships that you have when you start, and the relationships that you build as you go. Not to mention the role the heart plays in the film: bridging the gap between the thinkers (the head) and the workers (the hand) as if class struggle could be so easily subsumed!!

Starting something new that you are passionate about, that you were put on this earth to do — whether it’s a business, or a non-profit, or a creative endeavour, etc. — does not occur in a social and emotional vacuum… especially if you are in a loving relationship(s)! And thinking that it does, feeds this masculine fantasy of a single male, striking out on his own to create his vision, a la Howard Roark of The Fountainhead. So much of the media around entrepreneurship tends to be about head, hands and the visionary singular genius.

This is not to say that vision is always compromised. It is to say that vision is always emotionally loaded. As it should be. This is, after all, what you were put on this earth to do. What could be more emotionally loaded than balancing your commitment to your creative work with your commitment to your friendships and your loves?