This site has been moved to
Please update your bookmarks, you will be redirected momentarily.

Written by Zainab Habib

I've noticed that we're good at asking for and taking up offers to help as an organization, particularly in Kanika's absence. Speaking for myself at least, I'm terribly stubborn... especially the kind of stubborn that will just do everything myself, so admitting that I can't do it all is a challenge that I've been working on for the last few years.

One way of being able to learn though is to stay open to the opportunities that come. Adults often come to their "education" and learning because there's something they want to get out of it - meaning they have expectations of some kind (think of the last workshop you attended or course you enrolled in). As Kanika has said before, it often helps to enter conversations without (great) expectations and for us, our biggest learning has taken place within conversations.

AJ has had an advisor for a while since she came on board full-time; one of Kanika's most trusted advisors has been working with her and has helped her ease into all things CEO- and business development-related. Though AJ already has great skillset, she's told me it's been so helpful having this support.

AJ went out to lunch today with a close friend of hers and she returned with good news for me: he had asked what he could do to help and AJ was taking him up on the offer because he's someone in the industry who understands content inside out. He will be able to act as an advisor to SoJo and particularly to me, especially because he's an award-winning journalist and he and I can both relate as writers. Though I can do almost everything related to our day-to-day operations in content, I have much to learn when it comes to thinking about content in more strategic terms. I also haven't been able to reach out to anyone who does content in a meaningful manner because I haven't met anyone really working in content full-time yet.

As AJ pointed out, there's only so much either of us can learn on our own, even if we're both really resourceful. What's exciting about these advisors is that they want to get their hands dirty when they're helping us; they're not just people who point you to your next resource without any real guidance on why you're following a particular process. They're willing to stand by us as we learn from their expertise and insights, and as we then turn our learning into ideas and later action. This accelerates our professional development, which allows us to spend more time actually doing something with everything we're learning.

I can't wait to get started on this process. I'm going in with an open mind and a blank slate for our content and though I have no great expectations, I know this will be a learning experience regardless.
When you're going through a stressful time, people often say talking about what you're going through will make you feel better. My mom often encourages me to talk through my issues to avoid stress from bottling up. Stress serves no-one any good, and in fact the negative energy impairs rational judgment and productivity.

 Below are three examples of intense conversations that were had over the past 10 days:

 My case interview last weekend was a great example of the value gained by 'letting it all out'. Not only did sharing all my challenges made me feel a bit better, the feedback I received simultaneously allowed me draw valuable insights and make realizations. Before that session everything was fuzzy and I wasn't able to articulate the source of my frustrations. Letting it out allowed me to make sense of those fuzzy dots floating around in my head; and this enhanced clarity has since allowed me to better navigate through this turbulent time.

 The day before yesterday I had dinner with a group of friends, among them a person who I consult often for advice. It is rare that we meet, so towards the end of the evening I took the opportunity of asking him how I should navigate one of my challenges around funding. I was pushed into a corner with really tough questions at 10pm at night; it was an intense conversation to say the least. In spite of the discomfort that was experienced at the time, I left that conversation in a better headspace. I did not receive all of the answers I was looking for, but he gave me a tangible suggestion on what my next step should be. One that I'm already acting on.

 Yesterday as part of a mandatory check-in for the incubator that SoJo works out of, I was required to give an update on our current status. These check-ins are used to set goals, and act as accountability mechanisms to share updates on progress towards achieving those goals. They are also an opportunity for my peers (other entrepreneurs) and management to weigh in and provide advice. I was asked to talk about my challenges. Sharing your problems is not easy. Over vulnerability is the pain that comes with re-opening the wounds and reminding yourself of everything on your plate. At the table were 4 members of the management team who also act as advisors to all of the entrepreneurs in this incubator and only one other entrepreneur. I started the meeting excited, hoping for some breakthrough answers. Objectively speaking, I got very little tangible and concrete value out of that meeting. I did not walk away with a single thing that I can act on. I became more frustrated over the course of the meeting, and its clear to everyone that saw me shortly after that I was upset. I shut down my computer shortly after and went home early. It has been an exhausting couple of weeks and after pouring it all out on the table (for the third time in one week), the last thing I wanted to hear is keep fighting the good fight (which is the best feedback I received).  It felt like salt got rubbed into those wounds that I've been trying so hard avoid blood from gushing out (pardon the graphic analogy).

 Out of the three examples from above, I did not start either of the first two conversations with expectations. I did have a great deal of expectations from yesterday's meeting (given the nature of the meeting) and judging from my emotional barometer: I was disappointed.

 Lesson learned:
  1. You can't expect anyone to give you a silver bullet answer to your problems. Best is to enter every conversation without any expectations.
  2. Letting it all out doesn't always make you feel better. Use your discretion and open those wounds as far as you want to. 

Earlier today I had my first meeting with one of SoJo's crowd-sourced CTOs to learn about Project Management. As evidenced by the fallout from our server decision, up until now every decision has been made in an ad-hoc, do-what-it-takes-to-get-it-done fashion. This lack of organization and planning led us through a successful private beta, public beta, and post-beta launch. We were nimble, weren't bogged down with management and accommodated where we saw fit. Now that the scope and complexity of SoJo has grown, so has its need to get better organized and do things smarter.

To fill this deficiency, we invited an experienced project manager to join the team in an advisory capacity, lending off her 30+ professional years of experience in project management. This is a risk, as she has never worked with a start-up, and her methodologies may not necessarily apply to the needs of a fast-paced, ever-evolving organization such as SoJo. The biggest risk to seeking external project management support is getting slowed down by un-necessary processes and planning, when SoJo's greatest advantage has been our ability to implement and execute in a speedy manner.

Although a tad bit overwhelming, today's session was incredibly useful, and I learned a lot. I learned how to articulate our functional requirements at a high-level and the methodology used to break them apart into functions and prioritize. SoJo has always been victim to scope-creep, so having an objective process to prioritize features based on need, ability to implement, and risk will help the product team stay focused and on-track.

Making choices has historically been challenging, as I am always seeking an optimal solution with only incomplete information. She introduced me to a more structured way of making decisions, also referred to as triple constraint project management. As per the diagram, one side is the dependent variable (in the case of our public Beta launch, we were constrained by time to launch at the SociaLIGHT conference). Once you are clear of your dependent variable, you are then able to adjust the other constraints accordingly. Seems quite logical, but now whenever I make a decision I will visualize this triangle and remind myself that I cannot have it all. This will definitely help to keep me focused and grounded.   

To avoid the gerbil on the wheel syndrome, I'm hopeful that external project management support will help to keep us moving forward, without burning unnecessary energy.

Disclaimer: What I'm about to share is highly experimental and is not grounded in any theory or practice.

SoJo has many exciting product development decisions to make. Based on early insights from the strategic planning process, SoJo needs to improve the navigation, usability and interface of the public site. In parallel to making these improvements, SoJo is building its first-ever enterprise-level software product. The stakes are much higher now, and decisions have greater implications. I was able to guide the team to building a content site using a Wordpress framework in its most basic functionality. This next phase of growth is much more complex, and beyond our current capacity.

SoJo has great development team. When given proper direction and structure, they are able to execute above and beyond. That being said, both developers are fairly junior and SoJo is the largest technical project either of them has worked on. Trial by fire has been our methodology thus far,  however it can be a hindrance in moving SoJo forward. The entire organization needs to work at a more accelerated pace to achieve these next set of milestones.

When seeking advice, my challenges around the gap that exists between translating business requirements into functional requirements, the need for a CTO (Chief Technical Officer) came up quite often. Most successful technology companies are co-founded by a technical person, who becomes the CTO. Bringing on an external CTO at this stage of our development will be challenging. We have no intentions of selling SoJo for millions of dollars in the coming years, and the financial payout seems be to be a large motivator to attract good senior technical talent.

Technical recruitment has always been a challenge. Linus and Jesse joined SoJo right before major product launches. For the past 8 months, I've been keeping my eyes peeled for a technical partner. After 3 intense and focused months of searching for a technical team member, I've learned that effort will not always equal result. With the inability to offer a 6-digit salary and a highly competitive market, finding the right person will remain an ongoing challenge for us.

SoJo is in a conundrum where it needs a CTO to grow, however is unable to find one -- therefore the only logical solution is to create one. To fill its technical deficiencies, SoJo will be crowd-sourcing its CTO. This is highly experimental in nature. I have not found any successful case studies and I am still figuring out what it will look like.

Traditionally, crowd sourcing implies reaching out to the public for assistance. In this case, I will be reaching out to a closed network, seeking referrals to source individuals looking to commit their skills and experience to SoJo. Since SoJo is not building any unique technology, all development related activities can likely be covered by our existing development team. What we need instead is support in project management, information architecture, decision making and industry insights. Most of these skills come from experience, and so it makes sense to leverage the experience of many professionals, most of whom can complement one another. In addition to benefiting from the skills and expertise of experts in their respective fields, not having someone in the daily grind of the business can also provide fresh perspectives.

Product vision and business requirements will continue to come from me, so the crowd-sourced CTO will be used for technical guidance.

This approach is highly risky for many reasons:

Lack of ownership and accountability
SoJo will not the first priority of any of the individuals. Being a secondary activity, they may not dedicate the mental energy or time required for this role. A dedicated CTO invests in the company, both with their time and expected payoff. It will be difficult to hold a crowd-sourced CTO accountable to the advice that they provide, as the consequences of their advice may not directly impact them. Beyond goodwill and the opportunity to shape an organization with huge potential for impact, there is not much more that I can offer to our crowd-sourced CTOs in terms of compensation.

Effectively communicating the problem
A crowd-sourced CTO will not be able to get into the trenches or depth of problems. Only someone that works on a project day-in and day-out will understand all of the intricacies of certain technical issues and implementation problems. When only providing incomplete information, we risk getting incomplete or misleading advice.

With multiple brains giving out different pieces of advice, it is likely that we will receive conflicting and incomplete advice. Distinguishing between everyone's bias can result in a lot of inefficiencies or lead us down a wrong path. Similarly, the different features and technical elements to our products are all intrinsically linked. Each crowd-sourced CTO will likely look at their own issues in isolation. Without taking into account the technical inter-dependencies of each of the solutions, it is possible that solutions to one problem create bigger problems elsewhere. 


Having a dedicated CTO will free me completely of all technical related activities. With less focus on the product, I'll be able to dedicate my time to equally important CEO-type activities, such as getting funding, building the brand and supporting other functions of the organization. In addition to coordinating the schedules of the CTOs I will still be primarily responsible for relaying that guidance to the technical team.  

Risks considered, I'm quite excited about going ahead with crowd-sourcing SoJo's CTO. This could be an experiment gone wrong, in which case we know that we exhausted every option. On the other hand, this can potentially be a new model for what is possible, given limited resources.

_As of today, SoJo will be officially incubated by Ryerson University's Digital Media Zone (referred to as DMZ). We are excited to be in an environment that will provide us with the necessary technical, business and administrative support needed to bring SoJo through our next phase of development.

Although today is only the start of our journey in this incubator, it was a long road to get accepted. Multiple pitches (we were not accepted the first time we applied) and months later, the day has finally come when we can finally start working in a community of like minded individuals.

Located in the heart of downtown Toronto, DMZ currently incubates 27 digital media start-ups. I'm looking forward to co-working with other talented young entrepreneurs: seek their guidance as we build SoJo and also encourage them to think of society while they build their products and grow their companies. The mentorship, workshops, networking and visibility provided by this space will also be invaluable for us.

And of course, we finally have a proper office. There is no doubt that a proper workspace is important for productivity and overall happiness. Over the past 6 months, we've been bumped around between three different temporary offices and spent many hours at coffee shops. It is great have a proper base, so we can focus our energy on growing SoJo.

SoJo is the first company to join the DMZ this year. Being the "newbie" feels like the first day of school; I came into this space without any of my colleagues, don't know anyone here and don't yet have a proper desk set-up. I know it will take time to get settled, be acquainted with the other individuals and feel like I'm part of this community. For the time being though, I'm excited for this opportunity and hopeful that our experience with the DMZ will be integral to SoJo as we endeavour to achieve ambitious goals in Phase II.

_ Overwhelming is the one word I use to describe the past two weeks. I am overwhelmed reacting to the backlog of activities and overwhelmed trying to decide in which direction SoJo needs to proactively move forward.

Reactive mode-
November forced the team to be in laser fine focus mode. The key priority was to get the private beta ready in time for our launch, which resulted in me deferring all non-launch related items on hold until after the launch. Now that my head is out of the sand, it is not only overwhelming resuming a normal schedule, but more so, dealing with the backlog of correspondences for almost an entire month. This reactive mode of feeling the pressure to stay on top of my inbox stresses me and builds up negative energy. The feeling is one comparable to having a dumbbell tied to your ankle, which impedes me from moving forward and also makes for an un-enjoyable experience all around.

Proactive mode-
The launch has provided us with an incredible amount of momentum. Since starting SoJo, this has to be the single largest boost in energy. Knowing that we have some fairly ambitious goals ahead of us, there is a huge desire to capitalize on this momentum and run through our action items. There is temptation to implement feedback immediately from our users. We have so much good content that we want to put online everyday, however need to build up the editorial team to deal with the backlog. This momentum can also be used to our advantage when building new partnerships. This influx in positive energy places desires to push forward in so many different directions.

Striking the balance-
Feeling as though I have 100 different balls in the air creates a helpless feeling of not being in control of any one of those balls. Reconciling conflicting priorities is a challenge that I struggle with constantly. The last two weeks feel like a daze. Its feels as though a waterfall of ideas, emotions, pressure, expectations and work are now flowing through constantly.

Last night while talking about our launch, an advisor told me:
"You have to let this momentum ride you. Don't feel pressured to have answers, have a plan or respond to everything immediately. You've worked hard to get to this point, and in in order to progress further you need to listen. Use this time to listen, hear what people are saying and use that feedback to inform your next steps."

So on his advice, I will try to take a step back and listen. I'm still not entirely sure what that means, but I do know that getting overwhelmed is not a good way to proceed forward. We have nothing but possibilities to look forward to and it would be a shame to crowd all this positive momentum with negative energy and stress.

SoJo has taken an iterative approach; where we plan to release multiple versions of our site, have our users co-create the site and along the way deliver a product that meets the needs of our users and supports them in their journey of creating social ventures.

We released a closed Beta in July. Although we are very proud of this first step, it is now time to move onto our second version site and open it up to the public. The open Beta will have different functionality, more content and an improved user interface.

Having virtually no technical, web development or design experience prior to SoJo, I felt it'd be best to consult experts in the field and leverage their experience to make a more informed decision. Over the past few weeks I've been speaking with developers, designers and marketers - all with experience creating websites and established track records of delivering amazing work. Every conversation was stimulating, the average chat lasting about 2-2.5 hours - with ideas and possibilities getting tossed around. It was overwhelming at the same time, as all of these conversations went down very different paths.

Some said to focus on the technical development of the site and organization of information from the back-end. Some said to focus on the design and user experience on the front-end. Some said to shape the content and navigation to fit a brand. Even on the technical side, I was presented with 4 distinct options of how to proceed.

The bucket is full. My head hurts from all the confusion and attempting to reconcile the conflicting advice. The fact that there are so many ways to approach implementing SoJo's vision is encouraging, as it demonstrates that nothing like SoJo already exists and its going to take some serious innovation to come up with a good solution. On the other hand, I do wish the dots lined up more clearly together.  

Making decisions are often the most difficult parts of the journey. Once you know which direction you're headed, executing can sometime be as simple as creating a checklist of items and tackling them one-by-one. Picking the direction is the challenge.

I only have a few days to make a decision and pick the best course of action on implementing v2 of the site. With less than 2 months and minimal financial resources, I only have one shot at this decision and must stand by it until the open Beta launch.

Judgment and hunch go hand-in-hand when making a decision like this. There is no definitive consensus from experts on what is even possible given our timeframe and financial resources. There is no such a thing as a perfect decision, and perhaps I need to alleviate the pressure I self-imposed on making the "perfect decision," make a choice that feels right given the available information, take a risk and go with it...

For the longest time I thought business plans were quite un-necessary. In the entrepreneurial world, there are countless articles that talk about the uselessness of business plans and that "real" entrepreneurs don't really need one. My first "plan" was created on 11 slides...

Next week there is a grant application due. I believe SoJo has a pretty good shot at being considered for this grant, as we meet all of the criteria, and we have to start looking for external funding to take the venture to the next level.

I've known about this application for a few weeks now, but never thought the business plan would take so long, so I never bothered to look into it until now. Earlier today I proceeded to download the template provided on the grant-maker's website. The template is 47 pages. Although all sections don't apply to us, actual plans normally exceed their templates, as text  can exceed the allotted space. Not feeling like working through a 47 page template, I emailed an advisor to get a second opinion. He thought a 50 page business plan is absurd, but assured me that it will take about a week to complete this business plan.

This email was my much-needed kick in the behind. For the past 3 hours, I was successful in hammering out the Problem, Solution, Product Execution, Marketing and Business Model sections.  It's a start, but sadly still a long way to go.  While in the flow of writing it felt like I was driving at 200km/hour speeding through the words. But when I took a step back, I actually felt like I was strolling at the speed of a turtle!

Attitude and Approach
I don't think that a Business Plan can be created like an essay when you're in school with the arrogance of thinking it can be written in one night. Instead of feeling accomplished with the 2000 words of well written business plan content, I'm daunted and overwhelmed by the all of the blank sections that lie ahead and the unanswered question marks.

I'm not worried. If I'm committed to SoJo, then I'm committed to writing this business plan. Although its real-life application, beyond the grant application, is still questionable in my mind - it IS a great exercise to write out all the thoughts that have been in my head and will impose discipline as well.

The reason why I dislike business plans is because they are highly static and I honestly believe efforts should be focused on DOING rather than planning and saying what you will do. That being said, using this as an exercise to articulate different components of our venture, while not being limited exclusively to what is written will undoubtedly serve me well.

Wish me luck!

Last night I met with an advisor who helped me create the outline of SoJo's first "plan."

Although I'm fairly clear on SoJo's value proposition and our objectives our "plan" hasn't been written down anywhere. To prepare for this meeting, I created an 11-slide deck that answered the Who, What, When, Where, Why and How of SoJo. Because I've been so focused on executing the product, this is actually the first time since the initial backgrounder document (created back in March ) that I dumped everything from my brain into those 6 questions. It did not take long to write it all out, refining and re-wording did however. The beauty of a powerpoint is that is forces you to be precise (a skill I am keen to hone).

I arrived to my meeting with mixed feelings. Although I trust and respect this advisor and knew feedback would be given with SoJo's best interests in mind; I was quite nervous that my slide deck was going to get demolished. Sharing an idea is one thing. Sharing a document [for the first time] that represents the past 4 months of your life, your aspirations for the future and intense amount of emotional energy is unbelievably terrifying... In the end, it was actually an enjoyable experience! The difficult questions didn't seem so difficult, because for the first time I did not feel as though I was on "defence" mode. A difficult concept to articulate, but I think the act of writing out a plan gave me the courage to stand by what I did know and provided me the humility to acknowledge what I did not know.

My plan is at 30%, but was assured that with a little more work, it will be 90% there.  

When you're ready to create a "plan" and share it with someone external to the organization for objective feedback, here are some tidbits of advice that may help you remove those barriers:

- It doesn't have to be complicated. No one expects you to create a formal business plan on the get-go. The trick is to get what is in your mind on paper and manipulate it from there. Forget about structure and start with answering the 5Ws and How.

- The plan will change. Don't seek perfection, because the destination is an evolving target and there are so many unknown variables. Write your plan in the present, and forecast based on what you know today.

- Share with people whom you trust. I personally do not take criticism well from people where a trusting relationship has not yet been established. An attack on SoJo is an attack on me. Although last night I received a lot of feedback, working with someone who I trusted allowed me separate the emotions and objectively listen to the feedback.

- No one has all the answers. Everyone provides advice from their bias and perspective. Listen and take what makes sense to you, because ultimately you must trust your judgment as you will be solely responsible for driving your project forward.

An entrepreneurial journey is a rollercoaster. There will be ups and there will be downs. You cannot predict when the storms will hit you - as an entrepreneur (or someone starting a project) you need to remain focused on your goals at hand and humbly acknowledge that the rollercoaster is part of the deal you signed up for.

It can be really easy to get in those slumps - expectations are not being met, progress is not happening as quickly as you like, you question whether you're even on track, and the list of unknowns only seems to increase with time. Throughout our journeys, we're going to make mistakes, de-rail and feel completely lost. The challenge is remaining rational and collected, to not allow the negative emotional energy impede us from moving forward.

Although I agree that entrepreneurship is a 24/7 job, as your mind will always be processing ideas and you will be expected to deal with certain issues as they arrive -- does that mean we are also expected to be physically working on our projects 24/7? There will never be enough hours in a day and as a result the tendency to overwork ourselves seems to be the only reasonable solution out.

When starting out, why don't enough people talk about the importance of working smarter, not harder. I don't mean discount the hard work that goes into starting any project, because building a social venture is a lot of hard work, but is it possible for the human brain and body to run at optimal capacity all the time?

Last night a friend offered me critical feedback on SoJo - which I internalized as a personal attack. It triggered a downward spiral of negative energy, which I knew was unhealthy. Clearly, something was wrong. When seeking comfort from a friend, he shared with me a few words of wisdom from his experience as a serial entrepreneur and Venture Capitalist: Diversity will make you more resilient

I think it is OK to do a pulse-check. Aside from your venture, are the other aspects of your life that are important to you in check: relationships with family and friends, exercise and physical activity, or leisure activities? Attempting to include some diversity in your routine will not make you any less committed to your project -- on the contrary, it will make you more resilient and better able to bear those inevitable rough waters as and when they hit you.

Earlier today, SoJo was accepted to be a client with MaRS Advisory Services, operated in collaboration with Social Innovation Generation. 

What does this mean?

They will provide us with advice on business planning, help us figure out our funding strategy, and provide legal and intellectual property issues. We will also get access to market intelligence, among other helpful resources. These services are provided to us free of charge with the goal of helping us make SoJo a reality.

Sounds like a pretty sweet deal, right? Patience was required – it took us over 4 months to seal the deal from when we first approached them for support to finally receiving the official ok and discussing next steps. I was also forewarned about the backlog of client requests, which means it may take us a while to connect with the experienced advisors and derive value from the resources available to us.

Regardless, SoJo is at a place where we can really benefit from experienced advisors to guide us in the right direction, ask us the tough questions and provide us with the critical feedback that is needed to build the right foundation that will enable SoJo to be amazing. We are now entering a new phase: our idea has been validated; we’ve started building a community of supporters; and are ready to move forward.
Next phase is figuring out how we bring our site together, where the funding will come from, and developing a plan to launch the Beta. It is my hope that these services can help us in this next phase, and subsequent phases.

I will keep you posted on the evolution of our relationship with MaRS, the value that we derive from working with them – and of course, will share everything learned on the SoJo site for your benefit.

Don’t have access to a MaRS-like advisory service? Don’t sweat it – that’s why SoJo is here. We hope to build a site that will provide you with the information, tools and resources you need to get your idea up and running – and hope to connect you with other similar off-line networks and individuals who will provide you with that extra support you may need.

While I was in Montreal yesterday catching up friends and former colleagues, I took the opportunity to share the idea of Social Journal with people who I trusted and knew could provide constructive feedback. Two individuals in particular hold respected and distinguished careers in the Communications and Media field in Québec and are disconnected from the ‘social innovation’ world I’ve been immersed in for the past few months.

Although I consider myself fluent in French, I am only capable of speaking in standard “dictionary” vocabulary, as I do not read in French and am not up to speed with expressions and nuanced terminologies. Although I spoke about Social Journal with great enthusiasm and excitement, my tongue got twisted in knots (several times) and I was unable to articulate the essence of the idea as effectively as I can in English. I was frustrated at my inability to speak freely about something that I knew so much about! It is only through expressing myself in a different language do I now realize how many loaded “buzz” words I use and how I’ve adopted a whole new vocabulary.

And so I asked myself: Do I talk in a “different language (figuratively)” to everyone I speak with and assume they know what I’m talking about?

My take-away from this incident, practice your pitch using a Grade 5 vocabulary. You do not need to impress everyone with sexy buzz-words, but rather focus on articulating what you’re trying to achieve and why it is important in basic language. This will enable you to appeal to a much broader audience and allow people who speak different languages (figuratively and literally) to join the conversation.

PS: In case you’re wondering, both of the individuals have offered their support and will act as advisors to this project. Will keep you posted on the contributions they will make to Social Journal!