Thought Starters

Does the “Solopreneur and the Social Web” affect our understanding of Leadership?

I love live (well, I guess I love too) in Toronto, Canada and I have this website where I broadcast to the world my feelings and insights about a variety of topics on design, project management and leadership; the things I love live. In an effort to “up my game” I have hired a web developer in Boston to help me transition this site to self-hosting and to give it a more professional feel and some enhanced functionality.

That’s a pretty common thing to do so why am I writing about it?

Well, I guess I could have easily hired someone local. Why didn’t I? Several reasons. Some may not make sense to you but who cares, right? My decision. My web developer sold herself very well, the recommendations were good, her rates are very reasonable but most of all I wanted to take a chance. And I wanted to give the social web a fair shake and besides it’s kinda cool.

So off I go.

When we’re done, I will have a shiny new site and you will have a new place to visit.

Ah, the best of both worlds!

That process got me to thinking about leadership and the world of the entrepreneur or that new….ish term I keep hearing; solopreneur. How do the “solopreneur and the social web” affect our understanding of leadership?

Well, on that note, here are a thousand words or so (yowzer) broken down into bite-size chunks that form my vision opinion on this subject.

Is the self directed work model sustainable?

To set the stage let’s look at a ROWE [check it out here] one of the least “managed” work models that exists today. Even if it is a primarily self-directed model, a ROWE still has leadership and that leadership drives the direction of the business. Even for a model that celebrates the self-directed individual the business itself is not self-directed. Got it.

The social web appears, in its current state, quite the opposite.

If you look to classic storytelling as an example Lost or Lord of the Flies offers an interesting viewpoint to this argument (both extreme). In either case the world of the shipwrecked started in chaos and as time passed an organized system emerged. Leadership (and by nature politics) eventually evolved from the fray. By and large it’s human nature for us to organize ourselves. Now I am not suggesting the social web is in chaos but do you think it will evolve in a similar manner? It has certainly solidified the understanding of the individual. Just like being on an island where everyone starts out equally, all shipwrecked in the same manner, will the cream eventually rise to the top? Will the social web eventually self organize?

Who knows and maybe it’s ok not to know.

How do you now define leadership in the social web or can you even do so? Technology has facilitated a new way for us to communicate so the old definition of leadership needs to start to understand how to navigate this new world. The old hierarchical leadership models likely will no longer work. The idea of one level reporting to the next all the way to top of the heap, the ivory tower, is sustainable in many business models but in the social web it doesn’t seem to be viable.

Who are the leaders in this social web then?

It appears that the entrepreneurial attitude (yes, ATTITUDE) is the emerging leadership model; individuals and solopreneurs bringing ideas to the virtual table and sharing thoughts in order to test or evolve a model or an idea. Inherently we all look for leadership in some form or another and in this brave new “virtual” world, traditional leadership is segmented; fractured into a multitude of self-directed individuals happily putting themselves out there for the world to see. These are who appear to me to be the new leaders in the social web; together and as individuals.

But what about “ye old experience”?

It seems, in this brave new virtual world, the 99% no longer need to have an MBA, be Harvard educated or be elected to office to be a leader. We can all can take advantage of the free publishing tools out there and start to create influence. We can demonstrate our legitimacy. Today is the world of the citizen influencer; the 99% influencer. The D.I.Y. culture.

You CAN do it yourself.

D.I.Y. is now P.H.A.T. (pretty hot and tasty)!

It’s groovy!

Its hip, it’s cool, it’s sick (sic)!

Have I covered all the Generations? Fun times for all. “Go for it!” seems to be what the pundits (me included) shout from the treetops. Make hay while the sun shines.

Is there a downside?


How do you know I am a leader if YOU don’t know me? Are YOU going to hire me?

Is the social web like your virtual CV? Well, social proof seems to mean a lot in this world, doesn’t it? Everyone still seems to look for validation and social proof seems to go a long way but it’s a slippery slope and you know it. You have to be all MC Hammer and “too legit to quit” (sorry young folks, you might not get the reference) to make it in this world anyway and in the social web it becomes that much more difficult. These days, if you want to work with someone on the social web or you want to hire a solopreneur, the biggest challenge you might face is being able to look beyond the surface of someone’s credentials.

So what’s a brother to do?

Well, we all align ourselves to like-minded people, right? You do it in life. It’s a natural thing to do. When you want to hire someone you read their CV, you get references and you make a decision. It’s that easy. Same as the social web, right? Doesn’t seem like it though, does it? It’s easy to read a blog, surf a website, get opinions but opinions not based on experience are dangerous. You are almost forced to trust the opinions you get and you have to take the same entrepreneurial attitude and be willing to take a risk otherwise nothing gets done or nothing ever happens.

Do you shop around then?

In reality most people do very little research to find the right person or service. Yeah, you are going to oppose me here, I know, because of all the statistics and consumer reporting that says people are using the web to comparison shop at ever increasing rates to find the best deal on everything; a phone, TV, whatever. Shopping for ideas or services is not the same thing though, is it?

Why? Because services are not widgets.

As a business society when looking to engage a service are we too lazy to do the research or do we just not have the time? Is the “same old, same old” the right answer? The sure thing. Do we spend the time to look for opposing viewpoints or are we just taking what we are being offered for rote? Are we willing to take a risk?

I guess it’s really up to you to decide.

People who follow each other and align with like minded individuals certainly have similar values and that should mean something when looking for opinions on the legitimacy of a service or business. Is that the way forward? Is it legitimate trust or are we just being entrepreneurial minded when we hire on the social web? When we ask, we are placing YOU in a leadership position and trusting YOU to be honest and true.

And don’t forget, people know stuff!

You have to admit people are much worldlier today and that is surely due to the unlimited access to information at our fingertips. If you really want to know something you can find out. So, what does that mean for us that work (and play) on the social web? It simply means that we are all much more transparent and we all need to manage ourselves on a micro level. The privilege is that we get to know much more about each other and if we choose to be, we will always be connected. There are no filters anymore. We put it out there and once it’s out there, it’s out there and it better be legit!

We have an inherent responsibility, as individuals, to be real.

In this type of world we may need to redefine leadership and that may not be possible until a new language is formed that can actually help us define it. We are, together, rewriting the language of business and what it means to be a leader in that world.

But, for now, it’s really about connectedness, equality and sharing.

Isn’t it?


  • What role do you consider traditional leadership plays in the social web?
  • Are you participating to build a business or are you a passive user?
  • Have you hired a solopreneur and if so how did it go?


 Why are you just staring at this question? Write something.


About rdopping

interior design guy who loves other stuff; social media, photography, film, food and anything that is good for the growth of the self


4 thoughts on “Does the “Solopreneur and the Social Web” affect our understanding of Leadership?

  1. I think the traditional role has a place for those of us who have lived it and see what works and what doesn’t. In many ways, I think it gives us a leg up. However, we also have to be smart enough to see what’s working in the non-traditional way in here as well.

    I try to do business with people I know; I’m probably not going to do too much research (I’m the ‘just show up guy’ anyway) and rely on the relationship.

    I haven’t hired anybody because all financial decisions ultimately end up w/ my CFO (the wife) and she is Dr No on anything social until I start making money from it. Yes, my existence has been very passive to date….

    Posted by Bill Dorman (@bdorman264) | March 25, 2012, 08:55
    • Bill, thanks for your comments. Understood. Fortunately, I have a little more freedom on the financial front but the point really was centered around the ideas on how I see the social web affecting business in general. I know you got that but what’s interesting from the perspective of your response is that you are not a millenial (good guess, huh?) and your reaction to thes ideas is what I struggle with as I get more involved in thinking about how to navigate the web for business.

      Trust is a big deal and I stongly believe social proof is a starting point to develop trust in this space.

      Posted by rdopping | March 25, 2012, 09:08
  2. I feel a bit obnoxious saying this, but sometimes I feel like the millenials and I have so little in common it is like we come from different worlds.

    Posted by TheJackB (@TheJackB) | March 25, 2012, 23:34
    • That’s ok Jack. We are just people though remember (I know you know). Millenials are good people too and yes they do things differently but that’s what’s cool about it. In the workforce I love to listen to varying approaches to problems and younger folks have a different mindset and a different way of working which I think we can all learn from in some form or another. Social is interesting that way too ’cause it’s sometimes less obvious where some visitors, friends, etc come from. Their ideas are their ideas and we can accept or challenge them regardless of generation. Thanks for your comment. It got me thinking and that’s GREAT!

      Posted by rdopping | March 26, 2012, 06:37

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