The Unemployable Ones

Derek Skaletsky
6 min readSep 19, 2015


As the famous Apple Think Different campaign said:

“Here’s to the crazy ones. The misfits. The rebels. The troublemakers. The round pegs in a square hole. The ones who see things differently.”

I’d like to add to this list — The Unemployable Ones.

This post was triggered by the inevitable breakup between ESPN and Bill Simmons — which has created quite the stir:

For anyone who followed Bill since his days as a lonely (and amazing) Boston sports blogger, it was very clear to see that Bill was different. He had a new voice — a different perspective and a style unlike anything else that was being produced by the mainstream sports media of the time. He would swear; mix sports with obscure pop references; and be openly critical of anything (and anyone).

Of course, he was able to broadcast this perspective to the world because he published it all on an independent blog. He didn’t have an editor. He didn’t have a boss. He didn’t have shareholders. He was free to let his voice emerge without constraint. And this freedom was the reason for his success.

So, when he officially joined ESPN, it was clear that it was going to be a rocky road for both parties. Because it was clear to see that Bill, his voice, his perspective, style & talent — everything that made him successful — also made him part of a unique and complicated category of people — like David Letterman, Howard Stern, Steve Jobs, and many, many others before him.

And with his official breakup with ESPN, Bill officially joined the ranks of — The Unemployables.

The Work, not the Job

The Unemployables are a specific class people. They are highly talented people that find it very difficult to exist as a part of an established system. They earn their title because they are people that have a hard time keeping a job. They get fired — a lot. Not because they’re incompetent. Not because they’re lazy. Not because they aren’t talented. In fact, quite the opposite.

On the surface the Unemployables are unemployable because they are disruptive, stubborn, relentless, unprofessional, difficult…”just impossible” to work with.

And this is…almost always true. They can be complete pains-in-the-ass.

However, there is a big difference between someone who is unemployable (small “u”) and someone who is a member of the Unemployables (capital “U”). The big difference is this:

The Unemployables are inherently unemployable because they care much more about the WORK than they do about the JOB.


For most people, “work” and “job” mean the same thing. They make no distinction and use the words interchangeably.

I go to work to do my job. My job is what I do for work.


But this is NOT the case for The Unemployables. For these people, the WORK is what matters above all else. The WORK is their art. The WORK is the output of their efforts. The WORK is what they create. And the quality of it, the impact of it, the creation of it — this is what matters.

The job? It’s just a way to monetize the work. The paycheck is nice, but certainly not what drives them. In many cases, they would do the work without any job attached to it (Bill Simmons is a great example — the work was something he did at night while working random jobs in Boston).

For the Unemployables, when the WORK is threatened, things get ugly.

Organizations (especially big businesses, like ESPN), however have other concerns beyond just the quality of the work. Profit for example. Liability. Regulation. Efficiency. Schedules. Traditions. Relationships. Politics. Team harmony. General apathy. Etc. All of these are forces that can (and often do) threaten the WORK.

And for The Unemployables, when the job becomes a threat for the WORK (instead of an enabler of the WORK), things start to fall apart. This is when defense mechanisms start to kick in. Different Unemployables react to this in different ways — some get angry and disruptive, some become reclusive and removed. But in all cases, the path for separation starts to form.

Tribe Builders

The other thing that separates Unemployables from others who are just a pain-in-the-ass (again, besides talent) is their ability to build a tribe. Very often, Unemployables are able to build a very loyal base of followers who will travel with them anywhere.

Their ability to build a tribe transcends the job or the company that employs them. This is easy to see in the cases of media personalities like Bill Simmons and Howard Stern. Do you think Howard’s audience was loyal to Clear Channel or the radio stations that broadcast his early shows? Of course not…when he went to Sirius, subscriptions shot from 600k to over 6mm virtually overnight. Howard transcended (and still transcends) any company for which he works.

But this holds true even for non-media Unemployables. I’m sure you know some with whom you’ve worked. These people build a tribe of team members (and sometimes customers) that will follow them anywhere. If they leave and start something new, or join a different company, there will be a tribe of people that will come with him/her. When Steve Jobs was fired from Apple, he started NEXT and brought plenty of people with him — employees, customers, investors, members of the media, etc. He’s the most obvious example, but there are plenty of smaller-scale examples everywhere.

Can you Manage the Unemployables?

Now…I can speak about this because I consider myself relatively Unemployable. I’m certainly not saying I’m even close to the level of Bill or some of the others mentioned here, but I have always placed much more value on the Work above all else. And this has made me, at times, Unemployable. Yes, I’ve been fired or mutually split from several positions because of decisions made by management that has gone too far in compromising the Work (of course IMHO).

Now, as a founder/CEO, I aspire to look for ways to nurture the Unemployables that come my way. Obviously, I celebrate and value the Unemployables. I know their talent and passion can bring a ton of value to a business. Their presence can push you to places you might not go without them. Their focus on the Work can help to “raise all boats” — and elevate the efforts of everyone else.

So, creating an environment that can support Unemployables could be the difference between building a game-changing company and building…well…a regular company.

Creating that right environment starts with an understanding of what makes these people tick. What motivates them and will keep them producing at their best. Know that for these people:

  • the WORK matters more than anything;
  • “the way things have been” in the past matters very little to them;
  • ‘tradition’ is meaningless;
  • “fitting in” actually makes them uncomfortable;
  • freedom and independence are absolutely essential;
  • egos are a factor — they have them and do need them fed (at different levels);
  • their tribe is essential. They hold dear the people that value their work;
  • compensation is important, but not top priority. They will take a ‘home-town’ discount if they feel like they are in an environment that is supportive of the WORK.

The Unemployables should be given the resources….and SPACE…to do great work.

With that said, it’s also important to be realistic about the Unemployables. While I do celebrate them as individuals, I’m not saying that companies should never fire them. In some (maybe many) cases, it’s the right decision. But it’s a decision that needs to be made for the right reasons. It can’t be made because they:

  • don’t “fit the mold”; or they
  • “rub you the wrong way”; or they
  • “just create more work for me”; or they
  • “are constantly pushing back on things”; or they
  • “threaten my job!”; or
  • any other reason that is based on your own personal feelings

When the damage an Unemployable may cause outweighs the value they bring, it’s probably time to pull the cord.

And, for many of the Unemployables, even if you give them everything they need/want…they may still be Unemployable. But if done right, you can create great music (and a lot of value) together.

The Unemployables are a complicated bunch. But I’d hate to think where we’d be without them…



Derek Skaletsky

Tech founder (mostly SaaS). Latest — Sherlock (; Boston expat; Hollywood escapee; hack photographer; dad (x2)