What is your career “costing” you?

A couple of years ago, I had a serious career counseling session with a drug dealer.

The context of a former criminal prosecutor having such a meeting was strange enough. But, even odder, the young man was someone I knew from my work running The Learning Consultants.  He had been in one of our SAT classes.  I remembered him as a cheerful, hyperactive 16 year old.  ”Brandon” was now 21 and a college drop out.

The first part of his story was cliche.  Brandon discovered he liked partying more than studying while at college. 

The second part was disturbing but somewhat common: he started selling drugs so he could buy drugs.  

The third part was also along the continuum of someone losing his way: he liked the money that came from his new business.  

The fourth part was shocking from the perspective of a suburban Connecticut kid: he decided to drop out of college to become a full time drug dealer in New Haven, Connecticut.

In setting up the meeting, Brandon paid me what he said was his highest compliment: “I trust you.” He didn’t call it a career counseling session but wanted to talk about life.

Discussing the morality of Brandon’s work was a non-starter.  He thought drugs should be legal.  He didn’t sell to kids.  He thought he was doing the same thing that bootleggers did during Prohibition.  Discussions about meaning/purpose were not going to get anywhere.

So, we discussed his drug dealing business as I would any business.  

The money was good.  Very good for someone his age.  The autonomy was great – no boss. The “hours” were hard to pinpoint.  But, the irregularity of his work life did not bother Brandon.  From a practical perspective, he thought he was doing well.

How could I convince him to stop dealing drugs?  I thought. 

I asked Brandon his goals.  As expected, Brandon had high expectations.  He wanted to make a lot of money.  

My days in law enforcement helped as I walked Brandon through the likely outcome of his work life as his business grew.  

Brandon was a small time drug dealer at the moment.   Nonetheless, he likely would get arrested at some point because the weakest link in a drug dealing chain will eventually break.  Such breaks would lead to an arrest or two and maybe some jail time for Brandon.  

I then said, in a very matter of fact manner, that’s simply “the cost of doing business.”  

Brandon looked uncomfortable.  I pointed out that his parents would be shamed, his reputation in his suburban community along the Shoreline of Connecticut would be ruined, and he likely would not be able to get a job in any organization that did background checks. 

But, if you are going to be a drug dealer, that is the cost of doing business.  

I noted that the drug dealers that I knew were from the streets of Philadelphia.  For the most part, they didn’t have families that would be shamed; their reputations might even be enhanced on the streets if they were arrested; and they never envisioned working for organizations that would do background checks. 


The bigger challenge, however, would be when Brandon’s business grew.  As a small time drug dealer, he would not necessarily be on the radar of law enforcement, particularly federal law enforcement.  As soon as his business grew, he would be targeted by the federal government.  The likelihood of arrest and real jail time was nearly inevitable.  


I again commented in a purely objective tone: “that’s just the cost of doing business in your field.  The guys I know who dealt drugs didn’t mind real prison time because it gave them status in their community and they were used to dealing with prison.  You should know, however, that suburban types – particularly from soft places like suburban Connecticut – don’t do too well in prison.”


Brandon knew the type of prison horrors I was referring to and looked like he was going to vomit.   That, too, would be the cost of doing business.

I suggested that he use his experience to become a top salesman in a legitimate field.

Brandon hugged me when he left.  

I don’t know what became of him but at least I haven’t heard that he was arrested.  I do know, however, that “the cost of doing business” lecture may have saved him from a miserable career.

What is the “cost of doing business” in your career?