It was a Monday in January 2004. I had just decided to move to Boston with my girlfriend and leave the NYPD in search of new opportunities. I remember I sat down at my desktop computer and went to monster.com, and started looking for interesting jobs in Boston. I knew I didn’t want to do security, and I thought maybe insurance investigations would be something interesting. So I sent off some applications that morning and then checked back a few hours later. Nothing. By Wednesday, I was applying for security jobs, and by Friday, I was calling Blockbusters in the Greater Boston area to see if they needed help. It got dark. 

In the end, it all worked out, besides the girlfriend. I got into emergency management in state government and then ended up working in the private sector doing consulting, finally landing, for the last five years, doing gunshot detection. I managed to find my way through a process that was totally foreign for me, having only taken a police test and working in a structure that was incredibly regimented about process and next steps. And now that I’m on the other side of a paycheck from wearing a badge, I have some thoughts. 

It used to be that if you left a police department on good terms before retiring, you were almost always going to another department. If you left to do something else, people didn’t quite understand. What about the pension? What are you going to do? And while I have those answers now, I didn’t back then. I just knew that I was miserable and cynical, and the next 15 years felt like a prison sentence. And so I fled. And this is the first lesson. 

Run to things and not away from things. I got an offer from my new job, and the start date was two-and-a-half months before I was eligible to vest at five years. And I was terrified to ask them to push the date back, or even tell them about this, and was too young to know anything, so I just said yes. And months later, when I told my boss, she was horrified and said they totally would have just let me start months later. Had I known my value and been a little wiser, I would have slowed down, taken a breath and figured out what was best for me. 

I was on a work trip just recently in New York, and a young officer came up to me and asked if I liked working where I do. I said I did, and then he asked, “Do they pay for your lunch?” I laughed a bit and responded that they did indeed pay for my lunch. And this is my second lesson. There is a great big world out there, and you can do so many things. Sometimes we suffer from a failure of imagination, and if we only hang out with cops or have been in law enforcement for 15 years, we get blinders as to what opportunities are really out there. Police work has thousands of moving parts, and no one likes all of them equally. Some people love the investigations, some love the action, some love the paperwork (yes, it’s true) and others love talking to people or solving problems. There are all kinds of jobs out there that use these skills, and most of them have nothing to do with police work or security. We get conditioned to think of our pension time as the mandatory length of service, but it doesn’t have to be. 

Even if you decide to work until retirement, you can still start thinking about what comes next before you head to the pension section. You can take classes in other fields, like technology or writing, or get your commercial driver’s license. I know I sound like Matthew Lesko, who some of you may remember as the dude with the question marks all over his suit on late-night infomercials, but it’s true. I wish departments would offer career counseling, with workshops on resume writing or LinkedIn profile building. Here’s a hint for that last one. Putting Everytown Police Department, 2000–2020, is not a good idea. You need to tell a story, which too many fail to do. This is especially wild because the best storytellers I know are cops. 

When the NYPD had a 20-year retirement (22 for those joining now), the common adage was that there were four phases as a cop.

Years 1–5: This is great! I’m a cop! I’m helping people! I got a badge! I’m making a difference! 

Years 5–10: This sucks. You suck. Everything sucks. 

Years 10–15: Eh, what am I going to do? I’m halfway there.

Years 15–20: On no. I have no marketable skills. What the heck am I going to do when I retire?

In the non-police world, people change jobs often. Whether it be for more money, more responsibility, better work-life balance or more or less travel, it’s routine to see. In policing, it’s seen as a problem if you bounce around, when in reality, sometimes you need to try a few things before you find the right fit. Many cops don’t realize all the skills they have picked up while working during their careers. Conflict resolution, problem solving, mediation and decision-making are just some of the skills that you use daily while on patrol, never mind more specialized fields and training that you learn while on the job. 

If I see you while on a work trip and you ask if we’re hiring, I’m going to reply by asking what you want to do, what parts of your job you like and what parts you don’t like. It’s a big world out there, and there are lots of free lunches.