“Be a private eye,” they said. “It will be fun,” they said.

Some not-so-fun things about being a private investigator

Let’s be honest: Sleuthing for your daily bread can be a challenging gig. I’ve been doing this work for more than thirty years and have come to embrace this way of life and the downside that comes with it.

The following are a few challenges you might face in the private eye business:

The Hours Can Suck

In this business, we have a term for pre-dawn hours, late nights, weekends, and holidays: regular workdays. There is no downtime. The work can and does happen 24-7-365.

On one recent weekend, I traveled two-and-a-half hours (one way) in hopes of interviewing one witness. No one, including me, had been able to reach him on the phone. I thought a Saturday would be an excellent time to catch him. I found his house, but his vehicle wasn’t there, and no one was home. It was a late Saturday afternoon blending into the early evening.

I waited. And I waited a little more. Suddenly, a fancy Jeep parked in the alley behind the residence. The tattooed subject exited the passenger’s side and ran into the house. I caught him before returning to the Jeep, which was still running, and got him interviewed. Then I traveled the two-and-a-half hours back home and typed up my report.

Another fun Saturday night.

Uncomfortable Work Conditions

It has been said that to be a private investigator, you need to get comfortable with being uncomfortable.

Surveillance requires long hours of sitting, followed by the controlled chaos of following vehicles and people. The temperature in the surveillance vehicle can be brutally hot or freezing cold. And then, there is the need to use a whiz bottle.

Private investigator work will take you to some tough places, including surveilling or knocking on doors in the rougher parts of town and conducting interviews in homes where conditions are less than ideal. We are conditioned to take all this in stride. 

Uncomfortable Interviews

This job will require interviewing people from all walks of life. I’ve interviewed rich and poor people, people with and without criminal records, those with little education, and those with advanced degrees. A lot of this requires exiting the comfort zone, learning a new language to communicate with someone utterly unlike you.

I’ve also interviewed residents of county jails and state prisons. One such interview was with the leader of a prison gang. At first, he seemed like a goofy kind of guy. Then I told him something he didn’t like to hear. His face sank and went dark. Then he got real quiet.

I was able to lighten his smoldering anger with a few carefully-chosen words. But I was still glad his feet and hands were chained. 

Most interviews aren’t as uncomfortable as that one. But you never know how folks will react to certain questions. Wardrobe, zip code, and years of education aren’t necessarily a good predictor of who will be volatile.

One trick, to my mind, is to treat everyone like they matter. The interviewee gets my respect and my full attention, no matter who they are, what they earn, or where they reside. That’s the job.

Blending Family Time & Work Time

When my kids were younger, I often combined family errands with serving papers or doing spot-checks of residences I needed to surveil. I remember telling my young daughters to duck down as I needed to serve a subpoena. “And girls, by the way, here is my cell phone. Call 911 if I don’t come back. Keep the doors locked. And yes, we will stop for ice cream.”

Yes, I’m still married. And yes, my daughters still like me. I like to think they learned a little tradecraft on these “dual” missions.

Feast or Famine Existence

Work can come in waves. You’ll be out-of-your-mind busy for days on end, and then the work won’t come in at all, for weeks at a time. It can be that type of business, which tempts you to say yes to everything, even when you’re in an out-of-your-mind phase. Because you never know when it might all dry up again.

Don’t panic. During the downtimes, you get caught up on your administrative work, market your business, or take an online training class (PIeducation.comhint, hint).

Unpredictable Clients

You finally landed an excellent client. You’re doing a lot of work for them and maybe a few others, and providing a professional product.

Your big client seems quite appreciative of your work. You hire people. You invest in vehicles and equipment. You go into debt. That big client is now providing a fair percentage of your monthly income. Then overnight, that client is gone. No reason was given. They just quit calling. Half or more of your income is gone, but you still have expenses. You will probably have to lay people off.

You swear you will never do that again. But you most likely will.

Unhealthy / Unsafe

Sitting in a surveillance van day after day is not a healthy lifestyle. Nor is working cases that involve insinuating yourself into society’s darker subcultures. I remember sleeping with a gun under my bed while working a very off-kilter missing person case. I learned that the people I interviewed weren’t happy with my nosing around. They suggested I not return to their town.

A year later, the missing person’s skull was found. I was glad mine remained intact.

I have also interviewed people with a history of violence, like gang members, white supremacists, sex offenders, the mentally ill, convicts, and ex-convicts. I would characterize my attitude to these interviewees as “respectful and vigilant.” Some folks with violent pasts end up surprising me with their courtesy and insight. Others brim with menace and keep me on edge.

Sometimes the perils are ordinary enough. During a neighborhood canvass last winter, I ended up on my back while walking down icy stairs.

No Backup

Most private investigators work alone. Even if they work for an agency, chances are the daily work is all done solo. You need to have an independent streak and be okay living most of your time inside your own head.

Your safety is also important when working alone. The job requires us to walk solo on the shady side of the mean streets. I survived many sticky situations by exiting a scene ahead of the perceived trouble. Or calmly talking as I backed out the door. 

Talking to a fellow private investigator who has walked in your shoes can be very helpful and sound therapy for both parties.

Being a private investigator is a job like many other challenging jobs. If you have the personality to do this work, you will probably survive. And I do think it’s a bit cooler than most jobs.

End of Report


About the author:

Steve has been a private investigator for over thirty years. He specializes in criminal defense and attorney support investigations in Nebraska. You can find out more at his website at PrivateEye1.com. Steve has self-published fictional books, including his recent book, Unremarkable – Private Eye Story. You can find links to Steve’s books and his Pursuit Magazine articles at Stephen-Koenig.com.