Brian Willingham

I am a private investigator because I fell into the business. Truth be told, it was not my first choice. I hear people say, “You were born to be an investigator.” That’s not true at all. I was probably the most awkward greenhorn private investigator you will ever find. I hated being put in awkward situations. I wasn’t really good at thinking fast on my toes. I hated rejection.

Fifteen years ago, I was at a crossroads. I was working in the sports industry pursuing my dreams of being the head of the Major League Baseball Players Association. That was until an overconfident kid walked into their New York City office and blew the interview.

Crushed about my prospects in the sports industry, I ended up joining my father’s investigative firm to hold me over while I figured out my next move. Fast-forward 15 1/2 years and I’m still in the business.

I’ve been featured in Lifehacker and quoted in the ABA Journal, Fox Business and The Washington Post. I’ve been named one of the young, promising members of the Association of Certified Fraud Examiners.

The point is that you don’t have to be born to do the job. You don’t have to be a natural. You don’t need 20 years in law enforcement.

What you do need is some grit and determination, a few tools to help you along the way and an insatiable appetite to learn more. Couple that with a strong sense of self-awareness, a little hustle, some humbleness and mindfulness, and you have the makings of a private investigator.

I love what I do because this business shows me something new every day. It keeps me on my toes. I am constantly learning. I love helping people find answers.

And by owning my own business and building my business around being flexible and mobile, it gives me the ability to makes choices about my life, instead of people making choices for me.

I absolutely love what I do, but I became a private investigator, because that’s where life led me. Not because I was chasing a job I loved or was predestined to be an investigator.

What about you?


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13 replies
  1. Nanette Varian
    Nanette Varian says:

    Great blog, and thanks for sharing your story and inviting us to share ours! Two months ago I made the switch from journalism, joining the New York City Department of Investigation’s Background Unit. I love it. After being a magazine writer/editor/ researcher for some thirty years, I began about a year ago to think about what I’d want to do next (it was becoming very obvious that our magazine would fold–the ads just weren’t there). I decided to try switching to this field. I began doing some research, then after the (inevitable) folding last February, I answered any ads that seemed feasible. I also had many, many networking phone calls. (I am blown away by the kindness and generosity of people in this industry, in the public and private sector, and from large firms to one-person shops.)

    There were clearly transferable skills, but it was still tricky to break in. What I learned from these phone calls–and from reading blogs such as this one–helped me hone my resume and skills set, and proved invaluable during the interview process for the DOI gig. Great work for anyone who loves connecting the dots and finding things out.

    • Brian Willingham
      Brian Willingham says:

      Thanks for sharing Nanette. The mentality of a journalist, I think, makes it an easier switch skill wise, but breaking into the business is the hard part. Glad that things worked out for you.

  2. Dody Bullerman
    Dody Bullerman says:

    I am trying to get into the business. Any tips? Job openings? I love your sense of humor. Thank you for sharing your story.
    Best wishes,

  3. Jim Clark
    Jim Clark says:

    My initial career choice when I was 16 was to be a police officer. I was influenced by a couple of local police where I grew up in New Jersey. After I relocated to Kansas (if you thinking how in the hell did that happen, it was because my dad grew up in Kansas and wanted to get back to the good ole life), I went to college for a degree in Administration of Justice. My fiancé at the time didn’t like the idea of the varying hours in this line of work, and the fact that I could get killed.

    I changed my minor to Security Administration with the goal of working for a company that had a large Security department. A few years after college I started working for a major communications company in IT as I had a little experience in the field. I did IT stuff for a bunch of years, then was fortunate to get a Security Investigator position for the same company. Dream job attained!

    My immediate supervisor was also an investigator but she had many more years experience in this role. She was an absolute nightmare of a boss. She was insecure, petty, demeaning and a real you know what. I stayed in my dream job for less than a year and went back to a entry-level IT position.

    After many years with this company I was fired for expressing an opinion on what I thought the company was going to do in the future. Apparently, my opinion (not based on inside information) was too close to reality. Boom!

    Several more companies working in management roles in the IT field. Finally got the nerve to start a company while still working full-time. I combined my IT and management experience to be a digital forensics examiner and a licensed private investigator.

    I’ve had only one client in the last year. I’m still working full-time for a company managing an IT support group. My challenge is making the time to build my company while working full-time.

    My current need is to promote/market my business. If anyone has suggestions I’m all ears.

    Thanks for asking for my story. It was a little cathartic to put it in writing.


  4. Private detective manchester process server
    Private detective manchester process server says:

    Like you, I was never in the police, (or the armed forces, which is where many UK surveillance operatives learnt their trade). I find there are many situations where this is an advantage. There is never a colleague just minutes away to provide back-up, no badge to flash when things get awkward and no one track mind of Criminal investigation. In the UK criminal and civil laws are 2 entities with little in common. I feel I can switch by focus quickly onto either to suit the aims of an investigation, something I feel not all ex police can do.
    As for why I became a P.I.? I saw a course, it looked exciting so I skipped University and did that instead. The industry isn’t what I expected, but I love it.

  5. Scott Ross
    Scott Ross says:

    My story is too boring and I’m tired of telling it. I would like, however, to add the one ingredient needed to be a “successful” PI…Common Sense. In the words of one of my favorite clients (and convicted murder) Tyshaun Jackson, “The one thing I find in here [jail], is there is nothing common about common sense.”

    Thanks for sharing Brian, and I yearn for the day my office looks that neat, organized and clean.

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