5 Lessons Being a Private Investigator Taught Me About Freelancing

A decade ago, I worked as a private investigator. It was by far, the riskiest thing I ever did in my life. For a year, I learned how to follow potential criminals, photograph them and even worked undercover. Though the pay was low and the stakes were high, I got the kind of education about working that you can’t learn by reading books or studying in school.

There were actually five major lessons I learned that ten years later I still apply in my freelance writing business. Five things that taught me how to survive while chasing the bad guys and almost as scary, surviving the worsening economy as a writer. It’s funny how I got more warnings and advice from people when they found out I was leaving my cushy corporate job for a lifetime of writing than when I told them I was going to take a job as a private investigator. In some people’s eyes, the risks of fulfilling a dream are far greater than the risk of one’s life.

If you are on your way to pursuing your own freelance business, read this before you jump in. There are lots of life saving tips here. Take it from a past PI and a current freelancer who has done it before and survived.


Lesson 1: Always Stick to Your Morals and Values

For one assignment, I had to work undercover befriending co-workers so I could get information from them. The company wanted to make sure no more stealing was going on internally. But when I was offered the job, I was hesitant. It felt icky-like tattle tailing for money. With just a little bit of coaxing on my colleague’s part, however, I ended up agreeing to something I felt uncomfortable doing. Flattery worked in this case and I bit my lip and did it.

Pretending to be someone you are not in business is not a good thing. Doing something that feels unethical to you or compromises your values is worse. You are not only risking your reputation as a freelancer, but you are setting yourself up for years of regret (say like 10!). Although I was only “doing my job,” I can’t tell you how awful it feels to do something that feels wrong. I compromised my values and I had to live with it. Believe me, it’s not worth it!

Lesson 2: Climbing a Ladder is Harder Than It Looks

I mean this, both literally and figuratively. It was 3 am on a Friday night and I was scheduled to do rooftop surveillance with a co-worker. From the bottom, the white ladder in contrast to the dark building looked harmless. Nothing my six-days- a-week-of-exercising body couldn’t handle. But climbing it was a whole other matter. Halfway up, I panicked and stopped. My co-worker asked from below, “Are you okay?” For a moment, I wondered how I was going to make it to the top. My arms were shaking, I was out of breath and I realized I was too far up to jump. Either I had to face my fears and keep going or turn around and stop. But there would be as much work getting to the top, as there would be if I quit. I had no choice but to keep going.

Sometimes freelancing feels like that. There will be times when you won’t be sure you can make it to the top. You will see how far you’ve come and how far you still need to go and will want to give up. But it’s a lot easier to keep going on your path than it is to stop and go back to the job you hated or the life you led before you started this journey. What helped me get through it were courage and the belief that I was going to get there regardless of my fears.

Lesson 3: Know When to Fold It

The stakes were always high when I was a PI. When they got to be too high, when it was beginning to border on uncomfortable, I decided enough was enough and I pulled back. I realized that I didn’t have to put myself in unsafe situations just to prove that I could do it.

There are a lot of opportunities that will come your way in business. Some will be high-risk opportunities, but worthy ones. When you come across something that is a great opportunity, but not the right one for you, don’t risk taking it. The time, effort and energy you spend on the wrong job will take away from the right one. Don’t just do something because it’s an awesome opportunity. Do it because it fits in with you and your ultimate goals.

Lesson 4: Listen to Your Intuition

On one mission, I was assigned team leader. When we lost our target everyone wanted to know what to do next. I meekly expressed my opinion. But, in a sea of other thoughts and voices, my words went unheard. After the assignment was over, my superior pulled me aside. He wanted to know why I didn’t listen to myself. He said, “You were right. They were wrong. Why didn’t you say something?”

Oh how many times do we fail to listen to ourselves? In business, it’s so easy to ignore our gut feeling. But it’s a hard lesson learned. When you get a funny feeling about a potential client or an uncomfortable feeling about an assignment, trust your gut. Ask more questions and take the time to think about it. Figure out if what you are feeling is justified and you may save yourself from investing time and energy on an ill-matched client.

Lesson 5: Use Skills and Abilities and Be Adaptable

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I was surprised that I was good at being a private investigator. I am petite, 5’3 and scared about almost everything. But I learned early on that for this job, my physical appearance worked to my advantage. Who would suspect that a shy, Japanese girl was a private investigator? There was something else too. In the midst of an assignment when I had to make quick decisions (sometimes life and death ones), fear was gone and I got in a flow. Once in training, a guy who acted as our target went into an apartment. I grabbed a towel and a book that was in my car and sat down next to a bunch of children playing. He came out and saw me, but later said he never expected I was following him because I looked like I belonged there.

Being a freelancer means you need to exercise your muscles in different areas.

On top of hard work and lots of practice, being able to adapt to new situations is key. Maybe you are an introvert who feels uncomfortable in crowds, but need to cover an event for a features story. Pretend to be an extrovert for the day. Learn to blend in by watching others around you. Or if you find that the energy spent on social media is taking too much time from your writing, stop, readjust and get back to marketing offline. The faster you learn how to be flexible, go with the flow and adjust to whatever situation you’re in, the faster it will take you to find the right groove toward freelance writing success.

Being a freelance writer, like being a private investigator, is risky. There are a lot of obstacles and challenges that will test your limits, your passion and your determination to stick with it. Part of that is learning what is really important to you and what you are willing to sacrifice to write for a living. In the end, freelancing does become a life or death choice. You either choose to live your life purpose or die trying.

Your Turn

How does freelancing compare to your past jobs? Did you take anything from your past jobs into your freelancing life?

Share your answers in the comments.