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5 Lessons Being a Private Investigator Taught Me About Freelancing

Posted May 11, 2011 in Inspiration

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.

Related posts:

  1. 4 Lessons 2010 Has Taught This Freelancer
  2. 3 Lessons Children Can Learn From a Freelancing Parent
  3. Freelancing Lessons from Tech Support
  4. Freelance Lessons Learned–Make Your Own Music
  5. 5 Freelance Lessons I Learned from Working in the Fast Food Industry

About the author: Brandi-Ann Uyemura is a full-time freelance writer and an associate editor for Psych Central. She writes to keep others motivated, positive and inspired on the path towards their dreams at The Inspiring Bee and tweets about writing and everything inspiring @TheInspiringBee



 
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37 Comments
  • User Gravatar
    Jake Hills
    May 11th, 2011 at 8:42 am

    I’m currently 18 and i’m in the process of leaving my ‘saturday job’ at a local supermarket to be a full-time web designer.

    As working in a supermarket seems such a demoralising job I don’t like to think i’ve taken much from it. And to be honest, the one and only aspect I have learnt is the fact that I need to do something with my life rather than just work in retail my whole life!

    Being 18 and going into full-time freelancing seems like the worst decision to everyone, but i’d rather that than make a shelf of cheese look pretty.

  • User Gravatar
    Morgan
    May 11th, 2011 at 11:21 am

    I took something away from every job. Whether it was how to manage employees better, how to treat employees better, how to create better policies and procedures, how NOT to treat customers and so much more. There’s always something to take away from any job you leave, especially if you’re leaving to be a freelancer. You need to be observant to what you liked and didn’t like about your job and how you can improve it as an individual to treat yourself, your empoyees (if you have any) and your clients, better than your corporate job.

    Cool article!

  • User Gravatar
    LJD
    May 11th, 2011 at 11:37 am

    Awesome article!

  • User Gravatar
    Brandi
    May 11th, 2011 at 1:22 pm

    Hi Jake! Congrats to you for taking that big step to following your dreams. I’d say learning that you don’t want to do a particular job forever is an important takeaway from your experience. Good luck to you!

  • User Gravatar
    Brandi
    May 11th, 2011 at 1:26 pm

    So true Morgan! I’ve had the opportunity to have had plenty of jobs and I can honestly say that there was a valuable lesson there even if it’s just what I said in comment to Jake-that I didn’t want to do it anymore. Sometimes a long list of jobs that don’t fit are enough of an incentive to up and quit your current job and pursue the one you really want. Thanks so much for your comment and compliment!

  • User Gravatar
    Brandi
    May 11th, 2011 at 1:27 pm

    Thanks LJD!

  • User Gravatar
    Cathy Miller
    May 11th, 2011 at 1:27 pm

    You know what is great about life? No matter how much you think you know about a person, there are still surprises. Who knew our little Brandi was a kick-butt PI? :-D

    Some of our best life lessons are when we step outside our comfort zone. I laughed out loud about your comment that you got more grief about freelancing than being a PI. I had the same reaction (from some-not all) when I walked away from my 6-figure corporate job.

    Like Morgan said, I think you learn from every job. Twice during my 30+ years in corporate I lost my job and took on temporary jobs. I realized years later that those times were the happiest I ever was. They opened my eyes to the need for work/life balance and realizing climbing the corporate ladder does not necessarily equal success and happiness.

    Great post, Brandi. Remind me not to mess with you. :-)

  • User Gravatar
    Rachel Small
    May 11th, 2011 at 1:27 pm

    Great post! Being a freelancer can be terrifying at times, and I’ve learned the hard way that you need to learn to trust your gut. I like the ladder analogy – whenever I have serious doubts (which doesn’t happen often), I remind myself that giving up would be just as hard as facing my fears. In the end, if you love what you’re doing, it’s worth it!

  • User Gravatar
    big blog monkey
    May 11th, 2011 at 4:26 pm

    I don’t have any job because I am still a student. But I do a lot of freelancing jobs during as a part time job. Well, I do a lot of lesson number 4 and will keep on doing it over and over again. Thanks for sharing all the lessons, there are all very useful.

  • User Gravatar
    Brandi
    May 11th, 2011 at 4:47 pm

    I love your comment Cathy! You’re so funny. =) I’m much more of a chicken than a lion. But facing my fears by doing it really made me realize how much I was capable of. It’s amazing what we learn in retrospect.

  • User Gravatar
    Brandi
    May 11th, 2011 at 4:49 pm

    Hi Rachel.

    That’s a great reminder. I think sometimes people don’t realize how hard it is not to face your fears. When you give up on your dreams it begins to eat at your soul. That’s something I tell myself too especially when I’m afraid and scared out of my mind. Thanks for your comment!

  • User Gravatar
    Brandi
    May 11th, 2011 at 4:50 pm

    Your welcome Big Blog Monkey!

  • User Gravatar
    TLC
    May 11th, 2011 at 9:54 pm

    So true about following your morals and values. Almost got fired once because I refused to accept an illegal bid. My boss said, “Sometimes we just have to do these things to keep the peace.” it may have given peace to everyone else on the committee, but mine would have been gone. I’ll never regret taking that stand even though I paid a very high price for it.

  • User Gravatar
    Juan
    May 12th, 2011 at 2:17 am

    Great post. And what an amazing life :)

  • User Gravatar
    Olatunji
    May 12th, 2011 at 12:46 pm

    whats a nice articles!, i find it lovely and useful .

  • User Gravatar
    tuba
    May 12th, 2011 at 7:32 pm

    Nice article, I always follow this: “Lesson 5: Use Skills and Abilities and Be Adaptable”. Thanks!

  • User Gravatar
    Christian Entrepreneur
    May 13th, 2011 at 11:17 pm

    Thanks for this. It sounds like you could write a book about your PI days! When’s it being published? !

  • User Gravatar
    Brandi
    May 13th, 2011 at 11:20 pm

    Thanks Juan!

  • User Gravatar
    Brandi
    May 13th, 2011 at 11:21 pm

    That’s so nice of you to say Christian! Actually a writer friend did suggest that a few times, but we’ll see. Truthfully, I’m working on the essay that will never end on this topic now and that alone is taking forever.

  • User Gravatar
    Thea | Write Change Grow
    May 22nd, 2011 at 1:31 am

    Hi Brandi

    I really enjoyed this post. Great to see how you can take transferable skills from such a different profession and apply them to freelancing. I used to be a PA and have now started freelancing. There are some skills from being a PA that I can use in freelancing but mainly they evolve around how to deal and communicate with people. Other skills like running a solo business for example have to be learned from scratch.

    Thank again for sharing. I will defnitely head over and check out your blog.
    Cheers
    Thea

  • User Gravatar
    Marcelo
    June 30th, 2011 at 8:23 am

    I still apply in my freelance writing business.

  • User Gravatar
    boss-dd-20
    January 30th, 2012 at 7:19 am

    Hello, this is a good post!

  • User Gravatar
    Penny Stocks
    February 9th, 2012 at 4:27 am

    Hello there! Quick question that’s totally off topic. Do you know how to make your site mobile friendly? My web site looks weird when viewing from my iphone4. I’m trying to find a theme or plugin that might be able to correct this issue. If you have any suggestions, please share. Thanks!

  • User Gravatar
    Kitchen Set Murah
    February 14th, 2012 at 7:23 am

    If you’re still on the fence: grab your favorite earphones, head down to a Best Buy and ask to plug them into a Zune then an iPod and see which one sounds better to you, and which interface makes you smile more. Then you’ll know which is right for you.

  • User Gravatar
    Inspirational Quotes
    May 1st, 2012 at 8:25 am

    Excellent post at 5 Lessons Being a Private Investigator Taught Me About Freelancing | FreelanceFolder. I was checking constantly this blog and I am impressed! Extremely useful information specifically the last part :) I care for such information much. I was looking for this particular info for a very long time. Thank you and best of luck.

  • User Gravatar
    S.16
    September 20th, 2012 at 3:24 pm

    Brandi, I have to ask something… I’ve always had the investigative edge, and I’ve always wanted to be an investigator but I’m going to college to follow my other dream of being a vet. Did you have to undergo training to be a private investigator? Or is it something I could follow into on the side? Investigating has always been a passion of mine.

    Thanks!

  • User Gravatar
    logan mckinney
    November 20th, 2012 at 5:45 am

    Hi I’m thinking about becoming a private invstigator when I’ve moved back in phx, az opportunity abounds there. I’m hoping its not hard to get jobs and clients for more jobs in the future. I’m thinking of hitting up the city courts and getting jobs that way at
    After I get my lisence.

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