How I Learned to Be the Boss

Be A BossFreelance Job #1

 After a forced retirement from an illness which involved multiple surgeries, I decided to go back to work. The Freelance market was like a neon sign flashing in my eyes,

“Work Here”, “Work Here.” I gave it a try.

With my years of experience, I landed an interview, I think, the second or third proposal I sent out. Excited!


On the Skype, call questions bombarded me about my experience, my qualifications – “Had I ever worked remote before”, “Was I experienced with Team, Slack, Outlook”, “Could I manage a virtual office?”

A virtual office? I’ve always worked on computers doing data entry, programming, an office manager – yes. But a virtual office? What the heck did a virtual office look like?

“Yes, I can handle it” – my standard response. I knew I could figure it out. I just hoped I could figure it all out sooner rather than later.

With job offered, I accepted with trepidation. “I can always figure things out,” I kept telling myself.

The Truth Comes Out

Then the “boss” on the other end of Skype told me his story. He told how he had worked for several big corporations, naming off the companies, and how he had been fired from each one.

Red flags began waving in my mind as he relayed his story, “Fired, why?”

“If he’s been fired from all these high-level companies, what kind of a boss is the going to be?”

“Should I take the job?”

“Oh, it can’t be that bad, could it?”

Long story short, I took the job. I loved the variety. I received a myriad of jobs, data mining, writing, maintaining websites, transcribing videos into text, loved the work.

We’d Skype every few days. He was fun. Then the other shoe dropped. Extra space in a document caused an explosion. “You’re taking too much time on that transcription,” even though it was perfect.

“Send me what you have completed, NOW,” the growl came over email.

I began pulling back from the intense tension and stress.

All the work ended, he lost his contracts. Now, I understood the growling, the tension, the stress, but, still, did I need to take that kind of behavior. I pondered for months.

The psych terms “transference, projection” came to mind. I understood I am a psych major, but the behavior still ate away at me.

Freelance Job #2

 On my Facebook page, I advertised as a Web Designer, Content Writer etc, etc. I got a call. A so-called family member, same name, yet not related.

She needed help finishing a website. She told me her story, of course, leaving out the most important part of all. The part about all the other web developers.

I took the job then learned about the others who had quit unexpectedly. The question of “why had so many people quit” loomed in the back of my mind. Questions plagued my mind again.

A few days later the boss and another freelancer exchanged very heated words on a three-way conversation, resulting in the other freelancer quitting.

More Questions

My question moved forward in my mind, no longer just a question.

Two or three weeks later with the website nearing completion, I received a phone call, “We have to slow this down, it’s moving too fast.” Even, though, I had received emails and text messages that the website had to be completed because she wasn’t getting any orders from her site.

In bewilderment – get it finished, no money coming in – stop it’s moving too fast.

Once again, my psychology came into play. “Did she really want the website finished? Was the weekly invoice too high? What was the real problem?”

In phone calls, I received the evaluation that I emitted a negative vibe and I needed to chill. Just days from completion I was told I was moving too quickly. I began receiving messages in a very passive-aggressive language that indicated she felt I was ripping her off.

Time to Be the Boss

 Months later, I received an email from boss #1 that I still owed him time or money. “I figure you owe me $1000 start paying me back at $83 per month.”

“No, I will not pay you back in cash, I will work off the time at an increase in hourly pay?”

Instruction came to scrape a website for data.

My response, “No, it’s illegal.”

After several boundaries were drawn, I received, “You don’t have to harass me.”

With an agreement reached, I smiled, the boundary worked.

Boundary #2 began to form in my mind. I did not need “micro-managing” on the website development.

Upon being informed of the new boundary, boss #2 sent an email with a barrage of words. I didn’t need to read it and put the negative vibe from her rant into my psyche. Instead, I told her this wasn’t working find someone else.

Lesson Learned

 Set the boundaries first.

Question the person about the job, don’t accept it sight-unseen.

Set my own price.

Be specific about what I will and won’t do.

Set a realistic time frame that gives me the flexibility to do the job with excellence.


After spending approximately 20 years as a programmer analyst working in both the private sector and county government, Dena Warfield returned to college earning a Masters Degree in Psychology and in Creative Writing. Since graduation, her main focus has been on marketing – Direct Sales, Copywriting, and Writing for the Web. She co-owned and managed a direct marketing company with her husband working, primarily, with local newspapers. She managed the business office, human resources, and helped with training and marketing. She also designed their company Web Site plus writing for other web developers. Dena’s years of business, computer programming, and writing have helped to focus her copywriting skills in the marketing arena. Whether she is writing content for websites, emails, brochures, catalogs, or direct-response her goal is increased traffic and sales to your site or business. Education Dena earned her Master’s Degree in Human Behavior and a Master’s in Creative Writing from National University in San Diego, California. She has also completed a certification program from AWAI (American Writers & Artists Inc., Delray Beach, FL.) with a focus in copywriting for the web. Author Dena has authored a self-help book designed to help people become aware of their negative thoughts and core beliefs that keep them from becoming successful. The techniques described in her book were used to help their sales rep to become more successful. Her book is currently on She also enjoys writing Flash Fiction which can be found on her Facebook page, WarStories by Dena – Flash Fiction with a twist.

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