How I Left My Job to Be My Own Boss

by | Last Updated: Apr 17, 2022 | Careers, Freelancing, Working From Home | 0 comments

How I Left My Job to Be My Own Boss

For as long as I can remember I’ve wanted to be my own boss. Even if I enjoyed the work I was doing for someone else, I wanted to do the work as my own boss. In 2014 I left my stable job as an Industrial Engineer and became a freelance writer. I didn’t have any contacts, clients, or even an idea of what I would be writing. It was the best move I’ve ever made. Here’s how I left my job to be my own boss.


The hardest part was choosing a business that I could afford to start and that I would enjoy enough to stick with. I put countless hours into planning. I knew if it was going to work I needed to find the balance between skills, cost, and demand. I didn’t dream about cars, boats, homes, and vacations. I dreamed about running my own business, making a living, and enjoying the work I did.

I drove two hours per day, so I listened to several business podcasts every day (mostly Smart Passive Income, Learning with Leslie, and High Income Business Writing, but there were MANY others). They were a big help in making the decision.

Finally, choosing to become a freelance writer came down to answering three questions:

  1. What are your strengths?
  2. Which of those strengths are in demand?
  3. Which of those demands can you afford to provide?

My Strength

My strength is writing. Of all my skills, writing is the one I’m the most confident in. From grade school through college (B.S. in Business Management/IT) my teachers and class-mates commended me on my writing. Even in college, my work was used as examples for students to follow.

Is that enough? Why would they hire me? There’s more to being a reliable writer than learning to correctly use words and punctuation. You have to be easy to get along with. You have to provide the articles that clients want, when they want them, at the price they can afford. Your research needs to be reliable and accurate. Another of my strengths was research. I was confident I could meet my clients’ goals and needs.

In Demand

Technical writing (my specific strength) is not only in demand but it’s stable and has excellent job-growth potential. All industries need something written whether it’s magazines, websites, ads, books, white-papers, brochures, how-to guides, etc.


Starting a writing business doesn’t cost much when compared to other business. I could work from home using my own equipment that I already owned. I just needed a website with samples of my work and money to live on while I built the business. The experts recommended having from 6-12 months’ salary.


I spent several months working on this idea – trying to prove it was a bad idea. I couldn’t. It was solid. The only regret from every freelance writer I learned from is they didn’t start sooner. I had the skills, it was in demand, and it didn’t require a large overhead. The business was chosen.

The next question was how to start. I had two choices:

  1. Work part-time at night after 10-12 hour days at my full-time job (including 2 hours driving)
  2. Quit my full-time job and focus on starting my business

I didn’t like the idea of having two jobs: my full-time job that was an hour away, and my business that would have deadlines and required a higher level of effort than just selling something on the side. To make it work I needed to focus on it full time.


I don’t recommend you do this. Let’s get that out of the way first. I was willing to take the risk. I had one year of salary in 401k. I knew if I couldn’t build my business before the funds ran out then I couldn’t build it at all. If it didn’t work I would have to go back to work somewhere else. My wife and I were okay with that. Fortunately, I didn’t need it all.

My First Client

I quit my job, got business cards, created a website, and started making contacts. My plan was to become a general writer. I would write anything and everything but not really specialize in a specific topic. I had a wide range of topics I was familiar with including WordPress and business. This plan didn’t last long. I landed my first client within the first month of starting the business. My very first client needed articles about WordPress and everything surrounding it including business and social media. I’ve been a WordPress (and all things related) specialist ever since. As expected I did have to start small and work my way up.

Growing My Business

Part of business planning is determining how the business can grow. Some problems with freelance writing are I can only write so much in a day and I have to price competitively. I needed a way to expand my business. Fortunately, WordPress is a large industry with lots of potential. To help grow my business I decided to develop child themes for Divi to sell from the marketplaces and my own website.

Tips For Becoming Your Own Boss

  • Start
  • Know exactly why you’re leaving your job and make sure it’s the best option.
  • Be realistic. Don’t get sucked in by big dreams and wild promises.
  • Know what your strengths and weaknesses are, what the demand is, what the competition is, and the costs involved. I recommend writing a business plan.
  • Be careful about who you talk to. Many of your friends will be skeptical and will discourage you’re rather than encourage you.
  • Make sure your immediate family supports your decision.
  • Have enough money to live on while you build your business.
  • Take lower pay or even work for free in order to build your portfolio and get experience.
  • Have a plan in case something goes wrong.
  • Don’t make it about you.
  • Set aside time and money to learn new skills and hone your current skills (especially the skills that are the most important to your business).
  • Look for opportunities for growth within your industry that’s related to the work you do. For example, if you write about WordPress you could create websites, child themes, a writing team, your own website with ads and affiliate programs, courses, books, etc.
  • If your business takes you in a good direction, go with it.
  • There will be hard times.
  • Start

How I Left My Job to Be My Own Boss

Final Thoughts

That’s how I left my good paying and stable job to be my own boss. I wasn’t leaving because I hated my job. I had a good job and I liked the people I worked with. I simply wanted my own business. This was a good choice for me. The experts say it can take 3-6 months to get your first writing client. I landed my first client on day 29.

Who is my boss, really? That’s a tricky question. I am my own boss… I decide which clients I want to work with and what deadlines I can meet… but I still have to work to my clients’ deadlines and provide the quality they need at a price they can afford. Being my own boss still, means meeting my customers’ requirements. My only regret? Not starting sooner!

Have you left your job to be your own boss?


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