From Insurance Salesman, to Poker Player, to Successful Freelance Writer – How I Did It! by Jon Sofen

From Insurance Salesman, to Poker Player, to Successful Freelance Writer – How I Did It! by Jon Sofen

In January 2010, a year removed from a failed attempt to work as an Independent Insurance Agent, I took a couple of days off work, drove six hours to Chicago for a mini-vacation and then, the day before I was supposed to go back to work, I decided to call my boss to inform him I was quitting.

I didn’t like my desk job as an Employee Benefits Coordinator and, quite frankly, spending a few extra days in Chi-Town sounded like more fun than going back to work. But there was only one problem: I didn’t have a plan to make money when I returned home. I hadn’t thought that part through.

Upon returning home, I played some poker for a few weeks, a game I’d been successful at for quite a while. But, I wanted a less stressful full-time occupation than playing cards. I just wasn’t sure specifically which career path I was going to take but I had determined it was going to be something that didn’t involve me having a boss.

A few weeks later, I searched Craigslist for ideas and happened to stumble across the “writing gigs” section. Writing had always been a passion of mine, mostly sports and poker-related content. So, I figured I would apply for some of the writing gigs on Craigslist to build up a resume.

Worst case scenario was I wouldn’t find any work and I’d need to take a different career path. Best case scenario was I wouldn’t have to go back to working a desk job.

The first gig I found was to write funeral planning advice, a topic I find uninteresting. But, I was appreciative of the opportunity, and hoped it would help me grow my portfolio. I was only making $15 per 400-word article, but it served its purpose: beer money.

The only problem was I found the topic boring and it showed in the content. After a month, I just couldn’t do it any longer, and told my client I appreciated the opportunity, but had to quit.

Despite hating the work, the opportunity was beneficial. I received valuable experience and got paid to get my portfolio started. Even more important, I learned that, if I was going to become a full-time freelance writer, I needed to stick to topics I find interesting or I wouldn’t enjoy my job.

After that, I stuck with topics in sports, gambling, insurance, marketing, travel, and a few other niches I enjoy. It turned out to be the smartest move of my life. I now have many great clients who pay far more than $15 for an article and I wake up every morning excited to get to work, instead of looking forward to an upcoming road trip.

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Jon Sofen resides in Las Vegas but remains a Midwesterner/Iowan at heart. He is a freelance writer, professional poker player, and die-hard sports fan. You can view his personal listicle blog at


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2 Responses to "From Insurance Salesman, to Poker Player, to Successful Freelance Writer – How I Did It! by Jon Sofen"

  1. writerleenda  May 21, 2018 at 2:01 pm

    advance, not advacne

  2. pamelaallegretto  February 4, 2018 at 4:53 pm

    Good for you. Cheers!