I am a researcher, so when I started freelancing in my late thirties, one of the first things that I did was research freelancing. Almost everything I read was geared towards much younger freelancers or those who were launching their first careers. There were numerous pieces about getting experience, building a brand, and leveraging social media to build one’s clientele.

All of this was valuable and proved to be helpful at various stages during my transition, but I wasn’t receiving what I needed.

I didn’t want to freelance just to freelance. I didn’t want to freelance because it was a fun hobby. I didn’t want to freelance just to survive. I wanted to freelance to thrive and to sustain the quality of life that I had grown accustomed to as an academic. I’m allergic to the starving artist mantra.

Then reality hit. There were many opportunities, but the pay was very low.

One night, I even calculated how many low paying articles I would have to write in a week just to make a fraction of what I was making before. My heart sunk—maybe I was being foolish and this life was not for me, at least not at my age. Clearly, I was doing something wrong. I had the skill set; I had a portfolio full of diverse samples; and I had a vision, but the income was not coming in. Something was missing.

I assumed that with my credentials and years of experience, I simply had to let people know that I was now freelancing and they would respond accordingly. Wrong!

I am not an essentialist, so I don’t believe that only people of a certain group can speak about/for that group. However, real-world life experiences sprinkled with candor carry far more weight than an intriguing Internet article. So I reached out to a dear friend who had also left academia and launched a successful second career as a creative independent in his early 40s.

As I explained my level of frustration and expressed a desire to just quit, he listened attentively. As the conversation unfolded, I realized that I was making several mistakes.

  1. I was being too restrictive and I needed to diversify the types of writing projects and clients that I wanted to work with. The nature of freelancing is such that, for many of us, we can live anywhere and work from anywhere. I was concentrating too much on building up my local clientele. Yes, I am in the Midwest; however, I have a service that is of value for people on the coasts, places in-between, and overseas. I had to rethink how I was marketing my services and to whom I was marketing them to.

  2. I was only focusing on two types of freelancing—academic and curriculum writing. It dawned on me that I had also developed pretty acute editing skills (all of those years of grading English papers and teaching grammar in intro to writing courses), so I added editing to my toolbox of services. This created an additional stream of income. I cannot emphasize enough the importance of having diverse income streams—some people even refer to these as profit centers. The value of this is that if one area is not producing enough income, you will still have revenue coming in from another stream of income. And this brings me to the biggest mistake that many second career freelancers make…

  3. Freelancing is not the same as working for someone else. When you have worked within a system for most of your adult life, you grow accustomed to the processes that work within that system. For example, having a supervisor, having structure, having a built-in accounting system, earning paid time off, receiving merit pay, and enjoying cost of living increases are often outgrowths of working for someone else America.

When you strip away that system and find yourself in a new space, you have to change your way of thinking. I had to think about writing as art and as commerce. If I wanted to enjoy the benefits of writing as a business, I had to treat it as a business enterprise. This meant that I had to create systems. Why? If you build it, they still may not come and when they do, you need to be ready.

All of these mistakes were preventable, but I really didn’t know that at the time. They were valuable, yet costly, exercises that reinforced that what worked in the academic/education space (my first career) would not necessarily work in the world of free enterprise.

So, before you launch your second career as a freelancer, take the time to find someone who has a track record of doing what you desire to do. Seek the advice or counsel of other freelancers. Learn from that person’s mistakes and successes. I know one conversation, when I was on the cusp of giving up, was the turning point for me.