The Downsides of Freelancing: Why it’s Not a Long-Term Strategy

Note: This blog post reflects my personal opinion about freelancing and is not a critique of freelancing in general. It focuses on the drawbacks I have observed from my own experience and why I believe freelancing is better suited for starting an independent lifestyle rather than as a long-term career strategy.

Having worked as a freelancer and contractor for ten years from 2008 to 2018, I’ve come to understand the nuances that differentiate the two terms. In my view, freelancers take on multiple flexible jobs simultaneously, whereas contractors typically have one primary client whom they bill on a monthly basis.

Rather than diluting the answer to the question of what’s wrong with freelancing, I’ll get straight to the point and say that the major downside is the fact that you are essentially selling your time.

Time is our most limited resource. While money can be earned and spent, time can only be consumed; it cannot be created or replenished. When you create a website or design for a client, you are paid based on the number of hours you put into the project. If you don’t work, you don’t earn.

As a freelancer, your time becomes directly linked to your income. This correlation can eventually restrict your freedom and prevent you from pursuing personal activities. For example, taking a skiing trip would incur not only the cost of the holiday but also the income lost from not working during that time.

Being an employee brings its own set of challenges, but it has its advantages too. While you may sacrifice some freedom, you also have the benefit of leaving work behind at the end of the day.

Yes, billing high hourly rates can be enjoyable, but in the long run, you will likely seek an alternative approach. The ideal scenario is to separate your income from the hours you work and eradicate this strict time-money correlation.

Detaching the effort you put in from the money you earn may be a difficult concept to grasp, especially if society has conditioned you to believe otherwise. You might find yourself self-sabotaging, thinking, “I don’t deserve this” or “I didn’t work hard enough to charge that much.” If no one in your immediate environment is challenging the link between time and money, it can be hard to break free from this mindset.

Jobs such as working in a shop, office, as a driver, delivery person, accountant, or attorney are all tied to the concept of time.

Since reading “The 4-Hour Work Week” and launching my own business in 2008, I have been constantly brainstorming ways to separate time from money. I wanted to create a “passive income” machine — something I could produce once and sell multiple times, independent of my ongoing efforts.

It was important to me that this income stream could be highly automated. As an aspiring or seasoned developer reading this blog, you likely share my affinity for automation. No more phone calls, real-world meetings, or anything that isn’t streamlined.

I experimented with various avenues, but nothing initially produced the desired results. However, I persevered and after exploring different industries and product types, things began to fall into place.

Looking back, I consider my freelancing days as a necessary stepping stone towards achieving my goals. It provided a means to pay the bills while I searched for the type of business I truly wanted. Freelancing was not the final destination, but rather an interim phase.

This realization was similar to when I worked as a dishwasher in hotels during my college years. I knew that I would not be doing that forever; it was just a temporary job to sustain me at the time.

Today, I work incredibly hard. I spend months creating products, serving my audience, expanding my reach, and selling valuable products to them. While it’s not exactly the passive income that allows me to lounge on a beach and do nothing all day, it does afford me the opportunity to sell something long after the initial effort is made. I can sell a product a hundred times, even though I only worked on it once.

By separating the time I work from the income I generate, I have built the kind of business I always aspired to create.

Freelancing can be a perfectly valid choice for those who find fulfillment in trading time for money. There’s nothing inherently wrong with it if it aligns with your true calling. However, for those who seek alternative ways to make a living, it’s crucial to recognize that there is another path available.

tags: [“freelancing”, “contractor”, “time management”, “passive income”, “lifestyle”, “career strategy”]