‘Freelancing’ once meant ‘sword for hire.’

A ‘freelancer’ is literally a professional mercenary.

Some kings and queens of the realm have their own sworn knights to fight for them in the joust. Other lords and ladies, and especially the rich merchants who want to set foot in court, have to rely on mercenary muscle.

The ‘free-lance’ was a knight without colors in medieval times. For a price, you could hire this free-lancer to joust in your honor, and a victory would mean increased prestige for the patron.

These hedge knights were different than their loyal counterparts. Knights beholden to their oaths both rose and fell with the fortunes of their liege. As royal families rose and fell, they took the fortunes of their retinues with them. But not freelancers.

In modern times, as companies rise and fall, the employees are often powerless to separate their fate from that of their employer.

• Economic downturn? Employees get layoffs.
• Bad press? Employees handle disgruntled customers.
• New management? You serve the heir to the throne just as diligently as the predecessor, whether qualified or competent or not.

The ‘freelancer’ still retains the same flexibility as medieval artisans. If you were a stonemason five centuries ago building a big tavern, and the town where you worked was struck by a plague, you could pack up your tools and go somewhere else. But those working in the tavern were tied to the fate of their employer, trapped in the town.

This is the risk:reward tradeoff in employment vs freelancing. Employees have the illusion of long-term safety and stability, in return for relinquishing authority over their work.

Freelancing gives you control of your money, your time, and the decisions you make. A boss can fire you, or change your responsibilities, hours, or pay. But a freelancer only answers to the marketplace of clients, and has the authority to change anything they want about their work.

In 2019, freelancers added approximately $1 Trillion to US economy. One quarter of freelancers surveyed said that if they needed to, they could find work within 24 hours. 60% make more money than they did in employment, and 64% said no amount of money could make them go back to working 9-5 for someone else.

It is estimated by 2027 that more than 50% of the workforce will be freelance. This means we are going to see more people exiting the corporate labor market, and going into business for themselves.

Over the past 15 years, I’ve gone freelance a number of times. Any brief employment I have had was always supplemented by freelancing, because whenever a job ended (and let’s be honest, nowadays, jobs always end) I wanted some clients and some revenue ready as soon as I was.

Staying employed for decades is risky, if your pension can disappear through no fault of your own. If you trade some short-term risk for long-term results, freelancing clients can cushion any transitions you make in the future. You can also earn more discretion over how you allocate your time, and you will be able to turn down work that doesn’t align with your highest values.

I have 4 spreadsheets you can use to calculate your solopreneur success. Whether you are an experienced freelancer, or thinking of getting your first client, these spreadsheets can help you identify what’s working, and what’s a waste of time.