1. Are you comfortable with uncertainty?
Contracting can mean gaps between roles, last-minute extensions, or sudden project changes. If you thrive in a structured, predictable environment, this might feel unsettling but if you enjoy variety and can manage financial planning during downtime, you’re already thinking like a contractor. Ask yourself: Can I handle a few weeks without work and still feel confident?
2. Do you enjoy hitting the ground running?
Contractors are often brought in to solve problems quickly. There’s little time for hand-holding. If you’re someone who enjoys diving into new systems, learning fast, and delivering results under pressure, you’ll likely thrive. Ask yourself: Do I enjoy being the “fixer” or “safe pair of hands” in a team?
3. Are you self-motivated and Independent?
Without the structure of a long-term team or manager, contractors need to be self-starters. You’ll often be expected to manage your own time, priorities, and even training. Ask yourself: Can I stay productive without someone checking in on me?
4. Do you like variety in your work?
As mentioned in a previous article contracting offers exposure to different industries, systems and teams, If you get bored easily or love learning new things, this can be a huge plus. Ask yourself: Do I enjoy change, or do I prefer consistency?
5. Are you comfortable selling Yourself?
You’ll need to market your skills, interview regularly, and negotiate rates. Confidence and communication are key. Ask yourself: Am I comfortable talking about my strengths and value?
6. Are you financially prepared?
Contractors typically earn more per day, but without the benefits of holiday pay, pensions, or sick leave. You’ll also need to manage taxes and possibly set up a limited company. Ask yourself: Do I have a financial buffer and understand how to manage my income?
7. Does it fit your career stage?
Some professionals contract to gain experience quickly, others do it later in their careers for flexibility. It’s not about age it’s about timing. Ask yourself: What do I want from the next 2–3 years of my career?
