Your First Contract Role: What You Think Will Be Hard vs What Actually Is

Making the leap into contracting can feel like a major career shift - and it is. Before I took on my first contract at Activus, I’d spent years in permanent roles, operating as part of a team, with processes and expectations clearly defined. I thought I knew what would be hard. I thought the challenge would be the project work, the new tech, and the speed at which contractors are expected to deliver.

It turns out, I was wrong.

The technical side was the easy part. Sure, migrating a legacy WinForms application to MVC and Razor had its complexities, but those were solvable with experience and time. The real challenges came from everything else - identity, responsibility, and business management.

What caught me off guard most was the mental shift required. As a contractor, you’re not just a developer; you’re a business. There’s no manager making sure your workload is balanced, no HR team ensuring your benefits, and no one chasing you to upskill. That responsibility falls entirely on you. It’s liberating - but it’s also heavy.

There’s also the perception challenge. You walk into a team as an outsider, yet you need to build trust, lead change, and deliver results, often without any formal authority. At Activus, I found myself mentoring the team and leading architectural changes, not because I was asked to, but because it was needed. That kind of leadership has to be earned quickly, through action and empathy.

Then there’s the financial side. I expected to make more money as a contractor, and in headline terms, I did. But without understanding VAT, corporation tax, and cash flow management, those numbers quickly became meaningless. I didn’t anticipate the stress of unexpected tax bills or the risk of mismanaging company finances. It’s a hard lesson when you realise that profit isn’t what’s in your account, it’s what’s left after obligations are met.

What I thought would be hard - tech delivery - was what I was most prepared for. What I didn’t anticipate were the softer skills and business acumen contracting demands.

If you’re stepping into your first contract, expect to feel stretched in ways you didn’t plan for. Be ready to manage more than code. Learn the financials. Lead when the opportunity arises. And most of all, embrace the responsibility that comes with calling yourself a contractor.

It’s not just about filling a gap on a project. It’s about stepping into a space where your ability to own, deliver, and adapt sets the tone for your success.

That’s where the real learning begins.