Main image of article How to Land That Perfect Gig as a Contractor

Summary

After you’ve worked a few years as a developer for an organization, starting out as a junior and moving up to at least mid-level, you might be interested in becoming a contractor. How do you start? And how do you land a gig that’s perfect for you?

As a contractor, you’ll get to be choosy about what gigs you take. In addition, you’ll get to choose a gig that fits into your schedule. If you only want to work 20 hours per week, great! Or if you want to put in more than 40, that’s also great. Or you might want multiple part-time gigs. (Just a tip on the lattermost: That’s a good way to ensure continual income; if a gig runs out or stops abruptly, you still have the other gigs to help you get by.)

To find the perfect gig, you need to define perfect. Maybe you love working for nonprofits and helping them iterate their tech stacks. Or maybe you’re coming at it from a purely technical perspective; for example, you love coding in C#, with specifically MongoDB. Here are some ideas to consider as you define perfection:

  • Are you looking for remote, in-office, or hybrid? (By choosing remote, you open yourself up to a lot more opportunities, but a lot more competition as well.)
  • Do you prefer working hours to be shifted from the time zone you’re living in? (For example, are you a night owl?) Then you might want work with a company in another time zone so you can easily attend meetings.
  • Are you looking for something short, like a couple months, or longer-term, like a year? (A quick note on that: If you’re planning on a gig becoming permanent, you might need to reevaluate whether you really want to be a contractor. But on the other hand, if you see it as a way into an organization, that can work out too; you just need to solidify your plans).

Make a list of exactly what you’re hoping for. In the list, rank each item on how flexible you are. If hybrid would be nice, but you would be willing to be in-house, note that, too.

Special note for junior developers: If you’re interested in becoming a contractor, you’re going to need at least a few years of experience behind you. That’s because contractors are expected to be up and running right away, and there typically won’t be anybody available to go to if you need help. You’ll be expected to work independently and create good, clean code without much oversight. If your goal is to eventually become a contractor, then go for it! But first plan to put in at least four years, probably five or so, starting as a junior developer and moving to mid-level.)

There’s no single method for landing the perfect gig; instead, you need to do multiple things, starting with networking and advertising.

That’s where LinkedIn shines. It isn’t just a networking site; it’s also your place for promoting yourself and your work. Add your current and former colleagues, assuming you’re on good terms with them; ask them to give you an endorsement.

Then, Wwite posts about technology, make them public, and allow public comments. Write about the topics you specialize in. Give out “free advice” in the posts to help others. Why? Because it will help define you as an expert in the field. Try to write such posts at least once a week. Over time, people will view you as an expert.

And yes, you should respond to other people’s posts—but keep your comments polite and encouraging. As tempting as it is to write a negative comment under a post that has blatantly incorrect material, be careful. You don’t want to come across as an angry snob and push away potential clients. For your polite comments, on the other hand, avoid trite things like, “I agree!” or “Great observation!” Instead, start with something like that but add to the conversation with something like, “In fact, I was working on a similar project and…”

Write a great intro paragraph for your profile. Describe yourself and the services you offer. Make your profile publicly viewable so everybody can see what services you’re providing.

Don’t be afraid to make use of the features that promote yourself. There’s nothing wrong with adding the “Open to work” banner around your profile picture.

In addition to LinkedIn, there are lots of Discord servers, Slack workspaces, and Subreddits devoted to highly specific areas of technology and geographic areas. Join these, because sooner or later you’ll see people mentioning jobs. In the meantime, stay active and involved. And as with LinkedIn, stay happy and positive, and avoid posting negative, angry comments.

While LinkedIn is vital to promoting yourself, there are some sites set up specifically to land contracting gigs. Two sites come to mind immediately:

  • Upwork
  • Fiverr

Upwork lets you put build a profile and a portfolio and apply to job postings. But there’s a secret part to Upwork: If you have a great profile and portfolio, clients offering positions often skip posting jobs and instead contact contractors directly. We can’t know what percentage of jobs are landed this way, but many of us who have an Upwork profile can say we’ve landed several gigs exactly that way. (I personally have landed a few gigs this way through Upwork and I have a 100 percent success rate; I’ve landed every gig when somebody contacted me directly.)

Fiverr tends to be a bit more for people who offer small slices of services. While people do land contracts that span a few months to a year or more through Fivrr, most people coming to the site to find contractors are looking for smaller, highly specific jobs that take hours rather than weeks or months, like, “Write the text for an About Me page on my website.” Still, Fivrr is an option if you’re looking for such short-term gigs.

When applying for a contract position, consider including a note along the lines of, “If I’m not a current fit for your open positions, I’d love to keep a dialog open so that as new positions open, I might be available. Please add me on LinkedIn at…”

Make sure you have a public-facing GitHub profile, and that you have at least a few repositories that are viewable to everyone. If you haven’t built any such projects, start right away. They don’t have to be huge projects, but they should demonstrate your abilities. Include links to your GitHub everywhere you can, including on your resume.

A hard truth about contracting is that you really do need to be better than most. How do you get better than everybody else? You practice, practice, practice. During your downtime, build side projects that fit in with your idea of the perfect gig. Today, you may feel like you’re very good at what you do—but trust me, if you keep pursuing it even further, a year from now you will be even better.

By building projects and putting them on GitHub, you’ll build a portfolio to prove you’re great at what you do. And this will come out during the interview, too, as you’ll have a natural confidence about yourself and you’ll be able to easily answer any questions they throw at you.

Do not – and I repeat! – do NOT undervalue yourself! Don’t set a low rate.

Look at it this way: If you’re worried the client will balk at your high hourly rate, then you probably don’t want them for a client anyway.

The reality is contractors get hit hard in two areas: taxes and health insurance. With employment, the employer pays half of your social security and Medicare taxes, which for 2025 is 15.3 percent. That number can hit hard, because typically contract software developers don’t have a whole lot of deductions they can take. If you bring in $100,000, that tax alone would be $15,300 that you owe the federal government, in addition to regular income taxes.

Also, consider that most employers handle a huge part of the monthly health insurance premiums. As an independent contractor, you’re on your own with that too. Together, the taxes and health insurance can be a big hit, and suddenly that six figure income is, in fact, much lower.

So price yourself accordingly. In general, plan on taking a typical employment salary for your area, and multiplying it by at least 1.33, probably even 1.5, and you’ll get an equivalent contractor salary to cover the additional taxes and health insurance. But don’t stop there; because contractors are specialized and valuable, consider even double what you would get as an employee.

There’s also a hidden side to this: Potential clients view contractors with higher rates as being better at what they do. If somebody severely underbids for a contract gig, they will quite likely be viewed as an amateur. (Need proof of that? The vast majority of good contractors made that mistake in their early career, so just ask around. You’ll hear stories.)

Even though the client is purchasing your services, there’s a good chance you’ll still have to do an interview as you would with a regular job. In general, you can expect such interviews to be a little bit streamlined. Why? Because they already trust you. They’ve seen your LinkedIn profile and they know you’re good.

As a result, this interview will likely be less about coding challenges and more about the services you can provide for them. That means you should ask plenty of questions such as:

  • What stack they use.
  • What IDE and other tools they use.
  • How is the team put together, as well as the team’s size. For example, will you be answering to a manager or will you be leading the team.
  • Ask about agile and whether they do weekly sprints, and so on.

The perfect gigs are definitely out there. As a contractor, really it’s just a matter of being selective and pursuing the gigs that fit with your definition of perfect… and skipping those that don’t. You got this!