Should You Become a Contractor?
The tech industry is still in the midst of layoffs. When permanent roles are so precarious, is it the right time to make the move to the freedom of freelance software development?
Contract work — whether it means lending a hand on short-term projects or tech consulting of a wider scope — is a staple of our industry. It brings with it the independence to be your own boss and to pick when you work and what you work on. But traditonal employment comes with many benefits — health care, retirement plans, consistency and team camaraderie.
For this installment of Tech Works, we talk to developers who have worked long-term as contractors — and people who hire them — to understand the risks and rewards of breaking out on your own.
Stopgap Role or Career Pivot?
If you are struggling to find a permanent role, a contract developer gig is a good stopgap to pay the bills.
It also keeps your technical skills sharp for interviews, closes the gaps in your resume and increases your professional network. Especially in this market, no one is going to judge that decision, and these temporary roles are easier to drop if something more permanent comes along.
Make sure, even if you work via an umbrella company, list your third-party clients as your employers on your LinkedIn and resume. You can clarify that it was contract work, but don’t think that diminishes that experience. The tech industry, after all, is used to software outsourcing of all kinds.
“The way the resume is written is key,” Sidney Miller told The New Stack. In her current role as senior talent partner at veterinary medicine startup Loyal, Miller hires technologists to work as individual contributors.
After all, you need to write your resume in a way a human or an AI can scan in a moment.
Via direct online message, she recommended the following: “Tell me what you built and the technologies you built them in. Be razor sharp on that. Things like ‘responsible for the distributed systems written in Go’ are too vague.
“I need more on this, like ‘Built the system architecture (15+ microservices) for the Cloud Contact Center platform — multitenant (thousands of agents), omnichannel (text, video, email, SMS). Technologies: Golang, Java, Docker, Kubernetes, Nomad, Spark/Databricks, Mesosphere.’”
Before you make a move to a career as a consultant/contractor, know that it can be harder to move back to permanent roles.
One tech recruiter, who asked to remain anonymous to protect their employment, told us that, in their experience, companies tend to reject contractors.
“Usually they have big issues to adapt to the norms of the organizations and are a bit free souls,” the recruiter said. “They are more demanding in some cases and less committed, work for several companies at the same time and are more distracted.”
Quick Hire, Quick Fire
One of the biggest allures of being a consultant is the freedom you get.
“You can work as much as you want, as little as you want,” Dean Summers told The New Stack. “And work on stuff you actually want to work on.”
Contract work, according to Summers, who has spent 10 years as a contractor and now has his own professional services company, is usually what companies wouldn’t want to do in-house. His agency — Lampata, based in Cambridge, England — has carved out a specialty in building data maps, such as for grocery chains, which is useful to those companies but is not core to business.
Because consultants are usually brought in to fulfill an urgent need, the placement process for temp workers is quick, often just a single technical interview. By comparison, a traditional tech recruitment process — which involves long-term contract negotiation and exploration of culture fit — can take weeks.
But that works both ways. David Gimelle, a Java developer and automated testing consultant for 15 years now, told The New Stack that he particularly likes the option for a quick exit when he doesn’t like the company. He can do this without the usual judgment that comes with changing traditional jobs too quickly.
He can take more days off than his full-time colleagues, with fewer eyebrows raised.
“As long as you meet the objective,” he said. “If you meet the objective with less days, that’s a win-win for clients,” when you come in under budget.
Ditch the Office Drama
Contract workers often exist outside the company hierarchy.
In fact, a contractor can experience “a more balanced relationship with your manager and the entity you work with because you don’t have this feeling of subordination you can have when you’re permanent,” Gimelle said. “You also don’t have to feel too constrained by all the company culture.”
There’s less of a feeling of being trapped if you don’t like what you’re doing.
“If it’s not working, you have an end date,” Stuart Axon, a full stack developer working mostly freelance for the last 25 years, told The New Stack. On the other hand, “If it is working, then the idea that you may not be renewed keeps you doing good work.”
Your impermanence can even be an added value to an organization.
“As a consultant, you don’t need to worry as much about the internal politics or history when suggesting changes,” Ian Miell, cloud native consultant at Container Solutions, wrote on his personal blog. “You both get to tell the truth, and get listened to more when you’re a consultant.”
Often, a consultant is brought in by the most open-minded leaders within an organization. On the other hand, you are often pulled onto a project because in-house solutions have failed. This makes your project more urgent.
“Contract work can sometimes mean working on high-pressure projects with tight deadlines, as you’re often brought in to solve specific problems quickly,” said Miller. Before her current role as a recruiter, she worked as a contract engineer, which she said could “lead to a more intense work environment compared to the often more balanced workload of full-time roles.”
And contract development work can feel isolating.
“Not having permanent co-workers is a blessing and a curse. Working relationships are more fleeting,” said Elizabeth Barron, an open source community manager who has worked both in-house and freelance for more than 20 years. “You don’t have to worry so much about office politics or power dynamics. You can just focus on the work.”
Freelancing vs. Contract for Hire
As you start on your solopreneur developer journey, you’ll come to a fork in the road: go freelance or work through a recruitment or umbrella agency.
“Some people do it by having a big network of people they know and never use a recruiter,” Axon said. “I use recruiters. When a contract is coming up for renewal, I start answering the phone to them and see if something that matches my skills is starting soon.”
The introduction of regulations like the U.K.’s IR35, has created another obstacle for a lot of contractors, leaving many businesses reluctant to hire individuals directly. This has seen a surge in umbrella companies and interim hiring agencies.
Gimelle also finds most of his work through recruitment agencies because “big companies won’t sign you directly. They will sign with an entity.” Smaller companies will sign with individuals, but, he warned, those roles typically pay less, while larger organizations like governments and multinational corporations usually come with more established, reliable budgets.
Most contractors interviewed for this piece find success subcontracting with large enterprises and governments, which are more likely to run multiple projects that require contractor help and offer more stable funding and predictability.
With smaller organizations, Summers said, “You basically don’t know what’s going to happen in the next six months, almost never, because nothing stops your clients from just saying, ‘Project’s done. Budget is cut.’”
Who’s Suited to Contract Work?
Contracting may fit best if you’re a senior developer rather than junior level. You are basically being hired on your technical experience alone. Axon reckoned that if you have about five years’ experience, that’s enough to then test out the contractor path.
Whether you are working with an agency or going out on your own, there’s a certain type of personality that seems to suit this balance of freedom and instability.
Contractors have “to be more independent with the work they’re doing,” Summers said. This dichotomy has “permies” going through lengthy multi-interview processes, while his freelance work is mostly referral driven.
“We contribute back to the open source ecosystem,” he said, which means “we get to meet the people that built the tools that everybody else uses. These people are likely contractors too.”
Target open source projects, he recommends, that already have some corporate buy-in but don’t have the most vibrant developer community yet. The small team at Lampata all contribute to a lot of open source projects, including PySpark and Pangeo, which leads to referrals.
“You have to be way out there with yourself, unafraid to go for a networking lunch or an event,” Summers said. “It’s going to involve quite a lot of speaking with people.”
You also have to be confident in your work, according to Barron: “There are no performance reviews and no promotions, so you have to be OK with that.”
Often the only raise comes when you change clients. “You can raise your rates, but that can also be tricky if you have a longtime client that is used to paying a certain rate,” she said. “You may not get positive feedback, but clients will definitely tell you when they aren’t happy.”
No Clear Career Trajectory
As a contractor, you stay tuned into the job market.
“You will never find yourself being laid off after 10 years not knowing how the job market works,” Gimelle said. As a contract developer, “You’re always ready.”
On the flip side, as a contractor you are typically hired for what you already know, not the potential to grow.
“At a permanent job, they can give you a chance to develop skilling in-sector,” he said, but “with a contract, you always need to hit the ground running. So we often have proposed jobs about the same things. If you want to change a career or to a really different technology, it could be harder.”
If you have the free time to study and contribute to open source code, you can add it to your resume as part of your freelance experience.
Consultants also gain experience in different industries or verticals.
“The benefit of taking on contracts is that you gain exposure and experience to several different tech stacks and a diverse set of problems,” Miller said.
However, she added, “contractors might work on short-term projects, which can mean constantly adjusting to new environments and technologies, and less time to delve deeply into long-term, impactful work.”
Traditional employment usually comes with more structured career development opportunities, she said, like training, mentorship and promotions. A contractor’s growth trajectory is less linear.
“You are continually thrown into new environments, forced to consider new angles on industry vertical, organizational structure, technologies and questions that you may previously have not come across, thought about, or answered,” Miell wrote on his blog. “You have to learn fast, and you do.”
Consistently Inconsistent
While no one we spoke to was planning to return to traditional employment, they all said freelancing can be brutal.
“It happened two or three times in my career to have a contract just brutally stop, with one week’s notice because they don’t have budget,” Gimelle said. Sometimes, he added, he will risk working without income for a couple of weeks while waiting for his contract’s budget to be approved —and then get a lump sum when it finally is.
Always have six months’ pay saved for downtimes, he advised, so “you can sleep well because you know you have enough cash if something ever goes wrong.”
This instability is not for everyone, Gimelle warned: “I have a few friends who tried to be contractors, but it didn’t work because they were too stressed to be out of contract that they didn’t go into the interview” with a good mindset.
If you can charge a rate that gets you enough money for the year in about nine months of work, then Axon argues that gives you a sense of stability — and can finance some time off
“Best thing about contracting,” he said, “is finishing a contract and having money in the bank and free time.”
A Recipe for Burnout
When your next paycheck isn’t guaranteed, when do you turn off?
“How much do you actually work as a self-employed person? Do you work five days a week? Six? Seven? You end up working all the time,” Summers said.
While his team is very flexible, he acknowledges, “I’m working basically 24/7. I love the stuff I do. In my free time, I’m studying.”
Especially at the start of a project he feels pressure to over-deliver. But, once the relationship is established, he said, he pulls back a little bit to a steady rhythm.
The ability to choose clients can be both a good problem to have and an ongoing challenge for those prone to overwork. It can be hard to walk away when the money is good.
“It’s hard to say no to awful clients who are overly demanding but who pay well,” Barron said. “No matter how desperate you might be for a client, it’s not worth your mental health. They will always want more. It’s OK to fire them, and it’s OK to say no.”
Developer burnout is pervasive in the tech industry and contractors can be at even higher risk.
“It’s easy to burn out because if you aren’t working, you aren’t getting paid,” she said. “One of the benefits of contracting is control over your days, so take time off.”
