Info: This is part one of the Freelance & Prosper series, a series about how to prosper in a job that can feel very insecure and not very stable to some.

Saying that I “choose” contracts and clients indicates I have plenty of offers, and I can pick and choose. The reality is a bit different. What I mean is: There are plenty of contracts out there, but I’m not interested in working on everything. After all, I have the luxury of not needing to be because my financial situation allows me some breathing room. I am privileged, but it’s not simply luck. Early in my career, I decided to cut down on things I didn’t need, so I didn’t have to make decisions based on my financial needs. I’ve lived in a cheap one-room apartment, cooked all meals at home, and steadily built up savings. I’ll go more into why and how I did it in part 2, but it’s essential to understand that what I did required knowledge, planning, and willpower, not just luck. With that, let’s get into it.

More than one, less than five

Let’s start by talking about how we get sourced for contracts. There are many agencies out there, and they’ve all got the same reason for wanting to keep you employed. This is a good thing because it means they’ll keep matching you with clients and offering you contracts where they feel you fit. Keep in mind, though: you’re free to say no. It’s part of the game, and any recruiter worth their pay would rather have a happy freelancer than close on a deal at any cost. At the end of the day, it’s your job to say no to contracts and clients you don’t like.

It’s fair play to say no, but you can’t expect a single agency to bring multiple contracts to your door every month. That’s why I made a rule; More than one, less than five. Always contact more than one and less than five agencies because while one won’t bring something every week, it’s likely that five will.

Occasionally, they will bring you the same contract simultaneously, which is where it gets tricky. As far as I know, there are no rules, but I feel the established good freelancer conduct is to let the first one that brings it have the first crack at it. Being forwarded through multiple agencies to the same client at once can create bad vibes, and I want to believe it’s in their own best interest that I keep it first come, first serve. As said, though, I’ve never been told about any rules, and I have shunned any agencies that try to force any “me first” rules on their freelancers. For one, they don’t employ me, and for another, there’s plenty of agencies out there that don’t try it. I also never bring info about a potential client to another agency or share information about terms and conditions. I don’t ask for client names unless I’m invited to an interview, and I usually try to be upfront about any prior experience with the client I might have.

Following these rules, I’ve never had any issues juggling multiple agencies. Choosing agencies is very much up to you, but they can be divided into national, regional, and international categories. As of writing this, I am in contact with three national agencies, one I would consider regional, and one international agency.

Don’t ignore requests

Beyond agencies, don’t neglect your online presence, especially on LinkedIn. Most contracts are handled through agencies, but agencies unknown to you will reach out if you are active. I regularly go to LinkedIn, and this year - in May - I launched a new website where I make code examples, write about things on my mind, and generally try to be active. This is new to me, and I’m still learning, but I’ve already begun seeing more visits to the website and my LinkedIn profile.

A recent random message on LinkedIn

Messages like the one above can lead to a quick talk about the specific task or a more general one about what you’re looking for. If you are unavailable, don’t ignore these messages. Responding and letting the recruiter know when you are available next gives them the info they need to reach out later. And usually, they will.

Need before Greed

It may sound self-evident, but thinking about what you need when choosing contracts is essential. If you’re in a position where you need the income every month, taking any contract offered becomes necessary. But after just my first 3-month contract, I was in a situation where I could cover my expenses for a few months without income, so I started thinking about what I needed, since income was no longer my primary focus.

Three needs, three pillars

When I’m deciding on taking a contract, I use the three pillars to evaluate the contract. I don’t want to make it too complicated, so I usually say if two are met, it’s okay. If I learn and it’s fun, money doesn’t matter as much. If there is lots of money and a chance to learn, It doesn’t need to be a fun project. Once, when I was uncertain, I used a more complicated system based on the same factors, but these are my key concerns.

I NEED to learn

If I had a Game of Thrones house, its words would be “Constant improvement.” It’s also my preferred coping strategy and coupled with my need to create the best possible solutions, it can become an obsession at times. This is a boundary for me, and understanding that it needs to be part of the equation when choosing what contracts to take. I don’t mind doing routine work most of the time, as long as I still feel like I’m improving. I could be getting faster at the everyday tasks, find a better solution, or have non-routine tasks to work on. If I can’t find it in the contract, I need to focus on something outside the contract, because the need will still be there. If I can’t fill the need, I become unfocused, lazy, and unmotivated.

I need to have fun

Everybody likes to have fun, and I need to have fun at work too. We work most of our waking hours away (even in Scandinavia), and I want that time to be fun. We only have one life, and wasting it on tedious work or with humorless people is just not something I’m willing to put up with. Not all projects will be exciting, but the people you work with and what you work with matter. I don’t really care what the subject matter is most of the time. I work with websites; at worst, I’m building something that gives people access to buying more junk they don’t need; at best, I’m building something that makes it more accessible to get help. It isn’t world-changing, but at least I have fun most of the time.

Money does matter

You thought I was doing this just to learn, have fun, and help out some companies who really need my help? Of course money matters; we’re freelancers. Money matters because it’s the key to being able to do and be what you want, where you want. I want that freedom, even if I don’t know what I want to do with it. I don’t like the idea of having to do anything I don’t want to, but off the top of my head, the only thing I know I don’t want to do is to have someone else decide my future. Depending on what and where you need money, and that necessitates work. So far, working as a freelancer is the most efficient way I know of doing that. But I’m not done looking - constant improvement, remember?

Red flags

Over time I’ve had both good and bad contracts. With time I’ve noticed a pattern, and I’ve formed a list of signals to keep an eye on. Some are more intuition than rules, but most are common sense.

If I am going to be part of an internal team with the client, I’d like to see them be involved in the recruitment process. Firstly, I’d like the team to want the extra help and not have it forced on them. Secondly, I’d like to get a sense of who I am going to be working with. No involvement from the internal team is a big red flag to me, because it can mean any number of things, none of it good. For example, I once took a contract where I spent most of my time dealing with a lead developer, who didn’t want me there but an end client who didn’t trust the lead developer’s technical skills, so they wanted me there. The situation quickly turned sour, and I spent an enormous amount of time soothing egos and having meetings, rather than coding and actually working on the application. In the end, the application didn’t need many tweaks, but I left the project stressed and drained.

The client having fuzzy goals is another good way to get into trouble. If I sense there is no plan or the goals are unclear, it’s an immediate red flag for me. Don’t get me wrong, sometimes the contract is simply “We have a pile of tasks and more coming in, we need extra hands,” and those are fine. But expectations should be the same. Walking into a messy project where everything needs to be done ASAP is an excellent way to raise stress levels, and those projects can really mess you up. You can do things during contract negotiations to mitigate problems. Agree on a reduced scope, extend the deadline, or add a no-limit hour cap. But if those are refused, you should definitely back away.

Unrealistic deadlines, extremely short contract lengths, “double up on lead developers,” and different direction roles are also examples of red flags. The general rule is; If it seems fishy, take a breath and ask. At worst, they’ll give you a non-answer, and that’s an answer too.

Chemistry and Trust

Personal chemistry can be hard to define, but it’s important. Maybe something the client said made you smile or laugh during the interview? Perhaps something was said that made you stop and think. Was it too formal? Too relaxed? I know what I like, but it’s very subjective. I always ask myself; Would I be comfortable telling this client the Truth should I need to? As developers, we encounter situations where we need to advise a customer on something they are going to take badly. Having good chemistry and established trust with key people will make that easier and will make the prospect a lot less daunting.

I’ve been on projects where the state of the codebase was such that rebuilding it from scratch was preferable to trying to untangle the spaghetti I was given. I call it defaulting on your technical debt. In that situation, having the trust of your client and a personal relationship with them makes things a lot easier. If they dislike you already, you’ve just given them another reason to. If they distrust you, they’ll likely wonder if you’re simply trying to get more money. It’s a complex topic, and I would never open it if I didn’t have the client’s trust and a personal relationship with at least some of the key players.

Always another contract

My best advice on choosing contracts is there is always another contract. It may not feel like it, and sometimes you run into a dry spell, but there is always another contract. Understanding your needs will make it easier to express them to recruiters and clients and make you Prosper in the long term.

Having trouble finding contracts nationally? Go regional or international. Having trouble getting attention from recruiters? Write them, ask them if they have any contracts matching your skills. Reach out to the community, use groups on LinkedIn, take part in conferences and community events. In short, make yourself available, and contracts will show up.

Key takeaways

  • Always have more than one, less than five pimps.
  • Determine what your needs are, and use them during contract negotiations.
  • Chemistry and Trust will make your freelance experience easier.
  • There is always another contract, even if you experience dry spells.