It was in the last great recession that I started doing contract software development, about 2008-2010. The bubble didn’t burst with as much force and shrapnel as in 2000, but it had a distinct dampening of the animal spirits of SOMA, San Francisco where all the startups lived.

It was somewhat by design. The previous job I had, writing Java and ActionScript for a marketing research company was chill enough but felt aimless. I had so little motivation I ended up coasting for a few months and playing a lot of pingpong. I wanted some new challenges, so decided to go freelance.

The first gig I got was off of Craigslist, although I imagine these days Upwork would be a better place to look for work. The project was very limited in scope; mostly adding a Google Maps visualization on top of some grant data for a nonprofit. It was a couple weeks of work, a couple grand, and time to move on.

Some time later a former colleague of mine hired me for some development work at a SF startup doing IP telephony combined with podcasting. This was 2009 so nobody had ever heard of podcasts and smartphones were still a fresh new technology people weren’t entirely sure what to do with. The gig was a fun challenge – enabling people to listen to and produce podcasts using only a telephone, no apps involved. I ended up developing some pretty innovative software that resembled a web framework but for touch tone and interactive voice response (IVR) phone applications. We successfully moved the application from an expensive managed solution to our own in-house platform that I designed, significantly cutting down operating costs.

After some time working on that project, I met a couple of guys who wanted to build a SEO-optimized directory of medical professionals, starting with Spanish-speaking plastic surgeons. I said I could cobble together a search engine in my spare time and was engaged. Some days I would walk the two blocks over from the small telephony company office to the small office housing the nascent doctor directory business and show my progress.

It seemed clear at the time that the podcasting telephony company while highly experimental, was professionally run. It had not one but two Stanford business school co-CEOs running it, with what amounted to a successful track record in the form of an early dot-com electronic greeting card company. Remember those? Weird shit. There were respectable investors, a small team of smart and highly competent professionals, and a beautiful office on Howard St. I recall situated on the floor below our office sat a little room consisting of no furniture save a well-stocked bar with never any people in sight, and a sign on the door reading “GitHub.” I felt like great things could happen.

In contrast, my side gig seemed like some small-time SEO hustling along with a smaller team and paycheck and no Stanford business vibes or major VC funding. I didn’t see anything wrong with that, and still tried to do a professional job, but it seemed like more of a dead end compared to the “real” engineering I was doing, fighting battles with touchy open-source PBX software and voice recognition grammars.

Then things turned out completely differently from what I expected. The doctor directory project kept growing, expanding, and taking on a life of its own. We got a proper office at 1st and Mission, hired an engineer, a designer, a salesperson. Plastic surgeons were mostly ditched, and now we were primarily helping American dentists establish a presence on this new “world wide web” technology they couldn’t quite wrap their heads around. This contacting gig that I imagined would consist of a couple months of basic work kept growing and there was always more work to do. Without any planning or expectations it turned into a real company, with eventually a staff of 25 talented and terrific people and an extremely respectable office in the Financial District. We built software to help all kinds of small medical practices in the US manage their patient communication, from appointment reminders to e-visits to actually useful online medical Q&A. Six years later we sold the company to a large practice management software firm in Irvine, CA.

Following that experience my business partner John and I started a new company together again, this time on purpose. We started hiring and training some of the best young engineers, taking on projects and filling outstaffing needs for our clients, staffing a couple offices in Eastern Europe until covid forced us to go purely remote. This has in effect scaled up from my original single-person consulting operation into a powerhouse team of crack young engineers ready to take on complex software projects.

The classic Silicon Valley VC-backed, Stanford-connected, hip startup went nowhere, and closed its doors. I got permission to open-source the IVR framework we built but little else came of it. As it happened, consulting across different clients helped me to gain a broader picture of what was actually possible and break my preconceived notions founded on image instead of substance. I accidentally ended up starting a company which went on to help make American health care just a little tiny bit less terrible, created a couple dozen jobs, and had the profound and unique experience of building up the software for a company starting completely from nothing up through due diligence and acquisition. Along the way I learned some lessons about software contracting I want to share with others who may be considering going rōnin and setting out on their own as freelancers.

Tradeoffs and Considerations

It’s my nature to think of everything in terms of trade-offs. Maybe because I have engineer-brain, or because I’m a libra, who knows. There are real benefits to consulting as opposed to being a full-time employee, but also some downsides.

Legal Concerns

In America at least, contracting means forming your own business, doing 1099 tax forms and racking up deductions, and drafting and reviewing contracts. It’s more effort and responsibility than being a full-time employee somewhere, as you’re now responsible for taxes and legal matters. Even if you’re not in America, being able to work across borders means creating a legal business entity.

I started by initially getting a DBA, or “Doing Business As” name, under which I could legally create contracts and other paperwork using an official-looking business name. Later on I “upgraded” to a California S-Corporation, which gives favorable tax treatment once your income reaches a certain threshold along with some legal liability protection. If your corporation is sued, all that can be collected usually is what the corporation has, shielding you personally to some degree. A Cali S-Corp will run you $800 a year not counting the time spent on paperwork and taxes you or your accountant/tax attorney will be doing.

Even getting a DBA or Fictitious Business Name is far from simple. In Contra Costa County for example:

Within 30 days after a fictitious business name statement has been filed, the registrant shall cause it to be published in a newspaper of general circulation in the county where the fictitious business name statement was filed or, if there is no such newspaper in that county, in a newspaper of general circulation in an adjoining county. If the registrant does not have a place of business in this state, the notice shall be published in a newspaper of general circulation in Sacramento County. The publication must be once a week for four successive weeks and an affidavit of publication must be filed with the county clerk where the fictitious business name statement was filed within 30 days after the completion of the publication.

https://www.ccclerkrec.us/clerk/clerk/fictitious-business-name/

You don’t need to do this yourself necessarily, services like BusinessRocket can take care of business formation and taxes for a small fee.

One of the first things you’ll need to do is ask your friends for legal services recommendations. If you know anyone who is a contractor or a small business owner they probably have lawyers they work with and can recommend. Or you can hit me up. I enlisted the services of a business attorney to help me draft and review contracts, and a tax attorney to take care of the corporation taxes and paperwork. Obviously lawyers are not cheap and in theory you can do all of this yourself, but they can also save you a great time of time and money as well by warning you about common pitfalls and fuckups, and suggest ways to better protect yourself or take advantage of favorable tax laws.

When you are going to agree to do work for a client they will want to know your hourly or project rate and a contract to sign. Understand that around a third to a half of your hourly rate is going to go to taxes, so adjust accordingly. A contract will need to have some important pieces of information. I highly suggest not listening to me and listening to an Actual Lawyer in your country or state about drafting a contract, but as far as software development you will typically need to include a “schedule of work.” This is the scope of what you will be expected to deliver in order to get paid.

Come at the schedule of work with a PM mindset – you have to figure out what the client actually wants and what actually needs to get built. If you end up needing to do more work outside of this scope then it can be a headache, and having a contract which spells out what you’ve been asked to do can make an effective backstop against scope creep. As a related matter, I highly suggest doing per-hour billing rather than doing projects for a fixed price whenever possible, because as we all know the best laid o’ work statement often go awry.

Technology

Sometimes you have a particular skill or framework or vertical or other some such specialization, and you can look for relevant gigs. When I started out it mine was actually Perl, and I didn’t have a hard time at all finding work. The first nonprofit project I worked on was already using my favorite Perl web framework. Some jobs will leave it entirely up to you to create something from nothing, and you can have your choice of technology for solving the problem. Sometimes you will go work for a company with their own existing codebase that wants to expand it, fix existing problems, or throw it away and rewrite from scratch.

For me this is one of the most thrilling parts of contracting; getting to see how different companies operate. I’ve gotten an opportunity to look at a good amount of different codebases and operational setups. It gives you a broader view of the landscape, allowing you to borrow best practices others have landed on, and learn from the mistakes of others. I’ve gotten to encounter a lot of technologies I would not have otherwise run into, like seeing different implementations of microservices, getting really familiar with SNMP, and deconstructing a J2EE application. When you work for one company or for yourself for a long time, it can be hard to stay current or get experience with other technologies. When working with different companies, you can rapidly take in and observe various stacks that organizations have coalesced around, usually ending up with good practices. There’s an infinite combination of frameworks, languages, architectures, libraries, development environments, and security practices and the state of the art is always in flux. Having exposure to new assemblies of technology keeps you curious and informed and better able to make decisions for your clients and projects.

Most of our business consists of either building new projects for people, taking over existing projects, or joining existing teams. We get to experience not just code of course, but see how different organizations are run, different business models, all kinds of personalities and team dynamics. It can potentially open you up to a richer tapestry of experiences and cultures than working on the same product and team for years and years will.

The technology you encounter will vary wildly, from hipster web microframeworks to ancient enterprise Java. Being flexible and able to rapidly adapt and figure out the basics of a lot of different technologies is a very valuable skill, as is learning how to start up every kind of bespoke development environment out there. I sort of have a weird perverted dream of going around rewriting ancient COBOL applications for desperate businesses to run on modern serverless cloud-first architecture.

Clients

The coolest thing about being a contractor is that you can be your own boss. You set your own schedule, work from where you want, and don’t technically have to wear pants a lot of the time. Maybe this is less of a big deal than it used to be thanks to the ‘rona but it is definitely something I value a lot.

Of course in the end, everyone has a boss, you can’t escape from it. The CEO has to answer to the board and investors, the investors have to answer to their partners, the partners have to answer to funds, and so on. Your boss is now the client, since they’re the one cutting your checks now.

In my experience this has been a good thing. I can report honestly that I’ve enjoyed working with 100% of my past and present clients and things have on the whole gone very smoothly. Much of it comes down to choosing your clients. You will turn some people down because they are looking for someone with different skills, don’t pay enough, have a Million Dollar App Idea I Just Need Someone To Build It, are unprofessional, or just not cut out for the whole business thing. Just don’t work for these people. It’s okay to turn down work and it’s okay to fire your client as long as you’re not breaking contract obligations. Always act professionally though, no matter what situation you find yourself in. Your reputation absolutely follows you around, and taking pride in your work and professionalism is a requirement for being a freelancer.

Another skill that you must be consciously aware of and always seeking to improve is communication. Being direct, open, and transparent with your clients can often mean the difference between a successful project and one that ends up in a mess of assumptions and bad feelings. Underpromise and overdeliver is the mantra. Over-communicate, bring any concerns about the project to the fore, have regularly scheduled progress meetings when applicable, and do demos for your client. Focus on delivering something visible, something the client can look at and play with, so you can get feedback early. There will almost always be some gray area between what your client has in their mind and what you envision in your own, not just in designs but in all the details in the details.

Sometimes a client may come to you with detailed designs and specifications, but I’ve never been in a situation where all the information needed to deliver a project was hashed out up front. Most of the time very little of it is. You need to establish a good two-way street of communication and always be asking for feedback and clarification of ambiguities. Get a MVP in their hands as early as possible and iterate on it.

Other Skills

Consider also what skills you can bring besides just writing code. Familiarity and expertise in UX and design is very valuable and basically a requirement for most software jobs these days. We’ve had clients come to us to help them perform due diligence on codebases of companies that they are considering acquiring. We’ve performed security audits on codebases, sometimes unbidden. And thanks to our extensive commercial experience building successful companies we also can provide valuable consulting services on marketing, sales and raising capital.

Whatever extra you can bring to the table for your clients be sure to market it and build up your experience and knowledge in that area. It can make the difference between being just another coder and a valuable partner to your client.

Getting Started

For many contractor-curious folks getting started may be scary or daunting.

If you’re a full-time employee, becoming a contractor means giving up some job security. You may not have a guaranteed paycheck for a while, if ever. Being a contractor, especially if you’re starting out and doing it alone, brings many uncertainties. However working as a full-time employee carries its own sort of risks. Job security isn’t what it used to be, spending time on bureaucracy and pleasing your superiors may not make you fulfilled, and there’s a real limit to how much you can accomplish for yourself as part of a larger organization.

There is comfort in working at a company; all you have to do is show up and be told what to do, you don’t have to think much about taxes or contracts, someone else can make a lot of the decisions about how to run the company. But if you want to take on more responsibility, have the opportunity to grow and learn to run your own business, and do things your way then consider becoming a contractor. Almost everyone I know who works for a company of any size will be happy to tell you all about the mistakes and boneheaded ideas of their superiors. Everyone has ideas of how the company they work for could be run better. I say if you really believe this then work for yourself.

So how to begin? You have two options: line up to your first gig, or join a company doing freelance work. You can put the word out to your network that you are available for work, or you can go look for jobs posted on sites like Upwork. There are also companies that specialize in doing contract work and are often looking for contractors to augment their pool of developers. If you go this route know that such companies may not always have work immediately lined up for you, but they may be happy to interview you and keep you on file in case some work comes up that matches your qualifications.

My suggestion is to do both; look at what’s out there, get a feel for what people are looking for and how much they’re offering and also check out companies that are doing the kind of contracting work you’re interested in and offer your services to them. There certainly is no shortage of work and job opportunities out there for contractors, it’s more a matter of finding a good fit for you that will be engaging work and well-compensated. Even if you start with some small simple jobs, they can definitely lead to greater opportunities as you gain more confidence, experience, references, and a better understanding of the market.

I would of course be remiss as a small business owner if I did not mention that our consulting company JetBridge is always looking for smart and talented engineers. If you’re thinking of becoming a contractor, feel free to drop me a line, and I might be able to help you get started or refer you to other work out there. I know it can be an intimidating career jump, but it can be extremely rewarding and full of new opportunities as well. And if the current tech bubble happens to pop again someday, it just might be a great time to try something new.

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