Uncharted Waters

Jun 7 2017   3:28PM GMT

Life as a Technology Contractor

Justin Rohrman Justin Rohrman Profile: Justin Rohrman


I have been doing contract work in technology for the past three years or so. I have always had the goal of doing independent work as far back as I can remember, but wanted everything to be just right to start. It was bits and pieces of work at first — an article here, some crowd source work there. Over time it was harder and harder to balance having a day job and freelance work. I ended up leaving the day job (as you already know) and doing this full time.

There seems to be a lot of mythology surrounding contractors and contract work, so I thought I’d share a little of my experience around some key points.

Probably the biggest fear getting in was that work would be hard to come by and wouldn’t last long. Basically, I was under the impression that I would sign up for a 6 month gig and a month in funding would dry up. I’d be left with no work for the foreseeable future and have to start from square one finding a new client.

Fortunately, my last two years have been nothing like that. My clients have lasted anywhere between two years and two weeks so far, but all of them have started and finished as expected. My biggest client started two years ago, I have written about them vaguely before. They are 90% remote with one small office. The development team is spread out all over the world and we talk over email or skype. They want the stability of a close to full time tester. Someone that can grasp the problem space, someone that can do more than fumble through the software. But, without the trappings of a full time employee.


The two week contract I mentioned as a staff augmentation gig while they were hiring a new employee. The product they were working on was very simple and didn’t require any specialist knowledge. I joined the team and about an hour into the gig was testing software. Over a two week period, I worked with the development team, reported bugs, attended scrum meetings, and generally helped them deliver software as fast as they could in the short time I was there.

In between technology contacts, there have been marketing gigs helping software companies develop content. Doing this was originally designed to smooth out the edges of contracts. When one contract ended, I’d still have income for the month. But it also works as a tool for personal marketing sometimes.

Finding work was my number one concern. Would I be able to find enough clients, and keep them long enough, to pay rent and support my family and save for the future. My experience was that this was less trouble than I initially though. Some months were better than others of course, but over all working as a full time contractor has been extremely stable. At least as stable as any full time job I have had. The last company I worked for had 2 layoffs in the year and a half I was there. Each company before that had at least one real layoff, a few layoff rumors, or let some people go not too long before I started. The stability myth in full time jobs is just as strong as the instability myth in the contractor/freelance world.

If you want to try contract work, dive in. You can do it piece by piece, taking small gigs here and there, until you find the right clients for you that will last.

There are lots of myths about contract work, I’ve just touched on the instability myth. If anyone is interested in others, I might write more on this in the future.

11  Comments on this Post

There was an error processing your information. Please try again later.
Thanks. We'll let you know when a new response is added.
Send me notifications when other members comment.
  • TodwynH
    Great article as I am considering stepping out into MDM support on contract in the near future. Great article.
    10 pointsBadges:
  • teresasatterfield
    I'd like to learn more.
    10 pointsBadges:
  • freweight
    Thank you for your article.  I just jumped into contract work as an IT Project Manager in April.  It is something I always wanted to do but was afraid to move away from the perceived security of my direct hire positions.  Initially, it felt like a cliff-dive.  I must admit that I am still a bit apprehensive but I am becoming more comfortable.  I am on a contract that is scheduled to last 24 months.  The sponsor retired and the project may end prematurely.  I already have new opportunities lined up. The next few months will test my resolve to stay in the contractor space.
    10 pointsBadges:
  • a1r9i5
    I do agree about the instability myth in contract work / freelance.
    2,620 pointsBadges:
    I would like to blatantly challenge the writer’s premise … Instability is not a myth. It is indeed a fact but maybe not 100% true for every person involved in all instances. I have had both experiences. I have had 2 month contracts and 2 months searching for the next one, and then contracts over 3 years. Some have even turned into FTE positions. In the lean times when the economy is not so great, depending on your skill set and your network, there could be difficulty in finding work. Additionally, concerns surrounding have a rate high enough to increase savings, pay for medical, taxes, etc. needs to be taken in consideration. Contracts may be short and finite in the product of the project. Many contracts are for specific projects and once the project is complete, if there is no additional work or funding, the contractors will be let go. Words of caution: though the writer has had a good experience, I challenge the statement regard the mythology. You must be skilled, often multi-talented, knowledgeable in the business and the technology, and you must be able to learn the environment and people to succeed.
    20 pointsBadges:
  • gtracy
    I"ve been doing contract work for over 15 years. Contracts are all over the map. Scheduled to go 6 months and die after 1 month. Scheduled to go 6 months and last two years. There is no consistency. You get the worst offices and the hand me down equipment. No training. Most places expect to pay you employee wages for a rate. They don't care that you have to cover time between contracts so your rate has to be higher.
    The key in contracting is be unique with unique skills. It will always bring work. Also, continue learning, that is  the key to continued employment and be flexible.
    Currently I get at least two recruiters calling me every day with new work opportunities. I have to turn them down.
    Finally, value yourself. Don't just take what is offered. Figure out where you stand in the marketplace and go for that. The rate the offer is usually the lowest they can get someone for. If it is worth you going to work for them go at your rate. You won't be happy otherwise. Finally, remember you are a contractor. You owe them nothing. They pay you for the time you work. Don't work for free. If they really need you to work they will approve it. Full time employees are the slaves and it's factored into their wages.
    Good luck and remember to take time to smell the roses. You learn more about the market and meet new people that full time employees just don't get.
    20 pointsBadges:
  • Justin Rohrman

    Yes, that's right. This isn't true for all people all of the time. This story was about my personal experience, and the experience of several technology contractors I know as well. Some of this is related to the market I live in, some to my skill set, and some to blind luck. I still think it is important for people to know that contract work isn't always the wild wild west. You can go independent and have stability if you design your work around that. 
    2,130 pointsBadges:
  • Justin Rohrman

    That is all good advice. Some of the instability of contract work can be shed by finding the right clients. This is a slow, and time consuming process. These clients are usually based on long term relationships with people. I find that when I understand the client and their situation, and they understand my skill set, things just work better. There are exceptions of course, sometimes budget problems pop up, but the relationship is a good place to start.
    2,130 pointsBadges:
  • Justin Rohrman

    I know exactly what you mean about feeling like you are walking off of a cliff. It is hard to get over the feeling that a full time job offers some sort of safety net even though that net really isn't there. 

    I made things a little more stable by having several different marketable skills to fall back on when the market isn't hot for one or the other.
    2,130 pointsBadges:
  • Matt Heusser
    One thing that might explain the disconnect between the optimism in this post and the pessimism of a reply or two is the value of a long-term partner company to do the sales and marketing work ... not that I'm biased ... :-)
    4,855 pointsBadges:
  • TheRealRaven
    As @ITPMSFCA says, there is indeed instability in the contract arena. But as the article points out, there is also instability in FTE work. The point of the article is not that contracting provides guaranteed stability, but it's rather that guarantees don't exist either way.

    I came out of college in the late 1970s and was picked up by a multi-billion dollar, multi-national, DJIA company. After some five years had passed, a friend approached me about coming over to be part of a small startup with an unpredictable future.

    I "knew" that I could stay in my position as long as I wanted; and if I really wanted, I could advance a long way as years went by. I also knew that it would be fairly boring conservative corporate work, and I also wasn't convinced that upper management assurances of future company direction in my region were totally truthful. The choice was essentially one of long-term security (stability) vs. a scary step into... who knows what?

    I let it roll around the back of my mind for quite a few days until a single clear thought came to mind, almost as if I'd heard it spoken aloud: "I am my own security." Decades later, I still remember that.

    A couple days after, I turned in my resignation.

    It only took a couple years before that startup crashed, and I was looking for projects on my own. Ah, well.

    OTOH, just about a year after I resigned, word came down for 'Corporate' that the existing western U.S. data center would be closed down, with everything being moved 50 miles south. And a year after that, it was moved again another 1000 miles to Dallas, TX.

    Many of those I'd worked with were left behind in the first move. I think none below manager level made it to Dallas. But I'd gotten out early. I'd been out doing some services in the area before the others knew that they might need to. When the startup folded, I was already a bit plugged into the area market. Sliding into contracting was almost natural, and that's where I stayed for the next decade.

    Ever since, I've taken some staff positions when appropriate, and stepped back into contracting as soon as it felt it was time to do something else.

    For me, the initial "instability" appeared in two forms. First, the 'security' of FTE work was shown to be a myth. I was lucky to reach my epiphany when I did. But second, it was indeed always looming during a few early years. Simply being younger and inexperienced at managing myself as a business brought irregular difficulties.

    My latest jump into contracting began five years ago. I wasn't enjoying the position I was in, so I resigned. There was more work available than I could handle, so I turned it all down for the first year, just letting myself enjoy whatever I wanted to do. After that, I accepted work that fully interested me and was never idle unless I chose to be.

    In short, the issue of "stability" is real, but it's not a matter of contract vs. FTE. It's highly individual. It's affected by market conditions that may be out of your control regardless of how you're employed. It's also affected by your personal attitudes and aptitudes.

    If your personality isn't suited to stepping out on your own, you're likely to have more trouble contracting than others might. Just don't be lulled into thinking to a "job" is the true source of security (stability).
    35,620 pointsBadges:

Forgot Password

No problem! Submit your e-mail address below. We'll send you an e-mail containing your password.

Your password has been sent to:

Share this item with your network: