Recently, a TechRepublic reader wrote into Career Management blogger Toni Bowers with the following question:

I am a retired vet completing me BS degree IT by December 2011. I majored in programming and trying to find a job working at home doing web development, database administration, or creating applications. Do you have any advice for me?

Toni passed this good question along to me, and I’m glad to have the chance to answer it.

The good news

First and foremost, you are a veteran in good standing — that is a fantastic item to be able to put on your resume. It is my firm belief and has been proven to me many times throughout my career that veterans of military service have a wealth of experience and training, as well as a fantastic attitude, that make them superior employees when all else is equal. Even better, many employers agree too. I’ve seen a lot of resumes go straight to the top of the stack based upon veteran status, even when the experience or training for the job was not on par.

I’ve got more good news: getting a BS in IT with a major in programming was the right move to make. Right now, computer science and IT graduation rates are dropping, while IT is one of the few fields desperately hiring. One reason why companies like Microsoft have been doing so much overseas hiring is because they cannot find enough qualified workers here in the United States, and the declining graduation rates play into that.

You know what else is good about your situation? If you are retired from the military, you hopefully receive a pension. This money can provide you with the financial breathing room needed to do what you want to do without significantly compromising your goals.

One final piece of good news is that telecommuting is more common in IT than most professions, and it is quite possible to do in IT and be successful. Something that is very common is for a consultant to be hired for a project and for that consultant to rarely if ever be onsite.

The bad news

The first issue is the desire to work from home. In IT, it is extraordinarily rare for a new hire to be given work-from-home status, especially on a full-time basis. When this happens, it is usually with a candidate who already has an established track record of working from home, or who has enough “pull” that the company is willing to not require them onsite. The issue at the heart of it is teamwork; working from home is tough to do while being part of a team. It takes time for employers to build up enough trust to feel comfortable with an employee telecommuting. It isn’t just trust that you will actually do the job instead of goofing off, it is trust that your personality works well with the telecommuter work style. Not everyone is equally (or more) productive at home as they would be at the office. That’s the really bad news. (Read: 10 signs that you aren’t cut out to be a telecommuter.)

The slightly less bad news is your use of the word “retired” to describe yourself. I know that people retire from the military at all sorts of stages in their careers for a variety of reasons, and it is perfectly normal to retire after 20 years of service and still be middle aged. The problem is, there is a big age discrimination issue in the industry, and there is no way to sugar coat that disgusting fact. The older you are, the harder it is to get a job in a field that many consider to be “a young man’s game.” In addition, people making a mid-life career change often have the deck stacked against them. The perception is that they have career and compensation requirements that someone who went straight to college from high school does not (mortgage, house, children, etc.) and will need more time off and a higher salary, while having less energy and desire to keep up with the self-learning at home.

My suggestion

When you add this all up, I think that finding a full-time employee position with a company will be a challenge. This doesn’t mean I think you should give up; it means that you’ll need to be willing to consider some alternatives, such as:

  • Start your own business
  • Do freelance consulting work
  • Volunteer/charity/unpaid work
  • Work for a smaller, local company, perhaps with a consultancy that uses a lot of at-home workers
  • Be willing to make significant concessions in the compensation negotiations to offset the risk of hiring an inexperienced person who wants to work from home

My suggestion is to combine all but the last item on that list into a shotgun approach. Start a small business doing consulting work. At first, do small jobs that you can handle with your current knowledge and experience, and ask a more experienced pro to be your mentor and review your work. If possible, target small, local businesses, because they have a lot more flexibility and are often willing to forgo the things that a “big guy” consultancy brings to the table in exchange for the lower rates that you’d be charging. At the same time, look for local charities to work with part-time on a volunteer basis; this will let you get your feet wet and hopefully have someone with more experience guiding you. You may need to be onsite periodically, but that will beat going to an office for 40 hours a week. As always, I recommend getting involved with an open source project, or doing work on your own. Think of a project and just do it! This shows employers that you have the self-discipline to work on a project at home without someone standing over your shoulder, and it will give you a lot of the hands-on experience with an actual project that most degree programs lack.

I know this is a tall order; I am suggesting that you start a business and do a lot of work with no immediate financial payoff. This would be pretty daunting to most people, but if you can put forth the effort, you’ll be in a position to pick and choose either your clients as a consultant to fit the work-at-home lifestyle, or with the proof that you can be hired by an employer to work from home.

Best of luck! I am sure that the other TechRepublic readers will have lots of good suggestions as well.