Seeking Advice as a First-Time Contractor Coming From Federal Service

SECURITY CLEARANCE Q&A
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Hi all,

I recently transitioned from federal service into my first contracting role after retiring from government, and I’m hoping to get some honest insight from those of you who’ve been contracting longer than I have.

I’m currently with a small consulting LLC supporting a DoD client. The pay is excellent—which is what initially attracted me to this path—but I’m finding that several aspects of the job are not what I expected. The benefits are fairly minimal, the company structure feels a bit disorganized, and leadership seems to take a very top-down, impersonal approach. None of these are deal-breakers on their own, but the combination has me taking a hard look at what I should expect (and avoid) if I plan to stay in contracting for another 9 years until I fully retire.

For those who have been in the contracting world for a while:

  • What are the major advantages and disadvantages you’ve experienced, especially compared to federal service?

  • What should a newer contractor pay attention to when evaluating whether a company is a good long-term fit—benefits, culture, contract stability, management style, etc.?

  • Are there red flags you’ve learned to watch for when choosing a contracting company?

  • And on the positive side, what traits have you found in companies that treat their people well?

I know contracting can vary widely depending on the organization, contract type, and leadership, so I’m trying to get a broader perspective before making any big career decisions. I want to do this right and ensure I’m positioning myself well for the long haul. BTW the client so far good.

Any advice, lessons learned, or honest assessments would be greatly appreciated.

Thanks in advance.

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I was a contractor for many years before a brief stint as a government employee.

It is very hard to figure out which companies are better than others. One person can have a very positive experience with ABC Corp while another swears he would never go back there no matter what the salary.

The key point is that you need to be prepared for that moment when the company no longer requires your services. Keep your resume up-to-date; have it security reviewed if necessary (that can take a few weeks). Keep in touch with former coworkers as best you can. LinkedIn is a pretty good resource but be security conscious.

Also be prepared to move when you get a better opportunity. Its a good job to always be looking even if you’re not particularly dissatisfied. Maybe try to get an interview every so often so you dont forget what that’s like. Seems like that won’t be much of a problem these days as people tend to switch jobs more often.

A lot of people, former civilians and ex-military alike, don’t know too much about the world of contracting and their first job can kinda suck. So make the most of it and keep your eyes and ears open.

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Another thing is to maintain awareness of what the hot new technology or tool or just buzzwords in your field might be, then try to get any kind of exposure so you can put something on your resume AND be able to speak about it intelligently in an interview.

Sometimes just some basic knowledge can be enough to put you ahead of the pack.

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Contracting is purely about money. The benefits and stability will never be anywhere near as good as Federal. Just better pay (part of why feds hate contractors). As far as company reputation, you can check it on glassdoor. If it’s really small then you have the advantage of being able to advance and have personal relationships with company leadership. But as soon as the contract ends, they will lay you off.

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Ah yes, the stability of the fed in the current environment is certainly enviable /sarcasm. lol

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well… historically anyway

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Still pretty good compared to private sector. Yeah 2025 has been a rough year but these things happen every so often. I think in the long term, being a fed is a good deal… but nobody thinks long term anymore.