Contractors — 16 min
Ending your time in the military is just the beginning of a new journey. Reentering civilian life after serving is an exciting time — and one that comes with plenty of challenges. Rebuilding relationships and finding new ways to apply your skills can take some time, yet the rewards are worthwhile.
While every transition is filled with new opportunities, this one can also be overwhelming. Finding a new job to start your second career can be a real challenge. In fact, nearly half of American veterans since 9/11 say transitioning back to civilian life after military service was either difficult or very difficult.
Veterans can face a variety of obstacles when they end their military careers, including:
One of the challenges veterans may face is how to find good, meaningful employment after service. Finding full-time employment can seem impossible at times, but it’s important for veterans to consider every option, not just traditional paths for employment. There are so many different opportunities that can help guide you to a path of financial stability. With the advent of remote work, veterans now have more choices than ever when it comes to finding great new careers.
Many veterans have begun working as independent contractors in a host of different industries to see how their skills translate to the needs of businesses. From software to communications and mechanical work to graphic design, contractor career paths provide not only flexibility but great earning potential for self-starters. Throughout this guide, we will explore the ins and outs of what it means to become a freelancer as a veteran.
Before we dive deep into how to obtain a freelancing job, we must establish what it is and how it differs from the other types of employment. Let’s take a closer look at the differences between freelancing, contract work, and traditional employment so you have a thorough understanding of each option.
According to the IRS definition of independent contractors, “The general rule is that an individual is an independent contractor if the payer has the right to control or direct only the result of the work and not what will be done and how it will be done.” Simply put, if you operate as an independent contractor, you are self-employed.
Because contractors are self-employed, they choose how often they work and what a typical workday entails. While the freedom can be enticing, this work style brings more uncertainty, less stability, and a responsibility to consistently organize more work. Contractors can make lots of money, but that all depends on how much work the person puts in to market themselves and their services.
Another difference between contractors and part-time or full-time employees is that self-employed individuals are responsible for managing their own tax obligations. The contractor must obtain any required documentation, like a 1099 form, and file their taxes on their own. Employees are sent their tax information from their employer, but contractors have to manage this process without assistance.
Contractors often work for agencies even though they’re considered self-employed. Agencies deal with finding the customers so the contractor can focus on doing the work. Of course, taking this path means the contractor typically earns less, as the agency has to make a profit as well.
One advantage to contract work is the possibility of finding more permanent employment with a long-term client. After both parties have worked together on a project or short-term contract, there is always an opportunity to convert from a contractor to an employee. A contractor may become a full-time employee of an agency or an employee of a direct client. Contractors may also use their time working solo to fill in gaps in employment history. If you provide freelance services for six months between jobs, you were not unemployed during that time — you were working for yourself.
It’s important to note that if you are employed as a contractor (working either in-person or remotely), any agency or client should treat you with the same respect as they would a regular employee. Many employers who want to demonstrate their care for contractors develop fair and equitable compensation programs that may even include offering benefits to contractors to match those afforded to employees.
Similar to contractors, freelancers are also self-employed individuals with time flexibility. However, where contractors can be either full-time freelancers or contractors for one company at a time, freelancers typically do not tie themselves down to any one contract at one time.
Businesses must avoid employee-contractor misclassification to steer clear of hefty fines and penalties. In a similar vein, contractors should typically avoid working for companies that have had issues with misclassification in the past.
If employers treat a contractor like an employee, even if both parties have agreed to a contractor relationship, regulators may still view that relationship as one between an employee and employer — which can lead to serious taxation ramifications. Although the dangers of misclassification are more significant for the employer, contractors must be aware of how to avoid misclassification, as crossing the line could lead to losing a client or other headaches.
Most countries levy heavy penalties against companies found breaking classification law intentionally. If businesses want to stay compliant, they must follow through on their good intentions.
Let’s take a look at a few contract job examples and the skills you’ve accumulated while serving in the military that can give you an advantage in the market:
Think about the skills you enjoy practicing the most, then research the specific technical requirements of each type of job that might require them. Following this exercise can help ensure you’re choosing a path that aligns with your skills and your goals.
Even if you don’t possess all the necessary skills for an opening, you can learn technical skills in a short period of time with commitment and focus. Lean on the discipline and training you have already received to learn and improve. Once you have the basic qualifications and certifications required, you can demonstrate how your previous experience has helped prepare you for the role.
A freelancer is someone “who earns money on a per-job or per-task basis, usually for short-term work.” Rather than working steadily for a company as a contractor or employee, you take on one-time gigs with as many companies as you please.
Freelance jobs come in many different forms. For example, some businesses will hire a freelance artist to paint a mural on their storefront windows for the holidays. Someone may hire you to build their company website. One project may last for an hour. Others might run for months on end.
The pros of freelancing as a veteran include:
Cons of freelance work include:
Before you decide to become a freelancer, you must consider whether you’re able to make a living with so much uncertainty. Veterans are encouraged to contact their local U.S. Department of Veterans Affairs (VA) office for resources on overcoming financial instability if problems arise.
Examples of freelancing jobs include but aren’t limited to:
Similar to finding contracting jobs, finding freelance work that highlights your skill set is a great way to put what you learned while serving to use. The pay for each job type varies based on your skills, experience, and location, but you are always free to set your own rates. Do plenty of research to understand the market, and don’t sell yourself short on the value of your services!
Part-time employees typically work 30 hours or less a week. The specifics on the exact hours a part-time employee works vary from employer to employer.
A few advantages of working part-time include the ability to create a more balanced work-life balance and open up doors to new job opportunities in different fields. Working part time also allows you to work freelance on the side with your extra hours. Part-time work arrangements could allow you to pursue other options outside work, such as caring for children or going back to school.
On the downside, working fewer hours also means less money on your next paycheck. Freelance work can help bring in additional income in between paychecks. If you’re able to balance part-time employment while you freelance, you not only earn more in the short term but can develop new skills to help grow your career. Frequent freelance work could potentially lead to full-time employment, depending on the company.
Some part-time employees are eligible for benefits while others are not. If you obtain part-time employment, be sure to discuss the organization’s benefits program with the hiring manager to understand your coverage.
There are many examples of part-time employment, ranging from retail and tourism to food and hospitality, music and the arts, and more corporate fields like publishing, media, and professional services. Let’s take a look at a few examples of stable part-time roles that could provide regular and flexible work ideal for veterans:
Finding part-time employment is a great way to get more freedom than full-time employment while maintaining the financial certainty that can be lost when freelancing or taking contract work. However, you still need to confirm your eligibility for benefits like health insurance before accepting any part-time employment agreement.
While there is no one set definition for full-time employment, the Internal Revenue Service (IRS) defines a full-time employee as someone who is “employed [for] at least 30 hours of service per week, or 130 hours of service per month.” The specifics of what it means to be full-time vary for each employer.
Working full-time means you are guaranteed a minimum number of work hours along with other benefits. A few advantages of being a full-time employee may include:
Of course, working full time has its benefits, but it comes with some comparative downsides. Those who work a full schedule are at a higher risk for burnout and often have less time to dedicate to family and other parts of life outside work. Further, people who are salaried (that is, not paid by the hour) may be asked to work extra time without receiving additional compensation.
Veterans should consider the advantages and disadvantages that come with a full-time schedule. Jumping into a full-time job right after service could take a bigger toll on you mentally and physically if you’re not ready for that type of commitment.
It’s worth noting that just because someone works full time doesn’t mean they’re guaranteed to generate more income than a self-employed individual. How a full-time employee is paid and the amount they’re paid varies with each employer — some are paid hourly, and some are paid a salary. In many cases, your benefits package may make a lower salary worth taking, especially for public sector jobs.
The number of full-time employment examples is endless. Virtually every company with employees has multiple full-time employees on staff.
To narrow it down, let’s take a look at a few examples of full-time employment that are A, work that can be done remotely, and B, may align with the skills from your military career.
Some veterans may even consider seeking full-time employment while doing freelance work on the side. Keep in mind that pursuing freelance work while holding down a full-time job would require long hours.
We’ve already addressed the advantages of freelance work in general, but it’s important to understand why this path is beneficial specifically for veterans.
Because freelance work means setting your own hours, wages, projects, and deadlines, your skills in time and project management are critical. Military life often involves creating order out of confusion, which is a common theme for freelancer life.
Veterans who freelance can dictate when and where they work, which may be helpful to those who would prefer not to be tied down to one place or schedule. Of course, the greatest benefit of freelancing (besides the flexibility of time) is the ability to earn as much as your skills can demand. Freelancers with experience in high-demand work, such as specialized machinery or computer engineering, can make significant money in a short period of time. For those without high-dollar expertise, though, freelancing still offers great opportunities to earn.
Working independently can be rewarding. You’re able to put your skills to the test and watch your vision come to life knowing you were able to accomplish it all on your own. However, working independently can also be just that — lonely.
It's important for veterans to rebuild their social life upon returning to civilian life. Your support structure is critical, and the more you invest in it, the more you are able to lean on it when times are difficult. Benefitting from a robust support network is not unique to freelancers who recently left the military, but anyone returning to civilian life should recognize the advantages of having a group. If you aren’t sure where to start, ask around to find others who served and may be facing similar challenges.
Finding freelance work that capitalizes on your existing skills is a great place to start. However, we’ve collected a few other tips to consider when seeking freelance opportunities:
Listed below are a few websites veterans can use to find freelance work:
Considering the advice in this article is a great start to finding freelance work as a veteran. If you want to take it a step further but aren’t sure where to begin, look into organizations that hire veterans. Prioritizing your search by looking into pro-veteran resources is a great way to get a head start in your post-military career — whether that means freelancing, full-time employment, or anything in between.
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