Top Freelancing Tips for Every Stage of Life


According to article after article, a substantial number of adults are engaged in freelancing and the number of freelancers is increasing. For example, Business Insider recently published an article from Vivian Giang titled 40 Percent Of Americans Will Be Freelancers By 2020.

But, did you ever wonder exactly who these freelancers are?

The answer is, they’re us. Freelancers are people at every stage of life who are choosing to leave the traditional workforce and strike out on their own.

In my experience, I’ve mostly encountered freelancers who are in three life stages. In this post, I’ll identify each life stage and outline some of the unique advantages and challenges freelancers face at each life stage.

It’s important to note that these are generalizations, so not every freelancer will fit perfectly into a life stage. And some freelancers may be between life stages.

The Business Beginner

Business beginners are typically those who begin freelancing while they are still students. Or, they may start freelancing right after they graduate from school.

The business beginner typically doesn’t have a traditional employment background as a professional, although they may have worked seasonal and part-time jobs in addition to their freelancing work. Often, they are driven to freelancing by the lack of opportunity in their chosen field. Or they may just have an entrepreneurial spirit.

Some of the unique advantages of being a business beginner include:

  • Easy access to peers and teachers. This is particularly true if the business beginner is still a student.
  • Recent training in their field, including training in new technology. Freelancers in this life stage still have their training fresh in their mind.
  • Relatively low living expenses. Most business beginners are at a stage in their life where they haven’t started a family and don’t have a mortgage. They may even be partially supported by their parents.
  • Energy and enthusiasm. This should be an exciting time for these freelancers as they make the transition from being a student to being a professional.

Unique challenges of the business beginner include:

  • Lack of experience. Many of these business beginners have not worked on many client projects before. They may be surprised by unexpected occurrences.
  • No portfolio or thin portfolio. Because they don’t have much experience, the business beginner may not have a very large portfolio.
  • May take freelancing too lightly. Some young professionals may suffer from a casual attitude towards their business. They may not use contracts or they may procrastinate.

The Flexible Freelancer

I call the freelancer in this stage of life the flexible freelancer, not because they are flexible themselves–but because they need a flexible work arrangement. Their search for work/life balance is the primary reason that they turned to freelancing.

These freelancers may be struggling to juggle a freelancing career with caring for a young child, a sick spouse, or an elderly parent. Or, they may be part-timers looking for an extra income.

Flexible freelancers also have some unique advantages:

  • More experience. These freelancers likely have several years of experience in their field. They may have even worked in a traditional work environment.
  • Strong portfolio. Since these freelancers already have experience, they have had time to accumulate enough work samples for a strong portfolio.
  • Established professional network. These freelancers already know colleagues in their field and may even know prospective clients (including former employers).
  • Highly motivated to stay freelance. Their desire for a flexible schedule means these freelancers are highly motivated to succeed a freelancing. If offered traditional employment, they may turn it down.

However, flexible freelancers also face some distinct struggles:

  • Time management. These freelancers are very busy in both their personal and professional lives. Their time is at a premium and they must make the most of it.
  • Stress. Because they wear so many hats, flexible freelancers face a lot of stress. If you’re a flexible freelancer, it pays to learn some stress management techniques.
  • Finances. This group of freelancers may also face the biggest challenge financially. They may even be responsible for the financial support of other family members.

The Second Career Pro

A final life stage that is attracting a lot of freelancers, is the pre-retirement or early retirement years. These freelancers have already had a full career, either in their field or in another area.

They are now ready to start a second career and that career involves working for themselves.

In many ways, this group has more advantages than the others do:

  • Experience. The second career pro has years of work experience. Even if that experience doesn’t directly relate to their field, some of what they’ve learned is usually transferable.
  • Reputation. This professional may be well-known in his or her field. He or she may hold advanced degrees, they may have written a book, or have other significant accomplishments.
  • Extensive portfolio. The second career pro likely has an extensive portfolio and impressive achievements from his or her corporate career.
  • Connections. This freelancer may start out knowing the right people. They are more likely to be connected to upper level management and other decision-makers.
  • Financial stability. The second career pro may be more financially stable than those in the other life stages. They may even be receiving a pension or have significant life savings.

However, the second career freelancing pro does face some struggles:

  • Proving you are up-to-date. Sadly, many potential clients may assume that you are not technologically savvy, even if you are. It is up to you to prove that your knowledge is current and up-to-date.
  • Possible health issues. You or your partner may face health issues during this life stage. It’s especially important to develop healthy work habits.
  • Updating your image. As a freelancer, you will need an online image that you likely never needed in the corporate world. You will need to develop social media profiles and an online presence.

Your Turn

The truth is that you can start freelancing at any point during your life.

What stage of life are you in? What freelancing advantages and struggles do you face right now?