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5 Steps Older Workers Can Use to Launch a Freelance Writing Career


How to launch your freelance writing career when you're older. Makelivingwriting.comThink you’re too old to launch a freelance writing career? Think again.

Have you been working a day job for decades? Are you an empty nester with a few gray hairs? You might think you’re too old to go freelance, but you’re not.

You can do this. Believe me. I know what it’s like to launch a freelance writing career when you’re older.

For more than 30 years, I worked in banking and law, and did a lot of writing. I dabbled with freelancing to make extra money, and thought it might be my path to retirement.

But that all changed when my employer went out of business.

Not quite old enough for Social Security, I wasn’t interested in starting over in another office. But I still needed an income, and I wanted more time and more freedom to enjoy life.

Want to know how I made the move to full-time freelancing…at my age?

These five steps helped me launch my freelance writing career:

Freelance writing career path for older workers

After decades of writing for others in the business world, my first foray into freelance writing was for a content mill. It didn’t pay well, but it did help me earn top ratings for ghostwriting blog posts for attorneys. And it gave me a boost of confidence.

Realizing I could take the freelance leap and succeed, I planned to leave my job by cutting back hours as my freelance income grew.

But at my age, I’ve been around long enough to know life happens while you’re making plans. That’s not exactly how things worked out.

When my employer went out of business, the door opened to launch my freelance writing career. I didn’t want to get another day job. Instead, I used these five steps to go pro:

1. Take stock of your skills

I’ve spent better than 30 years working as a mortgage banking project manager, a compliance officer, and senior paralegal. I’ve been responsible for writing proposals, procedures, compliance materials, management reports, case summaries, white papers and legal documents, as well as regular business correspondence.

This little skills inventory gave me a lot of information to find my niche and the right clients as a freelance writer. How about you?

  • What industries have you worked in and already know a lot about?
  • What skills have helped you succeed at your day job?
  • Do you already have some writing experience as a staffer or freelancer?
  • Do you have a hobby, interest, or passion you spend time on when you’re not at work?

Instead of just thinking about this in your head, create a list of your skills, professional experience, life experience and interests. Write it down. And you’ll start to see some patterns that can help you identify your niche to build your freelance writing career.

2. Step up your marketing efforts

Are you going to launch your freelance writing career one day, and wake up the next with tons of client work and money rolling in? Probably not.

Be prepared to spend a lot of time on marketing when you get started. For most of us, that means sending query letters and LOIs, and following up.

I started out looking for any freelance writing gig I could find on job boards. I ended up with a series of writing assignments that paid better than content mills. Those early writing jobs were OK, but I needed to find better-paying clients and more consistent work. Some other marketing strategies that worked for me include:

  • Ask for referrals. This is huge for older workers, especially if you’ve been growing your professional network for decades. It’s easy. Just ask your former co-workers, boss, manager, or colleagues, “Do you know anyone who needs a freelance writer?”
  • Be selective about using job boards. Most job boards aren’t a good place to find freelance work. It’s usually a race to the bottom, because you’re competing with thousands of other writers. But I have found some good leads and client work thanks to the Junk Free Job Board in the Freelance Writers Den.  (Editor’s note: The Freelance Writers Den no longer includes a job board because so few jobs met our minimum requirements.)
  • Grow your network. For example, I’m still an active member of the Legal Assistants division of the West Virginia Bar Association. It’s a great way to stay on top of trends in my niche, and network with potential clients. Look for ways you can grow your network online and in person.
  • Optimize your writer website. Get a basic writer website set up. Then use search engine optimization to get found for searches like “West Virginia freelance writer.”
  • Make marketing your full-time job until you’re fully booked. Putting yourself out there as much as you can is the best way to jump start your freelance writing career.

3. Keep learning

You’re never too old to learn something new. In fact, you’ll have to if you’re an older worker who is serious about launching a freelance writing career.

I started by reading books and taking courses about freelance writing. That helped me develop new skills and build confidence. Then I joined an online writing community where I could swap ideas with other freelancers and learn from those with more experience.

  • Do you know how to write a query letter or LOI?
  • What do you know about LinkedIn to find clients and prospects?
  • What kind of information should be included in a freelance writing contract?
  • How much should you charge for your work?
  • What do you need to know about filing taxes as a freelancer?

These are all things you can learn about freelance writing, regardless of your age. Master one new skill, then move on to the next one. If you don’t know how to do something, ask for help.

Older workers turning to new careers is a huge thing, significant enough to warrant special programs by the Small Business Administration.

Your day job probably required on-going training and education, and it’s just as important as a freelancer.

4.Manage your time

If you’ve been used to a 9 to 5 schedule with a boss telling you what to do, you’ll need to take charge of your schedule when you launch your freelance writing career. For example:

  • Once you’ve got lots of work lined up, how will you get it done?
  • If you’re just starting out, how much time will you spend on marketing each day?
  • Can you develop a schedule and routine that will help you be more productive?

The beauty of self-employment is flexibility. After 30 years working for someone else, a flexible schedule was really important to me when I launched my freelance writing career. Think about how to plan out your day to get your work done, and still have time for family, friends and things you enjoy.

5. Plan ahead

If you’re old enough to remember the song, “Take This Job and Shove It” by Johnny Paycheck, you probably know better than to quit your day job before your freelance business is making money.

I wanted to transition gradually to freelancing, but when my employer closed its doors, I was forced to choose between self-employment or hunting for a new job.

My exit strategy was in place, geared toward retirement. My husband was already fully retired, and I planned to work until I qualified for Social Security. We had been building up our savings and had employer-based retirement accounts. We were debt-free empty-nesters, and our house was paid off.

After taking a hard look at the amount I had to bring in to cover our daily expenses, my health care premiums, and quarterly estimated taxes, I took the freelance leap. And it worked out.

Do you have an exit strategy?

If you’re an older worker leaving a day job, or coming back to work after a long break, you need a plan. An exit strategy to leave your day job, an income goal, and a clear understanding of how much money you need to make.

  • How much money do you need to make to cover basic living expenses?
  • Can you reduce or eliminate debt?
  • Do you have money saved for an emergency?
  • What about health insurance when you’re self-employed?
  • Will working for yourself save you money in other areas like commuting or childcare?
  • Can you turn your current employer into a client when you go pro?

When you take the time to develop an exit strategy or map out a plan for freelance success, you’ve got a clear path to follow to help you be successful.

Launch your freelance writing career…at any age

Becoming a freelance writer is the best employment decision I have ever made after 30 years with a 9 to 5 staff job. It’s been scary and thrilling, emotionally and intellectually challenging, and well worth it.

You’re never too old to assess your skills, learn new ones, and realize your dream to be a successful freelance writer.

Are you trying to break into freelancing as an older writer? Let’s discuss on my Facebook.

Debra Giuliano is an encore entrepreneur and freelance writer in the DC Metro area. She provides exceptional writing, editing and virtual support solutions for businesses.