Quit Your Job: Inside My Low-Risk Leap Strategy to Full-Time Freelancing

Evan Jensen

The Freelancer's Low-Risk Leap Strategy to Quit Your Job. Makealivingwriting.comReady to quit your job for full-time freelancing? Hold on just a second Ghostrider.

If you’ve got nerves of steel, piles of money in the bank, or you’re living rent free in your sister’s basement, go for it.

Or if you stare in the mirror every day and recite this old-school pro wrestler’s mantra: “I dine on danger and snack on death,” maybe you’ve got the guts to quit your job and walk out.

That wasn’t me. I’ve got plenty of hustle and freelanced on the side for years.

But making the leap from a job as a staff writer to full-time freelancing felt a little too risky. As in three kids, a mortgage, pending divorce, life…

Sound familiar?

If you’re a risk-averse freelancer, you need to find a practical way to quit your job for full-time freelancing with the least financial impact as possible.

When I finally walked away from my day job last year, I already had $4,000 in monthly freelance contracts lined up, and I’ve made more than that every month since.

Want to know how I did it? Here’s my low-risk leap strategy to full-time freelancing:

Be patient

Maybe you don’t love your day job, but it pays the bills. Stick around until you get your freelance life figured out.

It’s a much better way to make your exit than quitting without a plan in place, especially a plan to replace your income.

But don’t just sit around waiting for something magical to happen. Here are some things you can do:

Figure out how much you need to make

Crunch your numbers for stuff like your mortgage/rent, food, utilities, car, debt, savings, health insurance, spending money. Get real about how much you need to make to pay your bills.

When you set a monthly income target for freelancing, you’re a lot more likely to swear off low-paid content mill work for better paying clients.

Set a date

When will you make the leap to full-time freelancing? Be realistic. For the risk averse, you want to avoid living on bare bones rations after you quit your job.

When you set a date and commit, you’ll start thinking about your day job and freelance work differently. It’s the kind of mindset shift you need to make to be successful.

Note: I was pretty comfortable with my day job as a writer and a solid part-time freelance business. And then something happened. My employer announced plans to relocate in six months, turning my 20-minute commute into an hour-plus.

That’s when I decided I wouldn’t be joining my co-workers when the company made the move.

Map out an exit plan

You don’t have to have all the answers right away. Give yourself some time to think about how you’re going to quit your job and answer questions like:

  • What’s your exit date? Write it down. Commit.
  • When will you tell your employer? Set a date, and think about how to break the news. (This could be a opportunity to turn your day job into a client.)
  • What are you going to do about health insurance? Maybe you’re covered on your partner’s plan or you’ll purchase private insurance.
  • How are you going to find clients to replace your day-job income? Ramp up your marketing efforts. Ask your network for referrals. Map out an aggressive marketing plan if you don’t already have one.
  • How long will it take? If you’ve been tracking pitches and assignments, you should have some idea of what you can expect from your marketing efforts.

Want to quit your job for full-time freelancing? Set a date. Tell at least one person. And start planning to make it happen.

Pay off debt, save money

Here’s another low-risk strategy to help you quit your job for full-time freelancing. Pay off debt and save some money…first.

If that means you hang on to your day job for another six months or a year to pay off credit card debt, or a car loan, it’s worth it for the risk-averse. You’ll step into full-time freelancing with less stress and fewer financial obligations.

How much should you save? It depends on your comfort level. One to three months of expenses is a good place to start. But if you want even more peace of mind, save enough to cover six months of expenses like freelancer Emily Omier.

Note: I had about $10,000 saved from freelance work when I quit my day job and cashed out $5,000 in paid time off from my employer. And I had most of my debts paid off except for a mortgage and student loan.

Flex your marketing muscles

If you want to quit your job for full-time freelancing, flex your marketing muscles before you walk away. It’s a lot better to get a handle on this while you still have a steady income.

Why? At first, it can take some time to send out enough query letters and letters of introduction to start landing assignments. It’s where a lot of quit-your-job-without-a-plan freelancers go wrong, struggle, and too often give up.

But it doesn’t have to be that way. While you’re still enjoying the benefits of a day-job paycheck, make freelance marketing your part-time job. Here’s how:

Set a process goal

You can’t entirely control the amount of money you’ll make, but you can control your effort. So instead of measuring your effort in terms of income, use a process goal to measure effort. Here’s an example:

Send out 100 pitch letters a month. If you’ve been sending out zero, start with five a week. Move up to 10, and keep going.

You can measure a process goal like this, track pitches and assignments, and get an idea of what it’s going to take you to start earning the income you want from writing.

If you really want a stretch goal: The late Chris Marlow encouraged writers to send out 400 pitch letters a month, at least at first, as the path to becoming a fully-booked freelancer.

Note: Before I made the leap to full-time freelancing, I sent out an average of 150 letters of introduction to business in my niche (health and fitness) a month, usually on the 8 p.m. to midnight shift after I got my kids to bed. After a couple months, I had lots of warm leads and a handful of long-term contracts.

When can you fit in extra time for freelance marketing while you plan your exit?

Tap your day job

When my employer announced plans to move, I decided to make the leap to full-time freelancing instead of sitting behind the wheel-in rush-hour traffic every day.

If you quit your job for full-time freelancing, can you take your employer with you? Maybe.

  • If you’re in a hostile work environment or job you absolutely hate, its probably not an option.
  • If your day job doesn’t involve any writing, don’t rule it out. Reach out to the marketing director and ask about freelance opportunities.

If you’re on good terms with your employer, consider turning your day job into a freelance client. Here’s how I did it:

  • Map out your role as a contractor. What writing projects and responsibilities could you take with you as a freelance contractor? Define your role. Think about why you want to leave your day job.
  • Set your rates. How much will you charge your employer as a freelance contractor? Figure it out. Keep in mind, it should be considerably higher than your day-job hourly rate as Holly Hughes-Barnes explains.
  • Talk it out with a friend. Find an experienced freelancer, writing coach, or business professional who works with contractors. Share your exit plan and proposal to turn your employer into a client. Talk out the pros and cons.
  • Pitch the idea to your manager. It’s probably the scariest part of the process. What if your manager gives you the old Donald Trump line: “You’re fired?” If you’re on good terms with your employer, it’s unlikely. But it’s always a possibility. Just open the conversation by sharing your proposal, and see what happens. You might be surprised by the outcome.

Note: Even though I had a great track record with my employer as a health and marketing writer, I was still nervous about this. But it turned out to be an easy conversation. The CEO said: “We knew the move would probably displace some employees because of the commute, and you’re one of them. This sounds like a great option for you and for us.”

Can you turn your day job into a freelance client?

Find an anchor client

If you’re not going to be able to turn your day job into a client, find an anchor client before you quit. It’s the most risk-averse way to be a freelance writer vs. chasing one-off assignments all the time. These are clients that pay pro rates, pay on time, and always have plenty of work.

Looking for an anchor client? Carol Tice recommends:

  • Companies with 50-100 or more employees
  • National nonprofits with $10+ million budgets
  • National magazines with large circulations
  • Niche publications with a well-heeled readership
  • Companies or magazines with a publishing schedule of articles, blog posts, website content, and marketing materials that can keep you busy for months

Note: When freelancing was only my part-time gig, I chased a lot of one-off writing jobs. But it’s tough to create consistent income that way. Today, I have seven anchor clients, and I’m on track to earn $72,000 in my first year of full-time freelancing.

Are you targeting anchor clients in your niche?

Full-time freelancing doesn’t have to be risky

If you do it right, you can make more money writing than a lot of day jobs, manage your own schedule, earn consistent income, and enjoy work you love. Now I wonder why I didn’t make the move sooner. Thanks for the nudge, Carol.

Ready to quit your day job for full-time freelancing? Leave a comment below, and let’s discuss.

Evan Jensen is the blog editor for Make a Living Writing. When he’s not on a writing deadline or catching up on emails, he’s training to run another 100-mile ultra-marathon.
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  1. Lynn LeRoux-Pierre

    I’m an older retired lady who needs an additional income to retire comfortably. Always wanted to write and most people tell me I do a great job but I’m not published. Just need to be sure I’m headed in the right direction.

    • Evan Jensen

      Hi Lynn,

      The Freelance Writers Den would be a great place to start. Lots of info and resources there to help you get started. http://www.freelancewritersden.com

  2. Mmabotse

    How do I register?

  3. Cassie Journigan

    Great advice, Evan. I already have my timeline established so reading your suggestion there was reaffirming. But what I really love in your article is your advice to find an anchor client. I love it — or them — both the idea and term. Makes me feel like jumping up and down, smacking my forehead, and shouting, “Eureka!” Sometimes that’s enough — a concept contained in a single term. Wow. Thank you. I feel really inspired.

    • Evan Jensen

      Hi Cassie,

      Great to hear you already have a timeline to make your exit to full-time freelancing.

      Having just one solid anchor client with consistent work, pays pro rates, and on time every month can make the transition to full-time freelancing a lot easier/less risky.

      When I was planning my exit, I was looking for an anchor client that I could count on for $1,000 to $3,000 a month in consistent work/projects. And that’s totally realistic.

      Keep going.

      • Cassie Journigan

        Bookmarking this! Thanks for your reply and the additional info.

  4. Lyle K Weiss

    I would love to be able to make the leap but I am not sure full time freelancing is possible with my background. I have a doctorate in theology and a passion for history, philosophy, and movies. Are there enough opportunities with my resume to make freelancing a full-time job?

    • Carol Tice

      Lyle, in general not a ton of writing jobs that pay well in any of those areas. BUT…what you studied in school is only one aspect of what you know and are interested in. Linda Formichelli’s degree is in Slavic Languages, for instance, and she wrote a ton of health articles for major women’s magazines! And I’ve done tens of thousands in insurance-related content, which I got into because I had a passing interest and my dad sold insurance, so I had a basic idea of how it works.

      • Lyle K Weiss

        Hi Carol,

        Just when I had made up my mind to get a degree in Slavic languages to help with my writing career.:) Seriously, thanks for the feedback. I guess I have to think about what else I would be interested in writing particularly as a full-time profession. I love writing and would love to do it full-time. Do you love writing on topics you may not be passionate about?

        • Carol Tice

          Actually… I do! I’m a total business dork. I love the CHALLENGE of learning about a new thing and making it interesting for that companies’ clients. I’ve written about surety bonds, advanced washing-machine technology…you name it.

    • Evan Jensen

      Hi Lyle,
      I agree with Carol. There’s generally not a lot of high-paying work for history, philosophy, theology, and movies. But I’m sure you have other interests, talents, skills. Check out this post and start thinking about other areas you can focus on: https://makealivingwriting.com/freelance-writing-gigs-50-niches/

  5. Zaqueline Souras

    I am interested!

    • Evan Jensen

      Hi Zaqueline,

      Start where you are. Land some assignments. Keep moving forward. If you’re serious, you’ll find a way, not matter how long it takes.

  6. Kevin J. Duncan

    Hey Evan,

    I was a risk-averse writer too. Wish I’d read an article like this one ten years ago — I might have taken the plunge sooner. 🙂

    • Carol Tice

      I was always pretty risk-averse, too Kevin. I didn’t have the luxury of building up freelance and quitting the day job, since I got fired by a new editor, after 7 years at a publication. BUT… once I built up my freelance biz, I was always looking to find the next better client and THEN drop the one I wanted to get rid of. 😉


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