A Freelance Writer Reflects on Five Years In

In early 2018, I left my corporate career in human resources to go on what I then called a sabbatical.

Five years later, I’m a freelance writer, business coach, and writing mentor.

The in-between is a journey I reflect on often, and I’m grateful to have the opportunity to share it with you.

Why I Started Freelancing

I started freelancing accidentally. During my sabbatical, I launched a blog that partially focused on personal finance.

I made connections within the niche via social media and, after a while, wrote a guest post for a prominent website in the space. 

When I got paid for my work, a lightbulb went off. If I could earn $50 writing, I could earn $500, $5,000, and more.

So I immediately started looking for platforms I could contribute to regularly. My first steady client was Women Who Money!

As a few dollars turned to thousands, I realized I had met the goal of my sabbatical: finding a location and schedule-independent way to earn a living. That way, I could fully show up for myself and those I loved.

I could work around my life rather than live around my work.

Want to know more about my backstory? Check out this Women’s Money Talk article.

Benefits of Freelancing

During the last half-decade, I’ve enjoyed many benefits from freelancing — some expected, some a surprise.

Of course, I’ve loved: 

• Creating my own schedule, entirely in charge of where and when I work.

• Being able to scale my freelance business up or down based on the ebb and flow of my life.

• Choosing which clients to work with and which assignments to accept.

But I’ve also deeply appreciated:

• Forging relationships with other freelancers and entrepreneurs (they are your friends, not competition!)

• Gaining confidence when it comes to asking for money.

• Getting pushed out of my comfort zone (time and again!).

• Being able to fully step away from my business for more than three months when my dad passed away in 2019.

I knew from the get-go that freelancing would provide the freedom and flexibility I wanted.

But I didn’t realize how much that would matter until my father got sick. Then, I got to put everything else in the world on hold to focus on him, my family, and my mental health after his death.

Freelancing gave me the precious gift of time.

I also couldn’t predict how much growth I would experience as a small business owner.

I’ve met more people and gained more knowledge in the last five years than in the 30+ years before!

Related: Should I Quit My Job to Freelance? [The Pros & Cons]

Challenges of Freelancing

Naturally, my journey hasn’t been all chai lattes and impromptu naps. Despite mostly enjoying the ride, I’ve also dealt with my fair share of challenges.

There have been obvious issues, such as:

• Not having employer-sponsored benefits (namely health insurance and a retirement savings plan match)

• Not getting paid when I don’t work

• Having to navigate paying my self employment taxes (I recommend getting an accountant as soon as you start making real money.)

• Having to always hustle for new and better clients

• Budgeting with variable income (the feast or famine phenomenon is real!)

But I’ve also experienced some unanticipated hiccups, like:

• Losing multiple clients in a short period

• Having potential clients express interest in working together and then ghosting me 

• Dealing with projects that didn’t play out as advertised

• Chasing payments for completed work (I thought I would need a lawyer to collect several thousand dollars from a client. Fortunately, it didn’t come to that.)

My biggest takeaways from these challenges are continuously fostering connections in your network and getting all gig details ironed out in advance and documented in writing.

That way, you can call upon your circle when you run into tough times, and there’s never any question about how a project should go.

Plus, you have a legal document to back you up if a deal goes wrong.

Read: Before You Go Freelance, Do These Things

If I Had To Start Again

If I had to start again, would I do anything differently? Part of me says no, but part of me says hell yes!

On the one hand, I believe everything I’ve experienced has shaped me into who I am.

I like who I am and think I’m exactly where I’m supposed to be (even though I’m still far from achieving many of my goals). 

But, on the other hand, I’m wiser now than I was then, and it would be nice to use that insight to build a better business faster.

So, if we magically went back to February 2018, here’s what I’d do:

• Write more guest posts — and write them sooner. Doing so might have helped position me as a personal finance authority and led to gig opportunities.

• Buy fewer courses and take more action. I’ve purchased more courses about online business than I care to admit, and many of them sit unfinished and unimplemented.

• Develop passive income streams as early as year two. I’m still trying to get a few of those projects going. Had I started in 2019, I may be collecting a decent amount of cash from them by now.

• Work more hours. I’ve enjoyed the freedom of freelancing a little too much… and my finances reflect that!

Unfortunately, my Delorean is permanently in the shop, so time travel is impossible. But I’m trying to take my own hypothetical advice into consideration now!

Frequently Asked Questions

Here are a few things you may be wondering about:

How do you stay motivated to be your own boss when so many other things may pull you away?

The truth is – I haven’t always been great at this. There have been periods where I didn’t work nearly as much as I should have.

I can name many reasons for this (some legit, others not so much), but the bottom line is that my motivation has waned from time to time.

When I catch myself in a slump, I find that necessity and long-term goals propel me to action again. I need cash to pay my bills and fund the future I want, so back to work I go!

Has artificial intelligence (AI) changed your job, and are you worried about it replacing you? 

Many freelance writers worry that AI tools like ChatGPT will eventually replace them. I don’t think that’s true.

AI can aggregate and spit out information in an increasingly logical way. But the computer-generated words lack nuance and storytelling.

Human writers can develop connections, stir emotions, and prompt action far better than the digitally-created copy.

That said, AI tools can be useful to writers. They can help generate ideas for further research.

Should freelancers have multiple streams of income?

100% yes! When you have several income streams, you reduce your risk of financial trouble when one or more dries up.

However, freelancing (typically) inherently provides this buffer, anyway.

Each client or project is a source of revenue. So, you’ll have to think carefully about other income sources you’d like to incorporate into your business.

Personally, I provide coaching services to new and aspiring freelancers as well as professionals trying to become better writers.

I’m also exploring the idea of selling printables and freelancing-related merchandise.

Have you thought about going/gone back to any W-2 work? 

I maintained some part-time W-2 work for the first several months after quitting my full-time job.

Doing so allowed me to preserve my savings while I figured out a plan to earn a living going forward. However, once I started getting a lot of writing gigs, I quit those roles to focus on my freelance business.

Since then, I’ve admittedly contemplated returning to a traditional job occasionally because I sometimes miss the steady paycheck and benefits package I had in the corporate world.

I even got deep into the hiring process with one company. However, when I think about everything I’ve gained from self-employment, it becomes a no-brainer for me to stay the course!

Will you shift to a different small business that you own if you get tired of/burned out on what you are doing now?

I can definitely see myself changing gears at some point, which is another excellent reason to cultivate additional income streams.

Writing all the time can be a grind, so I won’t necessarily do it full-time forever. However, I highly doubt I will ever return to traditional employment.

How do you stop “chasing” money (taking on too much work)?

Just as there have been times when I worked too little, there have been times when I worked too much.

When I find myself chasing money, I remember why I took that sabbatical five years ago: to discover a way to earn a living and live my life.

I must never forget (at least for long) that the second part is the most important!

As my father often said, “You can always make more money, and you can’t make more time.”

Do you build in vacation time for yourself? Do you have set days off each week?

My schedule is extremely flexible. I take time off when I want to or when life demands it.

I strive to work 4-5 days a week, but the days aren’t always the same. I leave room for appointments, errands, events, illness, and even brain fatigue.

Since writing is mentally taxing, I’m sometimes not in the right headspace to do it.

When I take a vacation, I do one of two things. I either work ahead and tell my clients when I’ll be unavailable. Or, I’ll bring my laptop along and write when everyone else is asleep. Both have worked well for me.

What are some of your best and worst moments/experiences as a small business owner?

Here are a few of my best moments and experiences:

• Earning my first freelance dollars
• Exceeding my monthly corporate income
• Negotiating for more money (this one never gets old!)
• Meeting my freelancer friends in real life 
• Helping other freelancers with their business
• Speaking at a conference

And here are a few of my worst:

• Chasing a client for $6,000 — and being made to feel insignificant in the process
• Losing lucrative clients that I loved working with
• Owing taxes when I really couldn’t afford to pay them
• Watching websites I wrote for cease to exist (there go those links in my portfolio…)
• Doubting my ability to maintain and grow a business (this feeling creeps in periodically)

I’m sure that I’m forgetting many highlights and lowlights. But the truth is, freelancing has given me more than it’s taken, and it’s absolutely been a net gain for my life!

Final Thoughts

I hope this account of my journey has given you a glimpse into what to expect as a freelancer — both now and in the years to come. But if you still have questions, I’m a pretty open book. Feel free to email me to talk shop: [email protected]

Here’s to your freelancing success!