Freelance writer reflects on five years in

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

Five years later, she became a freelance writer, business coach, and writing mentor.

In between is a journey I think about often, and I'm grateful for the opportunity to share it with you.

Why did you start freelancing?

I started freelancing by mistake. During my time off, I launched a blog focused in part on personal finance.

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

When I got paid for my job, a light bulb went off. If I can make $50 writing, I can make $500, $5000, and more.

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

When a few dollars turned into thousands, I realized I had achieved my vacation goal: to find a schedule-independent place and way to make a living. This way, I could fully show up for myself and those I loved.

I can work on my life instead of living on my job.

Want to know more about my backstory? Check this out Women's money talk condition.

Benefits of freelancing

Over the past half-decade, I've enjoyed many benefits from freelancing — some expected, some surprising.

Of course I liked:

• Create my own schedule, where I am fully responsible for where and when I work.

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

• Choose which clients you will work with and which tasks will be accepted.

But I also greatly appreciate:

• Build relationships with other freelancers and entrepreneurs (they're your friends, not competitors!)

• Gain confidence when it comes to asking for money.

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

• Being able to completely step away from my work for over three months when my father passed away in 2019.

I knew from the beginning that freelancing would provide me with the freedom and flexibility I wanted.

But I didn't realize how important it was until my father got sick. After that, I had to put everything else in the world on hold to focus on him, my family, and my mental health after his death.

Freelancing has given me the precious gift of time.

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

I have met more people and gained more knowledge in the past 5 years than in the 30+ years before that!

Related to: Should I quit my job to freelance? (pros and cons)

Challenges of freelancing

Of course, my trip wasn't just a chai latte and an impromptu nap. Although I mostly enjoyed the trip, I also dealt with my fair share of challenges.

There were obvious issues, such as:

• Lack of employer-sponsored benefits (i.e. health insurance and retirement savings plan)

• I don't get paid when I don't work

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

• Always having to look for new and better clients

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

But I also encountered some unexpected hiccups, such as:

• Losing many customers in a short period

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

• Dealing with projects that were not implemented as announced

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

The most important thing I learned from these challenges is to continually strengthen connections in your network and settle all party details in advance and document them in writing.

This way, you can call your department when times are tough, and there won't be any question about how the project is going.

In addition, you have a legal document that supports you in case the deal goes wrong.

It reads: Before you start freelancing, do these things

If I had to start over

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

On the one hand, I think everything I've been through has shaped me into who I am now.

I love who I am and believe I'm where I'm meant to be (even though I'm still far from achieving many of my goals).

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

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

• Write more guest posts – and write them sooner. Doing so may have helped my status as a personal financial authority and led to job opportunities.

• Buy fewer courses and take more action. I've purchased more online business courses than I care to admit, and many of them remain incomplete and unimplemented.

• Develop passive income streams as early as year two. I'm still trying to implement a few of these projects. If I had started in 2019, I probably would have made a decent amount of money from them by now.

• Work more hours. I've really enjoyed the freedom of freelancing…and my finances reflect that!

Unfortunately, my Delorean is permanently in the store, so time travel is impossible. But I'm trying to take my default advice into consideration now!

Frequently asked questions

Here are some things you might be wondering:

How do you stay motivated to be your own boss when there are so many other things that might keep you away?

The truth is, I haven't always been great at this. There were periods when I didn't work as much as I should have.

I could cite 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 find myself in a slump, I find that necessity and long-term goals push me back into action. I need money to pay my bills and Fund the future I want, so I get back to work and go!

Has artificial intelligence changed your job, and are you worried it will replace you?

Many freelance writers worry that AI tools like ChatGPT will eventually replace them. I don't think this is true.

Artificial intelligence can collect information and release it in an increasingly logical way. But computer-generated words lack nuance and storytelling.

Human writers can develop connections, evoke emotion, and move on the spot much better than digitally created copy.

However, AI tools can be useful for writers. They can help generate ideas for further research.

Should freelancers have multiple sources of income?

100% yes! When you have multiple sources of income, you reduce the risk of running into financial problems when one or more dries up.

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

Every client or project is a source of income. So, you will have to think carefully about what other sources of income you want to incorporate into your business.

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

I'm also exploring an idea Selling publications And goods related to self-employment.

Have you considered going/returning to any W-2 work?

I maintained some part-time W-2 work during the first few months after leaving my full-time job.

Doing this allowed me to maintain my savings while I made a plan to make a living from now on. However, once I started getting a lot of writing work, I left those roles to focus on my freelance work.

Since then, I've thought about going back to a traditional job every now and then because I sometimes miss a steady paycheck Benefits package I had it in the corporate world.

I even delved into the hiring process with one company. However, when I think about everything I have gained from freelancing, it becomes a no-brainer for me to continue on this path!

Would you move to a different small business you own if you got tired/exhausted of what you're doing now?

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

Writing all the time can be daunting, so I won't necessarily do it full time forever. However, I highly doubt I will go back to traditional work.

How do you stop “chasing” money (i.e. doing too much work)?

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

When I find myself chasing money, I remember why I took it vacation Five years ago: To discover a way to make a living and I live my life.

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

As my father often said: “You can always make more money, but you can't make more time.”

Do you build vacation time for yourself? Have you scheduled vacation days each week?

My schedule is very flexible. I take time off when I want to or when life calls for it.

I strive to work 4-5 days a week, but the days are not always the same. Leave room for appointments, errands, events, illness, and even brain fatigue.

Since writing is mentally exhausting, I'm sometimes not in the right space to do it.

When I take time off, I do one of two things. Either I work ahead and let my clients know when I'm unavailable. Or I'll bring my laptop and write when everyone is asleep. Both work well for me.

What are some of the best and worst moments/experiences you've had as a small business owner?

Here are some of my best moments and experiences:

• Earn my first dollar as a freelancer
• Exceeding the company's monthly income
• Negotiating for more money (this never gets old!)
• Meet my independent friends in real life
• Helping other freelancers with their work
• Speaking at a conference

Here are some of my worst:

• Chasing a client for $6,000 — and feeling insignificant in the process
• Losing profitable clients you loved working with
• Because of taxes when I couldn't really pay them
• Watching websites I wrote to stop existing (those links are in my wallet…)
• Doubt in my ability to maintain and grow the business (this feeling creeps in periodically)

I'm sure I've forgotten many highlights and highlights. But the truth is, freelancing gave me more than it took, and it was definitely a net gain for my life!

Final thoughts

I hope this report on my journey has given you a glimpse of what to expect as a freelancer – both now and in the years to come. But if you still have questions, I'm a very open book. Feel free to email me to talk shop: (email protected)

To you Self-employment success!