14 Lessons I Learned My First Year as a Freelance Writer

Lessons as a freelance writerHeeeey guys. I know, it’s been a while. My sincere apologies!

My content writing business took off last fall which left me with little time to write for fun. A good problem to have, right?!

Some of you know, last January I took a risk and went out on my own as a freelancer. Something I’ve never done before.

It’s been a whirlwind of a year, to say the least. Complete with anxiety, success, failure, tears, joy, and laughter – all playing on repeat.

I have to be honest, I almost didn’t share this blog with you.

Right when I planned to post it at the beginning of the year, I found myself knee-deep in another big freelancing lesson. It shook my confidence and left me feeling incapable of sharing my own experiences (as weird as that sounds!).

I can’t say I’ve mastered freelancing, but I’ve learned a lot in a year.

The year was difficult. There were plenty of times I wanted to quit. I questioned my abilities and sanity more than once. But I kept showing up, I kept trying, and throughout the year, I experienced waves of success.

I learned many, many lessons last year and I wanted to share a few with you. Just in case you ever think about taking a similar risk.

Because 1) It’s not impossible, and 2) You’re stronger and more capable than you think you are.

1. Freelancing Isn’t a “Get Rich Quick” Method

I had high hopes of reaching my monthly income goals within six months (which weren’t extravagant). I knew building a client base would take time, but I didn’t think it’d take as long as it did.

I made most of my money in the 4th quarter thanks to the client who kept me busy. It took a lot of time, hard work, and patience to build a consistent stream of clients. Any freelancer will tell you it’s definitely not the route to take if you’re looking to get rich quick.

2. Taxes Are a Real Thing

When I got started, the online communities I was involved in seemed to skirt the issue of taxes and had the attitude of “worry about it later”. I get it, who wants to be on the line for giving tax advice?

I’m glad I didn’t get too deep in the weeds when I started, but I wish I didn’t wait until the end of the year to speak with an accountant.

As a business, you’re supposed to pay quarterly taxes or you could face penalties. That was news to me.

The best thing I did was track my income and expenses each month and saved 30% of my earnings aside so I wouldn’t be stuck with a huge tax bill at the end of the year.

Turns out, I didn’t face extreme penalties or a huge slap on the hand. Now, this year I’m set up to pay quarterly so my tax bill at the end of the year isn’t quite so big.

Thankfully, I had a bit left over from my 30% thanks to deductions and expenses. I’m just glad the money was there to pay for it!

3. Investing In a Coach Was Well Worth It

Even when not much money was trickling in, I invested in coaching at $60/week.

My coach was a huge influence in my first year of freelancing by offering support and helping me develop goals or build strategies to land new clients. The money was well spent and helped me grow my business faster than I could have done on my own.

4. You Are Not for Everyone – Not Everyone Is for You

Can we call this a work AND personal life lesson? The people pleaser in me wants everything to always work out and everyone to be happy. But that’s not always real life.

The best part about learning this lesson is you get to remove the pressure of being a literary genius, master business owner, or the perfect date. You get to just be yourself!

I learned my writing style, personality, and passions – they’re not for everyone. And that’s ok.

On the flip side, not every client is worth my time and energy. Once I had a good flow of clients coming in, I could say no to projects or clients who I knew could be better served elsewhere.

5. Freelancing Is Freaking Lonely

I spent most days working in my dining room with a nice big window to the outdoors. I seriously love it! But while working from home has awesome perks and advantages, it’s freaking lonely.

I’ve had to make a concentrated effort to schedule plans with friends to grab drinks and hit the trail on the weekends. It’s difficult at times because I genuinely like people and I miss face-to-face client interactions. So this year, I’ll be working on this more.

6. Community Isn’t Optional – It’s Required

I can’t reiterate this enough. You can’t be successful without community.

I found great online communities filled with people pursuing freelancing or creating businesses all over the world. I wouldn’t be where I am now without their helpful pointers, tips, incredible wit, friendship, and the daily dose of encouragement I needed to make it through my first year.

7. Back Up Your Client Work! Even Apple Can Fail You

The biggest, most painful lesson of 2015 was when my Mac hard drive crashed and I lost all my client work, income/expense spreadsheets – EVERYTHING.

I bought a Macbook Air over a year ago thinking surely Apple would never fail me. Thankfully it only cost $280 to replace the hard drive and battery, but it cost me time, energy, and anxiety to rebuild my spreadsheets, sort through emails to track down client work, and start over from scratch.


8. Everyone Wants a Deal – You Don’t Have to Give It to Them

It’s a normal practice across industries for clients to make low-ball offers. The problem is, if you constantly hand out discounts, it communicates that you’re not worth your rates.

My time is valuable and I produce good work, so sticking with my pricing communicates confidence and reiterates my product and services are worth it. If all they want is cheap, they can find that elsewhere.

The good news is, I had clients offer to pay above asking price, so it’s nice to know those clients exist too! Or maybe I’m not charging enough? Hmmm.

9. Say “Yes” to Opportunities

In the Spring, I responded to a random email from a copywriting email list seeking someone who could write about insurance. This email changed the trajectory of my entire year of freelancing.

I began doing contract work with this company in the summer and their projects took up the majority of my time in the fall. Beyond content creation, it involved project management which I discovered I LOVED and I was good at.

Working with this client was a huge confidence booster and a large part of my financial success in 2015.

10. Plan for Success and Growth

When I was slammed, I didn’t have time to maintain my regular client work on my own. I needed a backup plan to hire other writers for simple projects so I could spend my time on higher paying gigs. I started farming out work to other writers to keep growing my business.

11. Clients Are Buying the Product, but They’re Also Buying You

Sure, clients are buying the content I provide them. But they’re also buying the experience they share with me.

Am I responsive? Punctual? Friendly? Professional? I believe the relationships I developed with clients was a huge part of what kept them coming back throughout the year.

12. Too Much Time = Poor Time Management

Some think, “As soon as I quit my job I’ll have so much time to work on my business!”

That is until you have so much time you don’t know what to do with it. Starting out is rough when you have too much time and not enough clients to fill it.

This makes planning your time super important. Too much time on your hands is detrimental.

13. Eat Plenty of Tacos

For no other reason than they improve your quality of life. Amen.

14. You’re Stronger Than You Think

I’m a naturally independent person, but I never considered myself entrepreneurial. I had no idea I had it in me to take a risk like this and succeed within a year.

It’s empowering to go from never making money outside of a salaried position to working online with people I’ve never met who pay me for my time and experience.

Is this real life?! It’s crazy, but it is.

So, what’s next? I’m on to year two! Leap years ahead (no pun intended. Kinda) of where I was, yet realistic in understanding there’s LOTS left to learn.

What about you, have you ever taken a big risk like this? What stops you?

If you have questions, feel free to comment below! I’m happy to answer them.
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  • Michelle
    “Too much time = poor time management” – so true! I get so much more done now that I have a son and need to make good use of nap times. Knowing I only have 2 hours means that I’m not wasting that time.
    • Jen
      Yessss. I get so much more work done when I’m juggling projects or facing a tight deadline. Kids will definitely help with that! At least, I can imagine 😉
  • Hi there! Great read! I’m still struggling with a few of these issues and I’ve been freelancing for more then 4 years. If I may asked, what did the coach help you with? I’m also considering getting one, and creating a better plan for my business.
    • Jen
      Hey Anneke! Thanks for the kind words! My coach was awesome at helping me take a step back and think about the future. She started by asking me, “What do you want your freelance career to look like a year from now?” Then she helped me create manageable goals each week to help me get there. I’m guilty of getting so tied up in the day-to-day that I struggle seeing the big picture. She was also a HUGE source of encouragement during the difficult first months when I really needed a cheerleader. She believed in me when I didn’t always believe in myself. Anyway, if you need an extra boost in your business, I’d highly recommend finding a compatible coach – even if just for a few months to move you forward!
      • Hello Jen! Thank you so much for your reply and insight! I’m thinking it’s a great idea to do it. As a freelancer, it’s hard to be your own cheerleader, accountant and critic. 😉 Did you go for someone local, or did you do email/skype correspondence. I will definitely consider it.

        Do you have a FB page that I can like, would love to receive more of your content.

        Have a lovely day,
        • Jen
          A-men! I was introduced to someone local who had just finished school for coaching. It worked well for me because she was affordable (experienced coaches can be upwards of $500/mo! That just wasn’t in my budget). I think we could all use a little more face to face interaction in our lives, but Skype could be a great option too if that’s whats available.

          Unfortunately I don’t have a business FB page. And it’s funny, when you write so much content for others – it’s hard to keep up with your own blog! I’m on FB, Insta, and Twitter, but it’s mostly pictures of the outdoors these day 🙂 Shoot me a message to my email on this site (should be under “Who’s Jen?”) if you’re still interested to connect on any of these!
          • That’s great advice, I will look for someone starting out – to just give me some guidance and direction. I do feel like I’m stagnating a bit, and I don’t have a clear vision or goal for my business. Yeah, tell me about it – I’ve really be neglecting my own blog because I’m constantly busy with client work. I will pop you a mail shortly, would be happy to stay in touch. 🙂