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My name is Jamie. I’m a B2B freelance writer and blogger. And I'm here to help you take the guesswork out of content marketing and blogging. Thanks for stopping by!

5 Lessons I Learned in My First Year of Freelance Writing

5 Lessons I Learned in My First Year of Freelance Writing

In the fall of 2015, I reached a crossroads in my life. After spending over seven years as a stay-at-home mom I knew it was time for me to go back to work. I knew a 9-to-5 job wasn’t for me but I didn’t know what else I could do to provide a reliable form of income for our family.

Not really knowing where to turn, I did what many Midwestern stay-at-home moms do -- I joined an MLM. But after a year of constant Facebook posts and spinning my wheels I concluded that network marketing isn’t a great way for the averageperson to create a sustainable income. 

My Introduction to World of Freelance Writing

Then one fateful day, I met a girl in a Facebook group who told me how she had spent the past several years making a full-time income as a freelancer. And suddenly, I had a thought that would change the course of my life:

“I wonder if I could make any money as a freelance writer?” 

It turned out the answer was “yes.” My first client paid me $40 for four 750-word product reviews -- a figure that makes me laugh now because it’s so far below minimum wage it’s not even funny. But I am not exaggerating when I say that was the best $40 I have ever earned in my life.

17 months and several dozen clients later, I have learned a lot about freelancing. So because it’s the New Year and I’m feeling a bit nostalgic, here are five things I learned in my first year as a freelancer: 

1. DIY it for as long as possible

Yes, this is the part where I tell you not to run out and buy a course from some online guru. Bear with me here. 

Everywhere you turn, there is someone online trying to sell you an online course that promises to teach you how to do something. Business coaching. Course creation. Digital marketing.

And yes, freelancing writing.

And don’t get me wrong, some of them are amazing so I’m not necessarily against purchasing an online course.

But I think a lot of people -- myself included -- look to courses or coaching as a sort of shortcut to actually doing the work. And I am here to tell you that there is no shortcut. There is no course on freelance writing that I could buy that would teach what a year of working with clients taught me.

I think many people underestimate their ability to just jump in and figure things out on their own. So instead of buying a course to teach you how to find clients, why not go out and actually find a client? 

If you do need advice, just take in as much free advice as you can. After you’ve been working with clients for six months to a year, if you continue to run into the same roadblocks maybe then it’ll be time to consider a course or coaching.

2. There is nothing wrong with trading time for money

I love being a freelance writer, I really do. But for the first nine months of building my business, I kind of felt guilty about that.

After all, wasn’t I kind of settling by trading time for money? Shouldn’t I try to come up with a product or a way to make money while I sleep? After all, residual income is a huge buzzword right now. 

Here is what I have learned, though -- everybody trades time for money in the beginning. Everyone.

Maybe I’ll scale my business someday, maybe I won’t. 

Maybe I’ll earn residual income someday, maybe I won’t.

But working one-on-one with clients is the foundation for that because I am learning about what clients actually want. And ultimately, the goal (for me) isn’t residual income, the goal is to do work I enjoy that supports my lifestyle.

3. There is no certainty

This is probably the hardest and most frustrating thing about freelancing. I will never forget my first “big” client; from that one client, I would hit my income goal for the entire month.

Of course, since this client was going to be paying me more money there was obviously more work involved. As a result, I let go of another long-term client who paid a lot less because I didn’t think I would have time to work with him anymore.

Guess what happened next? My brand new client had a change of heart a week later and cut my workload down by about 75 percent of what we had originally agreed on. Obviously, the pay went down accordingly. 

I tried to go back to my other client and start working with him again. He very politely told me, “Thanks but no thanks.”

Freelancing is very uncertain and no amount of work is guaranteed forever. Looking back, I don’t know that I necessarily did anything wrong in that situation. I did the best I could with the information I had at the time. 

But the valuable lesson I learned is that freelancing is that you can’t rely on any one client for the majority of your income. And this leads nicely to my next point...

4. Never stop looking for work

Because freelancing is so uncertain you can never, ever stop looking for work. This probably sounds like an obvious point to more seasoned freelancers but it literally took me a good year to figure out. 

I would continually catch myself falling into the same cycle:

  • Step 1: I aggressively look for work, take every discovery call I can get, and accept every job that comes my way. As a result, I soon find completely booked.

  • Step 2: I become overwhelmed by all the work I have to do for my clients. As a result, I stop sending proposals or looking for new work. Why would I? I have all the work I can handle now! I don’t want more!

  • Step 3: A month goes by and I have finished all that work I was so overwhelmed by. (No matter how much work it is, I somehow always find a way to finish it all.) Now a new level of panic sets in as I realize that I have barely any work booked for the next month.

Lesson: Never, ever stop looking for work. Find a way to do it every day, no matter how busy you are. I promise you that you will figure out a way to get all of the work done. 

5. Find what works and stick with it

In the beginning, I found my first few clients on Upwork. For those of you who aren’t familiar with Upwork, it’s a global freelancing platform. Businesses post jobs for work they need to be done and freelancers can send proposals to bid on the jobs they want.

Upwork made sense to me right from the start. I made it my job to find a job and sent as many proposals as I could. This strategy paid off and I quickly started booking clients. 

And the best part was, it was a marketing strategy that took minimal time. Yes, those first few clients were low-paying but I was able to quickly raise my prices and book better-paying jobs within that first month.

Then I started to network with other freelancers and found out that many of them didn’t hold Upwork in high regards. Most people claimed that all I would find on Upwork is scammers and cheapskates. I was told by countless people that I should find clients in Facebook groups, on LinkedIn, by cold emailing businesses, etc. 

I think that one of the best decisions I made was to ignore all of those suggestions. I did branch out over time, but Upwork was where I found the bulk of my work for that first year.

If something is working, don’t question it just because someone who has more experience claims it doesn’t work. Maybe it didn’t work for them but that doesn’t mean it won’t work for you.

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