January of 2022 will mark my 7th year as a freelance writer. That might sound impressive and aspirational but it’s not. In reality, I’ve only been freelancing for three years. I was playing at the first four.
Of course, I thought I was taking it seriously at the time. Yet, looking back, I needed every one of the 30+ lessons I’ve learned the hard way since 2015.
Today, I’ll share a few of those lessons with you, all of which were born out of my most enormous freelancing failures.
Stumbling into freelance writing after surgery
Six months of (unsuccessful) physical therapy. Experimental knee surgery. 12 awful weeks on crutches. Six more long months of physical therapy. You’d better believe I was stuck at home.
But fresh out of high school with no job experience and no higher education, what was I to do with myself?
Writing professionally didn’t immediately come to mind. The out-of-touch, overly restrictive rules we’re taught in school had buried my years-long enthusiasm for the craft. But Google said freelance writing was the way to go so it’s the way I went.
The early (and gloomy) days of freelancing
I’d discovered the idea of freelance writing from oversimplified “10 Easy Ways to Make $1000 a Month” articles. So, of course, I started out working for content mills.
For the first year or so, I slaved for literally a few dollars per article on marketplaces with little to no consistent work available. By year’s end, I hadn’t even made $500.
At the time, it seemed like a step up when I left the content mills for Upwork, got my first few clients there, and started charging around $7 per article. As you can imagine, my earnings weren’t much better than the previous year.
Very slowly, I started raising my rates. Especially once I realized that there are distinct categories of clients and, therefore, distinct ways of marketing to each group.
There are clients who:
- Don’t take content seriously and, therefore, pay pennies for it
- Understand the value of strategically-driven content and, as a result, pay well
Over the next few years, I learned how to spot and avoid the first group, as well as how to attract the second.
My biggest fails and lessons learned
It’s been a slow climb to feeling more capable of running my freelance business successfully. However, I don’t consider any of my struggles a waste.
Some of my worst clients taught me the best lessons. And one of my lowest-paying clients has even become one of my highest.
For me, it proves that, if you take everything as a learning experience and stick around for the long haul, you’ll eventually find your way. But, of course, you don’t have to learn everything the hard way yourself.
There’s also value in learning from other people’s mistakes–mine included.
Fail #1: Setting low standards (aka no standards)
If you’re like me, being unsure of yourself comes more naturally than being confident and taking the reins.
I constantly dipped below my already-too-low minimum rates to win projects. I often budged at the first hint of pushback or hesitation from potential clients. People basically told me what they wanted to pay. (And I didn’t even have the good sense to fire low-paying clients in a timely fashion.)
Plus, while I did decent work for my experience level, the extent of my process was “Google the topic, then write.” Not defined or refined enough to demonstrate to higher-quality clients that my services were worth any decent amount of money.
Lessons: You have a business and you’re the boss
When it comes to standards, you must realize a couple of things.
You’re a business owner, not an employee
You have the right and responsibility to set the bar for your business. That goes for everything from your rates to how you work and beyond.
You may place a high value on flexibility and that’s fine. Yet, you want clients to enter into the business relationship with the mindset that you’re an independent partner, not a forced laborer. So you have to set that tone from the start.
Clients worth having value expertise
It’s much harder to showcase your expertise and land dream clients without a process. Saying, “I can get you from A to Z” isn’t nearly as effective as explaining how you’ll do it and why that process works.
So don’t wing it. And definitely don’t go along with whatever process potential clients ask you to follow, especially if they don’t have the expertise that you do.
Yes, it takes ongoing thought and effort to define and refine the way you work. Not to mention the guts to state what you charge, what you need from each client to get the best outcomes, and so on. But, if you want clients who respect you and pay you well, you have to get into boss mode.
Fail #2: Getting way ahead of myself
My second biggest freelancing mistake was swinging to the other end of the spectrum and setting the bar too high. Sick of not feeling in control of my business, I decided I’d had enough.
“I’m going to stop taking subpar projects just because I’d rather have a project than no project. My rates are going up and I’m only going to do the type of projects I enjoy most.”
That was my thought process as I decided to nix my other services and only write website copy for small businesses. With no real marketing experience outside of Upwork, no clue where to start, and no plan to figure it out. As you can imagine, it was a struggle to fill my schedule.
But I happened to win a consultation with a successful agency owner. Only then did I realize why I was failing.
I’d chosen a service that most small businesses only invest in once a year, if that. At the rates I was charging, I’d need to market to a massive audience every month to stay busy the whole year.
That was impossible given my lack of experience and aversion to networking up to that point. Not to mention that, even if I could’ve done all that marketing, I wouldn’t have had any time left to do my actual work! And goodness knows I couldn’t afford to outsource marketing or writing.
Lessons: Desire without strategy = risk
The two biggest takeaways from this major failure?
Balance your gut with strategy
People often debate whether marketing, writing, and business, in general, are more art or science. I think they’re equal parts both.
It’s okay to know what you want and go for it, to have a hunch and test it. But you can’t completely throw strategy to the wind and expect fantastic results. In such a case, you can only hope for a positive outcome and a business can’t survive forever on wishes.
Strategy is more than a list of ideal to-dos
It’s easy to say, “This is my target audience, these are the services I’ll offer, and Facebook will be my marketing channel.” But is that plan realistic and actionable?
Can you do well enough at Facebook marketing for that to be your primary channel? Is your target audience even on Facebook? Are the services you plan to offer aligned with their needs? There are many questions like these to consider before hanging your hopes on a tactic or strategy.
Speaking of tactics, I also found out the hard way why having only a single tool in your toolbox is an awful idea.
Fail #3: Putting all my eggs in the comfy basket
I tried marketing on Twitter for a month or two, felt like I was shouting into the void, and left. Cold pitching? Couldn’t do it because I was convinced I’d either be ignored or torn to shreds by angry recipients. Networking? As a hardcore (and shy) introvert, the thought of chatting with anyone who wasn’t directly offering me a project made my stomach turn.
I had excuses ready for each possible marketing method, many of which were based on preference and fear but disguised as logical reasons not to try. I thought: “I’m getting the hang of Upwork so I’ll just stick with that, improve my website, and I’ll be good.”
Yet, that thinking didn’t account for the fact that:
- Freelance writer websites don’t get traffic on autopilot. Unless, of course, they’ve been optimized for search engines or are otherwise being promoted. (I hadn’t done any SEO and was hardly promoting my site.)
- Only having one way to land projects is risky. It leaves you with no backup or momentum if and when it fails, even temporarily.
Eventually, it dawned on me that I had to step outside of my bubble if I wanted better opportunities than the ones I’d been getting.
Lessons: You have to be up for 101 challenges
The third thing it took me too long to realize?
You can’t operate entirely from your comfort zone
If being in that zone isn’t currently getting you the outcomes and opportunities you want, you have to step outside of it. And I’m not necessarily talking about throwing yourself in the deep end of difficult things. Even embracing the next level of challenge in your freelance business can reveal potential you’d have never discovered otherwise.
For example, a simple but impactful step out of my comfort zone was cold emailing agency marketing managers. The email was a straightforward ask to be on their freelancer list, which put less pressure on me to personalize and craft elaborate, direct-response copy.
The results were so-so. Lots of opens, several polite responses, and a couple of inquiries. And, although I didn’t get any clients from this small batch of cold emails, it showed me that:
- I could kick my efforts up a notch despite my self-defeating thoughts
- Things could turn out better than expected
This exercise put me in the mindset to embrace two of my best marketing and sales channels to date—LinkedIn and Twitter.
Wins on LinkedIn since 2020
I started doing cold outreach on LinkedIn, not to pitch but to make genuine, mutually beneficial connections. This has included having friendly chats in the DMs about marketing, writing, and freelancing and helping several connections fill open freelance roles by recommending fellow writers and pros.
And, although I haven’t pitched once, this outreach has gotten me several ongoing clients that are a joy to work with. What a shock it was to learn that, if you just get on the right people’s radar, many of them will pitch you!
Wins on Twitter since 2020
As for Twitter, I rejoined on a whim fully expecting to hate it like I did the first time. But, this time, my approach was different. Instead of trying to promote myself to people who didn’t know me from Adam, I started sharing my knowledge and lessons learned.
My reputation and network started to grow steadily. I began getting leads and referrals from respected pros who, although they’ve never worked with me, trust my expertise on the merit of my content.
The takeaway: I would’ve never known the potential of my current top channels if I hadn’t been open to giving them a go. Neither will you until you develop a willingness to take on new challenges and methods of promoting your freelance business.
The grass is only green as long as you water it
We’ve all heard that “the grass is greener where you water it,” and that’s often true.
But it’s worth mentioning that the grass is also only green as long as you water it.
To this day, I sometimes slip back into old habits and mindsets and, therefore, find myself staring the same old challenges in the face.
So, the bonus lesson is that lasting success requires consistency. It requires constant re-evaluation, constant correcting of your course, and constant shushing of the self-sabotaging voice in your head.
When you stay on your game, good things happen. For instance, compared to the $7 blog posts I was writing back in 2015 and 2016, my current highest rate for a blog post is more than 70x that! While I’m not a 6-figure writer (and am not aiming to be), I’d call that progress.
If you take the reins in your business, set attainable goals, and progressively push your limits, you too can progress from where you are now to where you want to be.