I’ve Been Freelancing For 3 Years. Here Are 7 Tips For New(er) Freelancers.
Photo by Jonas Leupe on Unsplash (also, this isn’t me ^)
In early 2017, I went to a happy hour that changed my life forever…
Which is a dramatic way to start an article. But it’s true. So deal with it.
I almost didn’t go to that happy hour at all though…
The weather was cold and rainy. And I only knew a handful of people who were going.
But out of loyalty to my friend Brittany — who had put the whole thing together — I sucked it up and went.
At the time, I was working as a Technical Writer at an information security auditing firm…
Which was about as interesting as it sounds.
Now don’t get me wrong — I loved the people at that company (and still do)
… but the work just wasn’t for me.
I didn’t care about firewalls, security tokens, or password managers.
I cared about freedom, independence, and the ability to make money on my own.
I wanted to be a freelance writer.
At the time, I knew next to nothing about copywriting. I’d heard the term in passing, but never dove into it.
I’d earned some money during college as a freelance writer. I even paid for a summer trip with money I made freelancing… which was an incredibly proud moment.
I had tasted the freedom and independence that came with freelancing — and I wanted more of it.
So while talking to a girl named Kelby at the happy hour, I told her about my dream.
“Well, I work at an auditing firm right now, but what I really want to do is become a freelance writer.”
Then Kelby said something that put me on the path to where I am today:
“Oh wow! I have a friend who does that. His name is Tim. I’m going to text him and tell him you all should hang out.”
Tim and I hung out a few weeks later.
Then I met Tim’s main client (who had a team of contractors working for his business). He asked me:
“So do you want to come work with us?”
Long story short:
I did.
June marks the 3rd anniversary of my freelancing career, and I have to admit:
I don’t like calling myself a freelancer anymore.
Because what I really am is a business owner.
My goal is no longer to float from gig to gig, making just enough to get by…
My goal is to build a sustainable business that will support my dream lifestyle.
But I’m getting ahead of myself. On the road from “freelancer” to “business owner,” I’ve learned a lot of things.
Here are a few of them:
1. Measure the Important Things
When I first started freelancing, I measured success based on the amount of hours I worked…
Which made sense, considering I got paid by the hour.
I was also working multiple days per week at a coworking space, and found myself wrapped up in the “hustle” culture.
And while I think there’s a time and place for that… I also think different people should measure their level of “hustle” with different metrics.
Put simply:
It doesn’t make sense to measure a writer’s productivity by the amount of hours he sits at a keyboard.
These days, I measure success based on the amount of work I actually get done.
Did I do the things I needed to do today?
Yes? Good.
Whether I got those things done in 4 hours or 8 hours is irrelevant.
Obviously, you have to dedicate time to improve your craft…
But a 12-hour workday is only impressive if you had 12 hours of productive work.
Otherwise, you spent a lot of time pointlessly staring at a screen.
So if you’re a creative freelancer, my advice to you is simple:
Track your time… but don’t measure your “success” by the amount of hours you spent chained to your desk.
Instead, measure it by the amount of work you actually completed.
(This means you’ll have to stop charging by the hour if you’re currently doing that. Charge per-project or set up a revenue share or retainer agreement instead.)
2. Don’t Fear Test Assignments
I don’t get pissed off very easily…
But there is one thing that frustrates the hell out of me:
Writers who say that you should never work for free.
While I think (or hope) this advice comes from a well-intentioned place…
It’s bullshit.
Here’s what I mean:
I think this advice is intended to help new writers value their time and their work, so they can avoid wasting it on clients who try to get free work with “test” assignments.
And I get that.
Doing a bunch of free work for a client who ghosts you is not likely to be a fun experiment.
But here’s where I think the “business owner” vs. “freelancer” distinction comes in.
A business owner is able to think long-term…
They’re able to make judgment calls and decide:
“Is potentially not getting paid for this worth the risk?”
And they’re able to recognize that (unless they have a legal obligation not to do this) they can use the test assignment in their portfolio to land new clients…
Or they can write a blog post about their experience that will position them as an expert in their field…
Or they can use what they learn from the test assignment in their next negotiation with a potential client.
Basically, business owners don’t just see things at face value. They look to leverage every situation to their benefit. (Not in a negative or rude way — in a smart way.)
Because here’s the truth:
If you want to work with large, successful companies — you’ll almost definitely have to do test assignments at some point.
But why?
These companies can afford to pay for your work — so why would they make you do a test assignment for free?
A ton of reasons:
They want to weed out people who can’t follow directions
They want to make sure your samples aren’t bullshit
They want to see if you can hit deadlines
They want to compare your writing style and thought process to other writers
And the list goes on
Bottom line:
Test assignments are part of the game if you want to work with big clients. Sometimes you’ll get paid for them. Sometimes you won’t.
Regardless, think long-term. And think about how you can leverage test assignments to your benefit.
(And as a general disclaimer — if you plan to use a test assignment for a portfolio piece or blog post… make sure it’s okay with the client.)
3. Give Yourself a Reason to Be in the Conversation
The best thing I ever did for my writing career was The 29x29 Project.
The first thing that I’ll point out is that it was A LOT of work — that I did completely for FREE…
But it’s led to massive breakthroughs in my writing career.
In fact, one month before I did the 29x29 Project, I quoted a sales page project at a VERY low price.
3 months later, I quoted a new sales page project at 5–10x that price, and I landed the gig.
(Full disclosure: I was also friends with the guy leading the project, and that probably helped me land the gig. But I would not have pitched the price I did — which was the highest price I had ever quoted — without gaining confidence from the free work I did during The 29x29 Project.)
But that was just the short-term benefit.
What The 29x29 Project REALLY did for me was give me a reason to be in the conversation.
Because I had the unique experience of writing 29 sales pages in 29 days…
I now had a reason to talk to copywriters who were much better and more experienced than me.
The simple fact that I had put in that amount of work showed them that I was serious about my craft — that I wasn’t just another wannabe copywriter who would stop writing when it got hard.
So, no matter what field you’re in…
And no matter how inexperienced you are…
How can you make yourself stand out? How can you give yourself a reason to be in the conversation?
Find out what that thing is, and do it. (And promote the hell out of it — without being a blowhard, obvi.)
In my experience, it’s one of the best things you can do if you want to make a name for yourself.
4. Pay for Coaching
Seriously. Just do it.
Obviously there are budget concerns here, but if you can swing it — it’s worth it.
Ideally, this would be a 1–1 coaching relationship.
Group coaching is good. Masterminds are good. And you should do both of them.
But early in your career, there will be few things more valuable than having a mentor who is dedicated to your success.
Specifically, hire a coach who has done exactly what you want to do.
While a general business coach might be able to show you some stuff you didn’t already know, someone who has walked the path you want to walk can give you a step-by-step plan to do the same thing.
Hiring the right coach could save you months (and probably years) of effort. And I don’t think that’s an exaggeration.
5. Get An Accountability Partner/Group
Wanna know a secret?
The reason I’m writing this article is because a small group of people expects me to. And if I don’t do it…
I have to buy them all a gift.
That’s accountability.
This is one of the reasons group coaching and masterminds are great. You can find like-minded people, decide on a mutual goal, and then hold each other accountable for completing that goal.
A phrase I often mention when it comes to copywriting and marketing is that “all ships rise.”
If the tide (skill level) goes up, then the well-built ships (well-run businesses) will rise with the tide (grow).
So find a group of people (or even just one person) who will hold you to a high standard — and maintain those relationships.
Your business will thank you for it.
(Okay, it probably won’t — because businesses don’t talk. But you know what I mean.)
6. Become Somewhat Competent at Project Management
Project management is a big fat turd.
There, I said it.
Seriously, if you don’t have a system in-place, trying to figure out project management is like rubbing lotion all over your hands and then trying to juggle chainsaws blindfolded.
And for the sake of transparency, I’m only just now getting the hang of this. (Project management, not lubed-up chainsaw juggling, FYI)
For the longest time, I just used a spreadsheet to keep track of everything. And for a while, it worked.
But recently I started using Monday.com, and I really like it.
You don’t have to use Monday — but you do have to use something. Because from my experience…
Flying by the seat of your pants isn’t a healthy long-term strategy.
You’ll spend hours responding to emails and Slack messages only to get to the end of the day and realize a hard lesson:
Even though your day felt productive… you didn’t really do any meaningful work.
Here’s what’s working for me right now:
Planning my week in advance.
I’ve found that I have my best weeks when I plan the entire week in advance — usually on Sunday night.
I’ll take an hour and plot out:
Every task for the week
Which day I will complete the task
What part of the day I will complete the task during (morning or afternoon)
And how long I expect the task to take
That way, I don’t have to waste brainpower trying to figure out “what am I going to do today?”
I know exactly what I have to do… so I can just sit down and do the work.
(Obviously, this doesn’t always work out perfectly, because sometimes things change or clients need a quick turnaround. But it’s a good goal to strive for.)
7. Listen to Your Natural “Work Rhythms”
If “work rhythm” wasn’t a term before… it is now.
When you’re a freelancer or a business owner, you have the unique luxury of working whenever you want.
Early in my freelancing career, I worked when everyone else worked. And that made sense, because I was part of a tight-knit team that worked in-person a few days per week and often required quick turnarounds on assignments.
But over the past year or so, I’ve been operating differently.
I know that I do my best writing in the morning, so I try to get started as early as I can. (And on my most productive days, I avoid checking email or texts until later in the day.)
I know that it takes my brain a while to recharge after a morning writing session, so I take a 2-hour lunch break.
And I know that I can only work productively for about 3–4 hours, so I chunk my workday into two 3–4-hour blocks (morning and afternoon).
Doing these things allows me to work with my natural “work rhythms” and…
Get more done in less time
Enjoy my work more
Embrace the ability to create my own schedule
This list isn’t exhaustive, by any means. If you want to be a successful freelancer or business owner — you’ll have to do a lot more than what’s mentioned in this article.
But nonetheless, I think these tips are great advice for anyone new(er) to the world of freelancing…
Or someone who dreams of freelancing one day — just like I was doing at that happy hour in early 2017.
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