500 Days of Freelancing: 6 Things I’ve Learned so Far

It’s been well over a year now since I went out on my own into freelancing;  511 days since I made the call to give writing full-time an honest go. If for nobody other than myself, I thought I’d write a quick little recap of some of the most important things I’ve learned as well as the challenges I’m working to overcome.

1. I’m (still) not sure how I feel about the word “Freelancer”

I’ve waffled on this somethin’ fierce. On the one hand is the argument that “freelance” implies cheap and unreliable, neither of which I want to be associated with.

On the other, there’s the thought that love it or hate it, this is the terminology people use when they’re looking for someone to write for them who isn’t employed by an agency.

Using something like “copywriter for hire” doesn’t really change the conversation that much.

I also feel like “Freelancer” is becoming less of a dirty word; I’m seeing – at least in my limited experience – a marked change in the way people seem to be thinking about outsourced help. So for now, I’m rolling with the word again and gauging how it impacts lead numbers and quality.

Early indications are that it’s actually helping – or at least not hurting.

2. Specializing is smart.

I think it’s almost inevitable that when you’re just starting out on your own, you’ll take almost any kind of project that’s thrown at you. I believe there’s actually a lot of merit in tossing yourself to the wolves and trying a whole bunch of things to challenge your assumptions about your own skill set. You can discover that you’re a dead ringer for something you never otherwise would have thought to try.

When I began, I opened myself up to every kind of written asset: Websites, blog posts, brochures, posters video scripts – hell, I even edited people’s LinkedIn profiles and CV just to see if I could have an impact. I learned a lot that way, worked with some fantastic people and rounded out my offering.

But at this point, I’m finding it’s time to put some boundaries on what I work on.

Offline assets are rarely worth the time invested, especially when I’ve got such a good rhythm with digital going. And while everyone and their dog wants blog posts, the return on time invested is lower than more permanent assets like landing pages or website copy, which I find more exciting and rewarding.

I used to oblige most requests if they could afford my rate; now I turn virtually all of them away.

I keep blogging relationships with a maximum of 3 agencies at a time and leave the rest of my month for more interesting projects. The main reason I hang onto blogging is a constant bit of exposure and a nice, reliable paycheck that covers all of my monthly expenses, from groceries to rent. If I didn’t land a single project outside of my blogging work (which has never happened), I’ll be financially OK, and there’s a value in having that security.

I learned that making yourself scarce is actually more valuable, and I’ve been able to significantly increase my rate for blog work because I’ve protected my name and kept those relationships special.

That said, at some point I’ll need to ante up and cut away that safety net. There are better income streams I can tap into that require less time and effort.

Speaking of which…

3. There’s money to be made in teaching/consulting that I’m definitely missing out on.

If you’re a freelance writer, would you like to learn how I made a 6-figure income  in my first year? Chances are, that information is worth a little somethin’ to you, especially if you don’t have a road map and you’re wondering how to get going.

If you’re a business who needs a fast, brutal assessment of your copy and a recommendations for success, wouldn’t you love to be able to get that kind of insight for $500 or so with a one or two hour intensive instead of waiting forever to have a top-shelf writer take a peek?

From writing ebooks and delivering lunch n’ learns to offering power-hour one-on-one consulting, I’m starting to play with some new ideas for taking what I know and what I feel I’m best at and offering it in condensed packages or products I can sell over and over again.

There’s a reason brilliant copywriters eventually stop writing and start teaching other people to write; it’s far more scalable than project work. I’ve known that for a long time, but haven’t been sure how to execute on it.

Now that I’ve got a bit of a story and a portfolio that’s growing more impressive, I need to start thinking about how I can head that direction.

4. Good help is (really) hard to find.

If you’ve followed me awhile, you might recall I had been building a little writing team. At this point, that team has been pared down substantially and I haven’t passed them a project in months. A few things I learned the hard way:

  • Even writers with great looking portfolios can be hellish to work with.
  • I paid my team too much too fast. There was nowhere left to go to reward writers who did exceptional work.
  • Bringing in an editor is a crucial step, but it also slices into margins. Unless you have a good process in place, prepare to burn cash in bundles.
  • You can’t be a perfectionist. I wasted HOURS revising pieces that probably would have been fine to go live, just because I didn’t let “fine” be enough.
  • My biggest gap was trying to find a software that could handle the project management for this, allowing writers to claim jobs. I had to do virtually all the organization via email, and even a jimmy-rigged Trello was a bit cumbersome to work with.

We did a lot of projects successfully – especially product description projects – but I was finding that given the rate I could charge for other work, the team was quickly becoming less and less lucrative – especially since it was sort of “make a killing or lose an arm”.
If things went well, I pulled a good number. If there were revisions, I’d lose money in spades.
So for now, that team has been reduced to a decentralized small few folks (5 or so) who I mostly just refer projects to or call in on bulk work. If I’m ever going to try to build a team for the long-term, I now know I’ll need to spend months up front refining the processes and finding a good platform. I’d also spend time digging into Copybloggers’ training resources – the reason they can do such good work is they invest into the team.
In any case, my focus on scaling up for the future will be with products and fast-delivery consulting. We’ll see what I learn there.

5. Saying “No” is awesome (and essential).

The very best, most wonderful position you can be in when working for yourself is being able to tell people “No” when the project doesn’t fit your game plan or a request is unreasonable.

Freelancing is all about confidence.

The confidence to charge what you’re worth. The confidence to pitch clients you don’t think you’re big enough for. And the confidence to push back, say no and have a backbone. You don’t need to be a jackass, but “no” is a word you’ll learn to love as soon as you start saying it in the right moments.

It’s somethin’ I am working on getting even better at.

6. It’s not all about the Benjamins.

The past two months have been some of the hardest of my short little self-employment. Not because the money wasn’t there, but because I simply took on more than I could handle. At this point, I’m working long hours to try and deliver on every project and I’m losing my mind a little in the process.

Exercise isn’t happening. Quality time is scarce. Diet is atrocious. And I’m not making music or putting time into endeavors that fill up other parts of my life.

But hey, I’m makin’ lots of money, right?


I realize how self-entitled and smug that might seem, especially if you, the reader, are dealing with a situation where money is your primary concern. But I think there’s sort of a Maslow’s Hierarchy of Needs for freelancing, with cash right at the bottom. Once you’ve reached that comfortable “don’t need to stress” stage, you start thinking bigger.

My next moves are going to be ones that help me design a lifestyle I can actually live with – Time for travel; time for others and time for myself. Less time in front of a keyboard, more time taking advantage of the flexibility I should be enjoying as someone with no boss to answer to.

To that end, I’ve got some really exciting plans in the works. I’m going on an adventure, and I’m going to be inviting a lot of my agency friends to come along for the ride.

More on that later – but let’s hope it’s not another 500 days.


3 Responses to “500 Days of Freelancing: 6 Things I’ve Learned so Far”

  1. carmyn says:

    loved this, joel! congratulations on reaching this milestone.

  2. Benjamin says:

    Sad to hear it’s not all about me :(

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