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Random Things I Did In My Freelancing Career That Helped Me "Make It"
By Daniel Kenitz comment 0 Comments access_time 14 min read

Random Things I Did In My Freelancing Career That Helped Me “Make It”

Date: 2009.

Location: My parents’ basement. 

Tool: A piece of posterboard tacked to the wall. 

Goal: $2,000 a month.

It felt like an ambitious goal at the time.

I had been laid off from my previous job. And while once again on the resume warpath, I noticed that there was a job board website where it was possible to get paid to write. Elance.

Hey, I thought. Why not?

And it worked. By charging pennies on the word, I got some people to give my new account on Elance a chance. 

But I wasn’t making much money for a while. Hundreds of dollars a month. These days, I look at how quickly some of my freelance-friends were able to get started and wonder what I was doing so wrong. It seems so easy now! But back then, I didn’t know any freelancers. I certainly didn’t know any other writers who were getting paid to write for a living. 

I just had my posterboard.

I didn’t immediately make $2,000 per month. It took a while to build up. But eventually, with the support of my parents and enough persistence to pick up a few regular clients, the arrow started pointing up. For a long time, $2,000 felt maybe just a little too ambitious. That would have been roughly equivalent to what I was making from my out-of-college job. And making a living online? Everyone knows you can’t do that.

I don’t remember what happened to that posterboard, but I can tell you how far I’ve come. If I had a month as low as $2,000, it would mean something is seriously wrong.

There are many great freelancers who can probably do a better job of telling you exactly how to get started freelancing. Heck, they even sell products on how to do it, they’re that good. And the lessons they share aren’t wrong.

But here are the dumb little things I did that I think helped a lot.

1. Contacted a successful freelancer and asked her what she did. 

Years back, when I was a new freelancer, I made some money right away. Key word there: some. Not a lot. I undercharged like heck. Pennies. It was brutal. I would slave over a blog post and get…what, ten bucks from it? Twenty? 

Intuitively, as a newbie, I knew I needed some experience if I was going to build a portfolio so people with more money would trust me with their blogs and whitepapers. 

Back then, in the primordial days before Elance was Upwork, it wasn’t hard to find the top performers. I remember looking at their profiles with awe. Here were people making 60k a year! All online! At the time, it seemed unimaginable. Clearly these were some major titans of industry and I, a mere peon. And, like the mini-fanboy that I was, I found some of their websites to see if I could email them and ask them a few questions.

A few responded. And one responded in depth, which is kind of funny, because I was essentially asking someone to help me be their competition. (Nice little tidbit: if you ask for what you want, and do it nicely, you’d be surprised how many people give you exactly what you want.)

One of the questions I asked must have been about her #1 key to success in freelancing, and here’s a paraphrase of what she told me:

Ultimately, your ability to drive opportunity comes down from how many proposals you send out.

You could apply the same logic to just about anything. As Jerry Seinfeld says about writing: it’s a tonnage game. You have to create your own opportunities. And you have to work harder to do so than is intuitive.

These days, I get most of my business through referrals. So I don’t necessarily recommend that you carpet-spam the world with lame, half-hearted queries.

But at the time, I needed to hear it: I just wasn’t putting enough out there. Like many beginning freelancers, I thought that if I sent out three proposals on a place like Elance and got no response, clearly the 0% rate meant this whole career could never work. Not unless I charged next to nothing, at least.

Wrong perspective. It did have the capacity to work.

I just wasn’t playing the odds. 

Sending out lots of proposals flipped the dynamic. I no longer expected to get every job; I just expected to set a regular habit of sending out a lot, and in the course of time, I would naturally get some responses from interested parties.

Over time, I did optimize. I created new “template” proposals for different types of projects so I could copy/paste certain parts. I started leaving in room for personalization. I experimented with different proposals and learned a lot about how to do it the right way. 

But hearing that even someone as successful as her simply needed to sit down and do the work like the rest of us was a big change for me. It made me see that the only difference between me and her was a matter of degree. Then, I worked to close that gap. 

2. Use separate Internet browsers for personal and business

It’s a pretty simple breakdown: 

  • I use Chrome (connected to a Google Suite account) for business
  • I use Firefox for personal stuff

This is one tiny, silly thing, but you’d be surprised at the little 1% benefits it has for the rest of your working life:

  • I no longer accidentally sign into client Google docs as my personal account
  • I can keep separate bookmarks for work and for personal use
  • My accounts are always logged into the proper email clients
  • If I ever need to share my screen, a client will see 100% client-ready content
  • There’s a nice little “mental boundary” that helps me delineate between work and play time. (Note: in one study, researchers found that in college students, even having something as simple as a “study lamp” to designate study time helped students reach an average of one grade better.)
  • I don’t have to keep switching accounts from business to personal
  • I can shut off one browser and be completely “done with” the other for the day
  • My separate browsers track more relevant history, rather than my personal surfing habits overlapping with client research, etc.

You get it. It adds up. I couldn’t recommend this approach enough. For bonus points, you might even consider creating different

3. Measuring my productivity in money

This one habit, more than anything else, is where I started noticing things changing from “meagerly paid but technically has a job” to “this thing is starting to feel like a real career.”

I started setting a daily quota of productivity. But rather than “I will write 2,000 words today,” I set it more like, “I will do $XYZ of work today.”

For example, let’s say I earned $100 for an article. If I completed two articles that day, I had a $200 day. Not too tough.

I used a simple formula here:

  • I calculated a goal income. 
  • I divided that goal income by 50 (weeks of work).
  • I divided that number by 5 (days of the week).

And just like that, you know exactly how much work you have to do every day. Try to hit that, and voila, you’ve got a system.

To this day, if I get an assignment for a $10,000 blog post (hey, round numbers) and I need to schedule one-half of that for Monday, I’ll write it out like this:

  • $5,000 – ½ blog post – (Client name)

Then, I’ll click and drag in Google Calendar

Here’s what it looks like. This is a real Tuesday from a few months back:

That’s a $400+ day, assuming I get everything done. I won’t tell you what my actual goal number is, since that will probably change by the time this post goes live. (Hello from the past! How are the Bears doing?)

But I will tell you this:

Ever since I started doing this, that number’s been going up and up.

You’ll also notice the precision of some of the numbers. 87? 296? Yep. If I split my work into segments, I will get it exactly right, treating every task as if it has an exact numerical value. 

My goal isn’t to make sure it’s dead-on accurate. I simply tabulate the dollar amount at the end of the week and hope it’s on pace for my yearly goal.

After that? I forget it.

When I measure my productivity in money, I trust that my output will roughly align with what I ultimately get paid.

Is it effective? Ridiculously so. Sometimes it feels like having a thermostat for your freelance income. Once you know exactly what you want, and what you can produce, the world has a way of lining up with your expectations.

It’s so effective that I wonder if I shouldn’t turn this into a $997 special offer on the One-Of-A-Kind Daniel Kenitz Productivity System™. Well, there you go. You have it for free.

One final note: what if you don’t have enough incoming work to meet your daily quota? You assign a dollar value to sending out freelance proposals, and then do that until you meet your quota.

Hasn’t failed me yet.

4. Saving as many items in my portfolio as possible

Over time, I came to realize that the majority of my new clients hired me for two reasons:

  • A referral from someone they trust
  • They liked my relevant experience

The former point is worth another post all its own. But when you’re contacting someone cold and asking them to trust you with their money, there’s no better way to earn that trust than to show them that you’ve done it before.

So whenever I write something a little public (with my byline) and that I’m proud of, I ask the client if I can save it in my portfolio. Here are my tips for making sure your portfolio is big and well-rounded:

  • Divide it into categories. Over the years, I’ve done this so often that I started organizing them by category. Sales writing. Blog content. Website writing (with screenshots). If a client asks me “have you ever done email newsletters before?” I can pull some out, show them some stats, and give them a definitive yup!
  • The Rule of Three. Psychologically, you’re going to want to send at least three items from your portfolio. Don’t ask me why; it’s just a nice round number when it comes to comedy, bullet lists, and portfolios.
  • The Rule of Three. I can’t think of a third. But having three bullet points makes my list seem well-balanced, doesn’t it?

5. Occasionally being on the hiring end

I’ll never forget creating a project on Upwork where I was doing the hiring. I received one of the best proposals I’ve ever seen.

The guy essentially did the work for free. He said “that’s easy. Here’s what you do.” And then explained it in detail. Ultimately, I couldn’t hire him because I required someone with specialized expertise, but his proposal made such an impression on me that I started incorporating it into how I send out proposals. I started winning proposals by outlining my exact approach to their specific project.

And that leads me back to the original point: if you’re a freelancer, try being on the hiring end once in a while. It will tell you a lot about yourself. For example, I learned:

I’m not as good a client as I thought I was. 

In my experience freelancing, the best clients are hands-off, trust you to do the work, and always pay you on time. I thought I would be like that. SPOILER ALERT: I was not. Once, when I asked a designer to make my business cards, I became a tyrant who had to do all the designing himself. How annoying! I realized I was only asking for changes because I had specific visions in mind, and I wasn’t open-minded to the superior design skills I was paying for. If I could go back, I’d just let the designer choose everything. They did a better job on their first draft than what I had in mind.

Now, I look for the same “red flags” in clients who seem like they’re going to be a little too pushy, and I avoid them.

People can resent you even if you pay them, so it’s worth learning some people skills.

I once hired a virtual assistant to do something—I don’t remember what—and I then gave her a critique of her work. She seemed a little peeved. I found myself with a classic professional quandary: how do I make her want to do it the right way? Fortunately, I’ve read Dale Carnegie and knew better than to argue about how I’m the boss and she should do what I say and blah blah blah. I decided to acknowledge that she probably had a point. 

A funny thing happened. She felt motivated to get it right, and her work instantly improved. Later, I learned this has a name: psychological safety. The more “free” people feel to make mistakes at work, it turns out, the more productive they’ll be. 

Not to use the word “I” when introducing myself.

“Hi, my name is Dan” is fine at a wedding reception when you’re sitting next to someone you don’t know.

But when you’re trying to get someone to pay you for writing?

Try an exercise. Don’t say “I,” “me,” or “my” at all. Talk about their project. Talk about what you’ll do to accomplish their goals. If you must say “me” because you’re bursting at the seams, do it in the bottom portion of the proposal when you introduce yourself and your background. 

The more I hire people and get used to a wave of incoming proposals, the more bored I get when someone tells me why they’re so great. I don’t want to know why you’re great! I want to know what you can do for me.

And everyone hiring you will feel the same way.


Like these words? Good, because I haven’t run out of them. Hire me to arrange words like these for your blog, business, or website.

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