10 critical lessons freelance writing taught me about success and being a boss

Hey everybody,

I know it’s been awhile but I’ve been a little busy working on my freelance writing business. I’ve made some great strides with it and have learned some great lessons along the way that I’d love to share with you.

So let’s start with why I started freelance writing in the first place – independence.


And this is what independence looks like.

Freelancers are their own boss. They set their own hours, work where they want and with who they want.

A perfect situation, right?

But along the way I’ve learned that freelancing has its downsides; what’s the biggest one?

We’re our own bosses.

Confused? Think about it. When you’re at work and you’re feeling lazy, do you just stop working? No! You keep going cause your boss will yell at you, ain’t nobody got time for that!

But if you’re a freelancer, you don’t get the “luxury” of having somebody “motivate” you to work.

So in a way, your boss is actually useful.

(In a way at least).

I had to adapt to that, still am in fact. Being self-motivated is TOUGH business, anybody who’s tried to add new habits to their life knows this. Imagine trying to make your work a new habit, working at home where nobody’s going to keep you on track but yourself.

At first I thought this was a problem that only freelancers or work at home people experienced.

But when I thought about it, I realized lots of people have this problem. How so? They aren’t the boss of their own lives, circumstance is.

Lots of people just let things happen to them. Instead of creating their own lives, they let chance decide things. That’s why it’s so important to understand what it means to “be your own boss.”

And that’s what I’m here to teach you.

1. Don’t waste your time thinking about past achievements

Whenever I’d write an article, I’d constantly go back and see how it’s doing. I’d always check to see:

  • “Did anybody comment?”
  • “How many social shares did I get?”

But I realized that it was pointless. I mean I had to respond to the comments, but really it wasn’t THAT important. I should’ve moved on and focused on building myself up with more writing and marketing.

So stop living off the high of a past achievement and start working on your next one. There’s ALWAYS something else to be done, that’s what freelancing has taught me.

2. Always commit to what’s now and what’s next

Once I stopped worrying about how my old work was doing, I realized I needed to 100% focus on what needed to be done now.

What can be done now? If you can’t figure it out then just do something, ANYTHING that’ll get you closer to your vision of success. Maybe you’re not being optimal, but you’re being something; you’re being a better boss than before.

And over time, you’ll get better at it. As long as you keep pressing forward, that’s all that matters.

3. Limit thinking to when you can’t take action, otherwise always act

It’s my philosophy that action is the most important thing you can do for yourself. Even misdirected action can be useful as it teaches you what not to do. And that kind of experience really sticks with you, much more so than reading about what not to do.

But there are times when you can’t take action.

When you’re driving somewhere, when you’re waiting in line… You know, those kinds of situations. At those times it’s best to think about how you should tackle the current step you’re working on.

What can I put in my outline? What should I do at the gym? How can I improve my form? Those kinds of questions are great since the answer is easily actionable.

You don’t want to be thinking too much when you’re actually working, it just ruins productivity.

4. Being good at your craft is far more important than credentials

When I first started writing, I thought that nobody would be interested in my work. I didn’t have a big portfolio to show off, and I only just started my own blog. “I don’t have the proof that I’m a good writer” I thought to myself.

But still, when I only had a few posts on my blog, I submitted a guest post to DumbLittleMan, one of the top personal development blogs around. The next morning I woke up and checked my RSS feed. What did I see? My article at the top of the blog.

Furthermore, I even became a featured writer at that blog. Not bad for a newbie, right?

I learned then that while people do like to see credentials, it’s much more important that you can perform your craft well. If you can provide the results, people will seek you and your skills out.

5. Discipline, attitude, and willpower are what matter; not talent

As a freelancer, you learn quickly how important it is to be diligent.

Cause if you aren’t writing or marketing, you have nothing to show for it; not customers, and not income.

Writing comes off as an easy thing to do, even if you were to do it all day long. But it’s not.

Sure, you’re sitting down comfortably on a couch or at your desk, but you’d be surprised how hard it is to create nothing from something all day long. It’s pretty mentally taxing.

I had to build up to it, still am in fact. Cause you don’t start off with good discipline and strong willpower, you earn those things.

Talent certainly won’t give you those things. It won’t even make those things easier, it just makes the craft you do easier. If you want to develop your discipline, there’s no way around it – you just got to sit there and do it, day in and day out.

6. Playing the blame game is pointless

When things go wrong, it’s normal to look for something to blame. But in reality there’s nobody but you. And even if there is something to blame, it doesn’t matter. You’re still in control of you, regardless of what those around you do.

Maybe you are being held back by something or someone, but just because you’re being held back doesn’t mean you can’t break free.

When I first started freelancing, I blamed my inexperience on not being able to get clients. And maybe that was partially true, but nothing was stopping me from emailing potential clients or asking to do guest posts on other blogs, only my fear of rejection was.

So stop blaming circumstances and saying you can’t do this or that. Circumstances can slow you down, but it cannot stop you from moving forward.

7. It’s important to network and know others

It’s not really my style to communicate much with others, but in the online world it means EVERYTHING. And if you want any amount of success (both online and off), you need to get your name out there in as many places as possible.

You want people to be like “you’re looking for somebody to do this kind of work? I know the perfect dude!” You need to leave your mark wherever you go.

So be loud and proud with you what you do, because it might just open a door of opportunity that you’ve never had before.

8. Get your work done early in the morning

The early morning is the BEST time do something important. Why? Two reasons.

  1. Our willpower is at it’s peak; we haven’t wasted it on any work for that day, so it’s easier to do things that matter.
  2. Nobody’s even awake to bother you early in the morning, that’s prime time for personal goals.

I got to admit, I HATE waking early. Really do. But when I pull it off, I can plop myself down on the couch and just write. And guess what, I get a TON of work done.

It really sets the tone for the rest of the day when you do the most important thing of the day immediately. In fact, I literally feel like it’s doubled my productivity because of it.

It’s that good.

9. The best way to learn is to apply and teach, but only learn as much as you need to move forward

In the online world, there’s an endless supply of information to learn. But an endless supply of data means nothing since we only have a finite amount of time to learn it.

As a freelancer, you’re going to write about things that you don’t know much about. This means that some research is needed, sometimes a lot. And to be honest, this is the most time-consuming part of any project.

I’m still experimenting here, but here’s what I’ve learned about research and learning in general.

  1. You should always dive headfirst into a subject and be able to teach others about it through personal experience
  2. Only learn only as much as needed to move forward

Reading about something is great and all, but nothing teaches like personal experience. Failure in particular really locks in a lesson hard. I’m not saying that reading and other learning mediums are useless, but having that experience makes your ability to adapt and make smart judgements much better.

This is especially important for snap judgements. You can’t make snap decisions based on what you’ve read, only on what you’ve felt (through your experiences). Basically, taking action improves your ability to take action.

This leads to my other point, only learning as much as needed to move forward.

Basically anytime you stop to learn something, you’re not actually moving forward. And it’s easy to get trapped in a “I need to learn as much as possible so I don’t mess up” type of mindset. So I recommend learning the bare minimum needed to maintain your action momentum.

If you do mess up, it’s okay. Just go back and fix it. Just keep moving forward at all costs, that’s what really matters. And if you do need to learn a lot before you can get started, like really have to, I still recommend my approach; learn as little as necessary and take action on it.

10. Embrace risk, fear, and failure

“Take small and medium size risks consistently.  Test your results and focus on what works. Taking action will make you feel alive. It’s where you personally grow.” – Justin Krane

This quote means so much when it comes to being successful. I honestly think it’s impossible unless you’re willing to fall face down and look stupid.

Failure is what cements life lessons into your character. If you’re weak, it’ll make you a worse person. But if you’re willing to proudly embrace your failures, you ALWAYS come out a better, stronger version of yourself than you use to be.

Over to you

My craft is freelance writing, and it’s taught me a lot about becoming successful. But my question to you is this, what has your craft taught you about becoming successful?

Leave a comment below and let me know!

Images via Peretz Partensky & Tina Lawson


  1. Love this post!! It’s so interesting to see the statistics of a lifestyle we are trying to make work for us.
    Great, great read. I thoroughly enjoyed reading about your journey. It sounds as
    if you have worked yourself to where you want to be . Congratulations and continued good fortune!

  2. Hello! Learn the 10 critical lessons that freelance writing taught me about achieving success and becoming the boss of my own life. By the way the best paper writing service that I saw: http://speedypaper.net/

  3. love this site. reading it while thinking about my own freelance writing dreams. Cool one!

  4. i like this one.
    great pointers.

Speak Your Mind


CommentLuv badge

%d bloggers like this: