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9 Things I’ve Learned from Freelancing for 2 Years

9 Things I've learned from freelancing for 2 years

If you’re reading this on the day of publication (Thursday, October 14, 2021), today is my 2-year anniversary as The Desk Dragon. Freelancing for two years has been quite a ride, and even though I sometimes feel as though I’m still just starting out, I’ve also learned and grown quite a lot.

So, in honor of my anniversary working as a freelance writer and creative assistant, I decided to share a few of the things I’ve learned along the way.

Here are nine things I’ve learned from freelancing for two years.

1. Never Edit Immediately

Especially when pressed for time, it’s tempting to finish a draft and turn right around to edit it. Or to edit each sentence as you go. But in my experience, it’s far better to put the draft away for a while and come back to it with fresh eyes. You need some distance from a project to be able to edit it properly and with a more objective perspective.

2. Desperation Is a Double-Edged Sword

Sometimes when you want to work badly enough that you’ll take whatever job you can find, you end up selling yourself short and/or getting yourself in way over your head. Other times, you strike gold with something you would never have tried otherwise.

How can you tell the difference? Do your research before committing to anything, and have a thorough understanding of your limitations and capabilities. Don’t be afraid to step outside your comfort zone, but pay attention when your gut tells you there are red flags ahead.

3. You’ll Never Be “Ready”

You might recognize this point from my very first post about what I learned while teaching in China. If you spend too much time researching and preparing, you’ll never end up taking that first step. There comes a point when you have to decide you’ve taken enough courses, studied enough, and done enough planning to go ahead and jump in, even if you don’t feel totally ready for what you’re taking on. All the courses and research in the world can’t teach you what practical experience can.

With that said…

4. Always Be Learning & Adjusting

The thing about freelancing is that you can change everything about your business at pretty much any time, however you choose to do so. This is one reason why you don’t have to know or decide everything before you start: there’s plenty of time and space to learn, pivot, and make adjustments as you go. In fact, I’d argue that if you aren’t constantly learning and adjusting, you’re not likely to get much of anywhere.

5. There’s a LOT of Advice Out There

If you’ve done any research at all about, well, anything, then you’ve seen a plethora of ads for courses, posts with advice and lessons learned (yes, this is one of them!), and so on and so on. But keep in mind that just because something works for one person doesn’t mean it will work for another. Whatever advice someone gives you, don’t take it as universal law. Test it out, see if it works for you, and know that it’s okay to throw it out and try something else if it doesn’t work for you.

6. Self-Motivation Takes Extra Energy

While I wouldn’t say this quite surprised me, it was definitely something that I became increasingly aware of as my workload increased over time. And I believe it’s an important thing for freelancers — and anyone who’s self-employed — to understand. Keeping yourself on task and setting your own deadlines requires more energy and focus than meeting deadlines set by someone else.

Which is why it’s important to understand this next point:

7. Capacity Is About More than Just Time

We’ve probably all heard people say something along the lines of, “You have enough time. If you don’t do XYZ, it’s because that’s not actually a priority for you.” I understand the point being made, but I also think this sentiment misses an important point: We can’t be running at full steam all the time.

You may have enough hours in a day to theoretically accomplish a certain number of tasks, but that doesn’t mean you have the physical, mental, or emotional energy to do so. So as you plan your schedule and set your deadlines, don’t just look at how many hours you have available. Also consider how much energy each task will consume, and external factors that will affect the energy you expect to have at certain times, and plan accordingly.

You can’t perfectly plan for the energy you’ll have at every moment, but you can give yourself a more accurate idea of what you can reasonably expect to accomplish.

8. Know Yourself

To reiterate an earlier point, what works for me won’t always work for you. The more you understand about your own capabilities, energy needs, planning style, etc., the more you’ll be able to successfully manage your time and resources.

9. It’s Not Built in a Day

Social media is inundated with overnight success stories and promises of six-figure income in so many days or weeks. But while those dream opportunities may be possible for some, most of us build our success much more slowly. (And it’s worth noting that “success” isn’t just about money. It also looks different for each person.)

To be fully transparent, I didn’t find my first consistent client until I was about six months in. And no, after freelancing for two years, I’m still not at dream income levels. But I have worked up steadily from that one client to several, and during that time I’ve been able to steadily increase my skills, efficiency, and yes, profits.

Bonus: Things I’ve Loved About Freelancing for 2 Years

Like any job, freelancing is hard work. There have been plenty of times I wondered if it was worth it, or if I should give up. I’ve spent money on courses and tools that didn’t help. And I’ve spent way too much time on projects and strategies that didn’t yield many (or any) results.

But there’s a reason (several, actually) I keep doing it. Here are just a few things that have made freelancing for two years worth all the difficulties and frustrations.

  • I’m constantly learning new things. I’ve written blog posts (and other things) on a plethora of topics. And that means I’ve researched a plethora of topics. Even if it’s not a topic I’m overly excited about at first, learning about so many different subjects keeps things interesting and fresh.
  • I have a lot of built-in flexibility. For many people, the appeal of setting their own schedule is one of the biggest draws of freelancing. And I’d be lying if I said it wasn’t a big factor for me, too. There is a caveat here in that I have to be strict with myself in setting personal deadlines and boundaries (see Point 6 above), but I definitely enjoy the flexibility.
  • My job incorporates my hobbies and passions. I get to write (something I already love doing) about things that I’m already interested in, both on my own blog and for other people — and often get paid to do it!

While I would never try to say that this is the ideal career for everyone, it’s certainly the right one for me at this point in my life. I’m excited to see where it takes me in the next two years, and beyond!

Social media is inundated with overnight success stories. But most of us build success slowly.

If you’re a freelancer, thinking about freelancing, and/or looking for some inspiration for planning, goal-setting, and self-improvement, check out my free resource library. I’ve put together worksheets, planning pages, and other resources to help you get started. Sign up below with your name and email to get access!


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