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First Year Freelancing: 5 Insane Things I’ve Learned

Hiring Is Hard. Admin Is Nuts. You’re Not Kanye.

I started my freelancing journey approximately 1 year ago, to date. I’ve learned some gnarly shit that I never expected would be on the damned syllabus.

I want to share these life lessons and observations about freelancing with you so that you can do the following —

  • Avoid the dogshit I stepped in.
  • Learn from my successes so you can thrive.

Be prepared — this is an honest hot-take. It isn’t some feelsy article (it actually is) written to make you think you’re going to digivolve into Kanye West the minute you quit your day job.

You’ve been warned.

Lesson #1: It’s not hard to find clients. It’s hard to find GOOD clients

I’ve written three actual guides on how to find clients on The Internet. If you can spare some time reading it, you’ll notice that it’s pretty easy for me.

I have it down to a science. Not like NCIS-level perfection, where I slap my hands on the keyboard and magic happens even when I type sdkgh idih rdGD asfdggh!! rdohgfhi. (Note: If you want to feel like a real hacker though, check this out!)

I mean science like Rick Sanchez’s version, except I’m not drunk all the time nor am I literally a sociopath.

The fact remains — for literally all freelancers ever in the world — that finding quality clients is a rough, rough go. At least to start.

How I deal with this problem?

The way I get over this hurdle is to make myself absolutely toxic to the people I’d hate working for, anyways.

I’m keen on rebels. I don’t care that much about large businesses.

If you can get past my general quirks — you’re the company or founder I want to work with.

Quality Client-Finding Pro-Tip : You attract what you put out.

Start content marketing like a beast, but do it for your intended audience. If you want help with this, I’m offering 100% free 15 minute consultations that don’t suck. Hit me up on LinkedIn — it’s a great place to start.

I implore you to scroll up and click those three links that all lead to guides, because I’ve already covered this in excruciating detail.

Lesson #2: Admin / grunt work is absolute ass. But you need to do it unless you find a competent VA

Even though I have a host of insane tools that I use to cover all my “grunt work” bases, it still sucks. It’s never not going to suck, unless you find a competent VA.

And let me just tell you right now — that’s probably harder than the admin work itself.

AND CO – Invoicing, Proposals & Expense Tracking. Completely Free! is the only tool I use for all my time tracking, contract making, client management, and invoicing necessities. It’s absolutely free, I do not work for them (though I’ve been trying to woo them feverishly for the past year to no avail), and I don’t trust anything else.

Here’s a super-fast review of other platforms that have similar functions —

  • Qwilr

Qwilr – Free software for creating proposals, quotes and docs

Basically Adobe Spark presentations with slicker permissions and passwords. It also offers payment portals for clients to put down cash money if they approve a proposal right off-the-bat. I’ve used it twice and it was “meh”.

  • Wrike

Your online project management software – Wrike

Kind of a pain in the ass. I don’t know if they’ve updated their Project Management platform recently, but it’s far more complex than I need. Better for small teams.

  • Airtable

Airtable: Organize anything you can imagine

The holy grail of content calendar planning. Airtable is basically a beautified version of Google Sheets. It includes passwords, permissions, reporting blocks (if you pay for it) and other neat features.

It can handle a lot of stuff, including project management, task management, social media spreads, article planning, and more. I use it frequently, but be careful on the free trial.

It’s not at all easy to end it, and their UI is insidiously confusing.

  • Trello


My go-to for project management and to-do lists. It has plenty of robust add-ons like Google Drive connections, Zapier automation, Mailchimp, Slack alerts, and more. It’s free, it works, it’s easy.

I encourage everyone to use it.

  • Canva

Amazingly Simple Graphic Design Software – Canva

Graphic design for graphic designers who just can’t even right now. Some people think this is a cop out, I consider anything that helps me get stuff done faster as a boon.

I obviously don’t use Canva for everything — UI Design is a Nope, Logos Are A Nope, Anything Super Duper Complex — Leslie Knope.

It’s free, it’s easy, I implore you to use it.

You’ll notice I wrote down proposals as “grunt work”. Let me take a hot minute to explain why —

At some point, you’re going to start repeating yourself, especially if you offer the same services, over and over and over and over again.

I have criminally defunct executive functioning (ADHD) and once something is no longer novel, it becomes mentally and physically exhausting. can help you in this case, and even Canva is a good option if you have a swanky template set up for proposals.

Freelancing Grunt-Work Pro-Tip: You need to work smarter, not harder.

You need to spend more time doing actual work, and less time doing the stuff that you don’t get paid for. The minute you realize that all this fluffery is costing you stupid amounts of time is the minute you become an adult. I’m serious.

Lesson #3: Hiring help is borderline impossible and hardcore dangerous

Trying to find competent help has been the #1 bane of my existence for this entire year. It drives me crazy.

I’m not going to pull a Junko from Tokyo Ghoul, but lord knows my level of frustration is definitely up there. Especially since I want to scale so bad it’s giving me indigestion. I’m just going to come out and say it —

Most freelancers suck at what they do.

  • They underestimate the time it takes them to get work done.
  • They overestimate how good they are at what they do.
  • Their rates are 90% arbitrary and 10% trying to get away with something.
  • Many are not reliable. Even worse, some are actually actively trying to screw you over.

Let me explain:

I’ve tried to delegate work. Believe me, I’ve tried.

I have exactly two people right now that I can confidently say are trustworthy, and a handful of people that, although not up to par, I can honestly say were pretty okay.

All the rest? Landmines that you never knew were there, blowing off chunks of your legs. Because once money is involved, people stop caring that you’re a person.

I no longer feel comfortable delegating. This is a serious problem.

In order to make your business work for you — and not you being a slave to your business — you need to delegate.

I’m slowly trying to build up a team, but I was so badly burned this past year that I’m having sincere trust issues.

Delegation / hiring Pro-Tip: I got nothing. Feel free to suggest some!

The cost and risk for a small business to take you on is ridiculously, impossibly high. It’s no wonder that hiring managers have a hard time finding quality help in the creative / tech sphere.

Please have a bit of sympathy for the clients you have that seem paranoid and ask you to sign 9649649 papers. They’re probably like me and don’t want to get their junk set on fire again.

Lesson #4: You absolutely have to take actual breaks, no exceptions

The hustle is dumb and killing you.

Having pulled 14 hour days on the regular when I started on my journey last year, I know it burns you out. And you literally cannot afford to be burnt out.

Last week I completely ditched the internet for 3ish days.

I had to go on an internet detox. If I hadn’t, the alligator death roll known as burn-out and anxiety would’ve stripped me of my productivity and all hell would’ve broken loose.

Break-taking pro-tips:

Sometimes when your work is staring back at you like the ass-end of a cat who insists on shoving their butt in your face, you just have to bounce.

  • If it’s possible for you to get up, out of the office, away from the co-working space, away from your house — please get up and take a walk.
  • Go get some coffee, go for a run — do something that will pro-actively help you set yourself up for success.
  • You must unplug. You must maintain a solid sleep schedule and practice good sleep hygiene.

I am telling you now that the “always on” approach will end in disaster. You cannot afford that disaster, so take care of yourself.

Lesson #5: “Okay” is better than nothing. Let go of being perfect

You know what’s worse than doing a “meh” job? Not doing it at all.

As a freelancer with a metric fuck ton of anxiety, and a penchant for perfectionism, I know how paralyzing a project can feel.

You’ll find that working a little bit at a time on your projects, and padding your timeline to account for low-energy moments, will help you get them completed. Deliver quality work of course, but the term “work in progress” exists for a reason.

Try to move the boulder a little bit at a time.

The work does not wait, and it must be done. Give yourself the grace of time to get the work done, and remember to include breaks.

And finally, a bonus Insane Thing I Learned That Isn’t Really Insane …

Lesson #6: Remember to be kind to yourself

Just because you run your own shit, doesn’t mean you are a non-feeling superhuman who never makes mistakes. You are the amazing master of your own career’s trajectory, but you aren’t omnipotent.

Clients will ghost, money makes people crazy, gigs fall through, stuff takes forever, projects scope-creep (please try to avoid this with solid contracts and proposals). The struggle is real.

But the worst thing you can do as a freelancer — bar none — isn’t really to fail other people. The worst thing is when you fail yourself.

You are your #1 priority.

Be kind to yourself, realistic about your goals, your skills, and who you are.

You are unstoppable.

If you have questions or comments, please reply below, or shoot me a message on LinkedIn. I’ll do everything in my power to help you through your struggles.

Kira Leigh is a snarky marketing nerd, writer, and artist. See her work here and send her a message if you want to work together.

You can also join her on Discord like the giant nerd you are — windows95toasteroven#3745

Special thanks to Renato P. dos Santos for his continued support.