Why I Started Freelancing

The answer is simple. I’m unemployable. 

Okay, okay. I know what you’re thinking. No, I don’t mean that in a negative way or an “I have a problem conforming to an office” way. I mean, I have too much of an entrepreneurial spirit and have too much creativity to work in a traditional office environment. Alright, that sounds a little hokey. How about this… My brain just works differently and that makes it difficult for me to work the ‘ol 9-5 and keep in line with the corporate structure. At least, that’s been the case to-date. 

But this newsletter isn’t about that. It’s about the why and how I started freelancing, so let me take you back a few years. In 2018, I was thinking about switching careers and getting a job as an in-house marketer at a company.  That didn’t pan out. I applied to 75+ jobs in the marketing space and didn’t receive a call back for a single one. NOT A SINGLE ONE. 

Talk about being discouraged. I had the skills, the know-how, and the ambition, yet something wasn’t clicking with myself and recruiters. I was unhappy with what I was doing at the time and, according to the application rejections, I had no other home I could go to. I felt stuck.

To get my mind off of things, I started taking on side projects to work on at night. It started off with a small social media management job here and a small Wix website development project there (for the record, I primarily design and develop in WordPress these days). But then those clients started referring others to come my way. People kept coming to me to be a freelancer for their projects and well, I just kept saying yes. 

After I hit $5k per month with this thing being a side-hustle, I decided that it was time for me to take things a little more seriously. I was enjoying myself, I loved creating, and I dug being my own boss – even though I was working up late at nights then going to my day job in the morning.

With this new ambition to do my own thing, I began to dive deeper into my crafts (and discovered how much I really love designing websites) and began studying what it takes to be full-time freelancer – the taxes, liability, etc…

I came across a lot of articles that told me no-one wants to actually hire a freelancer, they want to hire an agency. Being unsure about the best way to proceed to take this side gig to the next level, I thought, “Sure, why not?” 

That brought about the “I’m an Agency” era of my life from 2018 to 2019.  While business was still good, things felt a little disingenuous. I felt uncomfortable saying I was an agency when really it was just me and a couple of outsourcing partners. 

Then, in 2020, my friend, and fellow freelancer, Dann Petty gave me some advice – “Alex, where do you want to be at the end of the day? Do you want to own an actual agency? Because if that’s so, keep going with the agency appearance. But if you don’t and you just want to do your thing and build your brand, just be you, man.” 

I really took that to heart. 

After thinking a little bit about it, I realized that I just wanted to be me! I ditched the “Founder” title and just said I was a freelancer. 

And that move. That one simple move right there was a game-changer. The second I started promoting myself as a freelancer, work came flooding in. I mean 35% year-over-year growth. I don’t say that to gloat, but to share how one little mental shift that made me feel for genuine and comfortable was a huge opportunity and mental enlightening moment for me. 

As a freelancer going more and more full-time, I started to realize the benefits and what I loved so much about what I was doing. It was the freedom and the power to choose that I loved the most… and don’t forget the creativity part!

But, with going more and more full-time, I stated to appreciate that I got to choose what projects to pass on. I got to make my rules on work hours and communication.

If something fails, it’s on me. If something succeeds, it’s on me. Is it hard? Hell yes it is. There’s no doubt about that. But, there’s also a thrill to it that I’d like to hang onto for as long as possible.

Also, I was (still am!) having a hell of a lot of fun. I get to learn new things, solve problems, and create every single day.

Everyday is different, hard, thought provoking, and full of creativity, which is truly one of the greatest feelings in the world.

What can beat that?

And not to be all about the money, but what I have made in 2020 to-date, is more than I would’ve made at any of those jobs that I applied for.

I guess it was a good thing I was unemployable… maybe?

Anyway, I know this is getting long, so I’ll end things there. But that’s the how and why (at a high-level view) I started freelancing.  


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About Alex

Alex Medick is an entrepreneur and occasional investor from Las Vegas, Nevada.

If you want to jam about startups, growth, product, Bitcoin, punk rock, or surfing – he’s your guy.(more)

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