Quarterly Review: 3 Months into Full Time Freelance

I hate the word Freelance. It sounds disorganized to me, something that you would use to describe either a medieval knight or a hippie. I also joke that it contains the word “free” which is strongly juxtaposed to any number I could write down on a proposal. I’ve chosen to go with the word “Consultant” to describe what I do, but it’s a thinly veiled disguise. I’ve been full time freelancing for the past 3 months. It’s been an exciting adventure so far, and I wanted to share some of my experience.

A very hilarious and very real thing that happened to me…

Making the Jump

After 3 wonderful years at Domo, it was time to to try something new. You only get better when you’re exposed to new challenges and 3 years at a tech company might as well be a lifetime. I was chatting with my dad about it back in March and he said something that will stick around with me for the rest of my life:

As long as you work for someone else, they will define your ceiling.

It was a moment of instant clarity. It’s easy to fulfill a job role, but what do you do when you outgrow it? Ask for a raise, ask for a promotion? What if neither are an option? My former boss would joke with me that I had reinvented my own job 4 or 5 times over the years. Still, I wasn’t raising the ceiling, I was just finding a different one to hit. But what if there was no ceiling at all? This is what attracted me to foregoing the security blanket of the 9–5. I had freelanced before but never as a permanent fixture. It felt like a life or death decision at the time. I was literally staring down another completely remote full-time job with all the bells and whistles. I took a deep breath, declined the ceiling I was being offered, and jumped.

I Had Zero Brand

Like, just a few degrees more than absolute zero… I had:

  • A website that hadn’t been updated since the release of the first iPhone
  • A resumé I created for a job when I was 23
  • An outdated LinkedIn
  • A Twitter I didn’t use
  • A Dribbble account with 2 images.

When you’re gainfully employed you don’t think about these things, or at least you don’t really have to. I gave myself a deadline of 2 weeks to become a real person on the internet.

I wanted to give Angular 2 one more chance (I did and still hate it) so I got to work on building a personal site. It didn’t have to be anything crazy, just from this century and not embarrassing. I set a target for an MVP and was able to get something live within the week. This was probably the single most important thing I did out of the gate because every single thing links back to it.

I had no business card, no typeface, logo, nothing. Branding is also not my strong suit, although I consistently give it another shot. I wanted something simple that involved my initials, I opened up a scratchpad and played around with some fonts and shapes until I hit one I could live with. I ended up going with one that looked like scaffolding because it speaks to UX, DIN for my name just because I like it, and San Fransisco for the subtitle because of my love for Apple and mobile design.

I ordered my business cards and began to apply my little bit of branding in as many places as I could. I began to sort out any and all relevant portfolio images I could find. This is harder than it sounds when you work for companies that don’t allow you to share things publicly. I updated my resumé, got GSuite setup for my business, and started using my new assets. I got to work on me legal obligations; I already had an SCorp, but my previous contract template left a lot to be desired.

I also went on a mission to signup for / update every single service I could find on the internet. Pay no attention to the fact that I will never use some of these services, but they do offer new ways to be discovered and improve your SEO. This was a ridiculous undertaking, like it took days. Every new site wanted the same exact information about work history. A few were kind enough to have an “import from LinkedIn button”. Maybe someday I’ll build a service that does it for you. “Become a freelancer with 1-click”

Networking 101

Now that I had a business card to hand out, I was ready to work. I started with the people I’ve been privileged to work with over the past 11 years. I organized my business contacts and proceeded to reach out to every single one of them. To be honest, I felt terrible doing this. It made me realize how bad I’ve been about keeping up with people. Still, if your friends won’t hire you, how would you ever expect strangers to? I let everyone know I had gone out on my own and was available for new projects. I was able to reconnect with some old contacts and one of my mentors so it ended up being a positive experience in the end.

Sometimes your old colleagues hire you :). View more at https://dribbble.com/jamesmfriedman

I also began attending a local tech meetup. I know what you’re thinking “Tech in Ormond Beach?” Surprisingly yes, although the crowd is a bit older and retired. To my surprise though, there are a couple of ex-Googlers and a guy from Oracle! I’m looking forward to attending more of these events. These people are a lifeline and, at the very least, a group of people that understand what I do.

About those biz cards... I hate them. I hate them because I always forget them. I hate them because when I remember them, they get messed up in my pocket. I hate them because no matter what technology exists to replace them, they’re still universally used and accepted. I’ve partially solved this problem by stashing them in the car, all of my bags, and leaving one in my wallet to get beat up in case I’m ever in a pinch.

Time management…

You work for yourself, you can do whatever you want.

False. True on some days, but mostly false. I worked hard at my last job, but I find myself working harder. Freelancing doesn’t fit into a nice 40hr a week box. It’s more of an ebb and flow of projects and hours that you have to keep up with. I track time for everything I do: both clients and personal. Truth be told, it’s hard to get 40 billable hours a week, in fact I’d probably have to work a minimum of 50 to bill 40 and I consider myself a highly productive person. For every phone call, proposal, lunch, home repair man, doctor’s appointment, extended bathroom break, Medium post, or any other interruption, the clock stops. Even when doing my best to mitigate this stuff it’s going to happen unless I move my office to a full blown isolation chamber. Paid time off and sick time also doesn’t exist. On the other hand, I can bill 24/7/365. It’s a wonderful world of tradeoffs that I’m sure is not for everyone. As for me, it fits my lifestyle and personality well: Highly-motivated-early-rising-self-starting-workaholic.

“Have I Got a Deal for You”

Hey I know you said you’re only open to contracting but have I got a deal for you! This is a once in a lifetime job opportunity!

I am only available for project based, short term (3–6 months) contract work. 
I am only available for project based, short term (3–6 months) contract work. 
I am only available for project based, short term (3–6 months) contract work.

It doesn’t matter how many times I tell people that, they just don’t listen. Maybe I’m a bit of a Snowflake, but I don’t want their full time job. I don’t care about the benefits. I don’t care about the competitive pay and options package. I don’t care about the beer tap they had installed at work. The reality is, they want to build a for profit tech company that is going to either make millions of dollars or crash and burn. If they make millions, I’ll find out that my shares are worth enough to pay off my car loan, if they crash and burn I’ll end up working harder and harder to keep the ship a-float until I jump off myself. It almost feels like going to the horse track and putting everything on #3. The pay off can be great, or you can lose everything.

My motivations are different. I wholeheartedly love to learn, discover, and create. I especially love helping people build companies and products! I love being there at the start and helping form ideas. I love jumping in where someone left off and expanding on what exists. I love solving the difficult problems and designing for growth. For the clients I’ve been privileged to work with the past few months, it has been an absolute blast designing and building the future.


Warning, shameless plug: If one of my future clients is reading this, then have I got a deal for you! Let me help you get to where you need to be in a fraction of the time at a fraction of the cost. The current national salary average for a Senior UX / UI designer is 105K. Don’t settle for lower quality work because you can’t offer that salary. Hire me for solo work or to augment and guide your existing team. Visit my site for more info.


I’m Dreaming Again

The best part of this journey so far is that I find myself dreaming again. My proverbial creative juices are flowing and ideas are popping up everywhere. I have an entrepreneurial spirit that won’t be extinguished. The fact is, it’s hard to shave off 10 hours a week to pursue your own dreams when you’re already working 40. Even if you can, it’s going to be hard to find a tipping point for your business before you can quit the full time gig. In three months, I’ve come across three different Co-founding opportunities that I would’ve never been able to pursue before. The best part is, I said yes to all three :).

It has been a crazy first three months and it feels like things are just starting to settle down, but I wouldn’t change it for anything. Overall, I’m exponentially happier. I have less stress. I have a solid amount of business coming in. I’m free to choose my own adventure.

I know this won’t last forever, my personality won’t allow for it. I enjoy project work and making my clients happy. But thats not my ceiling, thats just the first step on a new and wonderful adventure.