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Freelancing is Hard.

I have been freelancing off-and-on…well…since I was in college, but in 2016, I decided to pursue it more seriously, because I was unhappy with the direction my career was headed.

In this post-mortem-like post, I’ll list some of my failures from the past three years and how I overcame them.

  1. I first sought out potential clients by sending out emails to local businesses I thought I could help. Turns out business owners are incredibly busy and cold-emailing (or going door-to-door) is the worst way to win over a client. It’s better to be approachable, let clients approach you, and know when the time is right to give a 5 second pitch during casual encounters. And follow up. And then follow up again. And then send a follow up a year after, even if it’s just a thank you!

  2. Super excited for a new opportunity, I worked in a…not so healthy environment for a 90 day contract, the result of a recommendation by a colleague I trusted. I learned that for my own mental health, I shouldn’t ignore red flags during interviews, and that butting heads with the CEO, no matter how optimistic and “correct“ you are, isn’t always worth it.

  3. I worked independently under the table for a past boss, which I hoped would lead to bigger contracts with the company. Instead, the next time a large project did come up where I could help, the team did not want to work with me due to mixed feelings about me working under the table previously. I didn’t know I was hurting feelings, so the next time a similar opportunity pops up, I’ll not step on toes and introduce myself to the team.

  4. I created a Meetup group with another designer, with the goal to create a community of local freelancers that could collaborate on projects. Turns out, we were the only two in the city with passion for this idea. You can’t trust others to be as friendly and open as you, when it comes to competing over a limited pool of potential clients. I am just non-competitive by default. I will always be receptive to working with other people collaboratively, but I shouldn’t expect it as the norm, and should strive for a competitive advantage.

  5. We merged our group with a newer UX-focused group…which promptly fizzled out in less than a month. I learned that others with lofty ideas may not have the drive to execute their ideas, and as exciting as an idea should be fully-executed, it’s important to remain cordial, but always have a backup plan.

  6. I came across as un-focused, or too-technical, to clients, since I have many different skills. The terms UX and Interface Design sound too fancy for most local business owners that just want a website. For most people I meet that could be a potential client, I describe myself as a web designer. I can also do all-flavors of graphic design projects, but I only offer it if I think they need it, as a part of a package. Overall, I learned to tailor my pitch, based on what the client needs and understands.

  7. I’ve been applying to full-time job opportunities this whole time, with handfuls of interviews but no offer letter! My website has been confusing, because I had two parts: one for HR and design teams to look over, and one for potential local clients to look over. Design-wise, I kept the parts separated, but anyone that really poked around could get lost. Now, I’m focused 100% on finding a full-time job to put all these lessons to work in an office or work-from-home setting. My portfolio page highlights the best of my UX work, and this blog will shine a light onto my personality as a designer.




Sarah Walters