Proud to be Self Taught: How I Pivoted to UX

Allison Milchling
4 min readJun 3, 2016

This is the story of how I redirected my career path. Having lived through it, I can say this (often uncomfortable) series of transitions has led me to the most gratifying stage of my professional life. My hope is to encourage others not to settle for the wrong fit, but to find the courage to carve out your own personal path.

When I realized I wasn’t in the correct place in my career.

I climbed up the “but what exactly am I doing with my life” mountain and it was hard. I didn’t always know which way I was headed, but I picked up some very different and very useful experiences along the way. They’ve all been essential in directing my journey — you can quiz me all the way back to my high school job at the ice cream shop.

The pace of this journey picked up around nine months ago. I ran out of steam over-working myself in a role I wasn’t passionate about within a startup that I wasn’t passionate about either. Instead of switching departments and seeing where that could go, I took a huge risk and jumped over as the fourth member, and first non-developer, of a tiny new project.

Three months in at that new opportunity, I had caught up on the company’s user experience history and had a solid understanding of the spectrum of pain points that needed to be tackled. Never before had I had access to such a broad range of data. Never before had I had the space to quantify the data into meaningful conclusions. It was so fun!

But shortly after laying out my work plan, I came to the realization that the company was headed in a direction that was not strategic for me to follow. All my fun wasn’t going to have room enough to pan out. So I quit.

What it was like being purposefully unemployed.

Quitting meant I became unemployed and the stigma of being unemployed was so immediately icky feeling. I had willingly left two opportunities in the startup world to dedicate 100% of my time to sharpen up my knowledge of UX, refine my process, update my portfolio, and figure out how I would enter back into the world rebranded as a “UX designer”.

To try and stay casual, I called this time “going back to school”, but because I was not enrolled in any kind of actual school, I actually felt like a huge liar that needed to be ostracized from society until she got a steady income again. Both meeting new people and catching up with friends and family was awkward during this time. Oh, what do I do? I’m not currently working and I have nothing at all lined up in the way of a paying job.

Spending my weekdays gaining skills, working on projects, and having no new deposits showing up in my bank account was weird and it never got normal. Luckily, during this time I came across a few resources that empowered me to collect myself and put my newly branded skill set out into the market.

The most influential nuggets that got me through.

When I was insecure about a decision I had made or I was self conscious about my professional life in general, I went back to these main themes.

Here’s what got me through:

Perfection isn’t attainable, so kaizen and wabi-sabi

Fake it till you make it because that is literally what everyone else does

Go after what you want because the worst case scenario (rejection?) isn’t actually that bad and definitely won’t break you

Entering back into professional society.

It was when I got my first freelance gig at the beginning of this year that I felt like I’d reached the top of that mountain I’d been climbing. High above where I had started, I could confidently contextualize and validate my journey to this point. And I could see a more straightforward and strategic path ahead in my continuation as a UX professional.

That was the beginning of what has now become the past 5 months of freelancing as a UX designer. It’s ruled. This time has helped me rearrange my skills into real experiences. Practice makes perfect, and I have noticed that since my early jump into freelancing, I have been able to refine myself at a much faster rate than when I was working alone in my secret bubble.

I believe freelancing is such a great playground for people on a new career path. It’s been an irreplaceable way for me to strengthen and expand my offerings as a designer. A big reason I’ve enjoyed it is because I get to spend this phase of my career committing to projects, and not a single company. It has been nice to focus on the task at hand without the threat of being hindered by quirky company culture, office politics, and other distractions that can create a more complicated environment for developing a new passion.

Enjoying the process.

It’s nice to be able to reflect on how I am snowballing my knowledge into bigger and bigger experiences that are making me a better designer and leader. My process serves as motivation during the day-to-day challenges.

I’m still undecided about whether my next big step will be to take my freelancing to the next level or to settle down with a single company, but I am proud to have these decisions to confidently face.