My career switch journey: tech support to UX design

I went into the pandemic as a full-time technical support manager and came out as a full-time freelance UX Designer in the social impact space. If the pandemic also forced you to reconsider how you spend your hours between 9 and 5, I’d like to offer one perspective for visualizing that journey.

For the sake of brevity, I’ll be summing up the decisions I made over the last 1.5 years but not going into all of the waffling I did beforehand; rest assured that if you’re agonizing over decisions, you are not alone. I owe everything to the people who trusted me, shared opportunities with me, and supported me along the way.

My circumstances

With any big decision, there are factors that “push” us away from the status quo and “pull” us toward an exciting but scary unknown. Here were some of the big “pushes” for me:

1. Compensation. The only way up for me within support was through management, and even then, the path was long and slow to get to my goal salary. After spending over a year as a people manager (under the financial pressure of living in New York City), I determined this was not a sustainable path for me.
2. Lack of purpose. While I loved the “helping people” aspect of support, I kept finding myself looking for opportunities to translate customer frustrations into root cause product solutions. As a result, I was always caught between working above my pay grade and solving the same problems over and over, both of which led to persistent burnout.
3. Lack of transferable skills. Despite the fact that I was doing UX work in every job I ever worked, I always held nebulous, non-descriptive titles that did not parlay easily into other opportunities. But more importantly, I wanted a technical skill set that would allow me to contribute directly toward activism and real world problems.

Phase 1: Marinate (April 2020 to December 2020)

I spent a long time thinking about UX Design before I knew I wanted to move my career in that direction. Here are some of the ways I dipped my toes into UX before making any big decisions:

Short courses

I am very much a “learn by doing” type of person. I am also a generally non-committal person that doesn’t want to bite off more than I can chew. Enter 4-week, part-time short courses, the perfect answer to my problem.

When I first started considering UX, I used my education budget (thanks Zapier!) to take a couple short courses with Designlab. I took Design 101 and UX Research & Strategy. These courses not only helped me get familiar with common tools (like Figma and Illustrator) but also allowed me to ask my mentors, who were working UX designers, questions about their daily lives. I figured that if I was still interested after this, that would be a good sign. (And I was!)

“If you give a mouse a cookie”

Zapier’s UX team allowed anyone at the company to sit in on UX interviews to hear directly from customers. After sitting in on a few of these, I asked a senior UX researcher if I could also shadow him during synthesis. Then, I asked if I could take the boring repetitive work off his plate (like transcribing videos and turning them into sticky notes). After a few months of informally working together, he gave me the opportunity to lead interviews, lead synthesis, and then publish UX reports to the whole company.

After a year of immersing myself in the world of UX (while still meeting/exceeding my core expectations), I decided this is what I wanted to do full-time.

Thank you SO much to Fernando for trusting and mentoring me.

Informational interviews

Lastly, I reached out to people in my network and extended network doing UX Design (shoutout Monica, Brandon, Zen, Eleni! ❤) who gave me a lot of advice, resources, and encouragement that helped me make the very scary decision to…

Phase 2: Take a leap of faith (January 2021 to April 2021)

Making the decision to leave my job was the hardest part. How could I possibly know what the end result would be? What if I ended up not liking UX Design? Or being bad at it? Looking back, the most helpful perspective to take on this was that — regardless of the outcome — this was an investment in myself and my skills. Once I believed that I deserved that, the answer was clear.

Quitting

I have many extremely talented friends who moved their careers fully into UX without ever quitting their jobs, by taking the “if you give a mouse a cookie” incremental approach to internal opportunities. Despite my efforts, this was not possible for me. So I made the difficult decision to quit and enroll in a full-time bootcamp.

Choosing a bootcamp

The first question going into my evaluation process was: What do I want to get out of a bootcamp?

From my reading and research, I had determined that the most important piece of the puzzle for me was a portfolio. While I had gathered UX experience from Facebook, Instagram, and Zapier, I wasn’t sure how to talk about it and was way too overwhelmed (and frankly burned out) by my full-time job to attempt such a massive undertaking alone.

More than anything, I needed time and mentorship.

Designlab’s UX Academy was by far the most affordable choice for my needs. I had taken 2 of their short courses, one of which served as a prerequisite to the full-time course, so it wasn’t a huge leap. Drawing from my experience during the short courses (which were great but exhausting), I knew that my mental health could not withstand a part-time bootcamp for 28 weeks on top of work (as opposed to 15 weeks full-time), even though this would’ve been the more financially prudent decision.

So I opted for the full-time track. I kissed my social life goodbye and moved from New York City back in with my parents in Houston for the first phase of the program.

Phase 3: Freelance (April 2021 to present)

Need experience to get work, need work to get experience.

“Real world projects”

For the second phase of the program, we were expected to do 3 capstone projects that would go on our portfolios. We had the option to either use mock briefs or find our own client(s).

If I wanted to graduate on the 15-week timeline, I would only have 2 weeks per project on the full-time track. But the word on the street was that if I wanted to go out and find real clients, I’d want to switch to part-time which gave me twice as much time with my mentor (but less frequent meetings).

I came into the program to make a portfolio that would get me hired (and I cannot function without 8 hours of sleep a night), so I knew I had to go part-time.

Finding work

In order to find clients, I asked friends in my network (directly and through social media) if they or anyone they knew needed help. I reached out to every non-profit I’d ever volunteered with and many more. I even sent out a few cold emails to more distant connections.

I employed a couple marketing strategies to make my services more appealing:

1. I advertised “web design” (and taught myself SquareSpace and Webflow on the fly) since it would translate better to non-tech small business clients, even though I went through the entire UX Design process anyway.
2. I was transparent about the fact that I was a student to give people the sense that they were also helping me.

Thanks to my friends’ invaluable support, I picked up 4 different clients by the time I finished the program. I had even been able to raise my rates each time from a flat fee that amounted to less than minimum wage to more than double the hourly rate I was making before starting the program. Thank you Jasmine, Tommy, Linh, Brett, and Chino. ❤

Note: There is considerable debate about whether freelancers should ever work for free. It’s up to you, but I believe that if a private company is getting value from the work you are creating, they can afford to pay you a fraction of that value (even as a newer freelancer).

I have my Designlab mentor, Erika, to thank for helping me navigate the intimidating tasks of writing contracts, defining scopes of work, and pricing myself (among many other things).

Despite extending my timeline, I still met the standards to graduate from the program early and learned a ton while doing it.

Freelancing sustainably

Among those I cold emailed was KettleSpace, a co-working company I’d used while working at Zapier and with whom I’d already made a few connections. A couple of conversations later, and I’d negotiated a one-month contract (which later turned into two).

Since I was technically employed by the time I finished the program, I was given 6 weeks (instead of 6 months) with my Career Services coach, Anthony, who helped keep me sane during the initial ups and downs of freelance life.

I also made a point to meet regularly with my friend turned UX mentor outside of Designlab, Monica, who taught me all about the government side of the social impact world (i.e. civic tech), helped me workshop my own story/pitch, and even mock interviewed with me for roles in this space. I cannot overstate how big of a role Monica played in not only my decision to go into UX at the beginning but also my ability to navigate the design world afterwards.

In June, a former coworker and fellow activist, Noah, reached out about an opportunity with his friend’s newly founded non-profit agency, Trestle Collaborative, that helps progressive organizations with their tech strategy. It was my dream job in every possible way. After a very fast but rigorous interview process, I was off to work by August. Since then, I’ve been in their rolodex of freelance UX designers to tap for future projects. I’ve already worked on another project since then with clients and colleagues that inspire me.

It was around this time that I realized my mindset had gone from seeing freelance projects as a means to woo full-time recruiters (or a stepping stone to full-time with a client) to a potentially even more sustainable option than tying my well-being to a single income source. It had always been a dream of mine to freelance full-time, but I didn’t know if I’d be ready right after graduating. Maybe it was the pandemic or maybe just growing my skills that made multiple streams of income feel not only possible but preferable. I guess the jury’s still out on this, but things have been going surprisingly well so far!

That takes us to today, spending about half my time working on projects and the other half of my time finding new ones. I’m still super early in my freelance journey and not sure what the future will look like for me, but I hope to keep this up as long as I can.

Conclusion

As I said in the beginning, everyone’s path is different but one idea is the same: Investing in yourself is worthwhile. If you aren’t getting what you want out of your career, if you find yourself perpetually burnt out or frustrated or just plain bored, it may be time to imagine a new path for yourself. I hope this article helped you a little bit along your journey.

P.S. I could not have made this transition without the help of my community, and I hope to pay it forward. Please don’t hesitate to reach out if you have any questions! ❤