Starting Point: The Bumpy Road to My Design Career (Abridged)

The super short summary version, until I feel like publishing the super long version.

This is a lovely sketch by one of the product designers at Udemy, fully utilizing my name as a pun.

Ihave just signed and accepted the contract to move to the Product Design team at Udemy. This is probably the seventh draft of this article so far; I hadn’t posted it earlier when I passed my interview because the contract wasn’t there and I just didn’t want to risk anything, you know? I’m anxious, but I’m excited. I’d like to share my journey, and hope that it helps in some way. To the people who helped me, who taught me, who were patient with me: I’m thanking you here in the beginning and at the end and the spaces between.

You can expect the following from this article:

  • Quick Stats
  • Top 3 Challenges
  • “(One thing I’d do) If I were to do this again…” (a full list to follow in a separate article, because let’s be real, one is not enough)
  • And because I have no shame and would absolutely benefit from the Spotify sharing feature that many folks have been designing for, I also have shared what is essentially my “KEEP GOING ROBBIN” playlist.
As the good Doctor would say…

Quick Stats

Chosen Path: CAREER CHANGE. Transferring within current company; otherwise, try for grad school.
Location: San Francisco, CA
Status: Bloody triumphant.

Background: Customer Support in an edtech company (currently, 4+ years) with no design credentials, save for messing around on Photoshop and doodling
Psychology/Japanese/Education, UC Davis; Designlab, UXA
Cohort: Ive, Full-Time
Graduation Date: March 2017

TOTAL TIME TO CAREER CHANGE: 1 year, 6 months (from beginning of UXA to interviewing and getting the verbal “You’re in”, plus a month or so for the contract and off-boarding from support)

Top 3 Challenges

I mean, yes, but also, really, no…

#1 No real-world experience

Not surprisingly, this was the biggest hindrance. Despite working on small projects here and there, there was never anything I could really say I worked on autonomously. I worked with designers and PMs and engineers, but I was not doing the work I’d learned from UXA.

My Response: I worked pretty much non-stop (I am the person who did my full-time job, design part time, group facilitation part time, and a part-time remote internship all at once). I made it a point to connect with as many designers as possible to learn what I can do in the maddening interim. I looked for any and all opportunities, pushing for them even if I didn’t make the cut. Feeling dejected from rejection was something I did not have time for.

And so I did give 110%. Or maybe more.

#2 External constraints

Half the battle was convincing the head of design to consider me for a rotation or a junior position. This was entirely something I could do on my own and this wasn’t so bad, because people were very supportive. The other half was the company. Simply put, there were no senior designers to take me under their wing, and on top of that, there wasn’t enough budget to take on a new recruit. Turns out you can’t just snag someone from one team to another when the company is in the midst of growing, because yes, all teams have a set budget and headcount, often per quarter or even half a year.

My Response: Always, always, always talk with the people who can help determine your future. Keep in touch with your manager, who will advocate for you. Keep in touch with the hiring manager, who will probably feel a little disconcerted at first but will later on commend you on your perseverance (true story). When you have no idea who to talk to, talk to people in HR so you can understand how the process works. It really gives peace of mind.

We can’t all go at the speed of Dash, unfortunately.

#3 Staying positive

Hands down, this was the most difficult thing for me to do. I can’t tell you how frustrating it is to be able to help students each week in group crits, often times outside of the hour I’m actually paid for, and then seeing them get a job long before I could even get a call. It’s bizarre getting messages on LinkedIn from strangers asking about my experience because they’ve read my articles or something when I’ve always been so close to moving teams, but never quite being there yet. It has been so close but so far for pretty much all of my journey.

My Response: Have a strong support network. My friends, family, and loved ones were always my #1 fans and encouraged me to keep going. The mentors I’d met were another kind of support; theirs wasn’t unconditional, so I appreciated that they were always realistic with me and didn’t give me false hope. I needed both the cheerleaders and the “let’s be real now” to keep going.

It helped to have some legit Jedi masters of design.

If I were to do this again…

The one thing I’d do is talk to more designers, PMs, engineers, HR folks, recruiters, and CEOs. I had all of these folks in front of me, but I was too afraid and uncertain to speak up. I was timid about wasting people’s time because I wasn’t sure who to ask or even what to ask. And yes, I am almost painfully introverted a lot of the time (to the surprise of many, for some reason). By talking to more people, I learned so much, and people are willing to help however they can. (Seriously, I have yet to meet an engineer who wouldn’t be thrilled to actually have a designer who is willing to work with them rather than just taking the redlining and hoping for the best.)

(Also, in terms of what to ask: I promise you, pretty much all of my conversations started with something along the lines of, “So what got you into design? What advice could you give someone starting out? What will be the hardest thing for me in terms of getting that first job, in your experience?”)

I’d tell myself not to grimace when I see the word “networking”. (I still grimace because I hate that word.) Inauthentic enthusiasm is pretty much the worst, and that’s basically what networking feels like to me. So I did what one of my design mentors told me: reframe it. It wasn’t networking to me; I was legitimately curious about how people got into design and why they loved it and why they stuck with it. Their stories mattered, not just to me, but to them, too. When someone loves design, you can see it in their eyes and in the way they talk and how they see the world.

Me after pretty much everyone I spoke to.

To me, this isn’t networking. This is connecting with another human being and talking about something they love. In my opinion, this is infinitely better than the cold, robotic nature of the word “networking”.

My completely shameless Spotify playlist that kept me going

Look, I’ll be real with you. This is probably not the playlist you want to break out at parties or anything, but it’s pretty much full of positivity and all that good stuff necessary to keep your head in the game. At the very least, you can have a laugh, or you can think, “Whoa, Robbin is weird” (or super cool). Here’s the Spotify playlist.

And now, some previews of the playlist, in GIF form.

Obviously, Hamilton made the list more than once, from not throwing away my shot to being non-stop.
I forgot how much I liked this song. Thank you, Fort Minor, because that’s legit.
And for all the times I wasn’t sure, I watched what is probably the most ridiculously epic self-anthem ever ala Disney.

Again: massive thanks to so many people that were involved in the process. I don’t know how to express my appreciation in so many words, but I am going to try my damnedest to thank you all individually. Thank you, thank you, thank you for believing in me and for all your support. Never underestimate what a “You got this!” can do for a person.

Product designer, puzzling over UX. Crocheting in between. Tea at all times.

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