A Creative Boss: 15 FINE years of Tsilli Pines

[caption id="" align="aligncenter" width="590"] Tsilli Pines. Photo by Richard Darbonne.[/caption]
Chances are, Tsilli Pines has made you look good. Throughout her 15 years at FINE, and now as Digital Creative Director, we know she’s always made us look good. And that’s just between everything else she does. Co-Founder and Director of Design Week Portland. Creative Mornings Host and Organizer. Master Time Manipulator.

Since she’s clearly lacking things to do, we tasked her with answering 15 questions (because, themes) on her time here, in the industry, and spent personally.

1. What’s kept you around FINE all these years?
   The co-conspirators. The work is great, but at the end of the day, it’s that we get to do it together. If you’re going to spend so much of your life at work, it better be with people you like, who challenge and surprise you.

[caption id="attachment_19282" align="aligncenter" width="590"] Co-conspirators conspiring at the FINE 2016 Retreat.[/caption]

2. Favorite FINE project?
   It’s always the latest thing we’re working on. We’re about to launch a site for a new winery in Napa called Ashes & Diamonds. I’m excited about that one. I also love the complex systems projects. We’re working on one right now that’s a platform for very different brands with a shared code base and features. The tension between creating a system across all of them, yet providing a basis for individuation, is an interesting challenge.

3. In your early days, what did people expect a website to do, and what's that evolution been like?
   I came up as the web was coming up, so I learned to design in a finite digital context. It was all pixel fonts and tables and Flash — a known universe. The responsive web shifted the sands significantly, and brought with it a much more complex set of defensive design challenges. The most interesting thing about the early days was the sense of driving on the road while it was still being paved. It still feels a lot like that, but the grain of the web has become a lot more apparent over the past 20 years, and though there are many more contexts and factors at play, there are also clearer practices and lenses for evaluating the work. It’s certainly never a dull moment, though.

4. What’s the most nonsensical piece of design advice you’ve given as a Creative Director?
   “This needs more Truck Nutz.”

5. How do you practice or ignore the design advice you’ve been given?
   As a designer, it’s your job to synthesize everything you hear into your next moves. It’s never a good idea to ignore anything, but the way it manifests can be unexpected. You have to listen, try to understand where the feedback is coming from, and use all of your skill to fold it into an elegant solution.

6. What’s your feedback tell? (aka, “interesting” really means you hate it)
   I’m too honest to have a tell.

{editor’s note: behind her back, we sometimes call her Tsilli “Ain’t Nobody Gonna Have To Read Between The Lines” Pines}

7. Describe you as someone else might.

https://www.youtube.com/watch?v=opkRF3UZSJw

8. How do you manage to do everything that you do?
   I work a lot, is all. Most people would rather do something else, and that’s cool — it’s probably healthier. I’m motivated by my passion projects, and I think about them all the time. There are early morning and late night hours where I’m pushing through something that needs to get done. I have a kid now, and it’s helped me balance my propensity for work, but it also means that there are times when I need to perform in a very focused way, so I take advantage of a 20-minute window like you wouldn’t believe. But at the end of the day, I do the work, and I have a lot of people running alongside me. That’s my big secret.

[caption id="" align="aligncenter" width="590"] Image credit: Ashley Courter[/caption]

9. What do you wish your brain was better at doing?
   I wish I were better at deep dives. My special move is scanning the horizon and connecting the dots. What I lack is the focus of a craftsperson who is willing to perfect and perfect and perfect a single skill. I’ve always been a bit jealous of people who are able to go deep.

10. We know what you’re great at, so what job would you be terrible at?
    I’m a terrible project manager. The unsung heroes of creative work are the producers. I’m too disorganized for that kind of work.

11. What habit of yours annoys you most?
    I have a bad habit of pretending like I know what’s going on when I don’t. It comes from being an immigrant and trying to blend in. Learning a new culture and language means you constantly need to catch up quickly. I still do this reflexively, and sometimes it would be easier and more conducive to learning if I were to just admit feeling lost. But it also works in my favor pretty often, so it’s a hard one to shake.

12. What is the luckiest thing that has happened to you?
    Being born to loving parents and given education, access to health care, and resources in a time and place where women can participate fully in business and public life. I basically won the lottery.

13. What are you most likely very wrong about?
    I’m in a permanent state of existential angst, so I’m pretty sure I’m wrong about everything. There have been times when I’ve doubted the very basis of everything I think and do, but I’ve learned to continue moving forward with my best possible guesses.

14. In what ways are you like your childhood self?
    I’ve always exhibited — ahem — leadership qualities.

15. How has your work, or the way you approach it, changed over the last 15 years?

*What the years teach you is comfort in the sticky bits. There are plenty of uncomfortable moments along the way when you’re trying to solve design problems, but you learn to work through them and believe that you’re going to succeed, even when you’re not sure how. *

Having shifted from working in the design trenches to more of a creative direction role, I’ve also changed the way I communicate. With greater power comes greater responsibility to be caring and precise. I shoot from the hip by nature, so I’ve tried to become more disciplined and sensitive in the way I communicate what I see.