🍔

Mistakes Were Made: A Career in Design

ExplodeConf • November 23 2017

Talks

I was the closing keynote at Explodeconf, a lovely little conference in London, Ontario.

I always joke that the talk I’m going to give at every single event is called “What Even is Design”, and I finally get to do it, thanks Explode Conf
but this talk is really called Mistakes Were Made: A Career in Design
because I think everybody’s career is going to be different than they expected and hopefully better than they expected
mine has definitely gone in some ways I sure wasn’t expecting
And I think it’s important for both personal and professional reasons to periodically look back at where we are to help us see where we’re going
How many people here are designers, or work in a creative industry?
That’s awesome
So: PLEASE DON’T use my career as a guide on how to be “successful” in a creative industry, there are a million paths to get where you want to be
but please DO try to take away something from lessons I’ve learned the hard way, even if it’s “definitely don’t do that”
hopefully here’s a nugget of wisdom in there that applies to where you are right now
Honestly I’ve had a great time so far as a designer and I’ve still got a ton to do and ton to learn
and I’m pumped that I get to share what I’ve learned so far

The reason I called this MISTAKES WERE MADE is that I think it’s easy to look back and go “oh man, whoops”
I tweeted this two weeks ago as a joke but honestly it’s more or less this talk in a nutshell
Everything in a career – even the tough, crappy parts we’d rather not talk about – has value. It’s all learning experiences.
Part of the journey of my career has been a voyage from being terrified at all times that I’d screw something up to being pretty okay with knowing I don’t know a ton of stuff, and being okay with OTHER people knowing I don’t know.
– before we dive into the story of how I got to where I am, I need to introduce the supporting character for my tale,

I call him CAREER SHARK
This is a true fact, some sharks will drown if they stop moving
And this is also a true fact: sharks are pretty scary
probably mostly due to the mouth area
And I feel like Career Shark has been responsible for a lot of my career progress due to those two facts
Specifically
Career Shark is always prompting me to to keep moving
Never feeling like I can settle for the status quo, always be thinking about what the next thing is, what is the thing I’m moving towards
… and

SAY “YES”
say yes … to … everything.
Do things that are frightening, things that you are not absolutely prepared for.
For example, I started doing particularly this kind of thing – speaking at events – in the spring of last year … so not quite two years ago.
You might not think so right now because I’m up here doing this, but I am a very shy, introverted person … so this was maybe the scariest thing I’d ever done.
And I think it’s fair to say I was probably a garbage speaker. But: that was my foot in the door.
And it’s been extremely rewarding to push forward and do the things that seem way harder than I’m ready for.
So let’s dive in.

Part 1 is the first part of every designer’s life: being a Junior
Maybe you’re fresh out of school, maybe you’re just winging it or giving freelancing a go, and trying figure out this whole “design” thing
there’s no right way to start out

but I personally started out in an agency, which looked sort of like this only less nice and less tidy
I spent the first part of my career there – nearly 8 years, which is an ETERNITY in this industry
a very small agency that kind of did everything.
Websites, print, packaging, branding, signage, video –
the whole gamut of “things that can be designed”.
And I think some people would find this lack of focus pretty concerning – like … oh, you want to be a – “whatever” designer?
you better double down on exactly that one thing.
right now I think “Product Designer” is the thing everyone wants to be.
But I think digging into the breadth of experience and deliverables was actually critical
because when I was starting out as a junior designer, there are definitely things I needed to learn
that every designer needs to learn –
that you’re not going to learn unless you do a little bit of everything

And this is important because one of the ideas I keep coming back to, in terms of how I think about creative work
– not just design but programming, writing, even art –
is that, at a high level, it’s just really, REALLY refined pattern recognition.
You become faster and faster and faster at recognizing the type of problem you’re trying to solve
this is a muscle you can build.
I don’t think I have more – call it “raw talent” – than a designer just starting out.
What I have is years and years of flexing that pattern recognition muscle.
We’ll come back to this.

So I was thinking about the framework of this talk
and I think at each stage of my career there’s definitely been some commonalities, some structure around my thinking
And that’s
1. What am I learning
2. What am I worried about, and
3. What comes next

So as a junior designer
you’re on the bottom of the ‘design pyramid’ [DESIGN PYRAMID]
I mean you don’t know *ANYTHING*
You are literally learning the craft of how to be a professional at the thing you decided you wanted to do as a job
Like, literally, the nuts and bolts of how – to – do – design
And that’s critical, that’s bedrock that you’re building your entire career on
So think having ALL of that experience on different stuff under my belt was an early boost
In my work as a product designer in my recent career, I never need to know how to specify weird fluorescent inks or talk to printers about paper weight…
That’s not DIRECTLY useful in my day-to-day now but it’s INDIRECTLY USEFUL
because design is HOLISTIC.
Every piece of knowledge you can bring to bear on a problem is a chance to flex that pattern recognition muscle.

and this also the reason why, when speaking to young designers who are looking for career advice, I think it’s easy for me to forget that they’re still dealing with all of that stuff
And also why I tell them their first job should NOT be in a startup, but that they should work in agency life for a bit
Because Agency Life is a harsh bootcamp in what even is design –

How do juniors do on our trifecta of questions?
What am I learning: look and feel
the actual boots-on-the-ground skills of DOING design – this is literally, like, how to construct a design in your tool of choice, how to apply pattern recognition and problem-solving to a specific kind of problem in a ‘design’ way.
This is very much a muscle.
What am I worried about: I mean … everything.
This is true of most jobs, I think. Just … how do I … job? Don’t worry! Everybody has to figure this out. Nobody jobs good right away.
What comes next: I dunno because I’m still worrying about how do I job.

Part 2 intermediate designer
Oh nice, I grew up a bit, I got pretty okay at design
As an intermediate designer, you’ve kind of got the mechanics of design down, you can be trusted not to go off into the weeds on a project

You start to see the ‘shape’ of what design looks like, how to consistently apply your skills.
Nice!
But this means – ESPECIALLY in a smaller company – you’re also given more responsibility.
And so I started getting invited to speak directly to clients
to understand where they were coming from
I mentioned earlier that Agency Life is a bootcamp in what even is design –
And the part that you learn when you’re not worrying SO MUCH about whether or not you can literally do the work
is that agencies live or die by getting business in the door and getting work out the door, and both of those things need to happen as close together as possible
I actually think this is great because you can have a lot of the preciousness around design ground out of you at this point,
and that’s because…

DESIGN IS A BUSINESS
you begin to get the impression that design isn’t just about GRIDS or CHOOSING A GOOD FONT
Because what I think you start to gather as you become a little more experienced is that
DESIGN ISN’T ART
DESIGN ISN’T FOR YOU
It’s solving problems.
It’s solving problems for MONEY.
And when people are paying you money to solve their problems, you better make sure you’re solving it.

I use this image in basically every talk I’ve ever done
and it should be used in every design talk ever
Because the learning, once you start talking with customers or clients, is that you figure out if you’re solving the right problems by understanding where your clients or users are coming from.
You get into their heads, gain an understanding of their context.
It’s the point in your development as a designer when you stop thinking about “how” to design and start thinking about “why” to design.

Let’s look at our three questions from an Intermediate viewpoint
What am I learning: Design isn’t look and feel, it’s about problem-solving.
You also realize – uh oh – that maybe a career in design is a series of escalating mental frameworks around the “work” itself
It’s not just about the work, it’s about contextualizing the work
What am I worried about: Well – do I know how to solve people’s problems?
As soon as you’re exposed to the PEOPLE – the CLIENTS, THE STAKEHOLDERS – in design, you realize that design is also about those soft skills. UGH
Remember when I mentioned earlier that I am a shy introvert?
Yeah, this was a painful part of my career. Like a really painful, terrible part of my career.
But also remember how I said that design is a pattern recognition muscle that you can exercise?
Turns out this also works with improving your communication skills.
What comes next: Figure out the framework around skills – what’s the BUSINESS of design?
There’s a reason that design sometimes used to be called “commercial art” – it exactly straddles both of those worlds – art and commerce – and both are important.
You OBVIOUSLY need to do good work – but you also need to pay the bills.
ESPECIALLY If you’re a freelancer – and I’ve been a freelancer three times in my career – you need to get PRETTY good at figuring out where that art/commerce line lies.
Whew. So that part lasted for a few years. Then what?

thinking about the design pyramid, logically the next thing should be becoming a senior designer, right?
I think the interesting thing about careers is that it can zig and zag in ways that you weren’t expecting
Here’s how I thought a career goes
A really nice, sensible progression
… AAAND …

and here’s how a career really goes
A huge squiggly mess
I decided, after being in the agency world for nearly a decade, that it was time to try something else
Career Shark in full effect here
This was possible the biggest change I’ve ever made in my career and also the scariest
I had no idea what I was doing, wasn’t sure it was going to work out, and was leaving behind my work family to do something possibly entirely foolish
It’s time for EXCITING STARTUP LIFE!
Let’s pump the brakes on this story – I said work family and the really salient part of that is, indeed, the word “family”
one of the best parts of my entire career has been getting to work with some truly stellar people and make friendships that are still going strong even after leaving the job in question
If you spend 8 years anywhere you’re going to see those people more than your actual family members
you ARE going to build meaningful and lasting relationships
that’s like ripping off the world’s biggest bandaid when you leave
I was so, SO comfortable in that agency world
But this is part of why Career Shark is scary
if you’re no longer growing, no longer being challenged, is that job still the right fit for you?
I mean, Maybe! But not for me.

okay back to EXCITING STARTUP LIFE
product vs. agency: the interesting thing to learn by making this jump is, despite both being concerned with ‘design’ and ‘experience’ as their output
agencies and startups work very differently
Agencies are trying to solve a lot of problems so they don’t run out of money
Startups are trying to solve exactly ONE problem BEFORE they run out of money
And that means the practice of design is very different
In agency life, you work on something and throw it over the fence: it has to be perfect … ISH, and done-ISH, and you’ll probably never see it again
In startup life, you are working on the same problem forEVER.
Where I am now at Wealthsimple, for example, every day is about solving the same problem: how do we make people feel good about investing online?
You need to think strategically instead of tactically – make sure you’re answering BIG PICTURE questions as well as the small day-to-day questions.

so
I wanted to share something that happened to me during the first time I worked at a startup
I took a big gamble and it paid off in experience and new friends and new knowledge and I got to work on cool stuff
and after a year … I got fired.
Was it because I wasn’t doing a good job? I’d like to think I was doing at least a pretty good job
but the upshot is I’ll probably never know
This isn’t something I talk about a lot and it kind of screwed up my confidence for a long time
And I think it’s worthwhile for me to share this, because you probably will have these kinds of crossroads moments in your own career and it’s hard and bad … but … it happens to everyone.
So what I’m saying is, this felt like the end of the world at the time …
but it also taught me how to have perspective and evaluate what parts of the job actually mattered to me.
And having perspective and being thoughtful about the work is a good way to get to ….

… Senior designer!
Sometime during this period I emerged from the chrysalis of an intermediate designer into a senior designer
I should say that all of these changes felt extremely gradual – they have the blurriest borders possible
you’re not going to wake up one morning and say “Oh dang guess I’m a senior designer now”
It’s more of a slowly dawning realization.

I think the perfect example of this is that I’ve been doing this for … … a long time. A real amount of time.
AND I work with someone presently who’s been doing this for, like, three years… but on a purely “skill” level, they’re a better designer than I’ll ever be.
Perhaps part of the process is becoming a senior is realizing you don’t have to be insanely great at every single aspect of the job.
Design is an umbrella that covers a LOT of things.
I am a senior designer because I’m quite good at a handful of things and pretty good at a few other things, and good enough at a LOT of other things to be useful … or dangerous.

We’ve leveled up
What am I learning as a senior: Design isn’t relationships, it’s value
You’re not just solving problems, you’re making sure the problems you’re solving actually have a tangible business goal
When you’re a senior you become expected to know WHY design matters to your clients,
WHAT is the outcome that they expect design to drive?
You begin to realize that design is often about information asymmetry –
they have the problem
and you have the solution
and you have to sell the idea that the solution you have is going to solve their problem
… and sometimes you’re wrong
… and it’s on you to figure out how to fix it
it’s not somebody else’s problem anymore
… and the other challenge with value is thinking about how horizontally or vertically you’re delivering that to your clients
you end up wearing a lot more hats
not just a designer but a client-wrangler and project-manager and direction-setter – that’s horizontal value – and
OR, go vertical, go deep, maybe think about becoming extremely good at one thing
like becoming an EXTREMELY good mobile designer or a REALLY technical designer who can also develop
Those are both ways in which you can add value to what you’re doing
To be fair I’ve always been a generalist but that’s definitely not the only way to do it.
What am I worried about: doing the right work, the work that moves the needle
When you start communicating at this level, you start getting to use fancy industry terms
like ROI and CAC and ARPU, which are all real things and you have to know why these things matter
What’s next: Fundamentally the first time I really thought about this
MORE career paths are open to you at this point than you might expect
Because one of the ways you get to be a senior designer is to be RELIABLE
and reliability is always in demand

SO:
Learned a bunch of stuff about product …
and took another zigzag and took those those learnings back to agency life!
The fun thing about being a senior in agency world is that maybe you get to work with the clients you never thought you’d get to!
This is absolutely something I haven’t touched on at all but when you get to a certain point you get to start working with, like, companies and brands you’ve actually heard of
and this is extremely exciting
and while you realize that while they’re really just like any other client, but the scope of their problems is much, much larger
THIS IS FUN
It’s FUN to solve problems that have BIG real-world impact.
Like: let’s say I did something that made 1 million people’s life easier, I shaved like 5 minutes off something that used to be annoying.
5 million minutes is NINE AND A HALF YEARS.
Design just created nearly a DECADE of saved time. How cool is that?
It’s so worth it to hang in for this part of a career in design. I think I kind of could have stopped right here and just done this kind of work forever and been pretty happy.
BUT

HEY
HEEEYYYY
WHAT IF YOU DID SOMETHING ELSE
WHAT IF YOU ASKED FOR MORE RESPONSIBILITY

We’re at the peak of the pyramid!
We’ve evolved from senior designer to lead, or team lead, or director, or whatever
This is where THE BUCK STOPS WITH YOU
This is where I’m at right now.
And getting here is a journey unto itself – when you actually STOP doing the thing that you’re really good at and have to learn a whole new skillset, if you decide to go this way.
You have to turn that pattern-matching muscle back on itself and use it to figure out how to design teams and organizations as well as you, or I, learned to design the actual work itself.
It’s hard. It’s really, really hard.
I don’t think I’m good at it … YET.

So what am I learning: Turns out Design isn’t about value, it’s about PEOPLE
You’d think it’d be about “VISION” or “INNOVATION” or some other buzzword
but not really
It’s about finding people to think about aaallllllll the concerns we already talked about and empowering them to act on those problems
It’s about clearing the way for THEM to climb their own pyramid.
What am I worried about: That I’m not doing enough. That I suck. That’s I’m letting my team down.
when I was responsible for my own success, no sweat
responsible for other people? Oh god, the daily fear.
Parents in the audience, I assume this what it’s like to have kids. I just want everyone to be happy and fulfilled all the time and that is 100% guaranteed not to be a thing.
this is the hardest I’ve ever worked and the thing that feels the least like “design”
But I have to balance all of this with delivering a product that works. That works on ALL of the other levels I identified as things that were design: – look and feel – problem-solving – value
It’s a real trip.

The realization I had as a lead is that your team is a small family that you need to nurture
and help them, you know, do all the other stuff I had to do as a junior and intermediate and senior
BUT
I haven’t talked about HOW I actually got the opportunities to move up the ol’ pyramid of design
Turns out “say yes to everything” means you go to a LOT of things and meet a LOT of people and make a lot of friends
even as a brutal introvert
One of the things I love about the design community is that it’s kind of grown up around me as I’ve grown as a designer
You’re building another type of extended family by making those connections and just putting yourself out there.
This ladders all the way back to the very beginning of my career
When I was a junior I didn’t know ANYONE
But I went to meetups BECAUSE I didn’t know anyone
and it was super awkward and embarrassing and I met some people who I’m still friends with, more than a decade later
So what I’m getting at is this –
you definitely DO NOT need to be a team lead to think about how you’re nurturing that family
you just need to start doing it, and eventually you have friends who might be like “Hey, I have this interesting position opening up, do you want to come and build something cool with me?”
So what’s next … WELL.

Well – this is something I’m still coming to terms with, myself.
This is a hard realization because I worked hard as hell so I could get from the BOTTOM of this pyramid to the TOP.
So what I’m learning now – and I don’t think I’ll ever stop learning or rediscovering –
is that in fact that it’s a pyramid at all.

It’s a path!
and … it just keeps going.
Career Shark is pleased because definitely frightening to be at a point where I have a huge amount of freedom to choose what to do next
there’s no guardrails, all I have is other people at similar stages of their own careers just trying to figure out the same thing.
I don’t know what my job is going to look like next year or even in a few months
But design – among other things – is people.
I don’t have to figure this out by myself, and nobody really has it all figured themselves.
Which is in many ways reassuring.

What I do know for sure is that mistakes will indeed continue to be made – and I’ll keep learning.
A career is really ultimately about forward movement as I continue to find out where that squiggly path goes.
And that’s very exciting.
thanks.