Be the first designer at a start-up.

So, a couple of years ago, I joined a start-up (of 6 people!) as the first designer. When I tell this to another designer, they’ll usually say something like this:

“I’ve thought about doing a start-up, but I’m just not sure, you know?”

I do know. And I know what you’re really asking: “Should I do it?”

Yes!

But, being a designer at a start-up isn’t what you expect.

I was definitely unprepared. Those first months, I was uncomfortable, insecure, and occasionally miserable because my expectations didn’t align with reality. I knew what agency life was like, what big corporate life was like, but when it’s you and a few friends trying to build a product, what is that supposed to be like?

Those challenges pushed me to become a better designer and a better person. I’m happy I made the leap. But man, if I’d been prepared, I could’ve avoided some of that pain.

So, if you’re considering becoming the first design hire at a start-up—or even becoming a designer founder!—ask yourself these questions before you take the leap. First off…

Do you want to do everything?

I mean everything.

Need wireframes for a new feature? That’s you. How about usability studies on a prototype? That’s you. Visual design for a new landing page? You again. T-shirts and stickers for an upcoming event? You too. Ads? You. Illustrations? You.

When the company is young and you’re iterating on the product on a monthly — sometimes weekly — basis, the design needs and your workload will change constantly. You need to be comfortable being a generalist for the early phase of the company, and switching context fast.

What if you won’t — or can’t — do it all? You have a couple options:

You can hire a freelancer or an agency to take some of these tasks off your hands. But if your company is young, your budget may be too tight to hire the big name designer you want for landing page illustrations.
You can hire designers to balance out your weaknesses. This requires your start-up to have the cash to hire more designers. Even then, you’ll still want to hire generalists as the product needs continue to shift.

You should walk into to a start-up accepting that your work will change drastically from one week to the next. You should be comfortable doing it all — even if you’re not a pro in every area.

So if you’re down to do it all, the next question to ask is…

Can you define your own direction?

As the first designer, you will be the only one determining the design direction for the company, and the only one determining your own direction. You are starting with a big, blank canvas.

You may find yourself deciding the following:

What does our visual identity look like?
What features do we prototype to determine product direction?
What are our user interface guidelines?
What’s the tone of our product, and how is that reflected across our marketing materials?
What is our company design process?
How do I solve [insert problem here]?

Yes, you’ll work with other stakeholders, including engineers, marketers, and even the CEO. But it falls on you to take a look at that blank canvas and make the first mark as designer.

Can you work alone?

If you are the sole designer in a company, there are no other designers to give you feedback.

You should ask your teammates for feedback. Their feedback will be valuable! But their feedback will be different than the feedback of a designer.

Consider these two comments:

“I’m not sure. Something feels a little off with the text here.”

“The all-caps, wide tracking on the CTA feels too uniform. It doesn’t stand out among the other elements on the canvas.”

There’s no one else to give you the latter feedback.

If you can look at your own work with ruthlessness and detachment, you can compensate for some of the risk of working without critique. But that inherent loneliness — no designers to bounce ideas off of — that doesn’t fade until another designer joins the company.

Are you comfortable with risk?

So let’s say you’re cool working alone and independently at the start, and you like a variety of work. You join or found a start-up. Yay! You probably want the following to happen:

You work on solving a problem that you find fulfilling which helps a lot of people.
You work with a team of awesome, intelligent people.
???
Profit!

But, you’re a good designer. You know this is The Happy Path™, and in our world, The Happy Path™ doesn’t occur often. Instead, you’re facing a number of possible obstacles:

The company runs out of money and folds.
The product isn’t gaining traction. You have no idea why.
The company pivots, and you’re not passionate about the new problem to solve. You like the team, but you’re disengaged.
You make a design decision, and your users hate it.
Cash will get tight, and your working environment may take a nose-dive in happiness.
And thousands of other speed bumps you can’t predict.

I guarantee that the start-up you join will change radically over time. But there’s a risk that the company may change for the worse!

But, be comfortable with risk! Be comfortable with the fear that something you build may fail, regardless of what you do, and potentially because of something you do. If you can accept this, you have the opportunity to take some even crazier risks with huge payoffs. But there’s another thing about taking risks…

Can you sacrifice perfection?

In the early days of the company, your team is figuring everything out. What is our product? What is our market? Who are our users? How do we generate revenue?

So, you‘ll try different things. A lot of things. Quickly.

For a designer, this means the following:

Lots of prototyping.
Lots of iterating.
Incurring design debt in early iterations of the product.

Because the product direction is uncertain, features may feel disjointed and inconsistent. If you’re a perfectionist, it‘ll drive you mad. And when the company finds product-market fit, you can polish your product and destroy design debt.

Ask yourself if you can live with the discomfort in the short term for benefits in the long term.

Are you comfortable leading design?

So let’s say things are going well. You have users — customers! — and the product is shaping up to solve their problems. The company is growing, and so are design needs. The company raises a round, and you hire a second designer. Then a third. Then more.

Suddenly there’s a design team. Wait, who’s leading that?

If the company is successful, as the early design hire, that might be you.

However, the very skills that made you effective as a designer when the company is small are not the same that help you lead a team. Unless you have previous leadership skills, be prepared to start from scratch. It will be just as uncomfortable as those first days at the company.

Perhaps you’re not comfortable in a leadership position. After all, being a generalist designer was one of the reasons you joined the company early on.

That’s fine! But you may have to hire someone to lead you. If you stay long enough with the company, be prepared for this scenario and keep an ideal candidate in mind.

Regardless of your choice, you’ll still have a massive impact on how design works at the company. You build the foundation for how products get made, how research is conducted, and how design is perceived across the company.

Consider the following:

Will you push for time to do user research when deadlines are tight?
Can you explain why that extra bit of polish matters right before launch?
Can you ease fears when you pitch a bold design direction?
Can you explain the value of brand equity when your team wants to cut corners?

As the first designer, your answer to these questions has an impact on the future of the product. It’s the small things that make a big impact, and you have an opportunity to build those best practices from the ground up.

So that’s a lot. Excited?

You don’t have to be the genius generalist, or the independent design lead when you start! But if you’re aware of what you don’t know before your first day, you can address these problems before they become problems. You won’t be blindsided. You’ll be confident! You can do it.

So, a start-up might be right for you! Next step is finding the right one. There are tons of articles out there on selecting the right company and founding one, so I won’t get too deep.

Two tips, though:

Make sure design has a seat at the table. This is hard to suss out beforehand, but look to your compensation, responsibilities, and the organizational structure for clues.
Actually, better yet, become a founder. The best way to ensure a product is design-driven is ownership. As a founder, you have a lot of ownership.

And if you’re doing it now — maybe you’re a designer-founder, or a first designer— here are my tips for enjoying the start-up rollercoaster:

Find a mentor.

If lack of direction and uncertainty becomes too overwhelming, talk to someone who’s been there before. You’ll find out that your problems aren’t as unique as you think, and a little bit of guidance can go a long way.

I talk to my mentor when things get tough, and there’s nothing so reassuring as hearing, “Yep, I’ve been there.”

Find another first designer.

Feeling lonely? Feel like you have no one to talk to? Find a lonely designer. Having a comrade to talk to is great for many reasons:

You two can let out steam and share support.
Sharing problems and comparing solutions.
Need design feedback? Do mini-critiques with each other on non-confidential work in progress.
Make a new friend.

I meet with my friend Jeff for coffee every other week. When things are tough, we brainstorm solutions. When things are incredible, we celebrate. It’s awesome talking to someone who’s in the same boat.

So go for it.

A new world of challenges await. Now that you know, you’ll tackle ’em with ease.

How’s your start-up experience going? Shoot me a hello on Twitter — feedback and discussion appreciated!