8 Lessons from My First 8 Months

About designing at a startup, remotely.

Andy Leong
Perpetual Perfection
4 min readMar 24, 2017

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Working at a startup is hard, but being a remote first designer at a startup is something I had no idea how to do 8 months ago.

I’m certainly still no expert, but here are 8 things I’ve learned along the way.

1. Commute Anyway

One of the perks of working remotely is that you can work from home. My advice: don’t. It’s hard to maintain work-life balance when your house is the venue for both work and life, so find a place you can physically go to that is just for doing work, and make it a habit to go there. It helps reset your mental space for getting stuff done, and then back again to relax and recharge at the end of the day.

2. One-on-One Often

It’s hard to connect with your team when your only interaction with them is through Slack or video all-hands meetings, but understanding the people in your organization is so important to doing good work.

One of the best ways I’ve found to fix this is to periodically schedule short 1:1s with each team member over video chat. Ask questions about what they’re working on and where they’re having pain points. Your designs will be better informed with that knowledge, but you’ll also establish stronger relationships with your coworkers, and that sort of regular engagement is a critical part of selling your work internally.

3. Ask Questions, Defend Your Answers

Especially in your first few weeks as a new hire, you’ll find there are lots of things you don’t know, so don’t be afraid to ask a lot of questions. Ask about your organization’s processes, how to get your work approved, clarification on business goals. As a remote team member it’s critical that you take the initiative because it’s much harder to observe and absorb those answers from far away.

However, don’t let those questions stop you from forming your own answers about how things should be done. You got hired because your company believes in what you have to offer, so put your skills to work and take ownership over your ideas.

4. Mark Up Everything

Don’t assume your work speaks for itself. When your deliverables are sent without context and you’re not around to explain them, odds are they won’t be interpreted how you intended. A lot gets lost when you’re not communicating face to face, so make sure you provide rich comments on all your work. It’s more work on the front-end, but the frustration it saves you on the back-end is more than worth it.

5. Never Stop Learning

It’s easy to get caught up in the day-to-day busyness at a startup and forget to take care of your own professional development, but you owe it to yourself to commit to your craft. It’s your love for design and the things it can do that got you into this game, so don’t forget to nurture that skill set as you go.

Besides, there are so many great resources available for designers you really have no excuse not to. Pick up a book, watch a tutorial, or go to a meet up and engage with others in your field. It’s easy, it’s energizing, and it’ll show up in your work.

6. Maximize Your Trips

Every now and then you might be fortunate enough to travel to meet with your team in person. These trips have lots of potential to be truly impactful for your work, so milk them for all they’re worth. Pack light and get into the office as quickly as possible. Shaving off a few minutes here or there in between the airport and the train helps to not only give you more time with your team, but also minimizes your mental drain on the commute, leaving you with more energy for what really matters.

Speaking of what really matters, make sure you plan ahead and schedule team meetings and 1:1s in advance. These trips are your chances for real face-time and collaboration, so don’t travel just to do individual work.

7. Take Actual Breaks

Twitter. Facebook. Dribbble. These are not actual breaks. When you’re working remotely, you need to get away from the screen, because the line separating your work from the rest of your life is fuzzy enough as it is. Combat that by getting away for a run, play a musical instrument, cook a fancy dinner. Avoid scrolling through a newsfeed, checking your email, or really just looking at anything with a digital interface. When you find ways to engage your other senses and give your visual cognition a rest, you’ll be restored and better equipped to see your work with fresh eyes.

8. Always Be Closing

The 80/20 rule says that the first 80% of a project only takes about 20% of the effort, but finishing the last 20% takes 80% of the effort.

The 80/20 Rule, in Giant Chart form.

Brainstorming, sketching, and ideating are often the easiest and most fun parts of the design process, but execution is the most difficult and arguably the most important.

If you want to be a successful remote designer, you have to be committed to closing. Shipped product is the best product, even if it’s not perfect, so see it through to the end and get it out there.

The next time you see a great opportunity to design remotely, don’t get scared off by the challenge. You’d be surprised how much you can handle when you give yourself a little structure, and with any luck, you’ll thrive in it.

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Andy Leong
Perpetual Perfection

UX Designer @karat. Formerly Design Lead @PlanetBravo. Living in SF but left my heart in LA. Eph 2:8–10