8 Lessons from a Decade in the Design Business

In a run-down, hidden building that used to be a movie prop warehouse is where I chose to start a very expensive experiment. It was July 2007 when I opened the doors of Transmitter Studios Inc. I had already been working as a freelance designer and had some incredible full time jobs. My first paid design gig was in December ’96. Despite a lot of learning in that time, the real education didn’t begin until I opened up my own shop.

*Not an actual picture of the studio… Unsplash/Patrick Fore

Seeing so much effort and so much hard work that often ended in failure didn’t diminish the drive to start a business of my own. I had also witnessed plenty of examples where it worked well. A desire for freedom, a creative imperative, a “fuck it, let’s jump in” attitude drove me to build Transmitter Studios. I wanted a home of my own. With good reason.

Leading up to the launch, I had just finished a year at small but very busy web development shop. It was a trial by fire. I wanted to learn how to lead a team as an art director so I agreed to an absurdly low rate and worked maniacally, often 12–14 hours a day, 6 days a week. Incredible lessons learned in working with a team as well as running a business. What to do and what not to do. Invaluable experience.

Nothing ever becomes real till it is experienced
- John Keats

At the end of a year, that company was about to be purchased and I made the choice to take a breath and not join in the transition. I was invited to join the production team at a growing DVD production company. I met with the owners, agreed on a rate, a start date, and shook hands. The idea of designing all day at a human pace after a punishing year, was enticing. The day I started one of the owners called me into the boardroom to sign the employment contract. Knowing that I had quit my last job to join them and had no other options, he reduced the salary offer by $5k. It was a long silent moment before I accepted it. I had no choice. Long after I left, that company took on investment, expanded dramatically and was sold to a much larger company.

Is the lesson that assholes win? Hell no.

It has been said before that business is war. It is. A war to get through each month. And then the quarter and then the year. Each battle getting you one step closer. It’s true that there are people who will try and steal everything in your pockets including the lint to win the war. Though I’ve found those people to be the rare ones. I have been disproportionately lucky to work with enormously talented, hardworking, and generous, designers, developers, writers, and filmmakers. I’ve had mutually rewarding client relationships that began before this studio and some that have spanned this past decade.

Unsplash/Lukas Budimaier

Continuous evolution requires continuous reflection.

I find myself considering successes and failures constantly, not just on New Year’s Eve and the anniversary of launching a dream.

Sure, when looking back I could meander into how the business has changed; the death of Flash, the battle over web apps or native apps, the rise of design thinking, and all the other exciting opportunities. Or I could rehash old business chestnuts; its easier to lose a client than win one, cashflow is king, a project can be good, fast, or cheap — a client only gets two, and on and on. That’s all ground well-covered elsewhere.

Scars have the strange power to remind us that our past is real.
- Cormac McCarthy

For this, I wanted to consider every success, every failure, every conflict, every love affair and friendship and then evaluate — how I felt about it all. And then consider what meaningful insights can be extracted. The hidden opportunities for growth.

Unsplash/Alice Donovan

The individual experiences of this past decade both devastating and elevating could fill 1000 pages. Here instead, bite sized chunks of hard-won wisdom.


1. Do something you’ve never done before with every single project that you work on.

Its easier than you think with the creative and technological options available. You’ll find the urge to re-do the same things over and over. From this assembly-line mentality we get some good things, like production standards. And some bad, like a homogenous design aesthetic found everywhere. Even a template can have its content, layout, palette, typography, functionality, and behaviour customized. Take advantage of the opportunity to learn. It has the added value of making you even better for your clients.

2. No matter how desperate you are for business, fire your worst clients. They will cost you far more than money.

Every single thing in your life takes up a certain amount of mental space and time. Neither of which can ever be replaced. Some people demand far more of your mind and your time than is reasonable.

A good client cares if you get paid a fair price, if your business does well, if you yourself are evolving & prospering. If they don’t — walk away. Focus on the relationships that hold the most promise for excellent work and long term engagements.

3. When you blow it (you will), apologize and back it up with action.

Consistently, when a project ran past scheduled delivery, a discount on the final invoice went a long way to make the client happier. The same remedy is true for all working relationships. Don’t just say you’re sorry, show it.

Anyone who expects you to be perfect or holds you to a different standard than they hold themselves is impractical. Apologize, make amends, or move on if your opposite refuses to find a middle ground. Some people will only ever see themselves as victims or exploit your mistakes for unreasonable gain. Reward the people who legitimately seek solutions not retribution.

4. Regardless of the “on-paper” skills, you will never know what it is like to work with someone until you do. References don’t mean shit.

If I had a dime for every time I was blown away by a developer’s skills only to witness unbelievable lack of professionalism, I’d be dead. Likewise, you might lack what that person needs to provide the necessary balance to get the work done. Finding out a critical skill holder is a nightmare to work with on your most important project is the very definition of excruciating. Trial projects are great opportunities — take advantage of them. They will help ensure the right chemistry for success.

5. Do not invest in employees, contractors, or anyone at all who does not care about; improving themselves, taking ownership of their work, the calibre of your business.

The business graveyard is littered with half-assed efforts. All relationships require investment, if you play the long game with too many team members, your immediate needs won’t be met. Your culture, your projects, and your business will suffer.

You can lead a horse to water but you cannot make her drink. Everyone needs to come to the table ready to contribute, challenge themselves, and play to win.

6. Choose your partners in life and business wisely.

If you come home from a 12 hour day right into another battleground day after day it can have a devastating impact on your endurance. And your overall mental health. Choosing the roller-coaster of entrepreneurship means a commitment well beyond a 9–5. Your limits will be tested. Make sure you have the personal support of the people around you — friends, family, and lovers. Otherwise you may as well hang an anchor around your neck and try to swim.

It is also true that partnership conflict remains one of the primary killers of businesses. A partnership means someone carries the weight when you cannot. They let you excel, without a bruised ego, when you do things they cannot. You, in turn, must provide the balance when needed. Complementary skills make all the difference.

7. Spoil the people around you who deserve it. If you’re lucky like me and have worked with amazing people — tell them. Tell everyone you can.

Did you know that James Reid is an amazing motion graphics designer and filmmaker? That René Ramirez is an incredibly talented full-stack developer? That Lisa Harvey improves the user experience of every project she works on? There is only one person I will ever ask about the music industry — thats Christian Hurst. I could go on and on. And whenever the opportunity arises, I do.

8. For the moment at least, all business is dealing with people. Or chatbots trying real hard to be people.

Entering the workforce and then working in it for years without strong communication skills or emotional intelligence will soon go the way of the fax machine. Check yourself, practice empathy, be worth knowing, and provide meaningful value to the people around you. It ain’t all about the dollars.


Education is hanging around until you’ve caught on.
-Robert Frost

Mistakes, failures, and setbacks are opportunities for learning. Getting better with every day is the goal. The only thing you should fear is dealing with conflict the same way, planning for success the same way, designing the same way — year after year.

The experiences we build in this coming decade will bear little resemblance to the Flash-intro’d, static brochureware of 2007. Better workflows, tools, design and technology standards, and most importantly —better skills for working with people, both creators and enjoyers of designed experience, will define the next wave.

For every single lesson, every tear and every laugh, from clients and co-workers over the past decade I am eternally grateful. Thank you.

See you in 2027.

Top left: Steve Ferrara, Lisa Harvey, Kristen Nakamura’s hair, Kyle Bing’s thumb. Bottom middle: Mr. Christian Hurst, Adam Leon. Bottom right: Nicolas Kadima, Ken Chong, Tracy Horner. Just a few of the amazing people that have made the Transmitter Studios experience a positive one. ❤