Having a job sounds really nice, sometimes.

What am I missing out on?

I’ve been running my design studio, Cottleston Pie, for 3 years. When I left my job as Principal Designer at Blue State Digital in 2012, I had a choice of what to do next. I loved working at BSD, the work was fulfilling and the people were my favorite. But it was time to switch it up. I was considering a few options of what to do next:

  • Getting a job at another agency
  • Going in-house at a product
  • Starting my own design studio

Each option presented some really great opportunities, and it was a choice that I wrestled with, and consulted with a few people about. Spoiler alert: I started my own company.

I’m really happy with the decision that I made. But every few months I stop and wonder if I made the wrong choice.

What am I missing out on?

  • I think about the amazing Creative Director that I could be working with and learning from.
  • The larger projects that I’ve missed out on that a small studio like mine might not take on.
  • Health insurance.
  • I live in New York City! Home to so many amazing creative people. Am I squandering my time here by not working with the talented folks here?

Maybe. Or is it just FOMO?

The freedom of being your own boss is really great. But thinking back on my time at an agency, there are a few things that I really miss.

Working with, learning from, and mentoring others

One of the most valuable parts of working for a company is the people. Working with people smarter that yourself is something that can’t be replaced. Having a mentor to take you under their wing, show you their approach, and trust you enough to do a great job, is invaluable.

Having a project manager

I didn’t fully appreciate project managers until I started my own studio. A great project manager enable designers to focus, and do their best work. They can serve as a surrogate for a client, by understanding the business goals of the project and can be a great gut-check to make sure concepts are on target.

Collaborating with other designers

I miss collaborating with other designers! I don’t often have budgets large enough to hire an additional designer for another direction, and I miss that. Working with a few people to think through a problem and come up with a solution is a great exercise. Whenever I work as part of an already existing team, I’m reminded how important it is to have people around to bounce ideas off.

That all sounds great. So why don’t I go get a job?

Hold on now. I’ve noticed a few things that I’ve learned by running my own business that I may not have if I worked somewhere else.

Having no backup can be a good thing

Running a studio without the infrastructure of an agency is a lot of work! You have to:

  • Talk to potential clients through the business development phase.
  • Sell yourself and your work to a client.
  • Be the point person for clients, meaning you have to meet with them, understand the immediate goals of the project, as well as the long-term goals for the business.
  • Learn about your clients and their position in their company, and empathize with them, to not only solve their business problems, but also make sure that they look good to their bosses.
  • Present your ideas directly to your client (and probably their bosses), with no PM there to back you up, or cover for you, which means you really have to understand the problem and to be able to back up your solutions.
  • Manage client feedback, and respond with your own thoughtful answers and questions.

That’s a ton of work! But doing all of that makes you a good listener, a good business owner, and a really good designer.

Being thrown (or throwing myself) into situations where I have to figure it out is scary! But what better way to learn?

Empathizing with other business owners.

Running a business is hard. Having that experience and understanding what other business owners are going through may give you a different perspective than other designers. You might connect with and empathize with the CEO of a company in a way that a designer from an agency might not. Take advantage of that.

Working with other people

The way Cottleston Pie works is often in partnership with agencies and other small teams. This gives me insight into a lot of different ways of working. Each new team I work with, I learn something new and can take that and apply it to my own process.


Every time work slows down, I start thinking about what could have been. But then another interesting problem comes along to solve, and I’m reminded of how valuable this experience can be. Onward!

Remember, comfort is overrated.