Finding full-time work as a designer
By: Darian Rosebrook
Tags: Year In Review, Freelancing, Design, Product Design, UX

Finding full-time work as a designer

This year is a unique moment to be writing a year in review post.

We just ended the decade of the 2010s.

We’re just now starting the decade of the 2020s

I graduated from high school in 2010, which seems like ages ago, yet not that far away. From there, I left for college, left college, got a banking job, started a design business, had two kids, got engaged twice, then married, left my job as a banker, got a job as a designer, and had as many ups and downs as someone should as a human being in a decade.

*breathes for a second

2019 was one of the craziest years I had so far.

Let’s look back at where I started and where I’ve been.

My first full year as a designer was hard for me (2016–2017), I had started learning design and deciding to leave my job as a bank teller and heavily research becoming a designer full-time. My second year was fun (2017–2018). I had opened the newsletter to the world and started building both the Compass of Design brand as well as my branding design practice, So Magnetic. My 3rd year, I kind of fell flat on my face. (2018–2019) I had planned on building the community site and the business to full swing, and I couldn’t focus on the right priority and lost myself a lot of money in the process. This fourth year of becoming a designer, I took on two massive goals and kind of hit both of them. Let’s look.

Hey, do you not have time for the full thing? Well, I respect that and here’s the high level of what I’ll be talking about (I do want you to know that these posts are usually full of resources that helped me get past painful points in the year.):

These can turn into long articles, so for a TLDR of what I learned this last year:

I had two goals for 2019

1. Switch from working as a banker full time to working as a designer full time

I successfully did this, but not in a way that I would have expected. I was looking to do this by going full time into my freelance business.

After a few months of no clients, I decided to look at finding a job but struggled to get past the interview stages with my non-traditional design background. Once I finally gave up on that and decided to pursue clients again, I got a call from someone staffing a job at Microsoft.

I had a phone interview on a Friday in May of last year, an in-person interview on the following Monday, and took the position before I left the campus.

2. Successfully charge $10,000 for a logo design.

I had billed almost $10,000 over three design jobs in 2 months. However, I didn’t get all the money from it. One of the companies that were supposed to pay my business for design services had a complication with a client and went bankrupt. But, now that I could see that I could command the amount in consulting fees that I wanted to do excellent design work, I had my eyes set for what I would like for my work as a designer.

Because of the results of the first goal, I ended up going a different route than client work. Even though the last project proposal I sent for the year was for $10,000 and we nearly started the work, I started earning the same monthly income that I had wanted to make with my own business, just for a single company instead of multiple clients.

The essential lessons that I learned

Companies can learn to value design, especially the value that comes from the work you do when designing an experience. It’s good to find companies that understand this already, however. The same creative skills you use for critical thinking as a designer can apply towards designing a design organization Breaking into tech is really hard if you’re on the outside looking in. It would help if you put the things that sell yourself, your skills, and your thinking into a comprehensive but digestible way. I’ll talk about this more this year, just not in this post. That taking the year off from Compass and content production was what I needed to get back on the horse That you can never have too much documentation on your work in order for it to scale well

To start the year, I had finished up a trainwreck of a client

I had recently finished the business bootcamp by The Futur crew, started applying the principles behind it, and working with a client that was giving the developer/strategist that hired me for the work a hell of a time.

In business, there’s always a chance that you’ll run into a nightmare client. The person we were interfacing with was great, but the business partner was trying to call too many shots of the nature of the creative work and just wanted the work done. My client (the developer) had done everything she could to save the relationship and project, but it went into a legal battle over the result of their arguments.

I decided never to work a non-design day job again.

The work I was doing at the bank as a mortgage loan officer was very stagnant. There was nothing I could do to improve the process or software as a whole. The banks don’t listen to people who work the front lines.

If you had been following my story for a while, you would know that leaving the day job was always the goal. This task has been a struggle to get anything done for it, however.

I started chasing every opportunity that came my way, looking for a way out.

These turn into a lot of “almosts.”

I had participated in the bid process for a “possibly 5 figure branding project.” I nearly secured a 100,000 user experience contract with Boeing I was in the interview process with large and small tech companies like Apple, Facebook (decided to not do it), Amazon, Expedia, GoDaddy, and more unfamiliar companies to me.

This process of chasing leads took nearly 4 months from when I set the goal to leave banking, up until my eventual exit from that company.

The hardest part was getting people to see the breadth of what I offer and could take on as a designer. Brand, UX, and strategy were all things that I did exceptionally well, but I felt the recruiters or companies were turned off by that and wanted someone who only showed one skillset.

How I got a job in tech

I’ve heard it a lot that people struggle to get into tech when you’re on the outside looking in. Either people who are in design school trying to get in now that they are almost done or people who are making career changes from outside of a design-related career.

It manifested itself when trying to find work as a designer myself. I had to leverage many references who could attest to the work I’ve done and could do.

I was hoping there would be more to learn from how I had gotten the work at Microsoft, however. The interview for that went great. I was able to talk with the principal design manager for Edge and we had a great conversation about what their vision was moving forward, it was something that I knew I wanted to be a part of.

During the interview, I had felt slightly overdressed wearing nice slacks with a button shirt and tie. My manager was wearing a metal band shirt with jeans and run down sneakers. haha

I matched his tone when giving responses to question and mirrored a lot of the actions he did when we walked around the room. This is something that I learned from a video on youtube years ago about how to interview. I feel like that was a good start. I walked him through the work that I have done on the Compass of Design Community, the user experience prototypes, and the work I’ve done for clients in the past.

Between being able to walk him through the old design work, and talk with him at a higher level about the design future for the project, I received the offer for the position before I even got off the Redmond campus.

I have thought a lot about this and how this process of applying to everything could have helped others.

I had to go through many interviews to get to this one. Several companies had said no to my application, some were nice to give feedback, and that feedback told me that there were things they didn’t see in my portfolio that would have made the decision easier. I had been refining the words that I use to present myself as a designer. In my resume, my portfolio, in my applications. It became a game almost of how much I had to reduce, elaborate, or replace parts of the ways I represent myself.

After trying many times with all of those edits, I feel like I had finally made a winning combination.

My work for Microsoft

On Tuesday this week, I left my position as a product designer there. It has been a wild run that felt like trying to drink from a firehose.

We shipped our product. That in itself is a huge win.

At Microsoft, I had three general projects.

The Edge Collections feature

Edge collections was a fun feature to work on. The teamwork here was very collaborative by nature. It felt like a game of Hot Potato where you’ll work on something and pass it off to other designers to work on and eventually it gets back to you.

I got to work on the internal branding for a first-run experience, got to work on the discoverability paths of the tool, the brand identity for the project, some thoughts about data presentation, and a lot of interaction design.

The hardest thing for me as a designer switching from freelance to a full design team was the lack of documented processes. There was no onboarding to the project at all; they expect that you pick up and start running as soon as you set up.

In the extra time around the work I was doing on Collections, I had started a document in our Figma setup that allowed people to:

get necessary information about Edge and Microsoft

get information about who is on the design team

the process of getting work approved

where to go for design resources

what to look for in our design standards

how to contribute and start new design files

After two months on this project, I got asked to start looking at how we do that at a much larger scale for the team.

Mapping and refining the product design process of Edge

This was one of the most fun projects that I have had the chance to work on in design. The early work that I did for this got passed on to the other leads to finish up.

Edge already has a very efficient process for product design. Microsoft is a company transitioning from being engineer heavy with design coming in the last moment to “do a design for this thing going out next week” to design being a more integrated process in product and feature development.

Through this project, I was able to sit in on my principal design manager’s meetings, make notes about the hierarchy and structure of design teams, sit with the Product Managers, in spec reviews, and with the team’s handoffs.

This led to presentation reports that I worked in tandem with the Principal Design Manager that I worked adjacent with to push for the specific tech we were building to improve the process.

If I ever get the chance to work on designing another design org, I would love to have that opportunity.

Leading the design initiative for Edge DevTools

After doing my work with that project, they relocated me to the DevTools team under Developer Experiences and with the manager that I had worked on that last project.

This project was a little bit special to me because I was the only design resource that was available for the project. The principal design manager I worked alongside was busy running the developer experience and core design/dev team. This led to me leading a large portion of the project on my own.

For this project as well, in any extra time I had, I worked on documenting our design process. The documentation included developing the design assets, creating components in Figma that was missing in the project, and finding any way to help this project scale after I would leave.

I got to attend user testing sessions where people would have prototypes and mockups to test and talk over things I designed with the people that would use it. I received invites to feature spec review meetings, user testing, and feature launches. It was a great experience to help work on everything from feature work, to design process.

After we launched this year on the 15th of January, that work wrapped up and now I’m looking for work again.

This entire last year was an extremely busy year, and now that I’ve got that work under my belt, there are a lot of things to explore and see how this work applies or maps to different companies, types of work, and anything else in my life.

I want to thank you for being here and reading this, if you reach this point at all in the review, I’d like to answer any questions you have about the work or processes I’ve set up. I know it can be a struggle getting work as a designer too, the months of searching alone was evidence of that. haha

But hey, let’s keep the conversation going.

What was it that you had learned in 2019? Anything you’re excited for or nervous about in 2020?

I think the best thing I’ve learned all year is that you can never have too much documentation on your work.

This year, expect to see me sharing more about how the work I did last year impacts my design work going forward. (:

If you would like to learn more about what we’re doing with the Compass of Design, you can check that out at compassofdesign.com where you can sign up for our newsletter for tons of design resources, and thoughts about how to improve yourself as a designer.