Making a Career Change Successfully, as Told by 3 People Who Did

The career changers:

Jess (left) is a Digital Project Manager. She joined Viget as a Project Manager after 3 years of software engineering in the financial services industry.

Annie (center) is a Developer at Viget. She started her career as a high school math teacher, then became a Program Coordinator for an education non-profit before learning how to code.

Dave (right) is a User Experience (UX) Designer at Viget. He spent the previous 10 years as a financial analyst, most recently as a Senior Portfolio Manager for the U.S. Treasury Department.

When did you start to think about changing careers, and what got you interested in your new field?

Jess (PM):

I studied engineering in college but all the jobs presented to me upon graduation seemed like the wrong fit for me. I finally landed on a software engineering role, thinking I was more interested in coding than in mechanical engineering. Still, I didn’t feel excited about the work. I enjoyed the problem-solving aspects of the role, but was restless by myself in front of a computer for hours on end. I realized that the parts I liked most about the job were understanding the need for the feature I was developing and seeing the stuff I built being used by other people, which was more like the role of a technical product manager.

Annie (Dev):

I was a program coordinator at a non-profit and they launched a new website. The webmaster went on maternity leave shortly after, so I started trying to figure out how to make small changes to the website myself. I liked this new challenge and I became interested in learning how to code from that experience. Knowing I wanted to do something different, I pursued learning how to code using online resources and then looked to see if there was a path for me to do it as my career.

Dave (UX):

I started thinking about a career change a few years ago, when colleagues that I admired started to move up or into positions that I didn’t see myself in. Around that same time, I was tinkering with connected hardware devices as a hobby, and I was slowly learning about the world(s) of code and product design. When I thought about what would make me the happiest, I kept coming back to this hobby. I wanted to design digital experiences across lots of different devices and learn more about user experience and product design.

What resource did you use that was the most valuable in helping you gain the skills you needed for a career transition?

Jess (PM):

I do think my experience as a software engineer was pivotal to quickly understanding the digital landscape I was entering. But project managers draw on a lot of different experiences and skills to be successful, and I don’t think there was any one resource that taught me what I needed to know. Many of the skills that make me successful were traits I already possessed that I’m just improving by being around other talented PMs here at Viget. A good PM generally starts as someone who is detail-oriented, organized, and eager to learn. Like most things, a lot of the actual learning will happen once you start the new role.

Annie (Dev):

Since this was 2013, code schools were just becoming a thing, and I didn’t know anyone who had been to one. After doing some research, it seemed like what I wanted to do, so I applied to a bootcamp in Chicago. I kept my full-time job in DC for another few months while doing the pre-work for the bootcamp, then left DC for the 10-week bootcamp in Chicago.

I tried to learn as much as I could in between realizing I was interested in coding and actually pursuing it as a career. I used online tutorials and books and blogs, and those helped me hit the ground running once I got to the bootcamp. I wouldn’t necessarily recommend bootcamps to others unless they’re already confident that they want to be a developer and have done a fair amount of coding on their own. The landscape has changed a lot since I went.

Dave (UX):

I eventually went the route of an online bootcamp, which provided me with the skills I needed, or at least helped me understand the ones I needed to learn on my own. But what was probably the most helpful, especially early on in my explorations, were some free UX classes I took at the library and an inexpensive, local UX conference I attended. Both of those experiences gave me access to UXers and other working designers I otherwise didn’t have in my existing network. I picked their brains about what their day-to-days were like and what they liked most and least about their jobs. It also gave me some early insight into the types of skills I would need to learn and/or continue to hone in order to make a career change.

When you were ready to start interviewing, what steps did you take to get your foot in the door in this new industry or field?

Jess (PM):

First, I spent some time crafting a “cover letter” that was a clear, persuasive narrative about why I was transitioning into a PM role and why I thought I would be successful in the role. Not only did this help me land interviews, but it helped me to clarify for myself the reasons why I was committed to the career change. This in turn made it easier for me to confidently express myself in interviews.

As far as getting my foot in the door, I just applied to as many positions as I could find online that matched what I was looking for, and I had that cover letter ready to support my resume. Carolyn, a recruiter at Viget, reached out to me through AngelList because I had made a profile there which included excerpts from my cover letter, and she thought I’d be a good fit. It might not happen like this for everyone, but I was lucky to find a company that values growth potential over years of experience.

Annie (Dev):

For my first job, I didn’t really do that much. I talked to someone at the demo day for my bootcamp, went on vacation for a week, and by the time I got back he had reached out about applying for his company.

Every job offer I have had in tech has been through someone I met in person. I’ve had opportunities originate at a meetup, at an event the company was hosting, and at tech volunteer events. My connection to Viget actually came from meeting Nate at my husband’s (non-tech) department holiday party.

My best advice for people trying to get their foot in the door is to do work and get out and meet people in the industry. If your goal is to find a job that’s a good fit, talk to people that you think are interesting about their jobs and see what that leads to down the line.

Dave (UX):

Well, my story may be somewhat unique in this regard. I really only wanted to work at one company: Viget. Viget was (and still is!) my dream job, the place I compared all other design agencies to. Although I did interview with other companies, that was really a means to an end. The plan was always to apply with Viget after I had some more direct experience to draw upon.

However, I realized that plan was just deferring a dream and selling myself short. After all, I did have 10 years of work experience and a number of skills that I knew would be valuable in any client facing role. So I reached out directly to Erica on social media and introduced myself. I basically followed-up with an open letter on all the reasons why I loved Viget and would be a good addition. From there we had a pretty honest exchange about the application and hiring process. And the rest is history!

How did you know when you were ready to make the transition, and what fear was in the back of your mind?

Jess (PM):

After a handful of interviews, I got a good feel for what a PM role entailed in different organizations. This process made me excited for the prospect of taking on that role, and by the time I got the Viget offer, I was ready to make the change.

While the PM role really appealed to me, I didn’t know what it would actually feel like to be on the other side of things. My biggest fear was that I would feel discontent without the satisfaction of building things myself. Having been in the role for almost 6 months now, I realize that I get satisfaction from other places: writing clear requirements that a developer can use as a blueprint, finding and troubleshooting bugs while conducting QA, guiding the successful synthesis of project activities to completion. I’m glad I made the leap and tried this instead of letting those fears hold me back.

Annie (Dev):

I was most afraid when I was living in DC with a full-time job but had accepted the offer to attend this bootcamp. I knew I was about to spend a bunch of money to do a thing that had no guarantees, but I was committed to pursuing this, so I made the leap.

After the bootcamp, I didn’t think I was ready for a developer job, but I felt ready to be learning on the job. When looking for opportunities, I presented myself as someone who was excited about continuing to learn, and I ended up with an apprenticeship, which felt like the right fit for my level.

Dave (UX):

When you’re learning new concepts and skills, you reach a point when you’re eager to put those things to use. I don’t think you’ll ever feel like “I’ve learned everything I need to” in order to change careers, and that’s okay. You have to accept that in order to take another step forward. The reality is you’re just learning how to learn in a new domain and you’ll learn the real stuff after you land the job. I reached a point when I felt prepared enough to tackle a new set of challenges and learn along the way. I was anxious for a fresh start, to show what I was capable of, to dig into the type of work I wanted to be doing.

My fear starting out was that I would be behind or make silly mistakes that others wouldn’t. But I’ve learned that playing into those fears is worse than either of those coming true. For example, not trying a method or applying a framework you’ve learned in fear of making a mistake robs you of a potential learning opportunity. It’s better to make the mistake and acknowledge it so that you can learn from it and know how to recognize it for yourself in the future.

What advice would you give someone who isn’t sure they’re in the right field but doesn’t know which one to try next?

Jess (PM):

Reflect on what makes you happiest and determine your strengths as an individual. They may not be related to the job you’re in at the time. I looked at all of my prior (non-work related) experiences and skills, and realized that a coding job wasn't making the most of my best qualities.

Ask the people who know you well where you shine and what they think your strong suits are. Then you can assess the fit of potential new careers with these characteristics in mind.

Annie (Dev):

If you can, talk to people in other fields about what their roles are like. There are always plenty of reasons to convince yourself not to do something or to stay where you are. Don’t get stuck thinking that you have to learn all the new required skills before you take on a new role. If you can develop a skill on the side while you’re still in your current job, that’s a start. Internships and apprenticeships are another good way to get your foot in the door once you’re ready to make a change. And once you have something in mind, set a timeline and goal and work towards that.

Dave (UX):

I would encourage others to seek out free events like meetups and talks to hear directly from practitioners and learn about the industry from their points of view. Going to these events were pretty low stakes but gave me access to and valuable insight from other designers. These experiences helped me understand what a career in user experience and design looked like and validate that it was something I wanted to pursue.