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Hey Girl Hey!

Aspiring Co. is here to remind you to chase your dreams relentlessly and to inspire you when you feel like giving up. We are telling the stories of women who are fighting everyday to pursue a life of meaning.




Name: Ashley Janelle
Age: 28
Job Title/Company: UX/UI Designer, Caterpillar Inc. + UX Career Coach
Education Background: Interactive Arts and Media, BA

1. Tell us a little about who you are.

I’m a UX Designer, UX Career Coach and tech influencer from Chicago! 

2. What sparked your interest in starting your business/ working in UX?

I’m always looking to create my own opportunities so that’s pretty much what fuels me. I’d love to be able to work full-time for myself in the near future so I’m hoping the businesses and opportunities that I create for myself will serve as the catalyst for that. I know that quitting your 9-5 and working for yourself is trendy right now, but I’ve always had this plan. It’s one of the reasons why I chose the profession I did where I’d be able to work from anywhere and create my own opportunities whether it be freelancing, working remotely, for myself, etc.

Work/Life balance is huge for me and I’ve know that ever since I entered the workforce. When I have kids one day, I don’t want to be held to a specific time I have to return to work after giving birth. I also love traveling and don’t want to have to worry about cutting my time short to be back at an office, so I’d love to just take my work with me. It’s those kinds of things that fuel me.

From a financial perspective I also don’t like the fact that someone else gets to dictate how much money I bring in  year. As a result this dictates everything else like where I can live, send my future kids to school, how often I can vacation, etc. You have to have multiple streams of income whether you’re working for an employer or yourself.

As for UX, I came from a graphic design background and after working in the field I just wanted more for myself. I knew there was much more that I could do with my skillset that would make me feel like my work was valued and really made a difference. I came across UX and the rest is history. 

Beyonce rehearsed for 8 months for a two hour performance. Remember that next time you wonder why things aren’t happening quickly enough.
— Ashley Janelle

3. Tell us about your full-time job and any side hustles you might have.

I work for Caterpillar, the construction company, as a UX/UI Designer. I’m doing everything from reviewing customer research to designing screens for our applications. I enjoy what I do because it’s not an industry I thought I’d see myself in. Because of that, it’s forced me to grow and develop in areas I hadn’t expected. I always saw myself at a beauty or fashion house working as some kind of visual designer so this is very different, but I’m loving it.

Along with that, I run a UX/UI career coaching business to help people bridge the gap between their UX training and actually landing a job. There’s a lot that goes into being fully prepared for landing that UX/UI role so I’m helping others by equipping them with the know-how to excel. 

I also am a tech blogger where I talk about and review my favorite tech and lifestyle brands. This is one of my favorite things to do because I get to express myself in different ways depending on the brand I’m working with. 

4. Who are you most influenced by?

Other women entrepreneurs who are accomplishing things in their perspective fields. Women are killing the entrepreneurial space and it’s not by accident. Seeing other women succeed reassures me everyday that I’m right where I’m supposed to be.


5. What was your first job and how long did you hold that position?

My first job was at Edible Arrangements. I stayed there for a few summers after turning 16.

6. Can you share one of your proudest achievements with us?

My proudest achievement has definitely been launching my UX/UI Career Coaching business this past April. It’s a combination of my professional work and my entrepreneurial side coming together. Literally one of the best things I’ve ever created.

Also my brand new website redesign that launched at the same time. That’s truly a reflection of me as a designer right now in 2019!

7. What were your initial goals with your work? How have they evolved?

My initial goals were and are still to help people while still maintaining a profitable business. My goal with every client is to make sure they leave each session ten times more enlightened than before we started. Giving tangible advice, resources, and guidance is what I deliver during each session.

8. What do you think is the most important life skill you learned through your work?

I’d say to keep going. I’ve had moments where I thought I wasn’t a good enough designer and thought about switching careers. But we all have those moments of imposture syndrome so I think me staying committed has made a way for me.

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9. Where do you hope to be in five years?

I’m not sure exactly where/what I’ll be doing, but I hope it’s something within tech, but on a much larger scale.  I can see my UX career coaching company operating on a much larger scale, and I hope to bring on other coaches to help grow it. I’d like to focus more on getting my company into new spaces so that I can scale. I also am working on getting into speaking more so I hope to be traveling to conferences and tech retreats to talk to people, women, kids of color, etc. about how to successfully navigate a career in UX and or entrepreneurship. 

Just keep looking towards your goals and eventually you’ll get what you want. 
— Ashley Janelle

10. What is a typical day like for you?

My typical day includes meeting with product owners and my team members to understand what everyones working on and what the goals are for the week. In between that time, I’m free to work on designs and meet with customers to review mockups.

My evenings are when I have my UX Coaching sessions and I’m working on my blog. I usually give anywhere from 1-4 hours a day after work on my own passions. During that time I’m also trying to get a workout in or meeting with friends.

11. What was the biggest obstacle you’ve faced so far in the process of pursuing your goals?

I’ve always known I wanted to pursue entrepreneurship and over the years I’ve had several business interests. Some of these I’ve turned into actual businesses after I’ve had time to expand the ideas, where others never came into fruition. So for me, it’s been trying to figure out what business interest would actually stick for me and be lucrative at the same time. At times I’ve wondered what I did wrong during those endeavors but I realized those were stepping stones for me to get to where I am now. Putting together my UX Coaching business was so much more seamless even at the point of launch because I knew what I was doing. I had been there before. So I realized that the challenges I went through with my other businesses really weren’t obstacles, they were just prepping me.

12. What is the best piece of advice you have received?

Don’t ever be in a meeting and have nothing to contribute. This is really key for new grads entering the workforce. 


13. When do you get your best ideas?

Talking to other creatives and entrepreneurs. Being able to bounce ideas off of other people who think along the same lines as me or share my interests is such a breath of fresh air. I’m always surprised how I can be struggling with something and talk to someone else and they seemingly have all the answers. 

14. Can you share with us one time that you failed and what you learned from that failure?

The day I launched my coaching business, all of the numbers of impressions I was getting did not meet the number of applications I received. Although some might not have seen this as failure because it was only one day, I believed something needed to changed. I thought about it and found that the questions I was asking in my application might not have been the best way to get to know potential clients. I framed my questions around “getting to know you” instead of application style and the next day saw an increase in them. I also removed the word “application” as I thought that might have been scaring people off.

I believe in quick course correction. It doesn’t always have to mean changing your business plan but just a small part of your business to see a different outcome. 

15. How do you unwind?

By fully getting away from work or anything that has anything to do with it. Anywhere I can be where I don’t have the urge to check my phone or carry my laptop around is an amazing feeling.

16. What would you tell someone else who is interested in entering your field?

Don’t stop learning. Keep taking courses and show up for meetups. The technology field changes everyday so there’s always something new to learn, even if it’s not directly related to what you do.

17. What do you hope people take away from your story? 

I hope you are inspired to keep going. My story hasn’t been a straight shot. There were times where I thought about a different field because my breakthrough wasn’t happening as quickly as how I thought it should. Just keep looking towards your goals and eventually you’ll get what you want. 

18. Anything we missed that you would like to share?

Beyonce rehearsed for 8 months for a two hour performance. Remember that next time you wonder why things aren’t happening quickly enough. LOL 

Follow Ashley Janelle:

Website | Instagram | Twitter