This Is What Happened When #IsaidWTF To My Comfortable Career
October 1, 2020  •  12 min read
It was risky business leaving my comfortable career of 12 years, but I've come to believe that sometimes you have to do uncomfortable things to grow, mature and improve yourself for your career.​​​​​​​

This story was originally posted on LinkedIn

Well, this is an extraordinary time for me. This is my first post on LinkedIn. I’ve spent most of my time on the network connecting with colleagues and companies while giving the thumbs up to some amazing posts full of dedication, creation and innovation. And seeing how the community works together to make connections, share experiences, and celebrate opportunities has always been very inspiring to me.
The reason I posted today is that LinkedIn is committed to helping make careers more productive and successful. For the past 3 years I’ve been productive and successful investing in myself full-time to prepare for new career opportunities by learning design software and addressing weaknesses in communication — both written and verbal. 
Today I'm more confident in my writing abilities and thought it would be the perfect opportunity to hone this skill by sharing my professional story while contributing to helping LinkedIn make more productive and successful careers.
And I mention helping because I think helping others is important. It makes me feel good, it gives me a “Helper’s High.” But I didn't first learn about this feeling doing the work that I do. I learned about it from my parents. I was raised by parents who do things out of the desire to help others in need. Who feel concerned and responsible for the welfare of others, without reward. They are empathic. They are humble. They are selfless.
So Who Are You Going To Help Next?
My mom’s love of children led her to become a teacher for over 20 years, and her first job was at a behavior disorder school. And after she started, I'll never forget how she would come home crying. Now at the time I was 14, but I remember it just like it happened yesterday. I will never forget it. I remember always asking her what was wrong, and she would just kind of brush it off and change the subject.

My mom’s class celebrating their achievement of reading 25 books by the end of the year with an ice cream party.

And the crying continued for a couple months, then one day it just stopped. That night during dinner I mentioned, “I noticed you weren't sad today, Mom.” And she replied, “That’s because I made a new friend.” And she told me about a student who would call her names, throw things at her, and even ignored her when she called on him.
But she remained tough, she remained strong, she remained helpful. “The adults in his life didn't help or care for him like they should have. But I cared, and I was there to help him, and over time he realized that and now we're friends.” she said with a smile. I laughed and asked,
"So who are you going to help next? Why don't you just save the world mom!"

Faded from years on my mom’s office wall, hangs my testimony to her virtue of compassion.

And the very next day I wrote those words on a Post-it note, and 26 years later she still has it. That experience very much defines how she sees her contribution to humanity, she can and will help anyone in need.
Sometimes You Have To Be Uncomfortable...
And by following in my mom’s footsteps to help humanity, I evolved from a web designer into a user experience (UX) designer. My role is to help make technology easier and more enjoyable for you to use. I create or refine products and interfaces to make them purposeful, meaningful and impactful to you.
When I began my career as a web designer I only had 4 months experience and was 1 of 3 employees. Twelve years later the CEO, a developer who was employee number 2, and myself turned a small web design company into a multi-million dollar lead generation empire.
The company grew to over 50 employees spanning 2 continents. We generated leads for over 550 clients in 2 highly competitive industries — moving and home remodeling. 
I emerged as the lead designer within a 10 member development team while leading and mentoring a design team of 3 senior level designers. And my greatest contribution to the company, increasing leads from 100k to over 1m by delivering a 5 year UX vision for our lead generation SaaS application.
I’m sure you would agree I built myself a comfortable career and was a successful UX designer, but after 12 years something connected deep inside me. I felt I was meant to do more. 

“Tom Cruise, Risky Business, 1983” copyright Warner Bros. Entertainment Inc. photograph by All Star Picture Library
Alamy image RWDK5C

Intuition can happen any time, and inspiration comes from everywhere. In the 80's movie Risky Business, Joel Goodsen (Tom Cruise) makes this statement about intuition: “There's one thing I learned in all my years: sometimes you gotta say WTF — make your move." And like Joel, I became inspired by the advice his friend Miles (Curtis Armstrong) gives him early in the movie:
"Every now and then, say WTF. WTF gives you freedom. Freedom brings opportunity. Opportunity makes your future."
Miles is trying to persuade Joel to “make a move” and be uncomfortable by taking risks that could have great reward without worrying about the outcome. I’ve come to believe in the power of his advice because of “making my move.” This is what happened when #IsaidWTF to my comfortable career.
WTF Gives You Freedom
While on my pursuit of personal development, I’m always curious, always learning, and this mentality has led me down many interesting paths. After moving to Chicago I became so inspired by how the Google Maps app improved my city life, I felt it was time to take the less safe path to learn how to design and prototype a mobile app.
So I took a risk and left my comfortable design lead role of 12 years to prepare for new career opportunities. I “made my move” back home with my parents to invest in myself full-time. And I’ll never forget the uncomfortable feeling that started creeping in as I left my home in the skyscrapers for my parents in the suburbs. Because I realized I just lost my freedom of independence to gain my freedom of opportunity.
Freedom Brings Opportunity
After being influenced by the rise of talent and capital in Silicon Beach (Southern California), I became intent on relocating to this tech scene. I believe it aligns perfectly with my industry experience while providing the opportunities I’m looking for to advance my career and where I want to live — around like-minded people and palm trees.
So I began my freedom-based opportunity by creating a 4 course curriculum for my education strategy using a creative problem solving approach.
1. CLARIFY (understand the objectives, problem, and opportunity)
By pursuing a new career direction in mobile app development, my greatest weaknesses were software and technical experience. 

After researching the hard skills of a preferred candidate with mobile app experience, I needed to learn Mac software (Sketch, Principle) and technical guidelines for Android (Material).

Working my entire 13 year career on the Windows platform limited me from using the industry standard Mac software used to design and prototype mobile apps. And by never developing a mobile app, I was not familiar with technical constraints and limitations for mobile devices.
2. IDEATE (think of possible solutions or approaches)
While living and working in Chicago, I had a negative first experience using a local public transit app and felt this was the perfect opportunity to teach myself how to design a mobile app, using new Mac software. 
Mockups from my mobile app project that made me more self-aware than ever, gave me a richer sense of what I’m capable of, what I stand for, and how I want to move forward in my career.
In 8 months I redesigned the transit app’s user experience creating 8 high-fidelity Android prototypes, 4 inspired by Google Cloud Vision, to demonstrate a working knowledge of the software (Sketch, Principle) and technicals (Google Material Design). I feel I accomplished this by achieving the following:
Using Sketch, communicated influence and guidance of a product design strategy from scratch. Using Principle, demonstrated meaningful mobile app improvements to actual user problems. Following Material Design, constructed prototypes aware of guidelines, constraints and limitations for Android.
After redesigning the app, I saw the I/O event introducing Google Lens, their visual search app. This inspired me to continue working on the app by envisioning how Google’s Cloud Vision, the technology behind Lens, could anticipate users' transit needs.
3. DEVELOP (build ideas into solutions or experiments)
One of the greatest things I did early in my career was establishing value for the company I worked for by positioning myself as being committed to its success and future. I was also lucky to work alongside an amazing developer Ed Caicedo, who I looked up to from day one. He inspired me with his knowledge and strong work ethics, which would very much shape the way I would continue to add value and improve my skills throughout my career.
Now 15 years later, I realized it was both a blessing and a curse working at the same company for my entire career. As a result of being so focused on the company’s success, I never made time to share my success by creating a portfolio or having an up to date resume and LinkedIn profile.
So I began by researching what the top skills recruiters and hiring managers were searching for in an applicant and what they wanted to see in their portfolio. This led to discovering communication and storytelling were among the top sought after skills. Using these insights, I thought of my new portfolio, resume and LinkedIn profile as products to help me “communicate” my skills and value through “storytelling”.
My UX product design portfolio tells stories of problems I've solved on my own and with the cross-functional development team I was on for 12 years at a lead generation company.
After 8 months of researching and overcoming writing challenges, I successfully communicated 14 years of industry experience by composing 4 comprehensive stories of my personal and professional experiences. These stories allowed me to establish a well-informed portfolio (using Adobe portfolio), resume and LinkedIn profile for my potential employers to experience the evolution of my career.
4. IMPLEMENT (form a plan and commit to next steps)
Finally, I analyzed companies of interest to determine career growth opportunities, culture fit and hiring process by evaluating their leadership, culture and vision. And one of the most interesting things that emerged was how lengthy and involved the interview process had become. 
The designers and developers I worked with had been at the company for years so we never used the multi-step hiring process of today:
By phone:
a. Recruiter interview
b. Hiring Manager interview
c. Product Manager interview
At home:
a. Design challenge
In person:
a. Design challenge presentation
b. Portfolio presentation
c. Whiteboard challenges
d. Design critiques
e. Technical interview
f. Cognitive interview 
g. Behavioral interview
h. Culture fit interview
Even though I hadn't interviewed in 15 years, I never would’ve expected these types of questions, challenges and presentations to get a job today. I was devastated. I was overwhelmed. I was uncomfortable. But I adapted and pushed myself to keep learning through 4 months of preparation and practice.

A whiteboard design challenge shows the interviewer how I approach a problem and how I’ll collaborate with their team by working with the interviewer to solve the problem together.

And I'm going to admit something to you I probably shouldn't. I still feel uncomfortable. But I’m going to trust the process and not worry about how things turn out, if I’m asking a dumb question or if I’m giving the wrong answer. After 3 years I completed my curriculum and graduated from self-education. I was ready to make my future.
Throughout this journey, I've come to understand the importance of communication in preparing for new career opportunities. Warren Buffett, the greatest investor of all time, talked about this in a video posted on LinkedIn by Michael Hood.

“9:30 AM ONE ON ONE Warren Buffett” by Stuart Isett for Fortune Live Media used under CC BY CC BY-ND 2.0

"If you can’t communicate, it’s like winking at a girl in the dark — nothing happens. You can have all the brainpower in the world, but you have to be able to transmit it. And the transmission is communication."
Well, I believe learning how to communicate better was the very reason that led me to take a risk for my career. With the freedom to invest in myself full time, I tackled weaknesses and learned new skills to transmit my value through all forms of communication: visual, written and verbal.
I shared my story on LinkedIn because I believe this professional community understands that sometimes you have to do uncomfortable things to grow, mature and improve yourself or in the spirit of LinkedIn: be productive and successful in your career.
The act of leaving a comfortable career of 12 years is risky business. In many ways life has taught us to be comfortable and think like Joel, "I don't want to make a mistake — jeopardize my future." Well, I’ve been persuaded we should do the opposite: take risks, get uncomfortable and “say WTF.” Because “if you can’t say it, you can’t do it.”
And for those of you who can say it, I simply want to tell you, “make your move!”
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