Hi there! I’m Katrina and I wanted to put this post together to help answer frequently asked questions I get about my career progression breaking into tech, marketing, project management, and program management.
Buckle up because this is going to be a long one. However, I can guarantee you’ll get most of the answers you need.
You can read my story below or jump to the “So if you are trying to navigate your career, here are my words of wisdom” section for a quick answers.
Alright, here we go!
What I Thought I Wanted
You know the question “What do you want to want to do when you grow up?” Well, that certainly changed many times throughout my (current) 30 years of being alive and continues to.
As a child, I thought I wanted to be a dentist. Growing up, my dentist was really cool and people always complimented me on how white my teeth were.
In high school, I thought I wanted to be a psychiatrist so I majored in Psychology. After one statistics class, several boring labs—plus the realization that I’ll need a PhD— later, I threw that “dream” away.
What I Always Knew (And How You Can Figure That Out)
Here’s the thing— even though I didn’t know what I wanted as a job title or career, I always knew what I enjoyed doing and experiencing.
Keep the above in mind because that will be the entire theme of this post.
Growing up, my parents were really strict (a Filipino mother and a Black father in the military). For them, they valued me going to school and graduating so I could have a “better life” than what they had. Slumber parties and movie nights were rarely a thing for me as kid.
School was my sanctuary so I did everything possible to get involved on campus so I could get out of the house. As I look back at my growth since high school, there are common themes to my personal career story that have shaped who I am today, and influenced where I am, that I can easily identify:
I’ve always enjoyed the act of planning things, being the life of the party, building community, and mentoring others. If I can sum up my collection of interests, I say they fall under the realm of “edu-tainment.”
In middle school, I was really good at playing the clarinet — to clarify, I was in a Dixieland jazz band performing across the country. (New Orleans, Sacramento Jazz Jubilee, a cruise ship, and local venues). My clarinet was blue and I led the band. I wish I still had photos share.
In high school,
I got involved with the Associated Student Body, eventually becoming ASB president. I planned every Winter Formal and Prom after my Freshman year.
I presented monthly status reports to the local school district and even delivered my graduation speech. No, I wasn’t valedictorian but I did have a 4.4 GPA and was in the Top Ten of my graduating class.
Although I wasn’t the best actor, I could sing and landed leading roles in musicals. (I mean, I do have a cover song on Spotify).
During my undergrad,
I worked as a peer mentor where I mentored 75 students annually by hosting weekly workshops and office hours, focused on personal and professional development.
I was an Orientation Leader (that person who gives you a tour of campus and hypes you up with all the screaming and chanting). I wrote for the core campus blog. I worked as a program associate planning on-campus after-hour events (concerts, karaoke, and more).
I only had one internship and that was during the winter quarter of my senior year. I moved to Washington D.C. for a quarter and interned at the Smithsonian planning 21+ after-hours educational events and programs. (Check out my core project, “Signed, Sealed, Delivered: A Party at the Postal Museum,” covered in the Washington Post and DCist).
This is all to say that I like to have fun, and I enjoy the process of creating fun experiences.
As you can see from the various roles and jobs that I had before I graduated, that theme is evident. From all these pre-graduation jobs and experiences I’ve had, I learned a lot about active project management and got my hands dirty by learning various marketing techniques, tools, and strategies.
The Start of My Post-Grad Career
With one quarter left of my undergrad, I was convinced I was going to be a full-time marketer working in a cool museum planning events.
Well, Life threw a wrench in that plan because I was hardly getting any callbacks for interviews. The companies that were interested in me couldn’t hire me because my graduation date was not lining up with their start dates (bye-bye dream job at the Smithsonian).
A month before my graduation, my campus held a “Last Chance” job fair (that’s literally what it was called. Depressing, I know, which is why I remember the name), which I attended. While I was running out of time, I knew I did not want to work in, or settle for, a customer service retail job (knowing the type of stress my mom experienced being in the industry for 30+ years and the fact I wanted a sustainable income for my personal needs) if I could avoid it.
There was a localization agency present at the career fair that was looking for project managers. While I did project management work, I didn’t realize this could be an actual career. I introduced myself and shared my resume. I was called for an interview one week later and was offered a job three weeks before my graduation. I started two weeks after I walked.
When I Realized I Hated My First Job
I thought I was so damn cool. I was officially a project manager, with an annual salary of $38,000. (Yeah this was in 2014 and I also didn’t realize they were lowballing me because I never researched information about negotiation and market value compensation beforehand).
I was working in a corporate office by the beach, in an affluent area. (I was commuting three hours a day, five days a week for a couple of years because I couldn’t afford to live in the area where I worked BUT that’s a story for another time. I was 21 and I had energy).
Even better was that another person who started the same day as me also graduated from my alma mater at the same time; we never met on campus. She became one of my best friends and we are still besties today.
I learned a lot of valuable skills. I managed vendors and teams across different time zones and learned how to balance timelines and budgets. I oversaw several client accounts and managed my communications with them directly. I moved up pretty quickly too — I was promoted to Senior PM then again to Program Manager overseeing a team of 15 PMs globally.
However, I was miserable.
I soon realized the environment I was in was toxic. Sometimes I’d find myself working 60-90 hour weeks, not leaving the office until 11PM at night, and crying over the belief that I “failing” at my job.
I’d tell myself “I have to stay at the office because x,y,z.” I would find myself begging my directs to do their job even when I myself felt I couldn’t give them the support they needed.
There were many things not automated so waking up to 300 emails was “normal.” Calling and pleading with translators and editors to get something done was “normal.”
The thing is, while I was working full-time at the localization agency, I was always working part-time elsewhere at the same time. Some stints included being a writer for a local news column, being a marketing assistant for a marketing agency, doing freelance social media work, and running my own career-focused blog focused on helping millennials navigate the workplace.
I started looking for other full-time opportunities and while I’d get some interviews, I wasn’t given offers.
That changed when I starting learning more about the mechanics of effective networking and mastering informational interviews.
It’s totally valid to hate your job and wanting to find a new one. Problem was, I hated my job so much that it became the only thing driving me to leave. By being in that negative headspace, it impacted how I went about my job search and that negative energy came through in my interviews, (which I assume may have been the reason why I wasn’t getting offers).
After switching my mindset to “I hate it here” to “I want to grow,” I felt I was in the proper headspace to see my true potential and was better prepared to position myself to hiring managers.
Effective Networking Is Key
I did more research and learned more about effective (emphasis on effective) networking and informational interviewing. I connected with strangers— people I found intriguing and/or shared a connection in some way, in roles and companies that interested me.
Every connection and “coffee chat” lead to a new door opening until I got an interview with an ed-tech start-up out of San Francisco as an events coordinator.
I felt the job was made for me; I already believed that role was mine and I wanted them to know it too.
After doing some research of their booth set-up at events and conferences, I swooped in with a multi-page deck complete with a mock re-designed booth, ideas for marketing, and an events plan, all before my first interview to so they could see what I was capable of when I didn’t have the job. (Imagine what I could do if they hired me?)
I got that job.
This tactic I used is known as a validation project and I feel it’s one of the best ways to stand out as a candidate. You can learn more about it here with some examples that worked for me.
Switching Careers Again (Thanks To The Pandemic)
I’ve finally moved away from my home town (and out of my parents) after 26 years and made my way to San Francisco to start a “new life.”
Seven months later, I was laid off for the first time in my life due to the Pandemic.
I gave myself three months to find a new full-time job, considering I recently moved to one of the most expensive cities in the USA, before considering part-time positions to pay rent.
Back to the drawing board of networking…
I came across this woman on LinkedIn who had this title I never heard of before but I knew I wanted (Program Manager, Recruiting Events & Partnerships). I reached out to see if she would be willing to have coffee chat but she was too busy. A few days later in the late evening, she shared a post about a job opening on her team.
I revised my resume and wrote a cover letter directed to her at midnight. At 3AM, I applied so I could message her at 6AM to reaffirm my interest in the position by re-sharing my application materials to ensure they landed in the hands of a real person.
She mentioned she would pass my materials to the recruiter. A few days later I received a call. Two weeks later, I was given the job— exactly in three months time, on my birthday.
Side note: I also went through four rounds of interviews and also presented another validation project. The job required I know how to use an event management and marketing tool call SplashThat. I’ve never used it so I signed up for a free account and created an event inviting the hiring manager to RSVP to an “Interview with Katrina.” I also presented a 10-page deck with event ideas and marketing tactics.
I am telling you, the validation project works.
Weighing The Risks
The thing is, I was offered a contractor fixed term position. It was also a coordinator position. They were looking for someone with one year of experience and I had five at the managerial level…in a different industry.
I’ve never worked as a contractor and I’ve only been working in events full-time for less than a year (not counting my undergrad experience).
I was afraid of how taking a role at a lower level may impact my growth. However, I did my research. The company was growing exponentially. Many employees had positive things to say and the direct team I would sit on made it clear there were growth opportunities.
I needed to get my foot in the door and this seemed like the best option for me.
Advancing On My Own Terms
Once I got my foot in the door at the company, I seized every opportunity to showcase my skillset and to get my name out there by working on stretch projects outside of my day-to-day to show how desirable of an asset I am.
Basically, I told myself I was getting converted. It was going to happen— and it did.
Remember when I said I like to have fun? Well…
One day, I decided to convert boring meeting notes into an eye catching e-newsletter. Suddenly, I was being approached by various teams to create their newsletters, including the VP of Talent. (I wouldn’t call myself a graphic designer but I do know enough basic graphic design to create materials that look good). Soon after, e-newsletters became a thing everyone started to do at the company.
I started creating branded Zoom backgrounds for our recruiting events to help distinguish employees from guest speakers. Now, our core marketing team has a library of backgrounds they’ve created for employees to use for a variety of occasions.
When there wasn’t the option to update our Careers Site at the time I was hired, I proposed creating the Interview Prep Guide and have it automatically emailed to applicants in the interim.
As an ex-Localization PM, I introduced opportunities for operational excellence via Project Management tools and standardization practices.
You can view my LinkedIn and portfolio here with more of my stuff.
This is all to say I know my skillset and I made it a goal to infuse my skills in areas across the company I knew could use the help. I pride myself on being creative and process-orientated. For example, I can design create content as well as map out a six month project plan with sub tasks of how to launch those content pieces.
By combining my interests in building community and improving operational efficiency, that has translated to project and programs I was able to build and launch from the ground up, no matter what industry I was in.
I was converted four months into my contract and moved up two levels during my first promotion. (Converted and then promoted twice. Yes, I am proud of that).
Okay so, what was the point of this long ass story?
The point is that this is my story and I’m proud of it.
It’s also fluid— it’s still a work in progress.
There are many paths you can take to get to your destination. You’ll likely encounter bumps in the road but being your own advocate will help you navigate those bumps even when you might be unsure of where to turn.
You don’t have to know everything or figure out everything right now. I learned as I traveled down certain paths what worked for me and what didn’t.
You can only move forward by doing. You don’t need to be fearless to take the first step forward; you only need to be brave.
And as my wise friend Nawara says, you have the power to own your story; don’t let anyone take that away from you.
So if you are trying to navigate your career, here are my words of wisdom:
Don’t know where to start? Get to know yourself. Whether you realize it or not, there is always a “common thread/theme” regarding the choices you make. A good way to identify those themes when you feel you don’t know what you want to do, what you’re good at, and how you can apply those skills, is by taking a personality test. In two minutes, I break it down in this post, where you can also view my test results.
Once you have a good understanding of your skills, what you like and don’t like, you can then start building a map of how and where you can apply those skills. Here’s a short presentation on “Confidence, Clarity, and Finding the Right Job” that outlines a methodology you can try. It’s boba themed!
Don’t have experience? Create your own. Here’s my take on what not having experience really means and why you need a “proof of concept.”
Get involved in stretch projects and side projects.
Stretch projects are those initiatives at work/school outside of your regular day-to-day to help build your reputation and to “get your name out there,” especially if you want to move laterally or have more advocates in your pocket when you’re looking for a promotion.
Side projects are those self-driven projects based on that things you personally love, enjoy, and are interested in that you can leverage professionally. This is a great way to build your portfolio and a “proof of concept” when it comes to applying to jobs. By being self-motivated and having something to show for it, this shows employers that 1). You know what you’re doing and 2). You have a clear understanding of what others are looking for and 3). You actually have a personality.
No matter how skilled you are, hiring managers want to hire real people, with real personalities which provides more insight into what kind of person you are and what it’s like to work with you.
Master your story. How and where you tell your story (website, portfolio, blog post as examples) will have have a different impact on your audience. Think about what impact are you trying to leave? What is the end goal of your story? How can you tell your story so people understand it? In this post, I talk about how to start telling your story.
Clean up your resume.Your resume is a snapshot of your most relevant information. Read that again. Especially if you are breaking into an industry or switching industries, you need to be able to connect the dots of how your previous experience is relevant to the role you’re applying for. Not all experience is relevant experience. Learn how to tell that story.
Your resume needs to tell a crystal clear picture of how your current skills and experiences are relevant to the next place you want to go. If it’s not relevant, don’t include it.
Understand that many skills are transferable. How you apply those skills may be in a different capacity in different roles and industries. Understanding how you can leverage X skill in Y role will help you break into a new career or role and also make you stand out as a desirable candidate.
Learn more about the nuances of the roles, industries, and career fields, in addition to the different niches within a chosen field. For example, marketing is a huge net. I’ve done customer marketing, SEO, social media marketing, and copywriting. I almost gave up on marketing career all together until I found employer brand and recruitment marketing which was the perfect blend of all the things I love. There is a difference project management and program management. Check out how Jean Kang breaks it down.
Don’t follow your passion; follow your curiosity. Follow what you can do well and get paid for it. Follow what you’re committed to doing. The reality is you can be passionate about something but often times, a lot of what you may like or be interested takes hard work. Are you committed to doing that hard work? Mastering that new skill? How easy or difficult will that be for you? Based on your personal lifestyle needs, is that passion sustainable to make a living? Would you view that passion differently if you now had to work at it as your full-time job? Your job should give you the means to do what you want to do; your job doesn’t, and shouldn’t, define you.
Leverage your network. Don’t have one? Build it. Networking does not need to be a long, drawn out process nor does it need to feel transactional. Here’s my free 17 page guide on how to network appropriately to find your next play.
If you want a job badly enough, you’re going to need to do more than “apply to a job” to get it. I know that may be annoying to hear but that pay off means a job that allows you to live the life you desire. Competition is tough and you essentially need to prove why you’re the best person for the job out of everyone else you’re up against. Here’s how you can do that.
Lean into your weird. We are all unique and your uniqueness is something you should sell and capitalize on because that is usually what makes you the best person for the job. Here’s more about how my love for anime helped me launch an ambassador program influenced by Attack on Titan and the importance of how your creativity can show up in a variety of different ways.
You’re allowed to reinvent yourself, whenever the hell you want. You will be working for the rest of your life. You are not obligated to stay at a specific job for a specific amount of time. Your career journey is your own. The toughest choices you’ll ever make are the ones that are best for you, despite what others may think.
Be your own advocate. There will be times when you encounter people who may not be rooting for you and that’s okay. Others will but YOU should always be your own cheerleader. You get to choose how your story goes and that’s your super power.
If you made it this far, thanks for reading and I hope this gives you a starting point to find meaningful work and to live the life you desire.
So proud of you!! This is such useful advice and Twilio is so lucky to have you 🤩