3 min read

How I change careers so "easily"

In 8 years of working, I’ve held 4 different roles in 6 companies, based out of 3 countries.

I went from Management Consultant to Product Marketer. From People Manager to Product Manager. I’ve worked for companies based in the Philippines, the US, and Germany. This has enabled me to work with people distributed across North and South America, Africa, North, South, and Southeast Asia, and almost all corners of Europe.

A question I get a lot is,

How do you do this?

The short answer is three-fold: I am flexible with my identity. I test new identities against the market. And I welcome serendipity.

Be flexible with your identity.

The first thing is I am flexible with my identity. I am not “precious” about it.

Early on, I learned there is no law stating I need to be a writing expert before calling myself a writer. I just needed to write.

Once upon a time, I was talking to a friend about pivoting my business to a “travel concierge.” While we were talking, someone called me to catch up. “I’m running a travel concierge business,” I said, when he asked what I’m up to. My friend was shocked at how fast this idea became real (after a few minutes of conversation). This is how I started “Location Asia,” the travel concierge business I ran in 2013.

In May 2014, I got my first job in tech by pitching Kevin Dewalt on analytics services. I was testing an identity. I didn’t know much about analytics, but I also didn’t want to waste time studying something I couldn’t sell. I knew if he hired me to do it, I could learn it. This is how I got my first Product Marketer role in a US-based tech startup.

Test your new identity against the market.

The second thing is I test my new identity against the market. I learned that career transitions don’t happen through endless introspection. I tell people. In fact, I treat it as a sales campaign.

In 2013, when I was self-employed, I tested different copywriting offerings by conducting quick and dirty email campaigns. I picked random personas, went down the list of US states, found lists of people, and emailed 100 people per campaign.

Dentists in Alabama?
Carpenters in Arizona?
Doctors in Arkansas?

I emailed them all.

These days, I’d do things differently and not spam people so much. But the principle remains. Every time I want to try a new career, I conduct a sales campaign and aim to talk to 100 people who might hire me. This “makes it real” real fast.

Welcome serendipity.

If the previous steps – being clear about my identity, what I can offer, and telling everyone about it – increase my “surface area for luck”…

The last step is about welcoming serendipity and being open to being lucky. Say yes to every meeting. This is a rule I have during every job search.

In 2016, before I had the opportunity to manage people for the first time in OnFrontiers, I was conducting a failed campaign to transition to biotech by applying to pharma jobs (not a good strategy, FYI).

By chance, Brian Caouette (CEO of OnFrontiers, and customer in a startup I worked for) reached out. They are opening an office in Manila. Can I meet with them and share tips?

Was it related to my current job search? No.
Did I say yes? You bet.

That was how I became Director of Client Services at OnFrontiers. That role put my career and my finances on a new trajectory. I couldn’t have predicted nor planned for it.

How to use this in a career transition

To summarize, be flexible with your identity. Test your new identity against the market. Welcome serendipity.

If you’re in a career transition, here’s a simple way to try these ideas out: Email 20 people saying you are transitioning to the thing you are transitioning to.

This is an actual email I sent for my Germany move in 2019. Feel free to modify as you see fit.

Hi George,

Big personal news: I am moving to Hamburg, Germany in August 2019.

I am currently looking for Product Manager or Product Owner roles at tech companies in Hamburg. By any chance, would you know of people there who I should chat with?

If not, no problem – just wanted to keep you in the loop.


P.S. What is new in your life? Would love to catch up.

My ability to move to Germany and the actual date were actually dependent on me getting a job. It was very far from a sure thing.

“Old me” would’ve needed to explain in five paragraphs all the complexities of my situation. “New me” just states this move as a fact.

This is what I mean by being flexible with your identity. State it matter-of-factly.

If you actually do this, most people will say they cannot help with the exact thing you are asking for. That’s fine. But would you like to catch up? Welcome serendipity. Say yes!

Let me know how it goes.