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Changing Careers in Uncertain Times

Greg de la Cruz works in the tech industry and is the author of two published titles on Amazon.

A woman holds an "Open" sign in front of a wooden door. Are you open to reimagining your career?

A woman holds an "Open" sign in front of a wooden door. Are you open to reimagining your career?

Staying where you are offers a comfort that you can depend on. Why look elsewhere when you know what to expect from your job? You’ve reached a familiarity with your colleagues, your boss, and your work environment. It’s a kind of stability that lets you sleep at night. And you’ve likely carved out a path that will make you a manager or an executive in a few years.

Why even think of leaving?

This career comfort used to envelop my fears of stagnation—it reassured me that I was fortunate where I stood. “Look at all those people still working for a labor contractor,” I would tell myself. I rationalized my significantly improved circumstances, and this comfort anchored me like my career was a ship that had reached its destination. I was safely docked in port.

And then, I began to notice that this same comfortable feeling was weighing down on me. It later turned into something terrifying. Because I had invested in making myself the man when it came to Environment, Health, and Safety (EH&S)—I received accreditations to be a company’s pollution control officer and its safety officer, I’d attended more seminars of the sort, networked with professionals, and even grew into becoming the company’s business continuity leader. And it all felt like I had more to lose if I suddenly went up and left.

But I did exactly that—I quit. It was a scary feeling, but I knew it was the right thing to do if I wanted to “get out.”

Quit Now or Quit Later

I wanted to get out of the box that I was wrapping myself in for many years. The path I was on from starting out as a building engineer to becoming a supervisor, then a site leader—was a fairly predictable one. Like Daniel Radcliffe, forever etched in our collective consciousness as the one and only Harry Potter, I felt that the longer I stayed on my path, I was doomed to be typecasted. In other words, since I had built my resume to be an expert on "corporate environment management," I was handcuffed to this field of expertise.

Yes, I was lucky to have a career path you could make sense of. Still, I felt it was unfair.

And so, one ordinary morning, just fresh off the typhoon Odette crisis that swept Cebu and many cities in the Philippines, I decided: quit now or quit later.

There’s no secret formula to jumping from maintenance engineer to technical writer in eight years. You might think that reinventing myself from ‘engineer’ to ‘writer’ was a downgrade. But no—it’s as good as I could have ever imagined. I had broken out of the box that kept me locked inside with its unspoken rules of:

  • You can’t work in the software industry because you took up mechanical engineering.
  • You’re not good enough to be a "product person."
  • Your getting hired by a Fortune 500 company was a fluke.
  • If you leave, you’ll start from scratch again.

7 Stages of Career Reinvention

All these musings of self-doubt added to the burgeoning weight of career comfort. But like Joseph Liu, who shared Navigating the 7 stages of career change, I went through a process of trying to leave the confines of familiarity. I went through my own seven stages of career reinvention:

  • Stage 1: Disrupting the Status Quo
  • Stage 2: Doubting Yourself
  • Stage 3: Reimagining Yourself
  • Stage 4: Procrastinating
  • Stage 5: Searching Relentlessly
  • Stage 6: Knowing Where You Really Want to Go
  • Stage 7: Leaving the Status Quo

Stage 1: Disrupting the Status Quo

When you’re trying to switch jobs, what’s the tipping point for disrupting the status quo?

Is it disenchantment? Frustration? Regret?

Joseph Liu “started to wonder if [he] truly enjoyed what [he] did or if [he] had been more enamoured by the allure of working for a cool brand.” He questioned whether he was doing the world any good if he was squeezing all the juice from his talents.

For me, I started to become disenchanted with my job during the on-off cycles of the Covid-19 lockdowns. I questioned whether it was the depressive mental wave of the pandemic that caused me to wonder if I was on the right path.

I experienced many good days at work, which kept me engaged for a while, but the ‘bad’ days kept creeping back. And by bad, I’m not saying I felt awful as I did my job—I simply found myself with incalculable dread on Sunday nights, squeezing in as many ‘fun’ things I could do with my time, knowing that when Monday came, I wouldn’t be enjoying my time at work.

It may sound harsh and smell of stinky entitlement, but as cozy as my corporate job was, the status quo sucked. I had to find myself hating the state I was in so I would want to break out of it.

Stage 2: Doubting Yourself

Having decided to take a drastic turn in my career, I kept searching for jobs shortly after typhoon Odette, which was around January or February 2022. I wasn’t applying for any of them yet because I wasn’t sure which jobs were the right fit for me or if I even had the right skills.

This was around the time when The Great Resignation was a phenomenon—people worldwide were leaving their jobs in search of better circumstances. The state of the job market then was a surplus of jobs over people. It was a feast for recruiters. And yet, I couldn’t find a match. I couldn’t find enough companies with job postings that demanded my skillset and experience.

So much self-doubt seeped in. I found myself in an awkward and depressing limbo—on the one hand, feeling demotivated in my day job and, on the other hand, frustrated I couldn’t find a role that was right for me. I was tempted to surrender back to the status quo (stage zero).

Stage 3: Reimagining Yourself

I could have stopped looking for jobs, but time did its magic and offered me some perspective. Throughout the wide job hunt, I kept crossing off non-negotiables in terms of what my next job shouldn’t be. I figured that:

  • I didn’t want to work in the safety and health industry.
  • I didn’t want a job that fragmented my attention into thin pieces.
  • I must stay as far away as possible from facilities and site operations management.

And conversely, I started making a mental checklist of what that next job should look like:

  • I wanted a job that focused my efforts into tangible goals.
  • I wanted to work on the company’s core product or service, not in auxiliary services or support (such as HR, finance, administration, or facilities).
  • I wanted as much as possible to work in technology, preferably in software.
  • I wanted to leverage a key skill that I already had and keep improving upon it.

With these two lists in hand, suddenly, it was easier to reimagine myself as someone else. For years I had fallen into the stereotype I had subscribed to and presented myself as. But with a little direction, the search for jobs suddenly became more doable. I could now customize my resume into fewer categories.

Stage 4: Procrastinating

Then came a roadblock. You know how in cases of Battered woman syndrome, the perpetrator somehow manages to make the woman stay, despite repeated cycles of abuse? During the tranquil or loving phase, the woman is fooled into thinking that the abuser has changed his ways. The batterer shows a tender and nurturing behavior, begging for forgiveness and throwing empty promises.

In the procrastination phase of my career reinvention, I found myself delighted in my work once again. I swept through small tasks in a flash, became proactive in coordinating with stakeholders for a project, and welcomed added work. I felt as productive as when I was just a new hire, hungry to impress.

This stage felt very confusing because all the great things about my job magnified themselves for me, such as:

  • Having an incredibly flexible work schedule (my manager didn’t keep time)
  • Being around supportive colleagues who were like old friends
  • Participating in clubs and engagement activities, making a day of work well-rounded
  • Knowing the whole organization looked to me and trusted in me for my expertise

My existing situation at the time was far better than what I had with previous jobs. It was difficult to throw all of that away, so I dallied and put off looking for jobs. I entered a momentary state of tranquility.

Stage 5: Searching Relentlessly

But this blissful feeling didn’t last very long. Soon enough, I was back to stretched-out Sundays and dreadful Mondays. And this was how I knew something was deeply wrong. This threw out any assumptions that I was just burned out—I was clearly unhappy.

The real, serious, targeted search began. From what was a fuzzy, unfocused search effort of a mishmash of open positions in February, came a definite job application strategy in June. Over the course of one month, I was trying my hand at these open roles, with the corresponding outcome:

  • Compliance specialist: got to the second round of interviews
  • Cybersecurity auditor: ignored
  • Security and compliance analyst: declined the interview (it was night shift and daily onsite work)
  • Business continuity analyst: interviewed
  • Content writer: interviewed

It might appear that I had a pretty solid conversion rate in terms of how many applications I sent out that turned into interviews. But what I left out here is how many jobs I actually applied for, which, trust me—is a very large number.

These preliminary interviews I had, even though none of them panned out, pointed me in the direction I was supposed to go in the first place. And instead of being worn out by all those rejections, I gained momentum. The relentless search continued.

Stage 6: Knowing Where You Really Want to Go

It dawned on me that there was a specific type of job that checked nearly all the boxes. And I had been doing some of the work for at least three years, not to mention doing a variant of it for the last six.

This was when I posed the question, “What if I stuck to writing as a full-time job?”

That’s when the proverbial light bulb went off. I tailored my resume for roles that involved writing. If you were to ask me how long I had been ‘writing’,’ I would say since the beginning of high school. Barely a teenager, I was already ghostwriting for classmates who couldn’t find the time or motivation to work on their journal project from our English class. And in college, I dabbled in online freelance writing—back when the art was still in its infancy. It wasn’t widely known as “content creation” back in the day. There weren’t lavish incentives for creators borne by ad revenue or sponsorships.

With the revelation that I wanted to work as a writer full-time, I saw the target and aimed for it. And lucky for me, the job market for content writers, technical writers, all sorts of writers—was hot. I narrowed down the positions I wanted to apply for, received multiple interview invitations, and ended up with multiple job offers.

Stage 7: Leaving the Status Quo

I was down to two good job offers, but my career reinvention wasn’t complete. Tough conversations were waiting for me back at the job I was about to leave. And the difficulty was compounded by three major things. It was especially hard to leave that job because:

  • My manager saw tremendous growth potential in me—he converted me to a regular employee earlier than standard, bumped my pay countless times, and gave me a platform to be the face of efforts that encompassed the entire company.
  • My teammates were as good as you could ever ask for. We had a camaraderie that encouraged openness and empathy, while remembering to hold each other accountable.
  • My workplace always breathed this atmosphere of there’s more to life than just work. Activities with co-workers outside the normal call of duty were organic. Nothing felt forced when employees came together to have fun.

But to truly leave the status quo, I had to stop thinking of the role I had as my job.

There’s a stickiness that you just can’t explain with some jobs you’ve worked. I remember quitting a job from several years back and walking to every corner of the office during my last week. I took a hard look at all the lights I helped fix, the clocks on the wall I had hung, the abandoned lockers I forced open so we could clean them out. And I felt proud that somehow, some part of me had mystically stuck.

But there’s a reality that people who have been in the same job for such a long time need to face: the job can exist without you. Absorbing this, I went and had those talks with people in the company to whom I owed an explanation. And they were kind and compassionate until the very end of our working relationship. They listened.

Having said my goodbyes and accepted one of the job offers, my career pivot was finished.

When Have Times Ever Been Certain?

There’s a secret lesson from my experience that might help you. It’s that there might never be a truly certain time to change careers. Things may always feel uncertain. Recessions, hot markets, global crises, labor shortages—yes, the backdrop will vary from time to time. But when was the last time you fought for less dreadful Sundays and for more meaningful Mondays?

I conclude here that work shouldn’t be an endless hope for Fridays.

This content is accurate and true to the best of the author’s knowledge and is not meant to substitute for formal and individualized advice from a qualified professional.

© 2022 Greg de la Cruz