in Startup Explorations

Startup explorations #18 / A reflection: Discomfort zones, and dealing with them

Talk of comfort zones is nearly always ridden with clichés but I’ll do my best. I’m a person who by now usually knows what I like and tries to only do things that I like. To quote Derek Sivers once again, “The real point of doing anything is to be happy.” At the same time, life offers better payoffs—not to mention it’s far more interesting—when boundaries are pushed and seemingly crazy things attempted.

I’m used to being outside of my comfort zone. When I was pursuing a music career I constantly had to “put myself out there” amidst fierce competition and try to get people interested in my work—by far the worst part of the music profession, and even worse for attention-hating introverts like me. Yet at the same time it was comfortable in a way because I was very confident in my abilities and had the experience and credentials to prove it.

When I moved back to the Philippines at the start of the pandemic and taught myself to build apps, and later started looking for software development work, I was yet again very far outside of my comfort zone. I had little programming experience and no related credentials to speak of. But simultaneously, I was in a comfortable position because I was back in my childhood home with no rent to pay, and I could keep up the job search for as long as I needed to. There’s also much less competition in the local job market than back in New York.

Disgruntled by my past failures, I had been wanting logical and “comfortable” work, and software development seemed to fit the bill (whether or not it’s true). Yet, after joining my current company, I found myself once again back in old discomfort zones: the chance to start my own project, which means going out into the wild and potentially making a fool of myself as I try to validate project ideas all before a single line of code can be written.

This latest example lies at the heart of a lot of reflection I have been doing lately as someone who has embarked on personal reinvention during this time of worldwide upheaval, when questions about the nature of work and what matters most are at the forefront. Lately, I have been asking myself: should a person really only do the things that they find comfortable or enjoyable? How does one discern between true discomfort as a measure of going the wrong way, as opposed to the good kind that leads to growth?

As I see it, it is a good clue that one is not going the wrong way when discomfort coexists with some comfort or another that serves as a stabilizer. People need stability. In the case of my recent work, which has been anything so far but comfortable, I’m comfortable at the same time because no matter the outcome, I get a paycheck at the end of the month. And no matter how far I have to go outside my comfort zone, all the work is on the internet—all from the comfort of my desk. I can even be anonymous if I wanted to. What’s there to get hung up on?

From here I’d like to offer a few more ways, though by no means the only ones known to people smarter than me, that I deal with discomfort.

The first one is a little naiveté—just a little of it can help one power through seemingly impossible situations. The naiveté that made me think I could pull off a music career is the of the same stuff that led me to believe I could teach myself a new skill and make a career change within months. And if I were not just a little naive about this project, I would never find it in me to get started, knowing all the difficulty in store.

The second is to not take oneself too seriously; what a miserable person who does so, whose sense of self collapses at the thought of any kind of failure, and who can’t have a laugh sometimes at the silliness of things.

The third is to decouple one’s sense of self from pure work. Work that fails is still all too human. I’m not sure that I believe in an “authentic self,” but I notice in myself and others that there are multiple selves, more than one of which can be just as authentic as another. There’s a large and genuine part of myself that values comfort, stability, and familiarity; and there’s no reason it should be threatened by the part of myself that wants to be much more adventurous.

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