Once Afraid...

On risk aversion & rethinking the concept of job security

I caught up with a friend recently -- one that I hadn’t spoken to in some time. We exchanged updates on what we’ve each been up to work-wise, and at a certain point in our conversation he summed up my career choices in an interesting way:

“You’re definitely not scared, hey?”

He was referring to the fact that I’m six months into having left a stable job for a categorically unstable one (joining a brand-new company), and to other similar moves I’ve made over the years. In 2012, I left a century-old insurance company I had worked at for the better part of a decade, to join a ~5-year old company that was much less of a “sure thing”. In 2016, I left a different secure corporate job to pursue even less of a sure thing -- starting my own company, solo.

To my friend, that series of moves makes me some sort of white-collar adrenaline junky, throwing caution to the wind in favour of a flair for grand adventure or ambition.

The truth is that I am scared. Or... I would be. Just not in the way that he was alluding to.

See, 2012 Me had my friend’s worldview. I was 30, had worked at the same giant institution -- err, company -- since I’d graduated from university, and my job was to put a price on risk. I don’t know what the average tenure was at the place, but I can tell you that at company ‘town-hall’ meetings, the list of people being recognized for 25-, 30- or even 40-year milestones with the company was longer than you’d find just about anywhere. And frankly, I had always assumed I’d be one of those -- some day posing for a photo on a stage, mid-handshake with a big grin, holding an inscribed telescope in my other arm.

Before being hired by the big insurance company to think full-time about risk mitigation, I was a straight-A student, which comes with its own implicit training along the same lines. Nobody tells the straight-A student to have a go at starting a rock band. They tell the straight-A student to take their pick of the most stable, respected (translation: least risky) jobs out there.

My point is: you could not have constructed a person better trained to value certainty than 2012 Me. So when I left the big, stable company to join a much newer, less mature one, I was whatever level of terrified is directly beneath the one of refusing to make the leap. What if the new company went under? What if I failed at my new job? Where would I go? What would I do?

Somehow, I still convinced myself to take the plunge.

And after I did, it didn’t take me long to realize... I’d made a big mistake.

The mistake was that all along I’d misunderstood the true nature of job security. I had always taken ‘job security’ to be a matter of having a “good job” with an employer that was unlikely to go out of business. And I was now realizing that while you could do a lot worse than to work for the big, steady employer, there’s a way better option available: make yourself un-unemployable.

Long-term service to the big, steady employer is a great way to be probably okay, but to ultimately leave your fate in someone else’s hands. If budget cuts or some other corporate headwind should happen to materialize, you may be on the chopping block regardless of your exemplary performance. And if that happens (particularly if you’re one of many, all being released into the job market simultaneously) you’ll be negotiating with new employers from a position of weakness. Here is your interviewer -- faced with an influx of labour supply -- and here you are, touting your deep, specialized experience in a work environment that... may or may not be relevant to them. Shit.

(I don’t love using real people’s misfortune to make a point, but a few years after I left, guess which big insurance company went through a ‘restructuring’, turning the last paragraph from a hypothetical into a real-life cautionary tale?)

I realized after my first big career move that, whatever else came of it, throwing myself into a new environment and a new challenge was making me stronger. And it’s not like it was a breeze. I felt legitimate culture shock at the new place, and of course had to grapple my way up the learning curve that comes with every new job or company. But I came to recognize pretty quickly that I was learning at a pace that I hadn’t in a long time, or maybe ever. And that -- professionally speaking -- when you stitch together different lessons and skills, hard-won in a variety of different environments and cultures, you become… ‘un-unemployable’.

Whatever else happens when you’re UUE*, you’re gonna be more than okay. Company fails? You’ll land on your feet quickly. Ready for a change? No shortage of options. Get fired? Even then, your next employer will mostly be interested in the skills you bring to the table. You basically can’t help but have great career prospects at all times.

(*Shit, if I’m going to make up a word, I might as well also make up a shorthand form of it while I’m at it, right?)

The UUE mindset has guided my career decisions since. As long as there’s something of value to be learned in the process, there’s no such thing as a bad move. (There are probably some caveats here -- the main one being “don’t burn bridges” -- but otherwise, the point stands.) And I say this as someone who’s tasted bona fide failure, in the form of that solo venture from 2016 ultimately falling flat. That failure had its downside, mind you, but my lasting impression from it is one of massive formative upside.

There’s one other piece of the puzzle, though: just recognizing the value of being (and therefore consciously endeavoring to be) UUE is only part of my motivation for making career moves.

I said earlier that I’m not immune to fear, but whereas my fears used to be the ones that were trained into me at a young age -- about being able to put food on the table, and the like -- these days I’m much more afraid of the prospect of... wasted time.

Sooner or later, we all come face to face with the realization of just how finite time is, or rather -- our own allotment of it. And having learned to be a student of my own life satisfaction, I’m hyper aware of the importance of allocating my time wisely. Career-wise, that means doing my best to ensure that I’m always working on creative things that are some combination of fascinating and meaningful (ideally both). I know now that had I stayed forever at the big insurance company, in pursuit of bigger salary, bigger title and an engraved telescope, I’d have lived to regret it. That sort of regret has come to be a way scarier prospect to me than the unknown. In fact, I now see the unknown as a thing of beauty: a blank canvas to be painted with all that’s possible.

So in the end, what my friend sees as me repeatedly taking risk turns out to be the way that I’ve learned to avoid danger… the danger of complacency, that is.

I guess I’m just as risk-averse as I’ve always been. Young Me would be proud.