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Swashbucklers have long captivated audiences with their daring exploits and charismatic personalities. From the likes of Errol Flynn to Johnny Depp's portrayal of Captain Jack Sparrow, these sword-wielding heroes have become iconic figures in literature and film. However, behind the glamour and excitement, there is a darker side to the swashbuckler – the curse that seems to haunt many who take on the mantle. This curse, while not supernatural in nature, is a burden that these characters must bear throughout their adventures. One aspect of the curse is the constant danger that surrounds swashbucklers. They find themselves in precarious situations, engaged in duels or daring escapes, risking life and limb for their cause.

They find themselves in precarious situations, engaged in duels or daring escapes, risking life and limb for their cause. Their skills with a sword may be unmatched, but they are always at risk of injury or death. This perpetual state of danger can take a toll on their physical and mental well-being, as they are constantly on high alert and in constant fear for their lives.

J-Curves vs Stairs: Two Approaches to Career Growth

For my first two years at Facebook, I worked on the People team. I worked on big, complicated, hard projects, learned a ton, and had a great manager. For all intents and purposes, I was happy and growing. I was planning to stay there for a while.

Then Chamath came to me and said, “We’re going to build a phone. Come build it with me.”

After a lot of deliberation, I decided to join him, and in doing so, I took the first big J-Curve leap of my career.

A J-Curve is what I call a risky career choice with a potentially big payoff. It’s a choice where you bet that you can transfer the skills you currently have to a completely new environment and the upside, if you do it successfully, is that you get to prove you are capable of more.

To me, the J-Curve is the alternative to taking the Stairs : staying in your comfortable role and getting promoted every 2-5 years, walking up to (hopefully) somewhere great. Growth is slower, but the stairs are a safer bet.

We can make a conscious choice to take J-Curves or stairs or a combination of the two throughout our careers. I personally think everyone can benefit from one or two J-Curves in their career, though I’m biased — my whole career is a sequence of J-Curve jobs.

My decision to join the phone project at Facebook felt risky at the time. I knew nothing about mobile, I wasn’t sure we should be building a phone in the first place, and even Sheryl told me the project would probably die but that I could do it if I wanted to. But then a wonderful friend, Larry Yu , said to me, “You’ve proven yourself on the People team. You know you’re good at that job. Why don’t you go see how actually good you are? ”

That quote always stayed with me because it was such a perfect way to explain the challenge that comes with a J-Curve risk.

I call it the J-Curve because of the trajectory of emotions you go through when you start one of these roles: you leap and for the first 6 months you’re falling until you hit the bottom – you usually feel insecure, stupid, and unsure of yourself among other things. Then, eventually, you realize all that pain was a side effect of learning, and you see that this job has catapulted you to places you’d never dreamed of.

The visual in my head reminds me of Paul Graham’s startup curve .

If you’re in your own personal trough of sorrow, you’re (hopefully) going through the pain of massively upleveling. The true shape of the J-Curve is not smooth like a J. It looks much more like wiggles of false hope in the picture above. It is a rollercoaster of feeling inept and crazy, starting to think you know what you’re doing, being humbled regularly, and then eventually realizing how far you’ve come.

When I took that mobile job at Facebook, for the first six months I felt like an idiot. I went from being an extremely high performer to feeling like a moron all the time. I literally got the lowest performance rating of my life at the end of the first six months.

But then, at around 9 months, I came back from a trip to Taiwan and drew the hardware layout for a cellphone on the whiteboard for Chamath. I remember explaining why the phone had to be a certain shape and being able to defend and discuss my ideas. I walked out of that room thinking, “whoa, I actually know something now.”

And that feeling continued. From 6-12 months, I slowly crawled out of the hole and started to feel like myself again.

The mobile job ended up being 3 of the wildest years of my life. I got to do hardware, industrial design, operations, product management, and bizdev with really big, complicated partners. I proved to myself and others that I was capable of much more than just People-related work. I ran teams that grew and morphed. I worked for 3 extraordinary, very different managers: Chamath, Dan Rose , and Bret Taylor . My next job at Quip, working for Bret, would never have happened if I hadn’t taken the risk on the phone job.

What a J-Curve looks like for you may not be the same as it is for someone else. These choices and risky bets are everywhere: joining the startup world, leaving the startup world, moving from marketing to product, CRO to COO, etc. It is also not always about titles; J-Curves can come with a much higher title or a title drop.

In my mind, it’s a J-Curve if:

(1) the change is big

(2) you could really fail

(3) the upside of success is big

It’s a bet on yourself – a bet that you can transfer your skills and prove to a new set of people that you’re great at your job in a totally new context.

J-Curves versus Stairs

I learned things about myself in those 3 years on mobile that I could never have planned or imagined. Among other things, I discovered that my unique skills are valuable for reasons that are broader than I understood. I also realized a bunch of stuff that I’m not good at and I don’t like doing, which saved me from future bad job choices. While the experience was not without cost, it is one that I would never trade.

I’ve chosen J-Curves over Stairs ever since and I am a bit… J-Curve biased as I said, but ultimately I don’t know that one approach is better than the other.

There are many positives to taking the stairs – it’s safe, predictable, and they can lead you to fun jobs if you’re good at your work. Some of my friends who stayed at Facebook or Google for 15 years have walked up the stairs to really interesting, huge roles at each company.

The downsides of the stairs are also relatively obvious: your growth might take longer, and you can get stuck in a bureaucratic organization that promises to promote you to VP but keeps kicking the can down the road.

You may also never know what you “could have been.” Sometimes, companies see you in an iterative way and you have to leave for other people to see you as a “grown up.” I was such a puppy when I joined Facebook and I think that, if I had stayed, that “puppiness” may always have been part of my story.

The J-Curve downside is worse than the Stairs, just like its upside is bigger: you never hit the bottom, you just keep falling. The role, place, or people weren’t right for you.

If you get to 1 year in a new job and haven’t had any feelings of competence … you may have made the wrong bet. You don’t have to feel completely competent but you should see glimmers of hope. The main thing though is do not make any value judgments in the first 6 months. In that first period, it’s hard to discern what’s the job and what’s just the newness and imposter-ness of it all.

Before making a J-Curve choice, you have to evaluate your appetite for risk including the financial and psychological elements. In the “easiest” J-Curve cases, you know there’s a parachute in your backpack or know that the fail won’t be that big of a deal.

When I took the role on the phone project, Sheryl did make it clear that almost no matter what happened, I probably wouldn’t get blamed and there would probably be a job for me at Facebook. It made it easier to make the leap. But sometimes you just have to decide that the opportunity of who you could become is worth the risk.

You can also manage risk by learning about yourself and getting good at communicating what you’re exceptional at and what your weaknesses are . My strength is figuring out big, ambiguous problems. I am the “figure it out” girl. When I took the job at Quip, I confirmed (and re-confirmed) with Bret that he was sure he didn’t want to hire someone who had built a SaaS business before. He was clear: “I want to learn together what is right for our business.”

And when I took the job at CZI with Mark and Priscilla, I confirmed with them that they wanted a first-principles thinker (me) and not someone that knew how to run a massive philanthropy (not me).

It’s healthy and helpful to make sure you’re on the same page with the people that are hiring you about what you bring to the table, and also what you are not.

Betting on yourself

One of our Glue People members recently shared that she had started a new job 6 months prior and was feeling so lost that she was questioning whether she was good at anything anymore. She was on a classic J-Curve, having switched from a consulting-type gig to an in-house operational role at a startup.

I told her about J-Curves to normalize those feelings but also to point out that they are a legitimate approach to catalyzing your growth.

As for me, the wild journey of the phone project gave me a hunger to always be on a J-Curve. I love learning curves so steep that I feel like I might fall off of them, and I love challenging myself to grow as fast as I can. I’ve had success and failure with these jumps but I have learned to be comfortable with the deep discomfort of throwing myself off a cliff every couple of years and to love the opportunity that comes with the risk.

The point of sharing all of this, though, is to help you figure out what is right for you. If you make these choices consciously, the whole journey feels less like tumbling down a mountainside than it does like an elegant base jump paired with the comfort of knowing you packed your parachute.

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The breakdown of the song sings these words:

Another facet of the curse is the inability to form long-lasting relationships. Swashbucklers are often portrayed as charming and charismatic, drawing others to them like moths to a flame. However, they are destined to be eternally alone, unable to truly settle down or find lasting love. Their constant pursuit of adventure and their nomadic lifestyle prevent them from forming deep connections with others, leaving them to wander through life, forever unfulfilled in matters of the heart. Furthermore, the curse of the swashbuckler extends to their moral compasses. While these characters are often seen as the heroes of their stories, they are burdened with a dual nature. In order to achieve their goals and save the day, they may be forced to bend or break the rules, resorting to morally ambiguous actions. This constant tug of war between their personal honor and the greater good can weigh heavily on their conscience, leaving them with a constant sense of guilt and questioning their own integrity. In conclusion, the curse of the swashbuckler is a complex burden that these characters must bear. The perpetual danger they face, the inability to form lasting relationships, and the constant moral ambiguity they encounter all contribute to their cursed existence. While they may be admired and idolized from afar, the reality of the swashbuckler's life is a lonely and challenging one..

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