The Uncapped Career

Gregarious Narain
Founder Craft
Published in
4 min readApr 9, 2019
Photo by Ian Schneider on Unsplash

It seems that no matter what side of the fence you sit on, the grass is always greener on the other side. This can be said, especially, for our own careers and personal development. But this rarely seems to hold when we look at the difference between the startup and corporate employees.

The stories of the startup life, what with its free meals, great perks, and a fun-filled culture and camaraderie. The added bonus of potential riches only seems like icing on the cake, even if it is on baked with long days and longer nights. Indeed, as a survivor of many the startup, the appeal is real. But is it worth it?

Startups begin their lives wandering an unknown path and require a special set of tour guides to navigate it. Early in their lives, even specialists and experts are required to “find themselves” and muster the fluidity and grace of the best generalist. Everything that needs to be done, must be done.

With time, this effort grows more refined, more dutiful. New employees augment missing skills, fill unknown ones, and even displace skills of the founders. But not all skills in the startup world are created equal and not all survive.

Startups have a lot to offer the right person

A startup poses three great challenges and opportunities simultaneously.

First, it represents an opportunity to build and create something on your own. For some, this alone is appealing enough. For others, it’s the pursuit of an unattainable mission that keeps them engaged.

Second, startups train all employees to operate and master uncertainty. The constant battle with the knowns, known unknowns, and truly unknowns keeps most biting their fingers and up late into the night. That may sound like a nightmare, but for some, it is the precise kind of adrenaline they need.

Lastly, if all else works out, startups provide an opportunity to learn how to truly scale and grow. While most problems can have tenuous solutions, the workings of a well-oiled machine are something quite different to marvel at. Solutions at scale are the closest that startups come to mimicking their corporate counterparts — and the closest the startup employee diehards hope to go.

For startups, the hiring floor is high, but is the ceiling?

Since startups are famously resource-constrained all the way until they are not, they are careful with who they hire. Most companies are highly selective, they can’t afford to make any mistakes (though they certainly will). They need the best they can possibly afford, with both the potential and appetite to go much well beyond.

Depending on when you join can become a predictor of your longevity, read, utility. The earliest generalists may return to their specialist roots. The experts continue to ply their expertise. But what of those in between? Has their career path become a trap.

It’s hard to imagine, but ask and you will find more and more employees who move from one startup to the next. Their path may certainly be intentional, but it’s hard to deny there are potentially 2 other main forces at work.

On the one hand, it’s hard to put the toothpaste back in the tube. Once exposed to the workflow and opportunities in the startup realm, most cannot fathom returning to the rigors of the corporate world.

On the other hand, and this one carries a far heavier heft, their skills may not be up to snuff. Startups, due to their rapid twists of fortune, may unintentionally force our own career development onto the rocks. Consider, one may develop the initial skills in the bootstrap phase, but the failure to launch leaves you lacking the skills for the next part of the journey and blemish of not doing so.

It’s possible to be good enough for a prototype, but not serious enough for scale. To be good enough for guerrilla marketing, but not ready to command millions in marketing dollars. An inspiration to the early, but not a leader for the later. For all the hard work, energy, and commitment we make, we know that there are no guarantees. We convince ourselves that even if we leave with nothing, at least the experience is invaluable. But is it?

Is your experience the feather or the cap? As an employee, what can you do to protect yourself? As a founder, what can you do to prevent it?

Gregarious Narain is a serial entrepreneur and founder, having founded more than a dozen companies over the past 25 years. He is the founder of Founder Craft — a startup advisory helping founders and founding teams to define, understand, and navigate the tools, skills, and experience needed to succeed.

Book some time with us at https://foundercraft.com

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Gregarious Narain
Founder Craft

Perpetual entrepreneur. Advisor to founding teams. Husband to Maria. Father to Solomon. Fan of fashion. Trying to stay fit.