The Challenge of Startup Life

Never let your day job become your life. Once upon a time I heard that advice and it stuck with me. Not because it was particularly unique, but it was particularly accurate in regards to exactly what I do when it comes to jobs and my life. Working for a startup to some extent requires you to dedicate many hours of the week to your day job, which very quickly becomes your night job as well.

Startups can be extremely fun and rewarding. I’ve worked for a few of them to date now. Some stayed small with no serious momentum at any point from start to the inevitable layoffs once funding runs out. Some have grown extremely fast only to teeter on the brink of crash and burning. I’ve never seen a real success yet. But I’ve been close and the closer you get the more your dreams of the big win plague the back of your mind while you’re trying to focus on getting an impossible amount of work done. No matter how great things are going, people get burnt out. Naturally, some days are less great than others, and those days are the hardest.

Working for a startup is more like having a work family than most any other job. That family needs to remain somewhat functional over the course of a many year period, bringing in new members that fit its DNA while expanding it genetic footprint. And everyday that family mades decisions together, or processes the output of those decisions, which determine the fate of the business. Every move matters in a highly competitive, fast-changing marketplace. It’s exciting. It’s exhilarating. It’s exhausting. 

Sometimes, it gets a bit rough. It’s a challenge to get through the hard days because you don’t want to share your fears with colleagues, that will only make the mood more sour, and you don’t want to take that pain home to your life outside of work. The few hours of it you have. So you see a therapist. Or you write an anonymous blog post. And you move on. Try to focus on just doing your job. Keeping your head down. Hoping that your little contribution to the greater good of the business will help shift the tides. And maybe it will. You know that, in a company this small, this young, this vulnerable, you can make a difference. Perhaps you can make all the difference.

That pressure eats away at people. It clearly fuels the mentality of many attracted to the startup environment. We’re all tired of being cogs in a giant corporate machine. We have some ideals. We want to not be stuck behind politics or process to get stuff done. But soon enough politics and process weighs down thea same people who sought to escape it. Typically the pressure put on the executive team from the investors is huge. This is not odd, as they’ve put millions of dollars on the line and expect an impossible return on this investment, all to offset their other failures. The pressure from the top burns through the organization. Everyone’s ass is on the line. One bad quarter and heads can roll. Two and shit can hit the fan. The more money you raise, the more opportunity you have to grow a serious business that can stick around, but you also have more chances of greater pressure. That pressure destroys people. It brings out their true colors.

So we’re all together running this marathon like it’s a sprint, from sprint to sprint, with no down time. It is painful to watch people I care about go through the rough patches. I generally avoid friendships with colleagues, but I can see how this pressure takes the toll on folks who desperately want to believe in the vision which ultimately brought them to the company in the first place. The one they were sold as they accepted a job with likely lower pay then a comparable position at a larger company. And everyone still sees that vision, though there are days they may wonder what has become of it. And other days when suddenly the world turns around and the vision is clear again, business is booming, and fears are set aside, replaced by a savage, dopamine-fueled state of victory against the competition and more so above the looming fear that the new market, the overall business need for the entire product you’ve spend years building, will not hold.

I’m trying hard to distance my heart from my job. But my challenge is always that I perform best when my heart is in it. I’m not the type of person that can turn off my heart from anything I do. It’s all art to me. And as I sit behind my cubicle walls, ones that have sprouted up in the growth of a company once contained in a tiny office with IKEA desks to one lost in a sprawling office park as a testament to its magical success, I peer through hazed glass, remnants of the open company that once was, and watch my colleagues all go about their daily tasks – sales calls, answering support requests, building product features, testing those features, launching those features, talking to customers, etc – and I see this whirlwind of people who I’ve grown to care deeply about, even though they don’t know that. And this doesn’t mean I actually like all of them. I know few of them personally. But they are my family. Many have their own families. Many have mouths to feed and partners to answer to, and full lives outside of their day jobs. But they all come in, 8am, or 9am, or even earlier, and eat lunch at their desks, and if they manage to leave at a reasonable time it’s clear they continue to work upon returning to their homes.

On the good days, the early days, perhaps the naive days, we secretly love this, as much as we may be bothered by the hours required to keep the business afloat. But then, it inevitably becomes tedious. We become the Aflec duck keeping the Titanic afloat, unable to breathe at the same time. It’s a challenge to remain consistently motivated while navigating murky, unexplored waters on a ship constantly being pierced with holes. That’s life at a startup. You are the modern explorers. Convincing residents of the old world that your new world is one they want to inhabit. And you spend lots of money to get them over to your new world, and to buy property so they stay. But how many new worlds do we really need?

Unless the product solves serious problems like poverty or disease, you quickly can loose faith in all humanity, pushing to bring folks to a new world by detailing the failures of their current state and promising the moon in return for embarking on a journey with us. It’s all quite a bit delusional, and cult-like, and yet in the end if we do this right some bigger company, some company that has a long time ago succeeded at the same mission, may come in and buy you for millions, billions of dollars. And you get swallowed up into a larger corporation where typically the original concept of your product fades away into a bigger machine. And all the good ideas, all the passion for new, for improving the status quo, dies with even most successful outcomes. That’s life at a startup. It may not always be this way, but it’s been my experience thus far. I wouldn’t trade it for the world. But it’s hard. It takes an emotional toll that few are willing to or able to admit. Or who have time to admit. So we plow on to another day, inviting visitors to explore our timeshare and purchase property in this new, questionably improved, land.



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