Startup Life is Hard. You Have To Know Your Why If You Want to Succeed

A Personal View On Working At A Start-up, Long Hours, Working Remotely & Burn Out

Cal Chan
The Startup


Photo by Mathias Jensen on Unsplash

There’s a common image that comes to mind when people picture a startup: a garage full of poorly-groomed, immature 20-somethings, munching on pizza, fueled by coffee and Red Bull, staring at a computer screen all day (and night).

The mental image is often times accompanied by a sort of montage of events that fast-forwards past the toil and strife to the cover of Time Magazine and the next ticker on the NYSE.

But this is an idealized picture, one entrepreneurial idealists and people in denial of the startup life try and perpetuate.

The reality is more like this:

Startup life is hard. Really hard.

Startup life doesn’t care how hard you work and how many hours you put in. It doesn’t care how intelligent you are, how talented you are, nor how much you’re willing to learn.

It doesn’t care how much experience you have in your field or how many degrees you have on your wall.

The startup life is hard, because you’re creating something from nothing, and that’s the harsh reality. There are no deep pockets of resources, there is no leg to stand on. In fact you have to build a leg, then two, then another while also trying to stay balanced on a tight-rope, while juggling knives.

Startup life doesn’t care if you like it. It doesn’t care if you hate it. This is just how it is, and there’s no way around it. You can’t trick it, you can’t hack it. You can’t negotiate it. You are not exempt from this reality.

Startup life is really hard.

It’s so hard that the average startup dies after four years. You can have the most innovative idea in the world, the smartest people, and the best investors, but in four years most businesses still fail.

Startup life is so hard that even if you are one of the few successes — even if you manage to make it after four years — you may not actually want to do it anymore. The glory of success is far less appealing, even after you achieve it, after years of being put through hell and back to earn it.

The pain is hard to justify. The sacrifices are hard to sustain. The reality is hard to accept. All this was true before Covid, and now is taken to the next level with social distancing, WFH, and the realities of days that bleed into evenings and that bleed into nights.

More than two years into this experiment, one has to consider, “Is it worth it?”

To answer that question, you may want to ask yourself this:

How long do you want to live?

Now, if you want to live for as long as possible, you have to make healthy decisions. And if you’re a human, you’re going to have to make a lot of hard choices to stay healthy.

At the beginning of the year, I made a commitment to myself: I would try to do whatever I can to stay healthy, by eating right, working out and avoiding unhealthy activities.

I’m not perfect. I have slipped more than a few times. But overall, I’m happy with my progress. I’m happier and healthier than I was two years ago. I’ve lost a few pounds and I feel better. I have more energy. I can run longer, wake up earlier, and have more focus than ever before. I’m more alert. I sleep better. I wake up less tired.

Going about the self improvement game is hard — especially while running a startup during a pandemic — and health is just one of the things that matter. There are many other things that matter too, like family, friends, love, and happiness.

One of the most important things in life is your network. And one of the most important parts of your network is your family. As messy as family can be, as dysfunctional as it can be, as much as it can frustrate you and make you want to tear your hair out, it’s still a really good thing to have. I’m extremely fortunate to have the family I have. Two beautiful boys, and a supportive, devoted wife.

To be honest, I‘m often distracted with them, thinking about work or in-between a text. This isn’t the best way to spend time with them, and it is something I’m actively working on.

Some of my best hours are spent with the team, on Zoom calls working through the big things and the mundane things, bouncing ideas off each other and getting feedback. I’m very grateful for the team, for the ethics we hold, the standards we hold ourselves to, and the support we give each other. Still, when confronted with an endless stream of tasks, I know many find it difficult to keep up. During these times I suggest taking a little breather. If you can, go outside for a walk. Get a breath of fresh air. Take a short nap.

Sometimes I might just reach out to a colleague for some advice, or to just chat about a random topic. It’s so easy for us to forget that “chit-chat” is a thing in remote cultures. Just taking a moment to say hello is helpful, even if it’s just on Slack.

I’m also fortunate to have friends, old and new. Many of them business contacts, some of them entirely removed from my work. People who believe in me and who push me to be better and to keep trying despite all the uncertainty, the frustration, and the adversity. I am thankful for these people, who accept a text and subsequent call from me, who are willing to hear me out about things I can’t share with my wife, kids, or colleagues. I wish I could grab a drink with them, but remembering to reach out, even via text, has really helped me stay grounded.

Several months ago a friend of mine asked me what I’m doing all this for. Is it the money? Success? To prove something?

He chose a very different life than mine, one focused on family, tangible, real-time experiences, and friends. When talking to him I remembered that all of us, even at my startup might have very different goals.

So, in the vein of his first question:

What are you here for?

Do you want to fulfill the Mitzvah of getting married and having kids?

Do you just want to find love?

Do you want to find happiness?

Do you want to find yourself?

Do you want to get a degree?

Do you want to climb the corporate ladder?

Do you want to retire?

Do you want to make history?

Do you want to cure cancer?

Do you want to save the rainforest?

Do you want to see the world?

Do you want to save the world?

If you do, for any of those things above or more, then you better make time for the people who can help you get there, first and foremost, yourself.

Yes, your health is important. Yes, your family is important. Yes, your friends are important. But if you have dreams and ambitions and goals like changing the world (maybe even just your world), you have to put in the time and effort to create a system that works, for you.

Even if you realize you don’t have entrepreneurial ambitions, you have to plan and execute your life so that you can achieve the goals that you personally have and are aligned with. If your goals aren’t aligned with where you currently are in work, that’s okay! As long as you put in a little effort, daily, to take care of yourself, you’ll get a little better, daily. Often times this means by taking care of those who are close to you. It’s funny how taking care of others really helps feed the soul.

If you feel like you can’t put in the time and effort, you have to know that soon, you won’t have a choice in the matter, so better to do it now, while you can — even if this means spending less time on whatever it is that’s keeping you from answering the questions above.

Something I’ve noticed from my time doing the Startup life is that there’s a lot of noise. It’s hard to sift through all the noise and find the signal. I feel like this is the age we live in — the age of noise — and if we can find the signal ourselves, we can amplify that and become a beacon for all of those around us. To those of you searching for a signal, join the club! You’re not alone, and you’re not that far from hearing it, if you take a moment to listen.