Reflections On Startup Life

Startup Life. These two words are often found together when someone is describing one of two things:

• How amazing their life is
• How stressful and intense their life is

Here’s an example of each.

• “We had beers with an amazing VC and he says he wants to see our deck, ah the joys of startup life!”
• “We spent all week pitching investors and are exhausted, oh and they hate us and we’re running out of money, startup life is rough.”

Of course in reality as a founder you’ll probably use “startup life” in both contexts as running a startup is a roller coaster ride where things can go from good to bad, or bad to good, in a day.

Before I quit my job I had always heard about startup life, I longed for it, oh and I thought I understood it. Now, almost a year into our startup and I realized that startup life is really different from what I thought it would be.

What I realized is that I thought I knew what startup life would be like, and I am happy to say I was wrong. Now that I’ve been living in a world that is still very new to me for almost a year I thought it would be a good time to reflect on what startup life has been like for me.

• Being your own boss means having the most demanding boss who is never satisfied. If you thought that working for other people full-time was hard, try working for yourself, it’s harder. As a startup founder you always have too much on your plate, you need to prioritize and you will run out of hours in the day. When you wake up at 6:00AM you could go back to sleep…but suddenly you become your boss, “get up, start working, you have SO much to do today!”
• You’ll never say the words, “I’m staying late at the office” again. There will never be enough hours in the day. I can still remember working in an office and waiting for 5:00PM, thinking, another good day of work is behind me! Say goodbye to that feeling because it never happens again. Most of our days don’t really have an end, they just keep going into the night. There’s no more notion of “staying late” and I don’t use that term at all any more. I find that my friend with corporate jobs seem to brag about working late, as a startup founder every day is late, there is no break, it’s always go-time.
• Everything takes longer than you think. I used to think I was good at estimating how long things would take. With a startup everything takes longer than you think and you need everything to move ten times faster than it is.
• A new feeling of satisfaction. When you work for someone else and close a big deal you feel good because you look good in front of your boss and you make money. When you are building a startup and close a big deal, you feel good because you did it yourself. It may sound subtle but it really is a different kind of satisfaction. Nothing is done for you, you have to do it all yourself, and when you make it happen, the feeling of satisfaction is like no other.
• A new feeling of defeat. Of course life is all about balance and while satisfaction might feel better, defeat feels worse, here’s why. When you work for a company it’s so easy to shift the blame. You say things like “well I could have closed the deal but the company I work for has ridiculous terms that the client wouldn’t agree to.” Or “I would have been able to do more business this month if my company just gave me the budget and headcount I deserve!” Alas, you can’t do that at your own startup, you and only you are to blame, for, well, just about everything. If something falls through it’s your fault, period.
• A new feeling of camaraderie. Last but not least is the incredible bond I feel with other founders. It feels like there’s this understanding that we’re all going through something very hard, yet very exciting and wonderful. Just like you relate to people you work with at an office because they’re going through many of the same things, you have the same connection with other startup founders who may be doing something completely different from you. The connections are no longer about what industry you’re in, it’s more broad because no matter what industry your in or market you focus on you’ll find founders going through many of the same trials and tribulations. The founder of a subscription candy service still has a lot in common with the founder of a startup that makes a to-do list app. Sure, they’re in completely different industries, but they’re both thinking about customer acquisition, hiring, branding, funding, etc.

Last but not least, what I’ve learned the most about startup life is that the further you get into it, the more you learn that you don’t know. Every day is a new challenge, a new opportunity, and in almost every case you’ll be doing something you haven’t done before. If you think you know it all, be prepared for a lesson in humility because at the end of the day all your really need to know about startup life is that you have a lot to learn every single day.