Why Startup Founders are Always Unhappy
I'm a startup founder and I'm very frequently happy... but I found this post quite sincere and poignant and potentially helpful to entrepreneurs.
I don't know Jess personally but I strongly suspect from her capsule bio that she's one of those people who was always great at school and work and never failed at anything major. On the other hand, you could argue that I've failed at everything I've done since grammar school -- except for one thing, which is learning to recover from failure.
A really big part of that for me was realizing that I actually did NOT feel happy as a first derivative of success. Some of my most miserable moments were during periods where others were congratulating me for some achievement -- partly because of that gap between how I knew I was supposed to feel and how I actually did feel. And remember that in the venture-backed startup business, there are frequently strong financial incentives for other people to make entrepreneurs feel "unsuccessful".
The part of this post I can definitely agree with is to get out there and talk to other founders, because "Without any perspective from other founders, my only data points on startups came from TechCrunch, which is filled with overnight success stories and positive spin. "
Silicon Valley trains people to not be happy with what we have.
It pushes people to do more, make more, raise the bar, keep improving.
You can't have your happiness tied to a milestone, or another milestone will make you miserable right after you hit your milestone.
It's not just TechCrunch that's filled with overnight success stories.
Pretty much all technology press is slanted that way.
 Perhaps, all press. Obama. Jeremy Lin. et. al
No, most mainstream press is about Dirty Laundry.
Kick em when they're up, kick em when they're down:
Happiness shouldn't be based on how well your startup is doing. 99% of startups eventually fail; basing your happiness on a 1% chance of success is sheer madness.
 This might be true in a vacuum, but I think we key our happiness relative to our friends, peers, etc.
Imagine an example. You wake up, scan your startup dash, realize that your key metrics have doubled. Your beady eyes crinkle into a happy face that lasts all day. That evening you happily walk into drinks w 3 friends who each run a startup. Their metrics *quadrupled* overnight. I would guess you are now a little bummed. Your individual rate of success has doubled, but you are not nearly as happy as you were when you woke up.
You can imagine the above where your metrics are flat, but everyone else's plummets. Your individual rate is flat, but relatively speaking you might be content, if not happy.
I believe that success = happiness. But all of that depends on how we actually define "success" (that o so elusive term). It's all in the metrics. If success is defined as "my startup is getting more funding" or "I am making lots of money" or "people are patting me on the back" then that is going to be an ephemeral moment of good feeling at best. On the other hand, if we define success in terms such as: I am doing something I am passionate about, I have close friends and family, I am living with meaning, or I am learning and growing (mostly from failures and mistakes). Those things last and won't be easily swept away by market conditions. I agree that Silicon Valley focuses us on what we have, but truly successful people focus on who they are, who they're becoming, and what difference they are making. One of my favorite quotes: "Success is how high you bounce after you've hit bottom." Veritas!
I agree with Chris and Jonathan -- happiness comes from friends, not startups.
Rich has a good definition of success: having close friends and family, working on something we care about, living with meaning, learning, and growing.
It's easy to forget that when we're up to our necks in our startups.
So I appreciate the reminder.