Expectations that we hold inside of ourselves can be a really difficult echo of identities we tried fantasizing about when growing up and as an adult. We want to do well, we want the approval, we want the validation.
The anxiety over expectations can kill you. It’s self abuse - people (investors, bosses, spouses) don’t invest in you for your anxiety driven productivity, they do it because of who you are outside of that worry. It’s hard to replace it if you consider it your motor. Let the desire to do well and good stay, but let the fear of others disappointment go, and the fantasy that we can control those outcomes by squeezing every last drop out of ourselves.
Identities shift over time whether we intend it or not. Who you were at 5, or 10 is not who you are at 20, 30, 40. We all pick up baggage, trinkets, burdens, and experiences.
One worries because it was a helpful strategy compared to not worrying, but some (like me very specifically) can get attached to that worry to the detriment of picking up other mechanisms.
It's always important to remind one's self that "who you are" is simply the story one is attached to. Things like meditation or psilocybin can help bring that to light.
> Then you look around and see "startup X gets to $1M ARR a month after launch" and shit like that and I'm feeling terrible about how we're barely growing.
Comparison is the thief of joy. I fall into this trap almost weekly. Success stories are incredibly rare and we only see the splash, not the iceberg of failure just beneath the surface.
I think about my current business constantly even though on paper we are making enough to keep this thing going forever but it never feels enough.
When doing my own startup in the past, the biggest pain were: loneliness and inexplicable paranoia. Which then lead to anxiety.
This, when unchecked, can lead to self inflicted, unnecessary pressure on myself. And failure to meet the impossible deadlines, created downward spiral.
I think this is normal, everyone went through the same thing. That’s why some VCs filter for megalomaniacs, zealots, or people who have no idea what pain is, because the journey is insane arduous.
The pain magnifies if the startup is located in VHCOL. Every month a whale appears and eat a big chunk of your runway. Who wouldn’t have anxiety?
Without trying to be glib about it, this post sounds like a description of second-system syndrome, applied to entrepreneurship. It happens to all of us.
Thank-you! It is great to read a honest and self-aware journal covering this.
As someone who fantasizes about running my own thing, working for a few start-ups have made me very stringent on what my requirements are for starting something (co-founders, investment, location, market). And also that these requirements have become so very risk-averse that I probably am not the personality profile to run a business! Nevermind the endless imposter syndrome.
This is exactly why I've avoided raising so far. Not because VC money is bad - obviously it enables things that wouldn't otherwise be possible - but because I know myself well enough to recognise I'd react exactly like this.
The author nails it: "I started to actually operate in a way that is counterproductive for my startup, while thinking I was actually doing what was best." That's the dangerous part. The pressure doesn't announce itself as pressure. It masquerades as ambition, urgency, drive.
Bootstrapping has its own version of this though. Instead of investor expectations, you've got the slow burn of "am I wasting years of my life on something that needs capital to work?" The grass is always greener. At least with VC money, you can move fast and find out if you're wrong. With bootstrapping, you can spend 3 years proving out something that would have taken 6 months with proper funding.
Neither path is inherently better. But knowing which one will fuck with your head less is worth figuring out before you're in the middle of it.
With boot strapping at least you can de risk with consulting/freelancing. And I think with the new generation of software development tools it’s much easier to validate the core business problems without grinding out code for weeks on end.
I have a few 1099 MBA advisors that I call Chief of Staff. I check my questions against what they think. When you get 3 MBAs with engineering, finance, or CS degrees agreeing independently, it bumps up confidence.
I think this is a case where this helps considerably. Its essentially the 'consulting' thing for small businesses.
I think everyone would seriously benefit from learning poker. I used to play professionally and the idea of looking at things as probabilistic bets, and in terms of expected value is so deeply rooted in my mind
Investments are bets. Most sane investors aren't putting it all on one thing
Startups are bets
Applying for jobs. Sales. Dating. Health. Basically everything
You risk $X money and time for a payoff of $Y that comes Z%
You can make the best decision and have a bad outcome because there are so many unknowns. This isn't chess
You can play everything wrong and still hit it out of the park
I mean this is one of the range of outcomes that could've happened. You can't declare yourself a success or failure from one project
Just keep making good decisions and don't risk it all, and you'll more than likely end up fine
I read about mathematical expectation in a poker book for the first time a long time ago and it's really an interesting way to think about the world. In real life, it's a bit different though since there are other factors than just raw percentages like poker hands. For example, you could do everything right and still fail while someone else (like a nepo hire) can do everything wrong and still succeed.
If you want me to ruin this for you, look up Bertrand's Paradox and The Problem Of Priors.
I recently had to deal with this, ugh, I just pick a prior or two and see what the outcome looks like. I'm not sure we can calculate probability of success, but rather use probability to find losing ideas that should never be done.
> You risk $X money and time for a payoff of $Y that comes Z%
Unlike in poker where you know those 3 numbers if you are paying attention, in real life you know only X, and sometimes not even that. The rest is a guessing game, and that estimation is the hard part.
Hey, author here. Totally agree on how helpful these people are. I have a psychologist and also some great mentors. This doesn't make you immune to things like I wrote about but helps you process and get over them when they happen.
As a side note, I'm in a much better mental space now, largely due to facing these things straight on. Things are good, and I'm motivated and sharp!
Nothing about this struck me as a sign that money wasn’t well-invested. From the headline, I was picturing “we raised and then I blew it in Vegas”.
Nothing wrong with admitting to uncertainty and insecurity. I mean, there are two types of people — those who suffer doubt sometimes, and those who don’t admit it. Give me the first kind any time.
Then I know they are capable of deep self-reflection. A good thing. Any founder without such thoughts and some point or another is either lying to you or will eventually fail big time.
Expectations that we hold inside of ourselves can be a really difficult echo of identities we tried fantasizing about when growing up and as an adult. We want to do well, we want the approval, we want the validation.
The anxiety over expectations can kill you. It’s self abuse - people (investors, bosses, spouses) don’t invest in you for your anxiety driven productivity, they do it because of who you are outside of that worry. It’s hard to replace it if you consider it your motor. Let the desire to do well and good stay, but let the fear of others disappointment go, and the fantasy that we can control those outcomes by squeezing every last drop out of ourselves.
Can you separate "who you are" from that worry? Seems to me it's a part of you and you wouldn't be you without it, for better and worse.
Identities shift over time whether we intend it or not. Who you were at 5, or 10 is not who you are at 20, 30, 40. We all pick up baggage, trinkets, burdens, and experiences.
One worries because it was a helpful strategy compared to not worrying, but some (like me very specifically) can get attached to that worry to the detriment of picking up other mechanisms.
It's always important to remind one's self that "who you are" is simply the story one is attached to. Things like meditation or psilocybin can help bring that to light.
A wonderful and personally relevant thing to read.
> Then you look around and see "startup X gets to $1M ARR a month after launch" and shit like that and I'm feeling terrible about how we're barely growing.
Comparison is the thief of joy. I fall into this trap almost weekly. Success stories are incredibly rare and we only see the splash, not the iceberg of failure just beneath the surface.
I think about my current business constantly even though on paper we are making enough to keep this thing going forever but it never feels enough.
I felt this post and appreciate the honesty.
When doing my own startup in the past, the biggest pain were: loneliness and inexplicable paranoia. Which then lead to anxiety.
This, when unchecked, can lead to self inflicted, unnecessary pressure on myself. And failure to meet the impossible deadlines, created downward spiral.
I think this is normal, everyone went through the same thing. That’s why some VCs filter for megalomaniacs, zealots, or people who have no idea what pain is, because the journey is insane arduous.
The pain magnifies if the startup is located in VHCOL. Every month a whale appears and eat a big chunk of your runway. Who wouldn’t have anxiety?
Without trying to be glib about it, this post sounds like a description of second-system syndrome, applied to entrepreneurship. It happens to all of us.
Thank-you! It is great to read a honest and self-aware journal covering this.
As someone who fantasizes about running my own thing, working for a few start-ups have made me very stringent on what my requirements are for starting something (co-founders, investment, location, market). And also that these requirements have become so very risk-averse that I probably am not the personality profile to run a business! Nevermind the endless imposter syndrome.
Loved it, understanding and working through your vulnerabilities is super hard but ultra rewarding. Bold but very altruistic move to publish this
This is exactly why I've avoided raising so far. Not because VC money is bad - obviously it enables things that wouldn't otherwise be possible - but because I know myself well enough to recognise I'd react exactly like this.
The author nails it: "I started to actually operate in a way that is counterproductive for my startup, while thinking I was actually doing what was best." That's the dangerous part. The pressure doesn't announce itself as pressure. It masquerades as ambition, urgency, drive.
Bootstrapping has its own version of this though. Instead of investor expectations, you've got the slow burn of "am I wasting years of my life on something that needs capital to work?" The grass is always greener. At least with VC money, you can move fast and find out if you're wrong. With bootstrapping, you can spend 3 years proving out something that would have taken 6 months with proper funding.
Neither path is inherently better. But knowing which one will fuck with your head less is worth figuring out before you're in the middle of it.
With boot strapping at least you can de risk with consulting/freelancing. And I think with the new generation of software development tools it’s much easier to validate the core business problems without grinding out code for weeks on end.
I have a few 1099 MBA advisors that I call Chief of Staff. I check my questions against what they think. When you get 3 MBAs with engineering, finance, or CS degrees agreeing independently, it bumps up confidence.
I think this is a case where this helps considerably. Its essentially the 'consulting' thing for small businesses.
I think everyone would seriously benefit from learning poker. I used to play professionally and the idea of looking at things as probabilistic bets, and in terms of expected value is so deeply rooted in my mind
Investments are bets. Most sane investors aren't putting it all on one thing
Startups are bets
Applying for jobs. Sales. Dating. Health. Basically everything
You risk $X money and time for a payoff of $Y that comes Z%
You can make the best decision and have a bad outcome because there are so many unknowns. This isn't chess
You can play everything wrong and still hit it out of the park
I mean this is one of the range of outcomes that could've happened. You can't declare yourself a success or failure from one project
Just keep making good decisions and don't risk it all, and you'll more than likely end up fine
I read about mathematical expectation in a poker book for the first time a long time ago and it's really an interesting way to think about the world. In real life, it's a bit different though since there are other factors than just raw percentages like poker hands. For example, you could do everything right and still fail while someone else (like a nepo hire) can do everything wrong and still succeed.
Life's odds are rigged.
I think the metaphor is pretty extensible to handle the things you point out.
> you could do everything right and still fail
Sometimes even a high probability draw doesn't get there on the river.
> while someone else (like a nepo hire) can do everything wrong and still succeed
Some people always start with pairs, Axs, or suited connectors.
One of my favorite star trek scenes: https://www.youtube.com/watch?v=t4A-Ml8YHyM
If you want me to ruin this for you, look up Bertrand's Paradox and The Problem Of Priors.
I recently had to deal with this, ugh, I just pick a prior or two and see what the outcome looks like. I'm not sure we can calculate probability of success, but rather use probability to find losing ideas that should never be done.
> You risk $X money and time for a payoff of $Y that comes Z%
Unlike in poker where you know those 3 numbers if you are paying attention, in real life you know only X, and sometimes not even that. The rest is a guessing game, and that estimation is the hard part.
In poker you learn to strategically size $X based on your estimates of $Y, Z%, and current bankroll.
Even if your estimates have large error bars, it can still be a good bet if you believe it’s +EV and have a large enough bankroll.
Finding the right psychologist/coach/founder to chat this over with will probably do you and the company wonders.
Hey, author here. Totally agree on how helpful these people are. I have a psychologist and also some great mentors. This doesn't make you immune to things like I wrote about but helps you process and get over them when they happen.
As a side note, I'm in a much better mental space now, largely due to facing these things straight on. Things are good, and I'm motivated and sharp!
Awesome to hear. Best of luck!
Imagine betting on someone and xe writes this ...
Nothing about this struck me as a sign that money wasn’t well-invested. From the headline, I was picturing “we raised and then I blew it in Vegas”.
Nothing wrong with admitting to uncertainty and insecurity. I mean, there are two types of people — those who suffer doubt sometimes, and those who don’t admit it. Give me the first kind any time.
if i bet on someone and they wrote this id know my money was spent well
Then I know they are capable of deep self-reflection. A good thing. Any founder without such thoughts and some point or another is either lying to you or will eventually fail big time.